Sailor Health (ashby) Opportunities

Full Job Description

🌊 About Sailor Health

America is undergoing one of the largest demographic shifts in its history as the Baby Boomer generation enters its later years. This shift will put unprecedented pressure on Medicare, which already spends more than $1 trillion each year caring for older adults. Yet the healthcare system is built backwards: reactive instead of preventative, measuring years of life instead of the quality of them.

Sailor Health is building a new care model for aging. We combine behavioral health, healthcare advocacy, wellness classes, and AI care agents into one virtual platform designed for older adults. AI coaches help patients navigate their health between visits, while AI copilots give providers the tools to deliver higher-quality, better-informed care. We partner with Medicare to make our platform affordable and accessible to older adults nationwide.

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: New York City (Soho), in office, 5 days a week.

We are looking for a relentless problem-solver to join Sailor Health as our Provider Operations & Strategy Lead. This person will build the operations and infrastructure that give every clinician who calls Sailor home an exceptional experience.

At Sailor, we are reimagining what it means to age in America by delivering exceptional geriatric care – and that starts with setting our clinicians up for success. That commitment runs deep: when we started the company, our co-founders brought geriatric clinicians out of retirement and personally taught them how to use Zoom.

The right person for this role brings that same range. You'll enjoy getting to know our providers and understanding their pain points as much as spending afternoons building AI-native operational systems with our engineering team – and you'll value long-term strategy as much as solving the problem in front of a provider today. It's a role with real ownership and visibility, close to a clinical team that's growing fast and a leadership group that sees provider operations as a core part of the business.

You'll report directly to one of our co-founders and work alongside our Clinical Director and Provider Growth Lead. You'll also coach the exceptional team currently running provider support.

💻 Your Key Responsibilities

• Represent the voice of the provider across the company: Be the voice of real provider pain points in rooms with product, engineering, and clinical.

• Manage day-to-day operations of our clinical team: Be the person responsible for ensuring provider operations run smoothly: supporting support escalations, work with clinical quality leads to enable exceptional care, and create the right systems and protocols meant for scale.

• Build support into an operating system: Take the function from an inbox to a scalable infrastructure so Sailor can absorb 10x provider volume scalably. You’ll build AI support agents with our engineers and own the support product.

• Write and enforce operational policies: Draft and roll out the policies that govern provider operations: payroll, holidays, patient no-shows…

• Deliver hard conversations directly: Own provider churn-risk and consequential conversations with providers. Communicate clearly and without ambiguity, while reading the room. Providers should leave the conversation understanding exactly where they stand.

• Close the provider feedback loop: Collect NPS and provider feedback, diagnose the real drivers, and push fixes into onboarding, clinical, and growth.

• Coach and manage the provider support team: Improve ticket quality, tone, and resolution speed through direct coaching, and build systems that enable this at 10x scale.

✅ What We’re Looking For

This is a high-ownership role for a builder who wants to get in early and shape something from scratch. The pace is high; people who thrive here move fast, take initiative, and get energized by dynamism and ambiguity.

• 3+ years of experience, with at least one of: prior ops or product role at a fast-growing startup; consulting or finance experience. Demonstrated track record of exceptional achievement in at least one dimension.

• Thrives in ambiguity — and structures it. Doesn't freeze without a playbook. Pattern-matches across situations and builds repeatable systems from messy problem spaces.

• Meticulously organized: Most likely praised by your teachers or peers about your to-do lists and organizational skills. You stay on top of time-sensitive tasks and attack projects proactively.

• Direct, high-stakes communicator. Can deliver hard messages clearly to external stakeholders — providers who can churn — without burying the point to protect the relationship, or blowing it up by being tone-deaf.

• People management instinct. You know how to improve someone else's output without owning it for them. You coach to the actual gap, not around it.

• AI operator. You build systems on Claude or ChatGPT to move faster and do more with less – either in your work or personal life.

• You take work personally. The clinician experience and the patient experience are directly connected. You feel that.

Our Offer to You

• 💰 Top quartile salary and 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

• 🕺🏻 Friendliest and most dynamic team culture

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

Our Values

• 💙 Make your Grandparents Proud: Remember why you’re here and build the standard of care you wish your grandparents received.

• 💡 Best Ideas Win: We strip problems down to first principles and challenge each other – but once a decision is made, we row as one.

• ⚡️Go Fast and Far: We have a burning sense of urgency AND we go the extra mile.

• 🥇 Do What It Takes To Be #1: We obsess over excellence and challenge ourselves and each other to actualize our best selves.

• ⛵ Happy Crew: A miserable crew rows slow. A happy crew rows fast. Fun is a performance metric.