Head of Finance

About Sailor Health

Sailor Health is on a mission to solve the mental health crisis among older adults. 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, and 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 serve thousands of patients across 49 states. We are honored to have the support and backing of world-class founders from Ramp, Nourish, Headway, Charlie Health, and Spring Health.

☆ About the Role

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

Sailor is hiring a Head of Finance to own the finance function and serve as a trusted partner to the founders. This is a high-ownership role where you will inherit and drive all key financial components of the business and work closely with the executive team on key capital allocation, forecasting & budgeting, and strategic finance decisions. As part of the finance function, you will also take on the Revenue Cycle Management (RCM) function - collaborating closely with our product and engineering team.

You'll report directly to the co-founders and work across every function at Sailor. At Sailor, operators ship product. You'll roll up your sleeves, write SQL, build dashboards, and be in the room for the highest-leverage financial decisions at the company.

Your Key Responsibilities

• Own financial planning and analysis (FP&A): Build and maintain our financial models, forecasts, and budgets. Translate operational data into financial insight for the executive team and investors.
• Drive KPI planning & reporting: Design and ship KPI dashboards and reporting infrastructure so the team has a real-time view of financial and operational health of the business.
• Own financial reporting: Together with our co-founders, own and maintain investor reporting, including board decks and investor packages.
• Drive revenue cycle management (RCM): Become the business owner for RCM - ensuring we collect revenue from payers. Own the product and team of billers in charge of net collection rate, days in AR, touchless claim rates, and cost to collect. You'll inherit a strong foundation and a top-tier AI-native stack. We'll invest in getting you up to speed quickly.
• Support strategic and operational finance: Own or support ad hoc financial work as the company grows - vendor negotiations, payer contracts, unit economics analysis, new venture launches and more.
• Serve as the finance business partner: Collaborate with the broader team to drive smarter investment decisions, improve unit economics, and accelerate growth. You'll be involved in high-states strategic decisions.

• What We're Looking For

This role is for someone equally at home building a financial model and digging through operational data. We care more about exceptional analytical instincts and a fast learning curve than a specific domain background.

• 6+ years of experience in investment banking, private equity, growth equity, consulting, or an operator finance role at a high-growth startup.
• You are analytically exceptional. You are comfortable building and stress-testing financial models from scratch. You know how to find signal in messy data. SQL experience is a strong plus.
• You learn fast and take ownership. You're not intimidated by a domain you haven't mastered yet. You'd rather take on something hard, figure it out, and own it than wait for someone to hand it to you.
• You're an AI operator. You use AI tools to multiply your output - and you're curious about what's possible, not just what's in the job description.
• You want to be close to the mission. You'll be working on financial infrastructure for a company serving seniors with mental health needs. That context shapes how you think about your work.
• RCM or healthcare operations experience is a plus, but it's not required. We have world-class RCM advisors to get you set up.

Our Offer to You

• Competitive salary and founding member-level 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, Teledoc Health

Our Values

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.