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Customer Experience Associate
Benepass · Chandler, Arizona, United States
Pay
$24/hr
Setting
Hybrid
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
TEAM & ROLE
As a Customer Experience Associate at Benepass, you'll be a critical member of our growing Customer Experience organization, reporting to a Customer Experience Manager. You'll help deliver an exceptional customer experience by supporting members across chat, phone, and email, ensuring every interaction is timely, accurate, and empathetic.
This role is designed for someone who thrives in a fast-paced, metrics-driven support environment. You'll be expected to efficiently manage work across multiple support channels, prioritize customer needs, and consistently perform against established service level agreements (SLAs), quality expectations, and hourly productivity metrics.
Success in this role requires balancing speed with quality. You'll be expected to self-serve by using internal tools, knowledge resources, and emerging AI technologies to research and resolve customer questions, while knowing when to collaborate or escalate. You'll continuously look for ways to improve efficiency and the overall customer experience.
As customer demand fluctuates throughout the day and week, flexibility is important. This role may require schedules that align with business needs, including earlier start times, evenings, holidays, or weekend coverage, to ensure we deliver outstanding support whenever our customers need us.
WHAT YOU'LL DO AT BENEPASS
- Deliver exceptional customer support across chat, phone, and email, providing a seamless experience regardless of channel.
- Confidently manage multiple live chat conversations simultaneously while maintaining accuracy, empathy, and high-quality customer interactions.
- Meet and consistently perform against established hourly productivity expectations, service level agreements (SLAs), and quality metrics.
- Learn and become an expert on Benepass products, internal systems, and operational workflows, proactively using available resources to build knowledge and solve problems independently.
- Self-serve by researching and resolving customer issues independently using available tools and documentation, while knowing when to collaborate or escalate complex cases.
- Partner cross-functionally with Product, Operations, Engineering, and Customer Success to advocate for customers and resolve issues.
- Identify recurring customer trends and opportunities for process improvements that enhance both the customer and teammate experience.
- Leverage AI tools responsibly and with curiosity to improve research, documentation, communication, problem-solving, and personal productivity.
- Contribute to maintaining and improving internal knowledge documentation and support resources.
- Be an active contributor to a collaborative, high-performing Customer Experience team.
ABOUT YOU
- You genuinely enjoy helping people and creating exceptional customer experiences.
- You thrive in a fast-paced environment where priorities shift throughout the day.
- You're comfortable supporting customers across chat, phone, and email and can confidently switch between channels as business needs change.
- You're able to manage multiple live chat conversations simultaneously while maintaining quality and attention to detail.
- You're comfortable working toward measurable hourly productivity goals, quality standards, and customer satisfaction metrics.
- You communicate clearly and professionally in both written and verbal conversations.
- You're highly organized, detail-oriented, and excel at managing competing priorities.
- You're eager to learn, enjoy exploring new systems, and quickly become proficient with technical products.
- You're curious about emerging technology and excited to experiment with AI tools to help you research, solve problems, improve workflows, and do your job more effectively.
- You're adaptable and willing to work schedules that align with business needs, including occasional early mornings, evenings, holidays, or weekends.
- You're resourceful and self-directed: you know how to use documentation, tools, and internal resources to find answers independently, while collaborating when needed. You're also a collaborative teammate who enjoys sharing knowledge, helping others succeed, and contributing to a positive team culture.
REQUIREMENTS
- 2+ years of experience in a customer-facing support role, preferably in a high-volume environment.
- Must be able to work a hybrid schedule, including required in-office days at our Chandler, Arizona office.
- Hands-on experience supporting customers across phone, chat, and email channels, with the ability to confidently move between channels as business needs change.
- Experience handling multiple concurrent live chat conversations while maintaining exceptional customer service.
- Strong verbal communication skills and confidence speaking with customers over the phone.
- Excellent written communication skills with exceptional attention to detail.
- Proven ability to prioritize work effectively, stay organized while managing multiple tasks, and self-serve by using available tools and resources before escalating.
- Demonstrated experience in a performance-based role where success is measured by output, productivity, service levels, and quality.
- Experience using modern customer support platforms such as Intercom, Zendesk, Salesforce, or similar.
