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Vice President, Marketing
HopSkipDrive · Remote
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Vice President, Marketing
Remote
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who we are
HopSkipDrive's go-to-market organization is the engine behind our growth. We sell to school districts, government agencies, and nonprofits — buyers who are mission-driven, relationship-dependent, and move on their own timeline. That means our marketing function has to do more than generate leads; it has to build the credibility, educate the market, and create the pipeline that a complex B2B sales cycle demands.
We're at an inflection point. We have strong brand recognition in our space, a maturing product, and an aggressive growth agenda. We are looking for a leader who can build a true revenue marketing function that operates in lockstep with Sales, is accountable to pipeline and revenue outcomes, and scales efficiently as we expand into new markets.
HopSkipDrive is a multi-sided marketplace. School districts, government agencies, and nonprofits are our buyers who organize and fund transportation for the students (and their parents) who use the service; and CareDrivers are caregivers on wheels who come to our platform to earn safe, flexible income.
As VP of Marketing, you will own the entire B2B marketing motion at HopSkipDrive. You will drive the full customer and user journey for our institutional buyers, who manage budgets and contracts, as well as the families and riders whose daily experiences heavily influence those buying decisions. You'll sit on our senior leadership team and report directly to the CEO.
Key responsibilities
Own the full B2B marketing function: brand, demand generation, field and events marketing, RFPs, customer advocacy, product marketing, sales enablement, lifecycle and growth marketing.
Lead product marketing as a core competency: market intelligence, client engagement and advocacy, competitive positioning, go-to-market launches, pricing and packaging strategy, and sales enablement that actually changes how a sales team sells. We use the Challenger methodology, and need someone familiar with how to sell, market, engage and communicate within that framework.
Build and execute a revenue marketing strategy where every investment connects to pipeline, revenue, and retention outcomes, not traffic, impressions, or MQL volume.
Drive the RFP function in partnership with Sales. This is a meaningful part of how we win new business in the public sector, and it needs to be treated as a strategic capability, not a reactive one.
Own the entire demand gen engine, which is not only our digital channels but also includes events as one of our most important marketing channels.
Oversee brand strategy and compliance across all external touchpoints, including earned media, events, digital, and content; serve as the steward of HopSkipDrive's voice and positioning.
Partner tightly with Sales and Customer Success on ICP, pipeline targets, lead quality standards, and expansion signals; hold Marketing accountable to the same revenue goals Sales is held to.
Build a lifecycle and growth marketing engine that reduces churn, drives expansion, and improves net revenue retention.
Oversee the marketing tech stack, attribution, lead scoring, and the data infrastructure that makes revenue marketing possible.
Drive the AI transformation of the marketing team’s capabilities, incorporating AI into every facet of the operating model. The expectation isn't that we grow our way to output; it's that we build AI into how the team works so we can scale impact without scaling headcount proportionally.
Own the marketing budget and be rigorous about ROI, CAC, ROAS, and marketing-sourced revenue as the metrics that matter.
Who you are
You've owned B2B marketing before, all of it, not just one function, but your foundation is in product marketing. You've built positioning that holds up in a competitive market (including against buyers who don't think they have a problem yet). You've crafted messaging that gives a sales team something real to say. You've created enablement that changed how deals get closed, not just the collateral library. You understand that "why us" is the hardest question in marketing to answer well, and you've demonstrably answered it well.
You've also run the full funnel and you understand demand generation. You've held pipeline and revenue targets, and you know how to build programs that tie marketing investment to business outcomes. You measure your work in marketing-sourced revenue, CAC, and time to revenue, not clicks and impressions.
Pricing and packaging isn't an afterthought for you. You've been in those conversations, you understand how those decisions ripple through positioning, sales conversations and competitive response. You know how to work across Product and Sales to get to something that is defensible and drives the market.
You're genuinely AI-forward. You’ve changed how you work because you are curious, you are an AI adopter and you know how to lead a team through that same shift. You think about redesigning workflows, what AI makes possible that wasn’t previously possible, and how to improve outputs before you think about what headcount would solve.
You're a clear thinker and a direct communicator. You can hold the strategic narrative and get into the details when the work demands it. You build teams that trust each other, hold each other accountable, and don't confuse activity with outcomes.
What you bring
10+ years of B2B marketing experience, with at least 3 years owning the full marketing function at a company with a complex sales cycle.
Deep product marketing background: you've built and owned positioning, messaging, competitive strategy, pricing and packaging, go-to-market launches, and sales enablement that demonstrably changed how a sales team sells.
Demonstrated accountability to pipeline and revenue metrics. You've held targets, not just reported against them, and you measure your work in marketing-sourced revenue, CAC, and time to revenue, not impressions or MQLs.
Experience building or scaling a revenue marketing function, including marketing operations, attribution, and the data infrastructure to connect marketing investment to outcomes.
A genuine track record of using AI to redesign workflows, drive team efficiency and productivity, and the ability to lead others through that shift.
Experience marketing to institutional or public-sector buyers (school districts, government agencies, nonprofits or similarly complex, multi-stakeholder environments) is a strong plus, as is direct experience owning or building an RFP function.
