Growth Lead / Associate

About Sailor Health

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.

⭐ About the Role

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

We're hiring a Growth Lead / Associate to scale Sailor’s patient growth engine. You'll report to the Head of Growth, work across nearly every team in the company, and own critical decisions that shape how care reaches older adults nationwide.

The role has two parts.

• Scale the engine: You'll be at the helm of Sailor's proven B2B and B2C distribution channels with a mandate to accelerate what's working at scale. You'll decode CAC, run the testing roadmap, and decide where the next dollar goes. You'll also build the team, playbooks, and reporting behind the engine, and use AI to uplevel our workflows so we move faster with every launch.

• New bets: You'll operate like a founder inside Sailor, with the budget and backing to test distribution channels that don't exist for us yet. Some weeks that means mapping the incentives of a Medicare Advantage plan. Others it means pitching a physician group or a senior center on why their patients need us. You'll turn the promising ones into pilots, measure them honestly, and scale what works.

Your Key Responsibilities

• Quarterback our proven channels. Be the connective tissue between the Head of Growth, our business partners, creative, and clinical ops. Set the weekly priorities, keep every workstream moving, and make sure the tests we agreed on actually ship.

• Launch new distribution channels. Identify untested channels, meet with the health plans, physician groups, and community organizations behind them, and turn the promising ones into pilots. Build the case, run the test, and make the call on what to scale.

• Own the growth analytics. Build and maintain the models we run the business on: CAC by channel and market, funnel conversion, cohort retention, and market level unit economics. Turn messy data into the analysis that decides where the next dollar goes.

• Rebuild our workflows with AI. Automate the work we run by hand today and build internal web apps that give the team better tools for reporting, forecasting, and campaign management.

What We’re Looking For

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.

• 2 to 7 years of operational or analytical experience. You've worked in consulting, banking, private equity, growth marketing, or the operations team of a fast moving startup.

• Scrappy with experiments. You'd rather run a quick test than debate a hypothesis for a month. You design clean tests, read results honestly, and kill what isn't working.

• A builder's instinct with AI. You already use AI to work faster and want to push it further: automating workflows, spinning up internal tools, and finding the next place it saves the team hours. You don't need to be an engineer, but you need to be curious and hands on.

• Strong communication and people skills. You can turn a complicated analysis into a one page recommendation, and you're just as comfortable building relationships with partners and coaching our Provider Partnership Managers to be more effective.

• Excellent spreadsheet and modeling skills. You build models other people can actually use, and you can defend every assumption in them. SQL is a plus.

• Deep empathy for the people we serve. Our patients are 65 and older, and many are navigating complex mental and physical health care for the first time. Everything we build has to work for them.

Our Offer to You

• Competitive 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

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

Our Values

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

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

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

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

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