- Proficient with Google Workspace and Slack.
BONUS SKILLS
- Previous startup or high-growth company experience.
- Experience working within fintech, payments, HR technology, benefits administration, banking, or another regulated industry is strongly preferred.
- Experience using—or strong curiosity about using—AI tools such as ChatGPT, Claude, Gemini, or similar to improve workflows, research, communication, documentation, and problem-solving.
- Experience identifying opportunities for operational improvements and process optimization.
- Familiarity with workforce management concepts such as staffing, scheduling, or service levels.
- Bilingual or multilingual.
- Passion for continuous learning and helping build a world-class Customer Experience organization.
COMPENSATION
- Base: $24/hour + Equity
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
Lead AI Systems Engineer
Benepass ·
Pay
$190k–220k
Setting
Remote
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
TEAM & ROLE
Benepass is scaling quickly, and the complexity of our product, engineering, and operational surface demands a modern, intelligence-driven approach to how work gets done. We are looking for a Lead AI Systems Engineer (P5) to build our internal AI platform from the ground up; from 0→1 foundation-building to 1→2 maturity and scale.
This role is deeply technical, highly strategic, and critical to Benepass’s velocity. You will own the AI systems roadmap and architect a shared internal AI platform that starts with the engineering SDLC, and is explicitly designed to scale into automation and agentic systems across the company (Operations, Product, Design, Support, and other internal workflows).
You’ll sit as a Staff IC in Platform Engineering, owning the platform while selectively embedding with teams to drive real adoption. Engineering is the first beachhead: coding assistants, CI/CD, quality automation, and knowledge systems. The platform primitives you build—agents, tools, retrieval, evaluations, permissions, and workflow runners—should generalize beyond Engineering so Benepass can automate high-leverage work company-wide without reinventing the stack each time.
This is a force-multiplier role. Near-term success looks like faster PR and cycle times, higher AI-tool adoption, faster and more reliable automated testing, better knowledge findability, and a measurably better developer experience. Longer-term success looks like the same platform powering durable automation outside the SDLC—SOPs, operational workflows, cross-functional knowledge, and internal systems—with clear ROI and adoption.
This is not a research/data-science role, a customer-facing product-ML role, a prompt-only chatbot job, or a manual process-ownership seat. This role is for a Staff-level technical leader who builds full-stack AI systems end-to-end, with strong platform, developer-tools, and infrastructure instincts. Your mission is to build the AI-powered guardrails and accelerators that let Benepass move faster, with higher confidence, and with less toil—first in Engineering, then across the company.
YOU WILL
BUILD BENEPASS’S SHARED AI PLATFORM (0→1 AND 1→2)
- Own the design and implementation of Benepass’s internal AI platform and strategy—engineered for company-wide leverage, not an Engineering-only toolchain.
- Use the engineering SDLC as the first beachhead, while designing platform primitives that extend cleanly to Operations and other internal functions.
- Stand up a pragmatic platform that combines industry-leading tools (e.g., Cursor and peers) with in-house systems, integrations, and shared infrastructure.
- Define the architecture for how models, tools, context, evaluations, secrets, and permissions are composed safely inside Benepass.
- Build reusable primitives: agents, tool interfaces, retrieval/context layers, workflow runners, observability, and feedback loops.
- Establish the foundation for reliable environments, secure access to internal systems and data, and patterns that new domains can adopt without a ground-up rebuild.
ACCELERATE THE ENGINEERING SDLC WITH AI
- Drive AI-assisted coding, review, and delivery workflows that compress time from idea → PR → production.
- Integrate AI into CI/CD so quality signals, summaries, risk checks, and developer feedback show up where engineers already work.
- Identify SDLC bottlenecks (local dev, code review, test wait time, release friction, knowledge gaps) and remove them with automation.
- Measure what matters: PR/cycle time, adoption, developer satisfaction/DX, test speed & signal, and time-to-find knowledge.
- Turn successful team-level experiments into platform defaults that scale across Engineering—and inform patterns for non-eng domains.
ENABLE AI-DRIVEN QUALITY, TESTING, AND RELEASE CONFIDENCE
- Own the strategy for AI-driven test generation, maintenance, and automation—especially where it unlocks broad end-to-end coverage.
