Strategy & Operations Lead / Associate

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, wellness classes, 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 growing quickly and have partnered with Medicare to offer affordable and exceptional healthcare to thousands of patients. We are honored to have the support and backing of world-class founders from Ramp, Nourish, and Headway.

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

We’re hiring a Strategy & Operations Lead / Associate to join our core team at Sailor Health and work side-by-side with the founders to build the backbone of care delivery. This role is a unique opportunity to architect Sailor’s growth infrastructure across operations, clinical delivery, and product. You’ll design workflows, lead complex cross-functional projects, and drive operational excellence at scale. If you thrive in zero-to-one environments and want to make an outsized impact, we’d love to meet you.

• Scale care delivery 10x: Build and optimize the workflows that ensure every patient and therapist has a 10/10 experience. You’ll be building the foundation for improving clinical outcomes and ensuring patients receive timely, consistent, and compassionate care.

• Own key operational levers: You'll be responsible for key operational metrics such as retention, NPS, and clinical outcomes.

• Launch our operations system: Develop KPIs and reporting to track program adoption, retention, and impact.

• 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.

• You’re an A+ player: You have a hunger to win and a proven track record of being a top performer in fast-paced environments. You want to be the best and help your team win.

• 1-6 years of experience: You’ve led high-ownership roles in fast-paced environments, whether in startups, healthcare, or finance. You've owned KPIs and moved them materially.

• First-principles thinker: You break down complex problems clearly, and know when to zoom into the details or step back to see the system.

• You’re relentlessly resourceful: new challenges don’t scare you. You move fast, leverage your network, and solve problems without needing a playbook.

• Analytical and decisive: You know how to set KPIs, find root causes, and make bold decisions. You value outcomes over optics.

• Collaborative & mission-aligned: You’re excited to work directly with founders, clinicians, and engineers. You care deeply about helping older adults access care.

• 💰 Competitive salary and founding member-level equity

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

• 🌴 Flexible PTO and sick days

• 🍱 Lunch and dinner in the office covered by Sailor

• 🎤 Team building events

• 🕺🏻 Friendliest and most dynamic team culture

• ✚✚ 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.