Head of Engineering
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Job Description
Head of Engineering leading the engineering function and team at Flex, specializing in HSA and FSA payments. Overseeing technical direction and infrastructure for a growing healthcare payments company.
Responsibilities:
- Lead and grow the engineering team – recruit, mentor, and develop engineers.
- Own the technical roadmap – partner with founders and product to define priorities.
- Set engineering standards – establish best practices for code quality.
- Drive delivery – keep the team focused and unblocked.
- Architect for scale – lead the design of HSA/FSA payment infrastructure.
- Engage cross-functionally – work closely with customers, sales, and operations.
- Stay hands-on – contribute directly to the codebase when needed.
Requirements:
- 8+ years of engineering experience, with at least 2–3 years in an engineering leadership role.
- Proven team builder – you've hired, grown, and retained strong engineers.
- Strong technical foundation – depth in backend systems and APIs, conversant across the full stack.
- Familiarity with TypeScript, Rust, Postgres, Redis, and AWS is a strong plus.
- Architectural thinker with experience designing and scaling distributed systems.
- Startup experience in a seed-to-Series B company.
- Operator mindset able to bring structure and clarity without bureaucracy.
Benefits:
- Competitive salary with meaningful equity.
- Medical, dental, and vision plans.
- Unlimited PTO and sick days.
- Paid parental leave.
- Flexible, remote-first team with quarterly in-person meetups.
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