Head of Engineering

Stealth Startup; Boston (MA); On-site; USD 180,000 - 260,000; Full time

Job summary

Stealth Startup is seeking a Head of Engineering to act as a hands-on leader and player-coach in the early-stage AI healthcare space. You will translate customer needs with the founders and product team into scalable technology and guide a growing engineering team.

You’ll stay actively involved in architecture, critical initiatives, and strategic decisions while shaping product direction and technical culture in a fast-paced environment. Boston-area preference with monthly travel considerations.

Qualifications

• Experience leading engineering teams in startup or early-stage settings.
• History building products and infrastructure from ground up.
• Strong software architecture, system design, and scalability knowledge.
• Product sense and understanding of tech-driven growth.
• Demonstrated focus on security and reliability in regulated environments.

Responsibilities

• Lead, mentor, and grow an engineering team of 4+ engineers.
• Remain hands-on and contribute to critical engineering initiatives.
• Own architecture, infrastructure, scalability, and tech strategy.
• Partner with founders and product leads to translate needs into solutions.
• Make pragmatic architectural decisions balancing speed and quality.
• Establish strong engineering practices and high-performance culture.
• Help recruit, develop, and retain engineering talent.
• Understand impact of tech decisions on adoption and growth.
• Identify opportunities to leverage AI to improve capabilities.
• Ensure security and reliability are built into the platform.
• Evolve technical infrastructure as the company scales.
• Balance near-term execution with long-term strategy.

Skills

Leadership

Startup experience

AI technologies

Security

Cloud infrastructure

Communication

Education

Bachelor's degree in CS

Tools

AWS

Kubernetes

CI/CD

Job description

Location: East Coast, U.S. — Boston preferred; NYC, Philadelphia, and Washington, DC metro areas considered

Travel: Monthly travel to the Boston area

Work Authorization: Must be authorized to work in the U.S. without sponsorship

About the Company

We are a seed-stage AI technology company building innovative solutions in the healthcare space. We are growing our engineering organization and are looking for a hands-on engineering leader who can help shape our technology, product, and team as we scale.

The Role

We are seeking a Head of Engineering to serve as a hands-on player-coach, combining technical leadership with individual contribution.

You will work closely with the founders and product team to translate customer and business needs into scalable technology. You will lead a growing engineering team while remaining actively involved in architecture, technical decisions, and critical engineering initiatives.

This is an opportunity for someone who thrives in an early-stage environment and enjoys building teams, products, and technology from the ground up.

Responsibilities

• Lead, mentor, and grow a high-performing engineering team of 4+ engineers.
• Remain hands-on and contribute directly to critical engineering initiatives.
• Own engineering architecture, infrastructure, scalability, and technical strategy.
• Partner closely with founders and product leadership to translate business and customer needs into technical solutions.
• Make pragmatic architectural decisions that balance speed, scalability, reliability, and maintainability.
• Establish strong engineering practices and contribute to a high-performance engineering culture.
• Help recruit, develop, and retain engineering talent.
• Understand how engineering and product decisions impact customer adoption and commercial growth.
• Identify opportunities to leverage AI to improve product capabilities and engineering productivity.
• Ensure security and reliability are built into the platform, particularly within a regulated industry.
• Help evolve the technical infrastructure as the company and product scale.
• Balance near-term execution with long-term technical strategy.

Qualifications

• Strong software engineering background with experience leading engineering teams.
• Experience working in a startup or early-stage environment.
• Demonstrated experience building products and technical infrastructure from the ground up.
• Strong knowledge of software architecture, system design, infrastructure, and scalability.
• Strong product instincts and understanding of the relationship between technology and business growth.
• High ownership, initiative, and ability to operate effectively in an ambiguous environment.
• Founder mentality and willingness to take on both strategic and hands-on responsibilities.
• Experience working with AI technologies and modern engineering tools.
• Strong understanding of security and reliability, particularly in regulated environments.
• Excellent communication and leadership skills.

Healthcare experience is a plus, but not required.

Location & Work Authorization

• Boston is preferred.
• East Coast candidates within reasonable travel distance of Boston will be considered, including candidates in the NYC, Philadelphia, and Washington, DC metro areas.
• Monthly travel to the Boston office is expected.
• Must be currently based in the United States.
• Must be authorized to work in the United States without sponsorship.