- Build systems that help engineers own quality: high-signal E2E coverage, faster feedback, lower flakiness, and less manual validation.
- Partner with Platform and product teams to put intelligent quality gates into CI/CD and deployment workflows.
- Use AI to improve regression detection, failure triage, and the loop from requirements → test plan → execution → root-cause analysis.
- Create clarity on ownership: what quality belongs to every engineer vs. what the AI/platform layer provides as shared leverage.
BUILD AGENTIC WORKFLOWS AND KNOWLEDGE SYSTEMS (ENG → COMPANY-WIDE)
- Design and ship agentic internal workflows that automate multi-step work, not just single-prompt assistants; starting in Engineering and expanding to other teams.
- Build knowledge/search systems so people and agents can find specs, decisions, runbooks, SOPs, and operational context quickly.
- Connect agents to the systems teams already use (repos, CI, docs, issue trackers, ops tools, internal dashboards) with clear permissions and auditability.
- Prioritize workflows with obvious ROI: repetitive operational toil, cross-repo changes, test authoring, incident/context gathering, onboarding, and cross-functional SOPs.
- Ensure these systems are observable, evaluable, and maintainable—and that the same platform can host automation outside the eng SDLC without forking the architecture.
PARTNER ACROSS THE COMPANY AS A PLATFORM FORCE MULTIPLIER
- Operate as a Staff IC on Platform: set direction, build the core, and embed selectively where adoption and design feedback matter most.
- Collaborate with engineers early so systems are testable, scriptable, and easy to integrate into existing workflows; then apply the same enablement model with non-eng partners.
- Work with Engineering, Product, Design, Operations, and other leaders to choose the journeys and workflows worth automating first.
- Provide documentation, reference implementations, guardrails, and golden paths so teams can adopt without heroics.
- Raise the organizational bar for what “good” looks like in AI-assisted work. Software delivery first, then broader internal automation.
DEFINE STANDARDS, EVALUATIONS, AND RESPONSIBLE ADOPTION
- Introduce standards for AI tool usage, prompt/tool patterns, evaluation, data handling, and human-in-the-loop controls that work across Engineering and other internal domains.
- Build evaluation harnesses and quality metrics so we know when AI systems are helping—and when they are creating noise.
- Make pragmatic build-vs-buy decisions, favoring speed and leverage while investing in shared platform where it compounds company-wide.
- Stay current on emerging coding agents, workflow agents, eval methods, and enterprise AI tooling, and bring the best of the ecosystem into Benepass deliberately.
- Help Benepass adopt AI in a way that reduces toil, increases speed and coverage, and keeps humans firmly in control of quality and production outcomes.
ABOUT YOU
A FULL-STACK AI SYSTEMS BUILDER
- You’ve shipped end-to-end AI systems—agents, tools, retrieval, evals, integrations—not demos or notebooks.
- You blend off-the-shelf tools (e.g. Cursor-class agents) with custom platform where it compounds.
- You’re AI-native in your own workflow and clear-eyed about where the tools break.
- Biased to shipped leverage over endless POCs; honest about AI failure modes.
- Believes AI should augment people and raise quality bars, not replace judgment.
A STAFF-LEVEL PLATFORM LEADER
- Proven staff or equivalent cross-functional/platform impact; you still write code.
- You turn ambiguous 0→1 spaces into sequenced roadmaps with real adoption metrics.
- Background in full-stack, developer tools, and/or infra automation—you build paved roads teams actually use.
- You embed selectively, prove value, then productize patterns onto a shared platform.
- You partner across Engineering, Product, Design, and Operations without becoming a bottleneck.
- You measure success by adoption and outcomes, not tool count or novelty.
REQUIREMENTS
- Staff-level (or equivalent platform/cross-functional) impact shipping systems others depend on.
- Strong programming fundamentals (Python and/or TypeScript/JavaScript preferred).
- Experience building internal platforms, developer tools, or automation integrated into CI/CD.
- Hands-on with modern AI systems: coding agents, LLM APIs, orchestration, and production operability.
- Experience enabling quality through automation (E2E/integration testing, intelligent quality gates).
- Solid systems instincts: APIs, permissions, observability, reliability.
