GM of New Verticals

Sailor Health is on a mission to reinvent the aging experience in America. Getting older in America is tough: 90% of seniors live with chronic health conditions, 40% feel isolated, and older adults have the highest suicide rates of any age group. Sailor exists to change that.

Sailor Health is building the AI-native health system for happier and healthier aging. Sailor offers virtual mental health, care navigation, wellness classes, AI coaches, and AI care agents. Our vision is to become the trusted household name for older adults in America, setting a new standard for aging with dignity and honor.

We are doubling every 75 days and serving thousands of patients across 48 states. We are honored to have the support and backing of world-class founders from Ramp, Nourish, Headway, Charlie Health, and Spring Health.

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

Salary range: $180k - $230k (total cash), plus top-quartile equity component

At Sailor, we believe the future of healthcare will be built on deep trust, horizontally integrated care, and preventative rather than reactive interventions. We’re now uniquely positioned to expand into adjacent care lines where our existing patient relationships, referral channels, and infrastructure position us to build the category-defining company for happier & healthier aging.

We are looking for our first GM of New Verticals to take a new care line from $0M to $5M in 9 months. You will be responsible for the P&L and the 0 → 1 buildout, and will work directly with the co-founders.

This role is designed for someone who wants to be a founder one day: you’ll have extreme ownership & autonomy, ability to build your own team, and lead projects projects across operations, product, and growth.

• Launch our first new care line 0→1, driving it from $0 to $5M in 9 months — first starting as an IC and then graduating into a player-coach.

• Own the P&L end-to-end for our new bets — revenue, margin, unit economics, and the capital allocation calls that decide where we double down and where we walk away.

• Co-design the clinical model with clinical leadership for each new vertical — care pathways, staffing ratios, protocols, and quality measures — so every new line clears Sailor's clinical bar before it scales.

• Build the operational backbone of each care line — intake, scheduling, documentation, billing, and the cross-functional workflows that wire new verticals into Sailor's core operations. Solve backwards of how to deliver a 5-star experience, in line with our NPS of 91.

• Partner with Product and Engineering to shape the roadmap for each new care line, combining human-led care with Sailor's portfolio of AI subclinical agents.

• Recruit and lead the team — operate as a player-coach early on, then build a pod per vertical (clinical lead, ops lead, growth lead) as each line hits escape velocity.

• Define the scorecard and report to the founders and board on clinical outcomes, patient NPS, contribution margin, retention, and growth — with a clear bar for what "working" means at every stage.

• Build and manage the external partnerships each new line depends on — payers, providers, channel partners, and vendors — including contracting and regulatory navigation.

• Bring structure to ambiguity — write the strategy docs, run the operating cadence, and create the decision-making artifacts that let the founders trust you to operate independently across multiple bets at once.

This is a high-ownership role for builders who want to operate close to the founders and build their own startup within Sailor.

• 3+ years of building experience. You’ve owned a P&L or business unit, and delivered exceptional results. Bonus points if you’re a former founder or entrepreneur at heart within your prior company.

• You're a world-class operator. You combine speed, operational rigor, and sharp judgment. You can hold a P&L, a clinical protocol, and a hiring loop in your head at the same time, and you see exactly how a decision in one ripples through unit economics, the patient journey, and clinical outcomes.

• You're customer-obsessed. You enjoy talking to customers and love building products and experiences they customers love. You’re excited to materially improve the lives of seniors’ patients.

• You're a data-driven operator. You go several layers deep before drawing conclusions. You live in spreadsheets, but you’re curious enough to check if the data and anecdotes match.

• You live in a culture of experimentation. You'd rather run five small tests than write one perfect plan. You think in Build-Measure-Learn loops.

• You're an AI operator. You are excited by using AI to drive better results and 10x your output. On evenings or weekends, you're on Claude or Codex shipping products, gadgets, or just experimenting.

• The people who've worked with you want to work with you again. Your former bosses, peers, and direct reports are your biggest promoters.

• 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.

• 💰 Top quartile salary and equity compensation

• 🩺 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, Teledoc Health