Head of Engineering

My People Person; United States; Remote; USD 180,000 - 240,000; Full time

Benefits offered by this job

Fully remote

Job summary

My People Person is seeking an engineering leader to own the platform modernization, team, and roadmap. You will report directly to ownership and influence overall company direction, not just engineering.

This is a mature, revenue-generating product, not a startup, with authority to decide what to rebuild, refactor, or retire. You will balance near-term delivery with long-term health, scale the engineering organization, and partner with sales, marketing, and product to align technical decisions

Qualifications

• 5+ years of software development experience, with at least 2 years in engineering leadership
• Experience in healthcare technology, EdTech, or subscription-based SaaS products
• Hands-on experience modernizing an established software product (cloud migration, platform consolidation, re-architecture, or similar)
• A proven track record building and scaling software teams
• Strong engineering instincts: good architecture, clean code, and scalable systems
• A track record of communicating with and gaining alignment from leadership and non-technical departments such as sales, marketing, and product
• Comfort taking ownership of execution and results in a small to mid-sized, family-owned company

Responsibilities

• Platform modernization: assess current architecture and build a pragmatic modernization roadmap
• Lead migration and re-architecture work balancing near-term delivery with long-term technical health
• Make build, refactor, or retire decisions that move the platform forward without risking customers
• Team leadership: hire, mentor, performance manage, and shape team structure
• Establish engineering processes: sprint planning, code reviews, incident response, and release management
• Stay hands-on at code/architecture level when needed while empowering the team to execute
• Business partnership: translate business goals into a technical roadmap and resource plan
• Report directly to ownership and align engineering with sales, marketing, and product
• Quality, security, and reliability: own delivery standards and ensure uptime/compliance in healthcare context

Skills

Software development

Engineering leadership

Healthcare technology

Cloud migration

System architecture

Cross-functional communication

Ownership mindset

Education

Computer Science degree

Job description

Our client has served healthcare institutions for more than 30 years. Customers rely on it every day, and it is ready for its next chapter. They are looking for an engineering leader who has taken a mature, revenue-generating product and modernized it without disrupting the customers who depend on it, and who wants to do that again with real authority and a direct line to ownership.

About the Company

They are a healthcare education and informatics company with over 30 years in the market. Their platform is used by healthcare institutions across the United States and globally. They are small enough that one leader can shape how engineering works, and established enough that the work matters to a large base of loyal customers.

The Opportunity

The Head of Engineering owns the technical side of the business: the team, the platform, and the roadmap. You will report directly to ownership and serve as the primary technical voice in company leadership, with a seat at the table to guide overall company direction.

This is not a maintenance role, and it is not a greenfield startup. It is a modernization role. You will evolve a proven platform in place, making clear, pragmatic calls about what to rebuild, what to refactor, and what to leave alone, while keeping the product reliable for the customers who use it today.

This Role Is a Fit If You

• Have led the modernization of an established product while customers kept using it, such as moving from self-hosted to cloud SaaS, consolidating fragmented products or services onto one platform, or re-architecting a legacy codebase
• Still enjoy getting into architecture and code, even though parrt of your time goes to leading people
• Have built and grown an engineering team, including hiring and developing leads or managers
• Can explain technical tradeoffs to owners, sales, and customers in plain business terms
• Want ownership and accountability in a smaller company rather than a narrow lane in a large one

What You'll Own

Platform modernization

• Assess the current architecture and infrastructure, and build a pragmatic modernization roadmap
• Lead migration and re-architecture work that balances near-term delivery with long-term technical health
• Make the build, refactor, or retire decisions that keep the platform moving forward without putting customers at risk

Team leadership

• Lead and develop the software engineering organization, including hiring, mentorship, performance management, and team structure
• Establish and reinforce engineering processes: sprint planning, code review standards, incident response, and release management
• Stay hands-on at the code and architecture level when needed, while empowering the team to own execution

Business partnership

• Translate business goals into a technical roadmap and resource plan
• Report directly to ownership and serve as the primary technical voice in leadership discussions
• Partner closely with sales, marketing, and product so engineering priorities line up with what customers need

Quality, security, and reliability

• Own the delivery of our software products and set the standards for quality, velocity, and reliability
• Ensure the security, uptime, and compliance posture appropriate for a healthcare data company

What We're Looking For

• 5+ years of software development experience, with at least 2 years in engineering leadership
• Experience in healthcare technology, EdTech, or subscription-based SaaS products
• Hands-on experience modernizing an established software product (cloud migration, platform consolidation, re-architecture, or similar)
• A proven track record building and scaling software teams
• Strong engineering instincts: good architecture, clean code, and scalable systems
• A track record of communicating with and gaining alignment from leadership and non-technical departments such as sales, marketing, and product
• Comfort taking ownership of execution and results in a small to mid-sized, family-owned company

Nice to Have

• Experience with security and compliance in regulated data environments
• Technical due diligence or systems integration experience following an acquisition
• Practical experience applying AI in engineering workflows or in the product
• Degree in Computer Science or a related field

Why This Role

• Real authority: you report to ownership and help set company direction, not just engineering direction
• A product with staying power: three decades in market and a loyal customer base to build on
• Visible impact: in a company this size, the platform and team you build will be clearly yours
• Fully remote, with the flexibility that comes with it