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VP/Head of Engineering

Sailor Health· Engineering
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New York City (Soho)$200k - $350kFull-timePosted 2mo ago

About the role

Senior engineering leader responsible for technical direction, product leadership across patient and provider platforms, and building AI-native software in healthcare. Reports to CEO and aims to establish a high-trust, high-performance engineering culture while scaling AI-enabled healthcare solutions.

Responsibilities

  • Build! This is a player-coach role. You'll ship production code weekly and set the standard for what AI-native development looks like at Sailor.
  • Lead product. You'll own the roadmap across our patient and provider platforms - we expect you to deeply understand business problems & decisions.
  • Run experiments. You'll bring a data-oriented, experimentation-first mindset to a consumer product for a generation that's never had one built for them. Launch fast, read the signal, iterate.
  • Recruit. You'll attract and close exceptional engineers, drawing on your network and making Sailor the place the best builders want to be.
  • Set technical direction. You'll make the architecture calls as we scale, balancing speed today against the platform we'll need at ten times the patient volume.
  • Reinvent how we build. AI is changing what a small team can ship, and you'll push that frontier inside Sailor. You'll define the practices, tooling, and culture that let us outbuild much larger orgs.
  • Mentor the team. You'll mentor engineers across experience levels and turn strong builders into exceptional ones.

Qualifications

  • You've led engineering at a high growth startup: you thrived in the chaos, grew the team, set the engineering bar, and made the people around you better.
  • You're a builder. You've written meaningful production code in the last six months and have no interest in becoming a pure people manager.
  • You're a talent magnet. You've hired exceptional engineers from your own network, closed hard candidates, and some of them would follow you again.
  • You've owned product, not just executed it. You've made roadmap calls, written specs, and sat directly with users without a PM in between.
  • You're AI-native. AI is central to how you build software, and you can point to concrete changes in your team's workflow and output, well beyond autocomplete.
  • You stay on the frontier. You're on top of the newest models and eng tools, and you're usually the one bringing them to the team before anyone asks. We're TypeScript full stack, and you're at home in a modern web stack.
  • You're analytical and experimentation-first. You've launched features, read the data, and killed or doubled down accordingly.
  • You work hard. You're energized by intensity and want to be in person in NYC building a tight-knit team.

Skills

Required:Leadership at scale / people managementProduction software developmentProduct ownershipAI-native development

Benefits

  • Top quartile salary and equity
  • Comprehensive benefits, including medical, dental & vision insurance
  • Flexible PTO and sick days
  • Lunch and dinner in our beautiful Soho office covered by Sailor
  • Team building events
  • Friendliest and most dynamic team culture
  • One Medical Membership for US employees, HSA, Talkspace, HealthAdvocate, Teladoc Health
Last updated Oct 21, 2026. Interested? Apply on the company site.

About Sailor Health

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