Senior Manager, Engineering

Location: Remote Workplace: Remote Hi, we’re Gravie. Our mission is to create health benefits that actually benefit small and midsize businesses and their employees. Our innovative benefit solutions and services are developed and delivered by a diverse group of unique people. We encourage you to be your authentic self - we like you that way. ROLE SUMMARY Gravie is seeking a technically engaged Senior Manager, Engineering to lead two teams, Carrier Integration and Platform Maturity, each staffed by a mix of full-time and contract engineers. Carrier Integration builds and runs integrations with insurance carriers, enrollment platforms, and HRIS/payroll providers, where data correctness directly affects members’ coverage and deductions. You will own outcomes for both teams, in partnership with your Product Management counterparts: what ships and how reliably it runs in production. You will be the face of these teams in cross-team, leadership, partner, and vendor forums, bringing decisions back and raising priorities and risks early. We are at a critical stage of agentic AI adoption. Engineers at Gravie use AI agents to develop specs and plans and execute multi-step engineering work, while owning guardrails, acceptance criteria, and the quality of what ships. This role is central to that shift. You will be an active champion for agentic AI adoption and accountable for how effectively both teams adopt these practices, including helping build the tooling that makes them work. The right fit solves problems creatively, gets directly involved when a team needs it (reviewing merge requests, helping debug production issues, and critically reviewing architecture and designs, though not necessarily writing code), and helps teams see what they’re missing, such as risks, gaps, or better ways of working. They challenge assumptions and improve how work is scoped. This is not a role for someone who only runs the process; we want someone who actively improves how the teams work and what they deliver. KEY RESPONSIBILITIES - Set clear expectations for every team member, including full-time and contract engineers, and manage performance against them, including difficult conversations. - Represent the teams in cross-team and leadership forums (EM/PO syncs, leads syncs, partner and vendor calls, RAID log reviews, Go/No-Go meetings). Bring decisions back to the teams and raise our priorities and risks. - Spot blockers early, work with owners across teams and vendors to resolve them, and escalate when needed. - Keep delivery health visible: maintain accurate Jira status and sprint commitments, send timely stakeholder updates, and flag risk early. - Make sure every epic, incident action item, and production-readiness checklist has a named owner and due date, and drive it to closure. Nothing important sits unassigned. - Own engineering quality for both teams: test strategy, contract tests between services, CI quality gates, and production-readiness reviews before go-live. - Ensure team ceremonies happen and are effective for both teams, including standups, backlog refinement, sprint planning, sprint reviews, and retrospectives, whether you facilitate them yourself or partner with Product and engineering leads to do so. - Evolve how the teams work as AI changes software delivery: research emerging practices, run experiments, and bring the teams along. - Lead a blended team of full-time and contract engineers, managing capacity and alignment to Gravie priorities. - Coach and mentor each direct report through regular 1:1s, a development plan for each person, and timely, candid feedback. - Grow the next generation of leaders by developing engineers into leads and future engineering managers. - Manage vendor partners end to end: SOWs, staffing plans, change orders, performance, and knowledge transfer so Gravie isn’t dependent on any one contractor. - Hire and grow full-time engineers as we move key capabilities from contract to in-house teams. - Partner with Product, Data, Security, and Infrastructure to translate ambiguous business problems into clear, deliverable work. - Partner with Security to make sure the teams handle PHI/PII appropriately and that security findings are owned and fixed. - Own the effective adoption of agentic AI practices across both teams: champion the change, set clear expectations for how agents are used, and measure whether it is improving outcomes. Help engineers raise the bar on problem framing, guardrails, acceptance criteria, and risk identification. - Build and contribute to the tooling, workflows, and shared practices that help teams get better results from AI agents. - Use AI in your own leadership work, such as planning, spotting delivery risk, drafting decision documents, preparing for 1:1s, and reporting, applying the same judgment and review you expect of your teams. - Participate in the on-call rotation for critical production incidents and drive follow-up and post-incident improvements. QUALIFICATIONS - Prior experience managing multiple engineering teams at the same time. - Experience leading teams that blend full-time and contract engineers. - A track record of developing people, including at least one example of someone you grew into a lead or manager. - Experience building and operating integrations with third-party vendors and partner APIs. - Experience building systems that handle PHI/PII in a regulated environment (HIPAA or similar). - Strong communication with senior cross-functional stakeholders, in writing and in live meetings. - Strong command of scrum and kanban and the judgment to know when each fits, plus active curiosity about how AI is changing the way engineering teams plan and deliver. Experience maintaining risk and dependency tracking (e.g. RAID logs). - Comfort with on-call responsibilities and managing critical production incidents. - Practical experience with AI coding agents and agentic development workflows, and a track record of driving AI adoption on a team, including building tooling or practices that others adopted. - Concrete examples of using AI to lead more effectively, beyond driving team adoption. - Technical depth to review merge requests, help debug production issues, critically review architecture and designs, and spot gaps in a test suite. This role does not require writing production code day to day. - A creative approach to problem solving, with the judgment to know when to dig in and when to escalate. A LITTLE MORE ABOUT US: - We know healthcare. Our company was founded and is still led by industry veterans who have started and grown several market-leading companies in the space. - We have raised money from top tier investors who share the same long-term vision as we do of building an industry defining company that will endure over the long run. We are well capitalized. - Our clients love us. Customer satisfaction rates among employees using Gravie health plans consistently rank above 80% – nearly 40 points above the industry average. - Our culture is unique. We tend to be non-hierarchical, merit-driven, opinionated but kind people who thrive working in a high-performance, fast-paced environment. People at Gravie care deeply about making a positive impact in the lives of the people we serve. BENEFITS Our unique benefits program is the gravy, i.e., the special sauce that sets our compensation package apart. In addition to standard health and wellness benefits, Gravie’s package includes alternative medicine coverage, flexible PTO, up to 16 weeks paid parental leave, paid holidays, a 401k program, transportation perks, education reimbursement, and 2 days of paid paw-ternity leave. JOB APPLICANTS If you apply for employment with Gravie, personal information collected via our applicant tracking vendor is subject to our standalone California Job Applicant Notice at Collection, accessible directly within the application workflow and separate from this Policy.