Strong executive communication skills; comfortable presenting to a board and investors, influencing at the C-suite level, and representing HopSkipDrive externally.
Experience in a growth-stage, VC-backed company where resources are finite and speed matters.
Our investment in you
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, mission-driven VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace.
HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $200,000–$250,000 + bonus. This position is primarily remote, with a strong preference for candidates in the LA area. Final compensation will be determined by relevant work experience, skill set, certifications, and specific work location. The total compensation package also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
This role will be fully remote in one of the following states: AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI.
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At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
By checking this box, you agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information you may obtain during your interview process. Read the full policy below.*
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You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
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Sr Counsel - Policy & Regulatory
HopSkipDrive · Remote
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Remote
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Sr Counsel - Policy & Regulatory
Remote
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
About the Role
HopSkipDrive is seeking a Senior Counsel, Regulatory & Litigation to own a significant portion of the company’s state and federal regulatory compliance program, lead engagement on legislation that shapes how we operate, and manage a litigation portfolio from onset to resolution. This is a high-visibility role for a lawyer who thrives at the intersection of policy and operations, builds credibility quickly with government agencies and internal partners alike, knows how to translate complex regulatory requirements into practical compliance strategies, and can oversee a litigated case.
You will manage HopSkipDrive’s regulatory obligations across multiple jurisdictions — monitoring the legislative landscape, managing filings and agency relationships, advising cross-functional teams on compliance, and positioning the company to respond to audits, public records requests, and enforcement actions. You will also contribute to emerging areas including AI policy, data sharing, and government contracting compliance. On the litigation end, you will oversee a small book of claims and litigation related to driver union and other civil matters.
What You’ll Do
Regulatory Compliance & Licensing
Own multi-state regulatory compliance obligations for HopSkipDrive as a transportation network company operating in the education sector, including TNC licensing, driver qualification standards, DMV record check requirements, and state-specific transportation regulations.
Draft and submit regulatory filings, advice letters, and compliance attestations to state agencies; track and manage agency review, approval, and disposition.
Advise on revenue contract and RFP provisions with regulatory implications, including background check requirements, reporting obligations, and driver and vehicle standards.
Advise internal stakeholders on regulatory requirements for new market entry and ongoing compliance obligations in existing markets.
Build AI projects and workflows related to regulatory matters.
Legislative Affairs & Policy
Monitor and analyze federal and state legislation affecting HopSkipDrive’s operations, with a focus on transportation network companies, school pupil transportation, and automated decision systems.
Develop legal and policy positions on pending legislation; collaborate with the Policy and Government Relations teams to prepare bill analyses, public comments, and engagement strategies.
Assist with bill review and bill drafting in partnership with the Policy team.
Identify legislative trends and develop proactive compliance strategies, particularly around TNC regulation, school transportation, and gig economy classification.
Represent HopSkipDrive’s interests in regulatory rulemakings before state public utility commissions and transportation agencies.
Monitor and manage responses to public records and disclosure requests from state and local agencies.
Leverage AI tools for more efficient legislative analysis.
Litigation
Oversee a book of claims related to labor and employment claims.
Manage a small number of cases or claims related to civil litigation including discovery strategy, preparing corporate witnesses, and directing litigation defense.
Support outside counsel in preparing for and conducting arbitrations.
Handle subpoenas, service of process, and regulatory investigations, coordinating with outside counsel as appropriate.
Build AI projects and workflows related to litigation.
Cross-Functional Advisory
Manage data use agreements and research partnerships with academic institutions and government agencies.
Provide legal research and rulemaking assistance as needed to support a busy and growing regulatory portfolio.
Serve as a legal subject matter expert on AI and automated decision-making, advising on compliance with emerging state AI legislation and internal AI governance frameworks.
Leverage AI-powered tools to increase efficiency across the compliance portfolio, and advise the business on legal exposure from emerging federal and state AI policy developments.
What You’ll Bring
Required
J.D. from an accredited law school and active license to practice law in the jurisdiction where you live.
8+ years of legal experience, including at 5 in a law firm or in-house role, with primary focus on regulatory and/or governmental affairs and meaningful exposure to litigation or claims management.
Demonstrated ability to work with AI tools in a legal context and uses AI consistently in their own legal work, whether for contract analysis, legal research and synthesis, matter management, regulatory analysis, or various projects.
Demonstrated experience navigating state regulatory agencies, administrative proceedings, or legislative processes
Proven ability to advise cross-functional teams on legislative and regulatory requirements and the legal implications of policy priorities
Exceptional analytical skills with the ability to interpret complex regulatory requirements and apply them to practical business operations
Excellent written and oral communication skills, with the ability to present information clearly to varied audiences and collaborate effectively across teams
Strong organizational skills and the ability to manage a high-volume, rapidly evolving regulatory portfolio with competing deadlines
Comfort operating in a fast-paced, ambiguous environment — bonus points for experience at a rapidly growing company
Preferred
Exposure to litigation or claims management, especially answering discovery and drafting court filings, and/or preparing corporate representatives for testimony.
Experience in transportation, mobility, gig economy, or a similarly regulated industry.
