Strategy & Operations Lead

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.

• Talent-dense team: We are a 25-person team in our NYC office and are backed by the founders of Ramp, Nourish, Headway, Charlie Health, and Spring Health.

Location: New York City, in office, 5 days a week.

We’re hiring a Strategy & Operations Lead to join our core team at Sailor Health and work side-by-side with the founders to build at the intersection of healthcare and AI. This role is a unique opportunity to architect Sailor’s growth infrastructure across operations, clinical delivery, and AI product.

If you want a high-ownership role at a startup with extreme product-market fit, we’d love to meet you.

We are growing very quickly, so we’re looking for Swiss army knives who are excited to tackle different problems. We hire for people, not roles - but here’s our best attempt at describing what you might work on:

• Launch a new care line: You could stand up and scale new offerings like care navigation, owning everything from workflow design to execution and performance.

• Own and scale a function: You could take over a core area like provider operations, RCM, or care navigation and drive it from scrappy to world-class.

• Drive AI transformation internally: You could deploy AI-powered tools, from vibe-coded internal apps to workflow automations, that unlock step-function improvements in how we operate.

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’re an A+ player: You have a hunger to win and a proven track record of being a top performer in high-intensity environments.

• You want to solve hard problems: You’re energized by complexity and have the work ethic to push through challenges throughout the week.

• You’re analytical and decisive: You’re skilled in Excel/Google Sheets and can perform deep analyses to inform fast, high-quality decisions.

• You take work personally: You take pride in what you build and care deeply about the impact of your work.

• You’re AI-native: You believe healthcare will be fundamentally transformed over the next decade and want to help drive that change in your day-to-day.

• 💰 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, Teledoc 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.