- Clear communicator who can set standards and drive multi-team adoption.
- Bonus: agentic workflows, eval harnesses, RAG/knowledge systems, or ops/workflow automation beyond eng.
- Bonus: fintech/regulated domains, or 0→1 platform ownership at a growth-stage company.
COMPENSATION
Base salary of $190,000 to $220,000 + equity.
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
Customer Experience Quality & Enablement Manager
Benepass ·
Pay
$90k–110k
Setting
Remote
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
TEAM & ROLE
As the Customer Experience Quality & Enablement Manager, you'll build and scale the programs that help our support team deliver accurate, consistent, and exceptional customer experiences. You'll own quality assurance, knowledge management, training, and support enablement across email, live chat, and phone.
You'll define what great support looks like by developing quality standards, scorecards, coaching frameworks, calibration processes, and reporting that help leaders improve team performance. You'll also own the Help Center, support macros, and voice and tone standards to ensure customers receive clear, consistent support at every touchpoint.
This is a highly cross-functional role for someone who enjoys building programs from the ground up, partnering across teams, and leveraging data and AI to continuously improve both the customer and teammate experience.
WHAT YOU'LL DO AT BENEPASS
- Build and scale Benepass' Quality Assurance program across email, live chat, and phone.
- Develop quality scorecards, audit processes, calibration routines, reporting, and coaching frameworks.
- Partner with Customer Experience leaders to improve performance through coaching, feedback, and training.
- Own the Help Center, support macros, and voice and tone standards to improve consistency and reduce contact rate.
- Design and deliver ongoing enablement programs covering product updates, call etiquette, communication, and support best practices.
- Analyze quality trends, customer feedback, and operational data to identify root causes and recommend improvements.
- Partner cross-functionally with Product, Engineering, Operations, Compliance, and Customer Success to improve the customer experience.
- Leverage AI and automation to improve quality monitoring, knowledge management, coaching, and operational efficiency.
ABOUT YOU
- You're passionate about building scalable quality and enablement programs.
- You have excellent written communication skills and a strong eye for detail, consistency, and customer experience.
- You enjoy coaching others and providing actionable feedback that improves performance.
- You're analytical and use data to identify trends, root causes, and opportunities for improvement.
- You're comfortable working across email, live chat, and phone support environments.
- You build strong partnerships and influence others without direct authority.
- You're curious about AI and excited to apply new technology to improve support operations.
- You thrive in fast-paced, high-growth environments where you're building as you go.
REQUIREMENTS
- 5+ years of experience in Customer Support, Customer Experience, Quality Assurance, Support Operations, or Enablement.
- Experience building or significantly scaling a Quality Assurance program.
- Experience creating QA scorecards, calibration programs, coaching frameworks, and quality reporting.
- Experience supporting multi-channel customer support teams across email, chat, and phone.
- Strong knowledge management experience, including Help Centers, macros, SOPs, and voice & tone standards.
- Exceptional written communication, analytical, and problem-solving skills.
- Experience supporting technical products and using platforms such as Intercom, Zendesk, Salesforce, or similar.
- Experience leveraging AI tools to improve quality, coaching, documentation, or operational workflows.
BONUS SKILLS
- Experience working in fintech, HR technology, benefits, banking, or another regulated industry.
- Previous startup or high-growth company experience.
- Experience with QA platforms such as MaestroQA, Klaus, Playvox, Observe.AI http://Observe.AI, or similar.
- Experience designing onboarding, training, or enablement programs.
- Experience improving Help Center performance, self-service, or contact rate.
- Bilingual or multilingual.
SUCCESS IN YOUR FIRST 6 MONTHS
- Launch a standardized QA program across chat, email, and phone.
- Implement quality scorecards, calibration, and reporting.
- Establish recurring coaching and enablement programs.
- Refresh Help Center content, macros, and voice & tone standards.
- Build quality dashboards and operational KPIs.
- Reduce customer friction through quality-driven process improvements.