Familiarity with public utilities commissions and/or transportation and education regulatory frameworks.
Experience advising on automated decision-making, AI governance, or algorithmic compliance.
Background in data privacy (CCPA, HIPAA) or government contracting.
Exposure to multi-state compliance programs or regulatory tracking systems.
Hands-on experience working with AI tools for legal or compliance purposes, or a demonstrated interest in building AI competency as a core part of your legal practice.
Who You Are
You build credibility fast. Government agencies, school districts, and internal partners take you seriously because you are prepared, responsive, and direct.
You don’t wait to be asked. You spot a compliance gap or a bill moving through committee and you’re already drafting the memo.
You can hold complexity without losing the thread. Multi-state, multi-agency, multi-stakeholder — you manage it without drama.
You’re curious about AI and legal technology and see tools like AI-assisted research and contract automation as part of how modern legal teams operate.
You communicate like a lawyer and think like a business partner.
Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $178,000.00 - $200,000.00 . This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
* This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**
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At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
By checking this box, you agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information you may obtain during your interview process. Read the full policy below.*
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You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
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AI & Automations Lead
HopSkipDrive · Remote USA
Pay
$120k–145k
Setting
Remote
The job you are looking for is no longer open.
Current openings at HopSkipDrive
Welcome! Please review our jobs and apply for what feels most relevant and exciting. We’re hopeful to get to know you!
HopSkipDrive will only collect personal information through our website (hopskipdrive.com) and/or greenhouse.io application form. Consider an email suspicious if the sender email doesn’t end in "@hopskipdrive.com." You would never receive an offer letter or an employment contract before starting the interview process. If you received an offer, but you haven’t been in verbal contact with a HopSkipDrive recruiter, we recommend that you do not share your information with that sender.
Hoping to become a HopSkipDrive CareDriver? We encourage you to Apply to Drive.
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Pod Lead, Specialty Account Management
HopSkipDrive · Remote USA
Pay
$70k–235k
Setting
Remote
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Pod Lead, Specialty Account Management
Remote USA
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are:
The Specialty Transportation team is the strategic engine behind HopSkipDrive's most complex, mission-critical services. This role leads the Professional Supply Pod, bringing together Business Development Managers and CarePartner Specialists into a single, high-performance unit focused on our professional WAV and Livery fleets.
The Role: As the Manager, ST Account Management, you are a strategic player-coach responsible for the end-to-end health of our professional supply portfolio. You will manage a team of multi-level professionals, bridging the gap between high-level supply contracting and daily operational fulfillment. You are responsible for ensuring that the "handshake" between sales and execution is flawless, documented, and scalable. This role reports to the General Manager, Specialty Transportation and is a critical leadership layer designed to drive consistency across our most complex markets.
You will be responsible for the following:
Unify the Account Management Lifecycle: Lead a specialized pod of 5–6 direct reports (BDMs and Specialists), ensuring that professional fleets are not just contracted, but successfully integrated and optimized for daily ride volume.
Drive Professional Supply Performance: Own supply-side performance for the WAV and Livery categories, ensuring we have the professional density required to meet district demand.
People Leadership & Development: Manage and coach a team of individual contributors. You will be responsible for their career growth, performance management, and daily tactical guidance.
Standardize Operational Blueprints: Eliminate "islands of process" by enforcing strict documentation standards. You will ensure every market launch and CarePartner relationship follows a consistent process.
Manage High-Complexity Portfolios: As a player-coach, you will directly manage a select group of high-complexity strategic partnerships, modeling excellence in account management for your team.
Act as the First Point of Escalation: Serve as the primary operational lead for complex CarePartner negotiations or significant service-level gaps within your pod.
Optimize the "Hunter/Farmer" Handshake: Partner with Revenue and Sales Ops to ensure that new supply acquisition is perfectly aligned with upcoming district demand and operational capacity.
Who You Are: You are a seasoned manager who thrives on building systems, developing talent, and leveraging modern tools to scale operations. You understand that scaling a specialized business requires moving away from individualized "heroics" and toward repeatable, documented processes. You bring:
Proven People Management: 5+ years of experience managing professional teams, including a track record of developing and promoting mid-level individual contributors.
Systems-Thinking & Rigor: You are obsessed with documentation and "playbooking." You have a proven ability to take complex, manual processes and turn them into scalable SOPs.
AI & Automation Tech-Fluency: You actively leverage AI and automation tools (e.g., LLMs for drafting documentation, workflow automation, or data synthesis) to accelerate team productivity, streamline communication, and eliminate repetitive tasks. You encourage your team to use AI responsibly to work smarter.
Player-Coach Mentality: You enjoy being "in the weeds" of a complex negotiation or operational challenge while maintaining the bird’s-eye view required to lead a department.
Collaborative Diplomat: You can fluidly navigate the natural friction between supply acquisition and operational fulfillment, finding the "win-win" for the business, the team, and the client.
Data-Driven Operator: You use supply-side metrics to drive team performance. You are comfortable using data tools to identify gaps and forecast supply needs.
Comfort with Ambiguity & Change: You thrive in a fast-paced, evolving marketplace environment. You can chart a clear path forward for your team even when operational blueprints are still being written.
