Head of Engineering

Leap

Head of Engineering at Leap shaping the technical direction and scaling a high-performing engineering team. Leading initiatives in AI, data infrastructure, and operational excellence in healthcare.

Posted 6/17/2026full-timeRemote • 🇺🇸 United StatesLead💰 $250,000 - $350,000 per yearWebsite

About the role

Key responsibilities & impact

Own hiring end to end — set ambitious targets, build the pipeline, and close engineers who clear a high bar
Grow the team from its founding core into a high-performing organization
Define what great looks like: the bar, the interview loop, and the standard the team is held to
Build the structure and culture a fast-moving team needs as it scales
Own and sequence the technical roadmap, making the prioritization and build-vs-buy calls that hold up as Leap scales
Build the cross-benefit drug identity layer that resolves one specialty therapy across NDC and HCPCS/J-codes as biosimilars multiply
Ship causal savings attribution that proves impact rather than projecting it — ROI an employer can defend in an audit
Build the intervention engine and AI workflows — at-risk prediction, prior authorization, formulary and site-of-care optimization — that turn analysis into action
Set the standard for how Leap builds: AI-native, fast, and correct by default
Make the foundational data and architecture decisions the rest of the roadmap depends on
Unblock the team, own the hard technical calls, and dive in when it matters

Requirements

What you’ll need

You've built and scaled an engineering team from a handful of people into a high-performing org — you've owned hiring, set the bar, and closed exceptional engineers.
You're AI-native: you've shipped AI systems in production with LLMs and agents, and you lead teams that do the same.
You've operated at a high bar at organizations known for exceptional engineering — your track record speaks for itself.
You're a lean player-coach who leads first but keeps the technical depth to make sharp architecture calls and own the roadmap.
You've shipped production systems on messy, real-world data — not clean benchmarks — and you build for correctness when being wrong has consequences.

Benefits

Comp & perks

Competitive salary
Eligibility for equity
Comprehensive medical, dental, and vision coverage
Access to 401(k) retirement plan
Flexible remote work

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI systemsLLMsarchitecture decisionstechnical roadmapdata analysisproduction systemsat-risk predictionprior authorizationformulary optimizationsite-of-care optimization

Soft Skills

leadershipteam buildingcommunicationproblem-solvingcoachingprioritizationdecision makingcollaborationadaptabilitystrategic thinking