[Remote] Engineering Manager

Note: The job is a remote job and is open to candidates in USA. Benepass is a fintech platform that helps companies customize, administer, and track employee benefits. The Engineering Manager will lead the Core Services backend engineering team, owning people development, execution, technical quality, and outcomes across critical systems such as ledgers, decisioning, integrations, authentication, and directories.

Responsibilities

• 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
• 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
• 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
• 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
• 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

Skills

• • 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
• • 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
• ### ROLE LOCATION & TRAVEL You will be expected to attend company-wide on-site events three times per year
• • 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

Benefits

• Equity
• 95% coverage of medical, dental, and vision
• $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
• Several team onsites a year
• Flexible PTO

Company Overview