Lead Engineer

This is a hands-on technical leadership role. Other possible titles for this role are Senior / Staff / Principal Engineer. Compensation $150-180K base. Plus equity in the company! Location Remote eligible but ideally candidates are based in ET or CT time zones and can fly directly to Washington, DC. Our team and office is in Bethesda, MD and we work in person every Monday, Tuesday, and Thursday so even better if you are in the DC area or are willing to relocate to be with us. If you're remote, you must be willing to fly to DC every month to work with our team in person. About Keep Company Keep Company is on a mission to make human connection an intentional, scalable asset in every workplace. As a venture-backed SaaS platform recognized by Techstars, Forbes, and SHRM, our patented talent platform delivers transformative relationship-based development experiences at leading professional services organizations. With our platform, talent leaders can launch, scale and measure innovative programs, including mentoring, coaching and ERGs, with little admin burden and maximum impact. We’re proud to support 20+ clients in professional services - with zero churn and multiple six-figure contracts. At a time when artificial intelligence is rapidly reshaping how we work, Keep Company is rebuilding the human layer of work, because we believe people are the most important asset that organizations can invest in to strengthen culture, retention, and performance in the moments that matter mos t. The Opportunity We're hiring an Engineering Lead at Keep Company. This is a hands-on builder role for someone who wants to ship code, own the full stack from frontend to security, and translate product vision into a lean, flexible platform that serves the business. You'll report to and partner directly with our VP, Product to make the architecture calls that matter — and then ship them yourself. Be the builder who turns Keep Company from a standalone dashboard into a platform our enterprise clients run on. We are leveling this role to the candidate. Strong applicants at Senior, Lead, Staff, and Principal levels are all in scope. What You'll Own Build the platform foundation — by shipping it yourself Design and ship the external API that moves Keep Company from a standalone dashboard to a platform that lives inside the tools our clients' employees already use every day. Lead the rearchitecture of our core data layer with API-readiness baked in from day one — not bolted on later. Own the integration story Sequence and build the integrations our enterprise clients expect: identity and access, Slack, Microsoft Teams, HRIS platforms (Workday, UKG), and ATS systems — including the build-vs-partner call. Deliver for our enterprise clients Co-own on-time delivery of our enterprise commitments — frontend to security, full stack, end-to-end. Bring engineering in-house Reduce our contractor dependency over time. Today, parts of our delivery surface live with external partners. Your job is to bring that expertise inside on a sequence and pace you set. Set the engineering bar Define the architecture reviews, code quality benchmarks, AI-native workflows, and release practices the team will calibrate against as we hire around you. Own the technical side of our SOC 2 Type II posture and the security expectations our clients bring to every contract. What We're Looking For You're a builder. You don't want to manage the work from a distance — you want to be in it, making the architecture calls, writing the code, shipping something you're proud of. You talk about what YOU built, not what your team shipped. You have current code commits and strong opinions about your tools. You've probably been a founding or early engineer at a company that didn't quite scale into a team, an architect ready to get back into code, or an engineering manager who's quietly looking to step back into IC work. The common thread: you have the muscle to own a full stack with minimal delegation, and you're energized by the breadth of the job. Required Experience 8+ years in software engineering with meaningful time in a senior IC or technical leadership role at a B2B SaaS company. Ideally who have worked in companies that navigated a consumer-to-enterprise transition or served regulated industries. You know how these organizations think, what earns credibility with their leaders, and where the real friction lives. A hands-on engineer today, not a former one. You still ship production code and can talk us through your most recent commit in detail. Direct experience with data architecture decisions that outlived their original scope — schema migrations, multi-tenant data models, and API surface design for third-party integration. An AI-native point of view. You have a clear perspective on how AI tooling changes the work: what it accelerates, where it fails, how you verify output, and how you bring a team along with you when they arrive. Comfort with integration-heavy work: identity systems (WorkOS, Okta, Azure AD), HRIS (Workday, UKG), collaboration platforms (Slack, Teams, Microsoft Graph), and the tradeoffs between native builds and iPaaS aggregators. You have clear points of view, held loosely. You make decisions with the information you have, name your assumptions, and update when the evidence changes. Nice to Have Founding-engineer or first-engineer experience at a small startup, especially one where you owned the platform end-to-end. A track record owning security and compliance as an engineering deliverable, not an external checklist — SOC 2, data governance, access controls, and audit readiness. Experience in HR tech, legal tech, or future-of-work environments — you understand how professional services organizations make decisions and what earns trust at the leadership level. Active in builder communities (YC alumni, Indie Hackers, Claude Builders, agentic-dev, Cursor power-user circles). How You Work We care as much about how you operate as what you know. This role is a strong fit if you: Decide with incomplete information, name your assumptions, and pivot when new evidence arrives. Close loops. When you own something, the next step is clear and visible without anyone having to chase you. Communicate directly — you flag risks early, ask the question rather than work around it, and tell us what you don't know. Volunteer to handle the thing rather than asking who handles it. Raise the engineering ceiling through your work. Your PRs, design docs, and architecture calls become the standard the team calibrates to once you start hiring around you. Partner with product. You think about the shape of what gets built, not just how it gets built. Why Keep Company + Benefits A small, mission-driven team that ships, celebrates, and grows together!. A pre–Series A company with enterprise revenue, named law firm clients, and a clear wedge into a large, underserved market. A genuine AI-native engineering culture, not a retrofitted one. We pay for 100% of the premium for one of our medical plans (and also offer dental and vision). We offer a 401(k) with a maximum annual employee contribution of $6K. We have a high accountability, high empathy ethos with a very generous time off policy.