Senior Stakeholder Presence: You have the gravitas and communication skills to represent the Specialty Transportation division in cross-functional leadership meetings and strategic planning sessions.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
* This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI, PA**
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At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
By checking this box, you agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information you may obtain during your interview process. Read the full policy below.*
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You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
This role requires deep expertise in complex B2B enterprise sales cycles (12+ months) focused specifically on hunting and closing net-new business, rather than managing existing accounts. Which of the following best describes your background?*
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How many years of direct people management experience do you have leading a team of 5 or more B2B Account Executives?*
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As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.
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Listed by HopSkipDrive for a position based in the United States. Employers on this board attest they are hiring domestically.
Strategic Account Executive
HopSkipDrive · Remote USA
Pay
$80k–205k
Setting
Remote
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Strategic Account Executive
Remote USA
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are
We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.
As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility—while making a meaningful difference for those who need it most.
As Strategic Account Executives, we provide this value to net-new prospective business partners in particular by telling the HopSkipDrive story, connecting our unique value propositions to their needs, creating urgency, and closing the deal to bring the solutions to reality. We achieve this by challenging the status quo and pushing our prospects to innovate alongside us.
To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:
Always be Closing: Effectively negotiate terms, and execute by closing new business. After the initial contract is executed, convert to a paying client, and grow that account during the initial onboarding period.
Always Build Pipeline: You will be supported by a worldclass SDR team but best performing AEs source around 20-30% of their own pipeline plus multithread all the time.
Challenge the Status Quo: Lead every conversation with an insight, not a pitch. Whether in person, by phone, or on video — Teach the prospect something they haven’t considered, Tailor the message to their specific situation and role, and Take Control of the process to create urgency and drive the deal forward.
Demonstrate Curiosity and Compassion: Ask targeted questions and listen to understand unspoken concerns, political dynamics, and the real decision-making structure across the buying committee. Use those insights to execute, teaching each stakeholder a new perspective on their problem, tailoring the message to their priorities, and taking control of the process to build consensus and create urgency toward a decision.
Multi-Threaded Stakeholder Engagement: Build and maintain relationships across multiple stakeholders in the buying committee simultaneously — including transportation directors, operations leads, finance, and executive leadership — mapping the full decision-making structure, identifying the economic buyer, and driving organizational alignment toward close.
Pipeline Qualification Discipline: Apply MEDDPICC qualification rigor to every deal. Prioritize finding the true economic buyer, the individual with real budget authority, early in the cycle, not at the finish line. Develop internal champions who will advocate for HopSkipDrive when you’re not in the room. Maintain forecast accuracy by consistently assessing all MEDDPICC elements on every active opportunity.
Partner Cross-Functionally: Collaborate with internal teams including Support, Product, Trust & Safety, and Operations to implement client feedback and optimize our offerings to their needs.
In-Person Prospect Engagement: Dedicate up to 50% of your time to travel within your assigned territory (including overnight) for invaluable face to face meetings, follow ups, unscheduled cold door knocking at district offices and transportation facilities, and cold prospecting with prospects within your assigned region or territory.
Operational Excellence & CRM Discipline: Maintain meticulous Salesforce discipline as a foundational element of your sales strategy. Ensure all interactions, pipeline stages, and MEDDPICC criteria are consistently documented.
Manage Your Territory: Build and execute a territory plan that prioritizes accounts by opportunity size, strategic fit, and probability. Know your whitespace, manage coverage proactively, and consistently generate the pipeline needed to hit your number.
Leverage AI Tools: Use AI-powered tools — including Gong, Salesforce Agentforce, Claude and others to research prospects, prepare for calls, surface deal risk signals, and accelerate your productivity. We expect our AEs to be active and creative users of available AI, not passive ones.
Who You Are
You excel at establishing new relationships, driving sales growth, and delivering impactful solutions to prospective clients. With expertise in pitching, negotiation, and closing, you can confidently sell the value propositions of HopSkipDrive to prospective clients and convert them into active paying clients. You’re motivated by results, and thrive in dynamic environments where our contributions directly drive to success.
With the required qualifications and necessary experience listed below, your impact will be tangible and immediate:
Strategic Sales Expertise: 8+ years of B2B sales experience, including 2+ years in enterprise sales, account management, or a related role. Strong background in developing and executing comprehensive tactics to get in the door, pitch the solution, negotiate, and then close. Experience selling into K-12 school districts, government agencies, or public sector organizations is a plus.
Goal-Driven Focus: Track record of consistently exceeding targets and achieving measurable results, with a sharp focus on delivering outcomes that align with company objectives.
Hunting and Prospecting: 5+ years prospecting by phone or in the field including cold dropping in, cold calling, and other common prospecting techniques.
Negotiation and Closing: Experience negotiating B2B contracts with multiple stakeholders and implementing tactics both internally and externally to bring the deal to a close including experience navigating strategy for RFPs before and after the proposal.
Executive-Level Communication: Proven experience communicating with Superintendents, Directors, and C-suite stakeholders (or similar titles) with authority and precision. Adapts messaging to executive audiences — translating operational detail into the business and mission outcomes they care about — and leads high-level presentations that influence client strategy and drive significant outcomes.
