Sailor System Engineer Jobs (NOW HIRING)

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.

We’re hiring our first Founding Data & Analytics Engineer to architect and scale Sailor’s data foundation, powering everything from clinical insights to AI copilots. You’ll work closely with our co-founders, clinicians, and engineers to build the pipelines and analytics that fuel care delivery and decision-making.

This is a ground-floor opportunity to build an AI-first data stack from scratch at a startup with extreme PMF. You’ll design the data models that measure patient outcomes, automate operations, and unlock intelligence across our platform.

We're honestly looking for a bit of a unicorn: someone who can architect pipelines like a data engineer, ship web apps like a product engineer, and reason about the business like a founder.

• Create data-powered web apps to solve tangible business problems

• Build pipelines in Snowflake and dbt that unify data from EHR, CRM, and communication systems

• Develop AI and ML-driven analyses of therapy transcripts and patient data

• Automate backend operations with Python scripts that power clinical and billing workflows

• Track and visualize clinical outcomes (PHQ-9, GAD-7, etc.)

• Collaborate cross-functionally with clinicians and founders to turn data into action

• Build long-term horizon data architectures and solutions that grow as our user base and internal teams grow

• Live in NYC and energized by in-person work

• Have 3-10 years of experience in data engineering or analytics

• Are fluent in SQL, Python, dbt, and Snowflake

• Have experience with GraphQL, REST APIs, and unstructured data (e.g., transcripts, FHIR format)

• Bring high EQ and can communicate clearly with non-technical teammates

• Move fast, set a high bar, and care deeply about improving mental health for older adults

• 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, Teladoc Health

1. Make your Grandparents Proud: Remember why you’re here and build the standard of care you wish you 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.