COMPENSATION
Base salary of $90,000 to $110,000 + Equity
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
Sr. Manager, Customer Success
Benepass ·
Pay
$150k–170k
Setting
Remote
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
TEAM & ROLE
As the Senior Manager, Client Success, you will lead our SMB and Mid-Market Customer Success organization, reporting directly to the Head of Customer Operations. You'll be responsible for leading a team of six Customer Success Managers overseeing approximately $5M in Annual Contract Value.
Your primary responsibility is maintaining and building a high-performing Customer Success team that delivers exceptional customer outcomes while driving retention, growth, and operational excellence. You'll coach and develop CSMs, establish scalable operating rhythms, and partner cross-functionally to continuously improve the customer experience.
This role requires equal parts people leadership, customer strategy, and operational execution. You'll serve as the primary escalation point for your segment while partnering closely with Sales, Implementation, Technical Account Management, Customer Experience, Product, Engineering, and Business Operations to ensure our customers realize maximum value from Benepass.
As Benepass continues to scale, this leader will play a critical role in evolving how Customer Success operates. We're looking for someone who is AI fluent and excited to rethink traditional Customer Success workflows by leveraging AI, automation, and scalable processes to deliver exceptional customer experiences while improving team efficiency and maintaining strong unit economics.
WHAT YOU'LL DO
- Lead, coach, and develop a team of Customer Success Managers through regular 1:1s, performance management, and career development.
- Own team performance across customer retention, renewals, customer health, product adoption, and expansion pipeline generation.
- Partner with CSMs on strategic customer relationships, executive conversations, and complex customer escalations.
- Establish scalable operating rhythms for account reviews, renewal forecasting, health monitoring, and portfolio management.
- Champion the adoption of AI and automation across the Customer Success organization by identifying opportunities to eliminate manual work, improve customer experiences, and enable the team to scale without sacrificing service quality.
- Analyze customer and team performance data to identify trends, coaching opportunities, and process improvements.
- Partner with Sales to ensure successful customer transitions and identify expansion opportunities.
- Collaborate with Implementation, Technical Account Management, Customer Experience, Product, and Engineering to deliver an exceptional end-to-end customer experience.
- Build and improve playbooks, customer journeys, and operational processes that enable the team to scale efficiently.
- Serve as the voice of the SMB and Mid-Market customer internally by advocating for customer needs and communicating product feedback.
- Help recruit, onboard, and develop future Customer Success talent as the organization continues to grow.
ABOUT YOU
- You love developing people and helping teams perform at their highest level.
- You balance empathy with accountability and enjoy coaching through both successes and challenges.
- You're highly organized and operationally minded, with a passion for building scalable processes.
- You're comfortable making data-driven decisions while maintaining a strong customer-first mindset.
- You enjoy experimenting with AI tools, automation, and new ways of working, and you know how to translate those innovations into practical improvements for both customers and internal teams.
- You thrive in fast-paced startup environments where priorities evolve quickly.
- You're an exceptional communicator who can build trust with customers, teammates, and executive stakeholders alike.
REQUIREMENTS
- 7+ years of experience in Customer Success, Account Management, or other customer-facing SaaS roles.
- 3+ years of experience managing Customer Success or Account Management teams.
- Proven track record of driving customer retention, renewals, and team performance.
- Experience coaching and developing high-performing customer-facing professionals.
- Strong analytical skills with experience using customer health metrics and performance data to drive decisions.
- Demonstrated ability to partner cross-functionally across Sales, Product, Engineering, Support, and Operations.
- Demonstrated experience leveraging AI, automation, or workflow tooling to improve team productivity, customer experience, or operational efficiency.
- Experience managing executive-level customer relationships and customer escalations.
- Experience working in SaaS, HR Tech, fintech, healthcare, or employee benefits is preferred.
BONUS SKILLS
- Experience leading SMB and Mid-Market Customer Success organizations.
- Previous startup or high-growth company experience.
- Experience building Customer Success operating models, health scoring, or scaled customer programs.
- Direct experience in the employee benefits space.
COMPENSATION
- $150,000 to $170,000 base salary + equity
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
Senior Customer Success Manager
Benepass ·
Pay
$100k–130k
Setting
Remote
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
TEAM & ROLE
As a Senior Customer Success Manager, you will manage a portfolio of customers, reporting directly to our Head of Customer Operations, Aileen Palmer. We are hiring two Senior Customer Success Managers: one to support our SMB customer segment and one to support our Midmarket customer segment. While both roles share the same core responsibilities, the size and complexity of the assigned book of business will vary.
