Engineering Manager

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 an Engineering Manager (M3) at Benepass, you will lead a team of backend engineers on Core Services — the systems that sit on our critical path: the ledger, decisioning, schedules, rules engine, HRIS integrations, authentication, and directory. These are the brains and books of the platform. Every swipe, payout, credit, and adjustment flows through them.

You will report to the Vice President of Engineering and split Core Services with a peer Engineering Manager. This is how we scale leadership without turning one manager into a bottleneck. You will own people, execution, and outcomes for your slice of the team. Engineers stay anchored to Core Services for growth and accountability; they ship through time-boxed projects with Product, Design, and Frontend Engineering.

This is a hands-on EM role. You have a strong technical background, stay close enough to the systems to review designs, spike prototypes, and debug when it matters, and you do not try to be the best IC in the room. You create the environment — clarity, staffing, and culture — so ICs can own architecture and delivery. Managers own team execution. Project leads own project outcomes. Engineers own the quality and impact of their work.

This role is a culture-carrier for how Engineering works. We hire managers who already operate this way — not people we have to convince.

HOW WE WORK

Our Engineering Operating Principles are the job, not a poster:

- Own Outcomes. Accountable for results, not activity. Ownership does not end when code is merged, a ticket is closed, or a project is handed off. Managers own team execution. Project leads own project outcomes. Engineers own the quality and impact of their work. The business experiences outcomes, not tickets.

- Projects Are How Work Gets Done. Clear goal, owner, deadline, and definition of success. Teams form around projects, execute, and move on. Core Services also carries operational load — production health, incidents, correctness. We plan for that instead of pretending every hour is roadmap.

- One Roadmap. Sales, Ops, Product, Security, and Data all have real priorities. A priority only matters if we are willing to choose it over something else. If everything is important, nothing is.

- High Trust, High Accountability. People decide and move without asking permission at every step. Mistakes get surfaced quickly, learned from, and fixed. We do not hide problems, shift blame, or wait for someone else to own it. Weak accountability produces process; we would rather trust people.

- Move Fast Through Simplicity. Complexity is expensive. Question meetings, approvals, handoffs, and tools. Prefer principles over rules and judgment over bureaucracy. Ambiguity is a tradeoff we accept for speed.

- Work in the Open. Share context early. Document decisions. Surface risks while they are cheap to change. Communication is everyone’s job.

- Be AI-Native. AI is a force multiplier and part of the craft. We expect you to use it heavily yourself — not as a talking point, and not only as something you encourage the team to try. People own outcomes. AI expands capacity.

- Deliver What We Commit To. Deadlines matter. If a timeline becomes unrealistic, we raise it, cut scope, and make the tradeoff explicit. We do not quietly slip. Reliability builds trust.

ROLE LOCATION & TRAVEL

You will be expected to attend company-wide on-site events three times per year.

OUR TECHNOLOGY AND STACK

Python, Django, Django Rest Framework, PostgreSQL, AWS, Docker — plus the adjacent client surfaces (React / TypeScript) your APIs power.

WHAT YOU'LL DO

LEAD PEOPLE AND RAISE THE BAR

- Manage ~4–6 engineers to start, with room to hire as we grow.

- Run 1:1s that are about growth, not status. Set expectations against our IC leveling matrix. Give feedback early, including the hard kind.

- Hire, onboard, and level the team. Design a hiring bar you would be proud to join.

- Coach project leads. They drive kickoff, technical approach, weekly updates, and release — you make sure they have the support and air cover to do it well.

OWN TEAM EXECUTION AND OUTCOMES

- Be accountable for results, not activity. Stay engaged until the problem is solved, not when the ticket closes.

- Translate company priorities into a sequenced plan the rest of the company can plan around. If a timeline becomes unrealistic, raise it, cut scope, and make the tradeoff explicit — do not quietly slip it.

- Protect operational load. Core Services carries production health, incidents, and correctness work that is not always a roadmap project. Plan for that instead of pretending every hour is feature work.

- Incidents take priority over roadmap. Escalate risks early.

STAY TECHNICALLY CREDIBLE ON CRITICAL-PATH SYSTEMS

- Lead design reviews. Champion simple, correct, observable patterns. Leave systems better than you found them.

- Jump into code, prototypes, or production debugging when it unblocks the team or validates a hard tradeoff — then step back.

- Hold the line on invariants that matter for money and eligibility: idempotency, auditability, reconciliation, and safe retries. Prefer a useful v1 over a perfect design debate.

- Partner with Client Apps, Platform, Customer Engineering, Product, and Ops so Core Services is easy to build on — not a bottleneck wrapped in tribal knowledge.

