Care Strategy & Operations (Lead / Director)

Sailor has exceptional product-market fit

• Exponential growth: We are honored to serve thousands of patients across all 50 states, with strong organic demand helping make Sailor one of the fastest-growing companies in healthcare.
• AI-powered, deeply human care: We harness the power of AI while keeping human connection at the center of care, creating an experience that feels personal, continuous, and deeply human.
• Talent-dense team: We are a 25-person team in our NYC office and are backed by the founders of Ramp, Nourish, Headway, Charlie Health, and Spring Health.

About the Role

Location: Soho, New York City

This is one of the most important hires we will make this year.

Our therapy practice is live in all 50 states and growing fast. Healthcare advocacy, our newest service line, is growing even faster. Patients come to us for therapy and quickly realize we can help with much more: finding the right specialist, untangling a Medicare bill, coordinating between doctors who never talk to each other. Demand is outpacing the systems we have built so far, and we need someone to build what comes next.

As our Director / Manager of Clinical Operations, you will own the care model behind all of it. You will scale therapy operations across a national footprint, turn healthcare advocacy into a world class service line, and launch new services that will define Sailor's future. Our case managers will report to you, and you will build the team around them.

You will partner closely with our Clinical Director, Dr. Daniel Burow, to design care that is both clinically excellent and operationally built to scale. You will report directly to our founders.

Your Key Responsibilities

• Build the care model. Design how patients move through Sailor across therapy, advocacy, and case management, partnering with our clinical, operations, legal, and engineering teams to bring it to life.
• Scale new service lines. Turn healthcare advocacy, our fastest growing service line, into a repeatable national operation with the workflows, playbooks, and metrics to match.
• Shape how AI supports our clinicians. Help design how AI copilots take administrative work off our clinicians' plates, so they can spend more time listening, connecting, and caring for patients.
• Lead case management and escalations. Manage and grow our case management team, oversee their caseload, and build the triage and escalation protocols for high acuity cases.
• Power whole person care. Build the connective tissue that unites our clinicians and care teams into one integrated model that sees each patient as a whole person, so their mental health, physical health, and daily life are cared for together, not in silos.
• Measure quality and safety. Track the metrics that tie our work to patient outcomes, and ensure everything meets clinical, privacy, and Medicare standards.

What We’re Looking for

• This role isn’t for everyone.
• It’s fast-paced, chaotic, and requires hard work.
• But if this excites you, we’d love to meet you.

• You have 4-12 years of experience (ideally in clinical operations): You've built and scaled care delivery at a high growth healthcare company, and you know what great clinical operations look like from the inside.
• You're a player-coach: You lead your team with clarity and warmth, and you're just as happy rolling up your sleeves to work a tough case yourself.
• You're a strong communicator: You build trust quickly with clinicians, engineers, lawyers, and founders alike, and you can get very different teams moving in the same direction.
• You thrive in ambiguity: You don't need a playbook to get started. When a situation is new and messy, you bring structure to it and keep moving.
• You think from first principles: You look at problems from every angle, weigh the tradeoffs, and land on a balanced decision you can clearly defend.
• You take work personally: You take pride in what you build and care deeply about the older adults who rely on it.