Challenger Mentality: Proven Challenger sales experience and mentality. Leads with insight, tailors the message to each persona, and takes control of the sales process to constructively challenge buyer assumptions and create urgency. Naturally reframes problems rather than validating them.
Professional Field Sales Skills: Comfortable traveling up to 50% (including overnight), practiced in cold door knocking, and disciplined enough to manage a high-volume field schedule and keep momentum across the territory.
AI Fluency & Tool Track Record: Proven experience leveraging AI-based or AI-enhanced sales tools to optimize the sales cycle (e.g., automated meeting recaps, prospecting research, and pipeline management)
Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is also proud to operate as a drug-free workplace. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $95,000 base with an OTE of $160,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
Role Clarification: This remote role requires frequent travel and in-person meetings.
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At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
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You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
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For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.
As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.
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A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.
A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.
An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.
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Why are you being asked to complete this form?
We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.
Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.
How do you know if you have a disability?
A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:
Alcohol or other substance use disorder (not currently using drugs illegally)
Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
Blind or low vision
Cancer (past or present)
Cardiovascular or heart disease
Celiac disease
Cerebral palsy
Deaf or serious difficulty hearing
Diabetes
Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
Epilepsy or other seizure disorder
Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
Intellectual or developmental disability
Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
Missing limbs or partially missing limbs
Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
Partial or complete paralysis (any cause)
Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
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Listed by HopSkipDrive for a position based in the United States. Employers on this board attest they are hiring domestically.
GTM Engineer
HopSkipDrive · Remote USA
Pay
$95k–180k
Setting
Remote
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GTM Engineer
Remote USA
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are
As a lean, high-impact Revenue Operations team, we build the scalable infrastructure and intelligent systems that power HopSkipDrive’s growth engine. We are an AI-first team obsessed with clean data, connected tools, and workflows that just work — and you will join us as the technical backbone who makes that possible. We do, and you will, support the business through the following responsibilities:
Administer and continuously optimize Salesforce — owning user management, custom objects, flows, validation rules, permission sets, and reporting dashboards to ensure it operates as a reliable single source of truth
Own the GTM tool stack end-to-end: maintain a live inventory of all tools, manage vendor relationships, track contract renewal timelines, and provide data-driven recommendations on consolidation, expansion, or replacement
Design and deploy new tool workflows and cross-system integrations that eliminate manual handoffs and increase velocity across Sales, Marketing, and Customer Success
Champion an AI-first approach to GTM operations — proactively identifying opportunities to leverage LLMs, automation agents, and intelligent enrichment pipelines to reduce manual effort and surface actionable signal for revenue teams
Build and maintain integrations across the GTM stack (e.g., Salesforce, ZoomInfo, Outreach, Gong, Spiff, Omni) via APIs, MCPs, native connectors, or iPaaS platforms to create a high-fidelity, connected data ecosystem
Document system configurations, workflow logic, and integration architecture to ensure operational continuity and enable self-service for end users and business stakeholders and also enable AI automations and agents. Document first and use that context layer to build.
Partner with RevOps leadership and GTM stakeholders to translate business requirements into scalable technical solutions, proactively flagging risks and surfacing opportunities before they become problems
You’ll report directly to the Director of Revenue Operations and work closely with senior team members and cross-functional GTM leaders.
Who You Are
You are a systems thinker and hands-on builder who moves fluidly between technical configurations and strategic context. You don’t just maintain tools — you make them smarter. With the following skills, you’ll make a tangible and immediate impact:
5+ years of experience in a GTM Engineering, RevOps Systems, or Salesforce Admin role within a high-growth B2B SaaS or marketplace environment
Salesforce Administrator certification or equivalent hands-on expertise, with deep proficiency in flows, validation rules, permission sets, custom objects, and reporting
Demonstrated AI-first mindset — a track record of incorporating LLMs, automation agents, or AI-assisted enrichment tools (e.g., Clay, n8n, Gemini, Claude, or similar) into GTM workflows to meaningfully reduce manual lift
Hands-on experience managing a SaaS GTM tool stack, including renewal tracking, vendor evaluation, and ROI analysis across tools like ZoomInfo, Outreach, Gong, Spiff, or comparable platforms
Strong technical aptitude for system integrations, including experience connecting tools via REST APIs, native connectors, or iPaaS platforms such as Zapier, Make, or WorkatoA builder’s mentality and ‘owner’ mindset — you proactively identify gaps, architect scalable solutions from scratch, and take pride in systems that others rely on without thinking twice
Comfortable building automations, debug integrations, and working with APIs — you don't need to ship production code daily, but you can read docs, use AI tools like Claude Code to close gaps fast.
Build AI agents and workflows that help reps prep for calls, auto-populate CRM after meetings, surface deal risk signals, and automate district research — shipping tools reps actually use
Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is 120,000-130,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
* This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI, PA**
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This role requires at least 5 years of experience in a GTM Engineering, RevOps Systems, or Salesforce Admin role within a high-growth B2B SaaS or marketplace environment. Do you meet this requirement?*
Do you hold a Salesforce Administrator certification or possess equivalent hands-on expertise with advanced configurations like flows, validation rules, permission sets, and custom objects?*
By checking this box, you declare that you have read and understood the HopSkipDrive Applicant and Employee Privacy Notice. Link to full policy below. *
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https://www.hopskipdrive.com/privacy_ae
At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
Voluntary Self-Identification
For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.