You will be responsible for managing and nurturing client relationships to ensure customer satisfaction, retention, and growth.
This role involves working closely with customers to understand their needs, providing tailored solutions, and ensuring they derive maximum value from our products. Depending on your experience and assigned portfolio, you'll partner with organizations ranging from growing SMBs to more complex midmarket customers. In addition to owning a book of business, the Senior Customer Success Manager will contribute to the continuous improvement of our processes by collaborating with Product, Sales, Engineering, Support, and Strategic Alliances teams.
Currently, our Customer Success team is composed of:
- 8 Customer Success Managers
It's an exciting time to join our Customer Success team as we continue to grow. This is a fantastic opportunity to shape and influence customer success processes while working with an innovative team. Whether your experience is managing high-volume SMB accounts or building strategic partnerships with mid-market customers, we'd love to hear from you!
WHAT YOU'LL DO AT BENEPASS
- Manage a portfolio of SMB and/or mid-market clients through all stages of the customer lifecycle, from onboarding to ongoing success planning
- Drive admin platform education and adoption by providing regular check-ins, product training, and best practice guidance
- Identify growth opportunities within your accounts and collaborate with sales on upsell and expansion strategies
- Monitor customer health metrics and proactively address at-risk accounts
- Gather and communicate customer feedback to product and engineering teams to help shape our roadmap
- Develop scalable processes and resources tailored to the unique needs of SMB clients
ABOUT YOU
- You are relationship-focused and enjoy helping customers achieve their goals
- You're organized and efficient, able to manage multiple accounts simultaneously while providing personalized service
- You're a clear communicator who can translate product features into business benefits
- You're adaptable and thrive in a fast-paced startup environment
REQUIREMENTS
- 3-6 years of experience in customer success or account management in SaaS, startup, healthcare, or the benefits space
- Direct experience working in the the benefits space
- Proven track record of managing and growing SMB and/or midmarket customer accounts
- Demonstrated ability to analyze data and business insights to influence stakeholder decision-making
- Ability to interact with customer teams at various levels of technical and non-technical depth, and across multiple levels from end users through C-level stakeholders
- Experience working with cross-functional teams and communicating common customer behaviors to the sales, marketing, and product teams
BONUS SKILLS
- Previous start-up experience
COMPENSATION
$100,000-130,000 + Equity + Variable Compensation
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
Staff Product Manager (Fintech)
Benepass ·
Pay
$195k–240k
Setting
Remote
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
ABOUT THE ROLE
We’re hiring a Staff Product Manager to own our fintech strategy and partnerships.
This role will define how we build and scale the financial infrastructure behind Benepass. You’ll manage our core fintech partners and determine how we leverage them to deliver differentiated product experiences.
A key part of this role is answering: where should we build vs. partner—and how does that evolve over time?
You’ll operate as a senior individual contributor, working cross-functionally and externally to shape our roadmap, improve reliability, and unlock new capabilities for our customers.
WHAT YOU’LL DO
- Own Benepass’ fintech stack strategy, including build vs. partner decisions, across multiple time horizons
- Manage and deepen relationships with key partners
- Ensure existing integrations are stable, scalable, and fully utilized
- Identify gaps in current capabilities and drive solutions with partners or internal teams
- Align partner capabilities with our product roadmap and influence roadmap decisions
- Evaluate and onboard new partners to expand our product offering
- Act as the primary point of contact for fintech partners across product, engineering, and executive stakeholders
- Lead issue resolution, escalations, and ongoing optimization work with partners
- Represent Benepass in partner conversations and industry events
WHAT WE’RE LOOKING FOR
- 6+ years of product management experience, with significant time building fintech products (e.g. card issuance, bank accounts, AR/AP, payments)
- Deep understanding of the money ecosystem, including card issuance, processors, payment rails, and bank cores
- Experience working directly with BaaS partners (e.g., Stripe, Unit, Marqeta, Lithic, Treasury Prime, Column, Increase, etc.)