WORK IN THE OPEN

- Share context early. Document decisions. Surface risks before they become problems. Ask for feedback while the work is still easy to change.

- Project teams are empowered to decide and expected to drive. Ownership includes gathering context, making tradeoffs, and unblocking yourself when you can.

BE AI-NATIVE — STARTING WITH YOU

This is not a “nice to have” and it is not a mandate you pass down while you keep working the old way. We want a manager who already heavily leverages AI in their own work, every week, across the job — coding, debugging, design, planning, writing, analysis, 1:1 prep, hiring, and communication.

Across Engineering, most new code is already written with AI in the loop. That is the baseline, not a future state. The managers who succeed here treat that as leverage: they get to higher-quality judgment faster, they automate the repetitive parts of the job, and they raise the team’s standard instead of lowering it.

What that looks like in practice:

- You use it yourself, daily. You have a real workflow — not “we bought Copilot.” You can walk through how you actually design, debug, write, and review with AI. You have changed how you work, not bolted a chatbot onto old habits.

- You hold the same bar. AI-assisted work is held to the same standard of correctness, security, and craft as everything else. On Core Services that is non-negotiable: ledger, decisioning, and money-movement mistakes are real. You review output. You do not outsource judgment. People own outcomes; AI does not.

- You increase leverage, not ceremony. You look for work to automate: tests, runbooks, design-doc first drafts, incident timelines, onboarding, repetitive ops. You kill toil. You do not add an “AI process.”

- You coach the team in the craft. Learning to work effectively with AI is now part of engineering. You set the expectation, share what works, and help people who are behind catch up — without turning it into theater or a purity test for one vendor.

- You are curious and unsentimental. Tools change. You evaluate new ones the same way you evaluate anything else: does this make us more effective? You experiment in the open, keep what compounds, drop what doesn’t.

- You do not hide behind it. AI is not an excuse for sloppy PRs, missing context, or skipped thinking. If the model is wrong, you still own the result.

ABOUT YOU

- Technical Expertise: Deep software engineering experience in Python/Django (or equivalent backend systems) so you can guide architecture, review PRs, and contribute code when it matters. You think in systems, not endpoints.

- Leadership & Empathy: Exceptional communicator who builds high trust and high accountability. You create psychological safety, coach engineers toward growth goals, and do not hide problems or wait for someone else to own them.

- Outcome-Driven: You own end-to-end results — from sequencing work to production health. The business experiences outcomes, not tickets.

- Disciplined Craft: You fight complexity. Clean code, tests, observability, and small building blocks. Principles over rules; judgment over bureaucracy.

- AI-Native: You heavily use AI yourself. This is a personal practice, not a talking point. You can show how it has changed your week: how you write and review code, how you debug, how you prepare for 1:1s and design reviews, how you draft and tighten communication. You are not waiting for a platform team to hand you a workflow. You hold AI-assisted work to the same bar as everything else, and you can teach that to a team without turning it into process.

REQUIREMENTS

- Experience: 5+ years of software engineering, including 2+ years leading teams of ~3–8 engineers (or equivalent scope), ideally in a startup or SaaS environment.

- Technical Leadership: Proven ability to lead design reviews, enforce engineering standards, and prototype in Python/Django (or a comparable backend stack). Comfortable on systems where correctness and reliability are not optional.

- People Development: Experience mentoring engineers through 1:1s, setting growth goals against a leveling matrix, handling performance issues directly, and hiring.

- Delivery Excellence: Track record of shipping on commitments, creating clarity from ambiguity, and running a healthy SDLC without turning process into the product.

- AI as a personal craft: You already use AI heavily in your own work — coding, debugging, planning, writing, and operating a team. You can describe your workflow in concrete terms. You have used it to increase your (and a team’s) effectiveness, not as a demo. You review and own the output. Candidates who “support AI adoption” but barely use it themselves are not a fit.

BONUS SKILLS

- Experience in fintech, payments, card issuing, wallets, or benefits platforms — especially ledgers, authorization/decisioning, or money movement.

- Experience owning high-integrity backend systems (financial, eligibility, identity, or large-scale integrations) where small mistakes have real customer or money impact.

- Experience splitting or scaling a team — taking a group that has outgrown one manager and making two healthy teams without creating an A/B split.

- Proven ability to set and use team KPIs (reliability, cycle time, incident health, delivery against commitments).

- Experience evaluating tools (CI/CD, observability) to increase leverage, not ceremony.

- Strong background in performance management: promotion cases, PIPs, and hiring pipelines you would send a friend through.

Not meeting every requirement but still feel like you’d be a great fit? Tell us how you would contribute.

COMPENSATION

- Base Salary $200,000 to 230,000 + 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.