As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.
Gender
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Are you Hispanic/Latino?
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Race & Ethnicity Definitions
If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:
A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.
A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.
An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.
Veteran Status
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Voluntary Self-Identification of Disability
Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 07/31/2029
Why are you being asked to complete this form?
We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.
Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.
How do you know if you have a disability?
A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:
Alcohol or other substance use disorder (not currently using drugs illegally)
Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
Blind or low vision
Cancer (past or present)
Cardiovascular or heart disease
Celiac disease
Cerebral palsy
Deaf or serious difficulty hearing
Diabetes
Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
Epilepsy or other seizure disorder
Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
Intellectual or developmental disability
Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
Missing limbs or partially missing limbs
Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
Partial or complete paralysis (any cause)
Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
Short stature (dwarfism)
Traumatic brain injury
Disability Status
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Listed by HopSkipDrive for a position based in the United States. Employers on this board attest they are hiring domestically.
Metro Service Manager
HopSkipDrive · Remote USA
Pay
$80k–90k
Setting
Remote
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Metro Service Manager
Remote USA
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are
This role will provide exceptional, proactive support for our clients throughout the operational lifecycle. This position bridges the gap between Implementation, Customer Success, and ongoing Operations to streamline service delivery and ensure a premium client experience.
The Metro Service Manager will take ownership of ongoing client operations and issue resolution. This new role will work closely with cross-functional teams to proactively address client needs, improve service quality, and optimize ride experiences. We are looking for creative problem-solvers who, like us, believe that challenges require innovative approaches, unique perspectives, and new ways of thinking.
Serve as the primary point of contact for assigned clients, ensuring needs are addressed and solutions delivered with urgency and professionalism.
Respond to and resolve complex client inquiries, leveraging internal resources and collaboration to provide swift resolutions.
Lead and manage the implementation of new business from contract signed through launch, ensuring a successful implementation process and maintaining communication with clients throughout the implementation
Act as a trusted advisor by continuously learning about HopSkipDrive's evolving products and services to best support clients.
Gather and analyze feedback on ride experiences to identify improvement opportunities and implement service enhancements.
Collaborate with cross-functional teams to address systemic issues affecting client satisfaction and advocate for impactful changes.
Partner with Customer Support Specialists to resolve real-time ride and account issues while delivering weekly optimization reports.
Conduct virtual and in-person client meetings to strengthen relationships, align on goals, and ensure adoption of best practices.
Drive the strategic planning and execution of business reviews to align ongoing service strategies with client objectives.
Who You Are
You’re a proactive and strategic customer success professional who excels at building strong client relationships, solving complex challenges, and driving measurable results. You thrive in fast-paced environments and are passionate about enhancing client experiences through data-driven insights and collaboration.
5+ years of experience in Customer Success, Account Management, or Implementation roles, preferably in a high-pressure or start-up environment.
Willingness to travel (10%-20%) to strengthen client relationships and support service strategies.
Proven ability to manage client relationships, resolve issues swiftly, and deliver exceptional customer service.
Strong communication skills, both written and verbal, with the ability to present insights and solutions effectively in meetings and reports.
Expertise in analyzing data, identifying trends, and implementing actionable solutions to improve client outcomes.
Experience collaborating across teams to address root causes of recurring challenges and enhance service delivery.
Proficiency with CRM tools such as Salesforce or Kustomer, and advanced Excel skills are preferred.
A proactive, problem-solving mindset with the initiative to drive continuous improvement and innovation.
You are tech-forward and committed to operational excellence. You actively leverage AI tools (such as Gemini) to streamline workflows, summarize complex client issues, refine communication, and derive insights from data sets, and you are eager to apply this expertise to enhance client outcomes
Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The base salary range for this role is $80,000 - $90,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
*NOTE* This role will be remote but candidates must be able to travel occasionally regionally (10-20%).
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"Do you have 5+ years of experience specifically in Customer Success, Account Management, or Implementation roles?*
Which CRM (e.g., Salesforce, Kustomer) have you primarily utilized, and what is your proficiency level with advanced Excel (e.g., VLOOKUPs, Pivot Tables)*
At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
By checking this box, you agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information you may obtain during your interview process. Read the full policy below.*
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You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
Voluntary Self-Identification
For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.
As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.
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A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.
A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.
An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.
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Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.
How do you know if you have a disability?
A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:
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Cancer (past or present)
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Epilepsy or other seizure disorder
Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
Intellectual or developmental disability
Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
Missing limbs or partially missing limbs
Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
Partial or complete paralysis (any cause)
Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
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Listed by HopSkipDrive for a position based in the United States. Employers on this board attest they are hiring domestically.
Sr. Regional Account Manager
HopSkipDrive · Remote USA
Pay
$90k–100k
Setting
Remote
Back to jobs
Sr. Regional Account Manager
Remote USA
Apply
About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are:
We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.
