Care Strategy & Operations (Lead / Director)

Sailor Health is on a mission to solve the mental health crisis among older adults. In the United States, older adults have the highest suicide rates of any age group yet receive the least mental health care. By 2030, over 65 million seniors will make up nearly a quarter of the U.S. population, creating one of the largest and most urgent challenges in healthcare.

Sailor is building the platform for senior mental health, connecting older adults, therapists, healthcare professionals, and insurance plans. Our AI-native operating system powers seamless care coordination, real-time clinical insights, and insurance billing – enabling therapists to spend more time delivering compassionate care.

We are growing quickly and have partnered with Medicare to offer affordable and exceptional psychotherapy to hundreds of patients. 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'll support you with relocation if you're looking to move to NYC)

We’re hiring a Lead / Director of Care Strategy & Operations to join our core team at Sailor Health and work side-by-side with the founders to build the backbone of care delivery. You'll be reporting directly to the co-founders.

Our #1 priority right now is scaling our operations to meet market demand while delivering a 10/10 experience – to clinicians and patients alike.

We're looking for exceptional operators who thrive in building systems from the ground-up – you'll go from strategy to execution, and work closely with our ops team, patients & clinicians to scale our care delivery 10x.

• Scale care operations 10x: Identify and break bottlenecks to unlock Sailor’s next 10x phase of growth. You'll go deep in our customer journey and find ways to enable a 10/10 patient and provider experience.

• Build and scale an Sailor's customer support function: You'll lead and grow our amazing support team. You'll launch systems, workflows, and KPIs so our customers receive timely and exceptional support.

• Drive Sailor's operations engine: You'll own key cross-functional operational levers such such as retention, NPS, clinical performance, and utilization. You'll work with our ops team to develop KPIs and reporting systems, followed by launching experiments to improve them.

• Design and collaborate on product roadmap: Work with engineering and design to turn frontline insights into product features that power care coordination, therapist tooling, and patient engagement.

• 2-6 years of experience: You’ve operated in fast-paced environments – such as high-growth startups, consulting, investment banking. Healthcare experience is a plus.

• Driven and highly ambitious: You care deeply about doing exceptional work and about being excellent at what you do. This desire to win has shown up before – whether in academics, team sports, or in your prior jobs.

• Curious & resourceful: New challenges don’t scare you. You move fast and learn how to figure things out.

• Analytical & decisive: You know how to set KPIs, derive insights from data, and digging deeper to find the root cause. SQL or Python is a plus.

• Team player & mission-aligned: You’re excited to work directly with founders, clinicians, and engineers. You care deeply about helping seniors get access care.

• 💰 Competitive salary and meaningful equity

• 🩺 Comprehensive benefits, including medical, dental & vision insurance

• ✚ Health benefits: One Medical Membership for US employees, HSA, Talkspace, HealthAdvocate, Teledoc Health

• 🌴 Flexible PTO and sick days

• 🍱 Lunch and dinner in the office covered by Sailor

• 🌅 Beautiful office in the heart of Soho

• 🕺🏻 Friendliest and most dynamic team culture