- Proven track record of owning both partnership relationships and technical implementations
- Strong product judgment and ability to navigate complex tradeoffs
- Excellent communication skills and comfort working with external partners and executives
NICE TO HAVE:
- Experience with brokerage or trading infrastructure
- Project management experience in BaaS partner migration
- Relationships and experience with sponsor banks
- In-depth knowledge of compliance requirements, including build vs. buy considerations
WHY THIS ROLE
- Own a critical and highly strategic part of the product
- Work on complex, high-impact problems at the intersection of fintech and product
- Partner with leading fintech platforms and shape how they’re used in a modern benefits stack
- High visibility role with meaningful influence on company direction
COMPENSATION
- Base salary of $195,000 to $240,000 + equity.
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
Lead Product Manager
Benepass ·
Pay
$180k–200k
Setting
Remote
ABOUT US
At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.
Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.
OUR MISSION
Helping companies reimagine how companies take care of their people.
OUR INVESTORS
We are backed by leading investors, including Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.
ARTICLES
- Founder Story - Jaclyn Chen https://bit.ly/3FpQ0ti
- Benepass Raises $40M Series B https://getbenepass.com/blog/benepass-raises-40m-series-b-to-help-employers-redesign-benefits-for-rising-healthcare-costs
CANDIDATE RESOURCES
- Benepass | Candidate Resource Page https://docs.google.com/document/d/1_OTFvktl-2SoxPn_tkZzyHECSKM0V14hVZOy1ZdZ8zE/edit?usp=sharing
- Benepass Listed on Inc. Magazine's Best Workplaces of 2023 https://bit.ly/3EAXv0Q
THE ROLE
Benepass is reimagining how employees discover, understand, and engage with their benefits – and we’re looking for a Lead Product Manager to own a major part of that experience end to end.
This role is for a senior product manager who wants real ownership in a small, high-trust team. You’ll take responsibility for a strategic product area, shape its direction, and drive it from early discovery through delivery and iteration. The scope is meaningful, the problems are ambiguous, and the impact is highly visible.
You’ll work closely with product leadership and cross-functional partners, with autonomy to run your domain and accountability for outcomes. This is a hands-on role for someone who enjoys both strategic thinking and building.
WHAT YOU’LL DO
As the owner of this product area, you’ll be accountable for setting direction, making tradeoffs, and driving outcomes. You will:
- Own a strategic product area focused on employee discovery and engagement, from problem definition through execution
- Reimagine core employee-facing experiences that help users better understand their benefits and discover relevant options
- Define the strategy and roadmap for your area, making and owning tradeoffs based on user needs, business goals, and constraints
- Lead product discovery to deeply understand employee and employer problems, and translate insights into clear product direction
- Partner closely with Design, Engineering, Product Marketing, and other teams to deliver cohesive, high-quality experiences
- Drive execution end to end, keeping work moving forward and adjusting course as new information emerges
- Use data, feedback, and judgment to evaluate impact and continuously improve what you build
You’ll be trusted to operate independently within your domain, while collaborating closely with product leadership on prioritization and broader context.
WHAT WE’RE LOOKING FOR
This role is a strong fit if you:
- Have 6+ years of experience as a Product Manager, with increasing ownership over time
- Have experience working at a startup or similarly fast-moving environment, where scope is broad and ambiguity is high
- Are comfortable owning a problem space end to end, from framing through delivery
- Can balance strategic thinking with hands-on execution
- Communicate clearly and proactively, especially when navigating tradeoffs or uncertainty
- Are curious, thoughtful, and motivated by learning in complex domains
- Take accountability seriously and follow through on what you own
We’re less focused on specific industries or tools and more interested in how you think, how you work, and how you approach ownership.
COMPENSATION
- Base salary of $180,000 to $200,000 + equity.
RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE.
WHAT WE OFFER
- 95% coverage of medical, dental, and vision
- Fantastic benefits (of course 😃), including:
- $250 WFH setup (one time)
- $500/year Learning & Development Benefit
- $150/month cell phone + internet
- $100/month Wellness
- $100/month Co-working and Commuter Benefit
- We offer several team onsites a year
- Flexible PTO
At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.
Listed by Benepass for a position based in the United States. Employers on this board attest they are hiring domestically.
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