As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what's possible in mobility-while making a meaningful difference for those who need it most.
The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. The Sr. RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.
This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.
To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:
In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions.
AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.
Who You Are:
Required
8+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
Proven ownership of retention and expansion revenue.
Strong executive communication and presentation skills.
Demonstrated success managing complex, multi-stakeholder accounts.
Advanced CRM discipline and data fluency (Salesforce or equivalent).
Experience leading cross-functional account execution.
Comfort operating in ambiguity with accountability for outcomes.
Experience in education, government, or regulated markets highly preferred
Familiarity with Challenger or similar insight-led sales methodologies highly preferred
Background in transportation, logistics, or marketplace platforms highly preferred
High operational rigor and the ability to leverage AI into daily workflows
Our Investment In You:
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $90,000-100,000 base with an OTE of $150,000 - $170,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
NOTE* The role will require 2-3 days on-site client visits regionally.
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Are you a current or former HopSkipDrive Employee? *
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What is your annual salary requirement? *
Are you currently authorized to work in the U.S.?*
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Will you now or in the future require sponsorship for employment work visa status?*
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Which state do you live in? *
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What encouraged you to apply to HopSkipDrive?*
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Do you have 8+years experience in Account Management, Customer Success, or Consultative Sales in a SaaS, marketplace, logistics or services environment? *
Select...
If you were referred by a HopSkipDrive employee, please include their name here.
At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
Are you willing and able to travel?*
Select...
By checking this box, you declare that you have read and understood the HopSkipDrive Applicant and Employee Privacy Notice. Link to full policy below. *
Select...
https://www.hopskipdrive.com/privacy_ae
By checking this box, you agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information you may obtain during your interview process. Read the full policy below.*
Select...
You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
Voluntary Self-Identification
For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.
As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.
Gender
Select...
Are you Hispanic/Latino?
Select...
Race & Ethnicity Definitions
If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:
A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.
A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.
An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.
Veteran Status
Select...
Voluntary Self-Identification of Disability
Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 07/31/2029
Why are you being asked to complete this form?
We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.
Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.
How do you know if you have a disability?
A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:
Alcohol or other substance use disorder (not currently using drugs illegally)
Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
Blind or low vision
Cancer (past or present)
Cardiovascular or heart disease
Celiac disease
Cerebral palsy
Deaf or serious difficulty hearing
Diabetes
Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
Epilepsy or other seizure disorder
Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
Intellectual or developmental disability
Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
Missing limbs or partially missing limbs
Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
Partial or complete paralysis (any cause)
Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
Short stature (dwarfism)
Traumatic brain injury
Disability Status
Select...
PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.
Submit application
Powered by
Listed by HopSkipDrive for a position based in the United States. Employers on this board attest they are hiring domestically.
Regional Account Manager
HopSkipDrive · Remote USA
Pay
$85k–90k
Setting
Remote
Back to jobs
Regional Account Manager
Remote USA
Apply
About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are
We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.
As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility — while making a meaningful difference for those who need it most.
The Role
The Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 2 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. With support from Regional Sales Management, the RAM sets and executes account strategy and provides recommendations to senior staff for required resources, collaborates cross-functionally with Metro Service Managers to drive operational excellence at the account level and plays an active role in identifying product-level gaps and strategies for product penetration by account.
This is a revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires strong client communication skills, demonstrated commercial acumen, high operational rigor and the ability to proactively coordinate and align both internal cross-functional partners and senior external stakeholders.
To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:
In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions
AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.
Who You Are
Required
5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
Proven ownership of retention and expansion revenue.
Strong executive communication and presentation skills.
Demonstrated success managing complex, multi-stakeholder accounts.
Advanced CRM discipline and data fluency (Salesforce or equivalent).
Experience leading cross-functional account execution.
Comfort operating in ambiguity with accountability for outcomes.
High operational rigor and the ability to leverage AI into daily workflows
Experience in education, government, or regulated markets.
Familiarity with Challenger or similar insight-led sales methodologies.
Background in transportation, logistics, or marketplace platforms.
Our Investment In You:
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $85,000-90,000 base with an OTE of $130,000 - $140,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
NOTE* The role will require 2-3 days on-site client visits every week regionally.
Create a Job Alert
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Create alert
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Last Name*
Email*
Phone
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Phone*
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Attach
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Enter manually
Accepted file types: pdf, doc, docx, txt, rtf
Cover Letter
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Enter manually
Enter manually
Accepted file types: pdf, doc, docx, txt, rtf
Are you a current or former HopSkipDrive Employee? *
Select...
What is your annual salary requirement? *
Are you currently authorized to work in the U.S.?*
Select...
Will you now or in the future require sponsorship for employment work visa status?*
Select...
Which state do you live in? *
Select...
What encouraged you to apply to HopSkipDrive?*
Select...
Are you willing and able to travel within a region specifically to visit clients onsite 2-3 days a week?*
Select...
Do you have 5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environment with proven ownership of retention and expansion revenue?*
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Listed by HopSkipDrive for a position based in the United States. Employers on this board attest they are hiring domestically.
