Sr. Regional Account Manager

HopSkipDrive · Remote USA

Pay

$90k–100k

Setting

Remote

Apply Sign in to mark as applied ← Back to all jobs

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. Get new jobs like this in your inbox We'll email you when HopSkipDrive posts a job like this one. Create alert Apply for this job * indicates a required field Autofill my application First Name* Last Name* Preferred First Name Email* Phone Country Phone Resume/CV Attach Attach Dropbox Google Drive Enter manually Enter manually Accepted file types: pdf, doc, docx, txt, rtf Cover Letter Attach Attach Dropbox Google Drive Enter manually Enter manually Accepted file types: pdf, doc, docx, txt, rtf LinkedIn Profile Website 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... 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.