Weekend Ai Operator Jobs in New York (NOW HIRING)

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.

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

We're hiring our first RCM Associate to own and scale revenue cycle at Sailor Health.

You will be the business owner and quarterback for RCM across product, engineering, and operations. You'll inherit a small team and a strong foundation: over half of our patients pay $0 out of pocket and our RCM KPIs already sit in the top 5% of digital health companies. We’ve invested heavily in a state‑of‑the‑art, AI‑native RCM stack, and we want a leader who can compound that advantage. We’ve gotten to where we are through a combination of operational rigor, in‑house RCM products and external vendors, and deep attention to patient experience.

You’ll report directly to both co‑founders and work shoulder‑to‑shoulder with Payer Growth, Patient Growth, Engineering, and Product. At Sailor, operators ship product. You’ll roll up your sleeves, write SQL, build internal tools, and run point on the highest‑leverage decisions in the function.

This is the rare RCM role that combines the scale of a fast‑growing digital health company, the bar of a top‑decile billing operation, the tooling of an AI‑native engineering team, and the autonomy of a first hire.

• Own RCM end‑to‑end: Be the business owner responsible for the KPIs and health of the function. You’ll sustain our top 5% outcomes, and will be responsible for growing the RCM team. Key metrics include: net collection rate, touchless claim rates, denial rates, days in AR, and cost to collect.
• Serve as the product manager behind our AI‑native RCM: Partner with our engineers to continue shipping RCM products. You’re not waiting for a roadmap – you’re co‑authoring it.
• Design and scale AI‑native workflows: Across claims management, denial resolution, QA, reconciliation, payment posting, and payer operations.
• Build real‑time RCM reporting: Build and ship dashboards, reporting infrastructure, and operational visibility across the revenue cycle for the rest of our team.
• Identify and break bottlenecks: Identify reimbursement leakage, process bottlenecks, and opportunities for automation or optimization.Drive revenue operations: Own credentialing, enrollment, fee schedule integrity, and the operational side of payer relationships in tight partnership with Payer Growth.
• Provide best‑in‑class patient billing experience: You ensure that our 5‑star patient experience extends across billing and payments.

This is a high‑ownership role for builders who want to operate close to the founders and solve complex problems. The pace at Sailor is high, and the people who thrive here are energized by autonomy, speed, and responsibility.

• 1‑3 years of relevant experience. You’ve led or been a part the RCM team at a digital health company, or come from an operator role at a tech‑enabled RCM company. Medicare / Medicare Advantage experience is a strong plus. Strong product, consulting, or banking candidates are also a fit.
• You are customer‑obsessed. You understand how RCM directly shapes the patient experience and you obsess over delivering a 5‑star experience to patients.
• You're a data‑driven operator. You enjoy going several layers deep into data to understand operational performance, uncover edge cases, and improve performance. You’re excellent with spreadsheets, and SQL experience is preferred but not required.
• 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.
• You take work personally. You take pride in what you build and care deeply about the impact of your work.
• 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.

• 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

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.