Senior Product Manager, Ops & Customer Experience
HopSkipDrive · Remote USA
Pay
$160k–180k
Setting
Remote
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Senior Product Manager, Ops & Customer Experience
Remote USA
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About HopSkipDrive
At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.
Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.
How we work
We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.
Who We Are
Our Support and Operational Productivity team sits at the intersection of customer experience, operational excellence, and business growth. We're a high-impact, collaborative group of product managers, engineers, designers, and operations specialists who build the systems and experiences that keep HopSkipDrive running — for our customers and for the teams that serve them.
Our support world is uniquely complex. We serve schools and parents coordinating their children’s transportation, school administrators managing district-wide logistics, drivers navigating complex pickup instructions and multi-stop coordination, and the operations team orchestrating it all. Every interaction involves multiple stakeholders, tight safety requirements, and real-time coordination.
Our work spans the full operational landscape of HopSkipDrive — from the customer-facing experiences that keep riders, CareDrivers, caregivers, and school partners informed and supported, to the internal platforms that power how our teams operate across support, sales, revenue operations, and safety. We think deeply about the people on both sides of every interaction: the customer navigating a problem, and the team member solving it. That dual lens — user experience and operational excellence, together — is what makes this work uniquely challenging and uniquely impactful.
We move fast, think big, and measure success by how much more effective we make our teams and how much better we serve our customers.
Who You Are
You are a seasoned, versatile Senior Product Manager who leads with curiosity and conviction. You don't just build features — you develop a deep understanding of your customers, your business, and your stakeholders, and use that understanding to make smart bets and drive real outcomes. You're as comfortable in a strategic planning session as you are in a sprint review, and you have a track record of bringing people together around a shared vision.
Minimum of 8 years of experience in product management, ideally spanning customer-facing platforms, operational tooling, or internal systems in complex, multi-stakeholder environments where reliability and user experience are non-negotiable.
Strong Customer Instincts: a proven ability to build genuine, nuanced understanding of users through research and data, and to translate those insights into product decisions that matter
Strategic Vision & Execution: You think in systems and over horizons. Skilled at defining multi-year product strategies, cutting through ambiguity to set clear direction, and driving execution from ideation through growth. You can zoom out to shape a roadmap and zoom in to unblock a team — and you know when to do each.
Cross-Functional Collaboration: A proven partner to teams across the organization. You navigate competing priorities, broker alignment, and build the kind of collaborative relationships that make hard things possible. You understand that great product work happens at the intersection of functions, not in silos.
Platform & Systems Thinking: Comfortable building internal platforms, CRM solutions, and operational tooling that scales business processes and enables cross-functional teams. You think holistically about how systems interact and how tooling choices shape team performance and customer experience.
Data-Driven Decision Making: Highly analytical. You leverage data, customer research, and operational metrics to inform product decisions, evaluate tradeoffs, and measure impact — and you foster that same orientation in the teams and stakeholders around you.
Preferred experience that will set you up for success from day one:
Hands-on experience with customer support or helpdesk platforms such as Zendesk, Salesforce Service Cloud, or Intercom. Understanding how agents work, not just how the tools are configured
Familiarity with CRM systems and how they connect customer data, workflows, and team operations at scale
Experience building with or alongside generative AI tools, whether LLM-powered features, AI agents, or conversational experiences, with a practical understanding of where they work well and where they don't
Experience building internal tools or operational platforms that meaningfully changed how a team works
Background in industries where safety, trust, or care are central to the product — transportation, logistics, healthcare, childcare, or similar
Our Investment In You
We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $160,000 - $180,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.
HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.
* This is a fully remote role. Candidates must reside in and perform work from one of the following states: AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, or WI. We are not currently considering candidates who will perform work from any other state.
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If you were referred by a HopSkipDrive employee, please include their name here.
At HopSkipDrive, we lean into technology to drive efficiency and impact. Please describe how you currently utilize Artificial Intelligence (AI) tools—such as LLMs, research assistants, or workflow automation—in your professional or personal life. Specifically, how has it changed the way you approach complex tasks?*
By checking this box, you declare that you have read and understood the HopSkipDrive Applicant and Employee Privacy Notice. Link to full policy below. *
Select...
https://www.hopskipdrive.com/privacy_ae
By checking this box, you agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information you may obtain during your interview process. Read the full policy below.*
Select...
You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.
Voluntary Self-Identification
For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.
As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.
Gender
Select...
Are you Hispanic/Latino?
Select...
Race & Ethnicity Definitions
If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:
A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.
A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.
An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.
Veteran Status
Select...
Voluntary Self-Identification of Disability
Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 07/31/2029
Why are you being asked to complete this form?
We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.
Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.
How do you know if you have a disability?
A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:
Alcohol or other substance use disorder (not currently using drugs illegally)
Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
Blind or low vision
Cancer (past or present)
Cardiovascular or heart disease
Celiac disease
Cerebral palsy
Deaf or serious difficulty hearing
Diabetes
Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
Epilepsy or other seizure disorder
Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
Intellectual or developmental disability
Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
Missing limbs or partially missing limbs
Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
Partial or complete paralysis (any cause)
Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
Short stature (dwarfism)
Traumatic brain injury
Disability Status
Select...
PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.
Submit application
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