VP / Head of Engineering

About the role

Sailor Health is seeking a VP/Head of Engineering to lead technology and product across both patient and provider platforms. Reporting directly to the CEO, you will shape technical direction while actively shipping code in a fast‑moving AI‑driven healthcare environment.

Key responsibilities

• Build and ship production code weekly, setting standards for AI‑native development.
• Own the product roadmap for patient and provider platforms, translating business problems into technical solutions.
• Run data‑oriented experiments, launch features quickly, and iterate based on results.
• Recruit and close top engineering talent, creating a small, high‑trust, talent‑dense team.
• Define architecture and scaling strategy, balancing short‑term speed with long‑term platform needs.
• Reinvent engineering practices to leverage AI, establishing tooling, processes, and culture that enable a small team to out‑build larger organizations.
• Mentor engineers at all experience levels, raising the overall performance of the team.

Required profile

• Proven leadership of engineering at a high‑growth startup, thriving in chaotic environments.
• Hands‑on builder who has written production code within the last six months.
• Track record of attracting and hiring exceptional engineers from personal networks.
• Experience owning product direction, writing specs, and engaging directly with users.
• Deep familiarity with AI‑centric development and modern web stacks.
• Data‑driven, experimentation‑first mindset.
• Willingness to work onsite in NYC and lead a tight‑knit team.

Required skills

• TypeScript
• Full‑stack web development
• AI‑native development practices

What we offer

• Top‑quartile salary and equity
• Comprehensive medical, dental, and vision benefits
• Flexible PTO and sick days
• Lunch and dinner provided at the Soho office
• Team‑building events and a dynamic culture
• Additional perks: One Medical membership, HSA, Talkspace, HealthAdvocate, Teladoc Health