VP/Head of Engineering

America is undergoing one of the largest demographic shifts in its history as the Baby Boomer generation enters its later years. This shift will put unprecedented pressure on Medicare, which already spends more than $1 trillion each year caring for older adults. Yet the healthcare system is built backwards: reactive instead of preventative, measuring years of life instead of the quality of them.

Sailor Health is building a new care model for aging. We combine behavioral health, healthcare advocacy, wellness classes, and AI care agents into one virtual platform designed for older adults. AI coaches help patients navigate their health between visits, while AI copilots give providers the tools to deliver higher-quality, better-informed care. We partner with Medicare to make our platform affordable and accessible to older adults nationwide.

Sailor has exceptional product-market fit:

• Exponential growth: We are honored to serve thousands of patients across all 50 states, with strong organic demand helping make Sailor one of the fastest-growing companies in healthcare.

• AI-powered, deeply human care: We harness the power of AI while keeping human connection at the center of care, creating an experience that feels personal, continuous, and deeply human.

• Backed by category-defining founders: We are supported by founders from Ramp, Nourish, Headway, Charlie Health, and Spring Health.

We're hiring a VP/Head of Engineering to lead technology and product at Sailor. You'll set technical direction, lead product across both our patient and provider platforms, and report directly to our CEO.

You'll be building at the frontier of AI and healthcare: our AI Health Coach that measurably improves health outcomes, copilots that give clinicians superpowers, and a longitudinal data platform spanning the full care journey. Just as exciting is the how, because you'll get gritty reinventing engineering practices for a world where AI changes how software gets built.

We're looking for a player-coach with high slope, someone who loves to build, and a leader wants to do the defining work of their career. On hiring, your mandate is to build the "Navy SEALs" of engineering: small by design, high-trust culture, and extremely talent dense.

• 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.

This role isn't for everyone. It's fast-paced, chaotic, and requires hard work. But if this excites you, we'd love to meet you.

• 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.

• 💰 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

• ✚ Additional: One Medical Membership for US employees, HSA, Talkspace, HealthAdvocate, Teladoc Health

1. 💙 Make your Grandparents Proud: Remember why you’re here and build the standard of care you wish your grandparents received.

2. 💡 Best Ideas Win: We strip problems down to first principles and challenge each other – but once a decision is made, we row as one.

3. ⚡️Go Fast and Far: We have a burning sense of urgency AND we go the extra mile.

4. 🥇 Do What It Takes To Be #1: We obsess over excellence and challenge ourselves and each other to actualize our best selves.

5. ⛵ Happy Crew: A miserable crew rows slow. A happy crew rows fast. Fun is a performance metric.