Head Of Engineering

Flex

3d•Remote

About The Position

As Head of Engineering at Flex, you'll own the technical direction of a company defining a new category in healthcare payments. You'll lead and grow a talented engineering team, set the architectural vision, and ensure we're building systems that are reliable, scalable, and ahead of the market. This is a rare opportunity to partner directly with the founders to shape how we build — not just what we build. You're the person who gets us from where we are to where we're going — building the team, processes, and infrastructure to match our next stage of growth.

Requirements

8+ years of engineering experience, with at least 2–3 years in an engineering leadership role (EM, Staff/Principal, or Head of Eng).
Proven team builder — you've hired, grown, and retained strong engineers, and you know what great engineering culture looks like.
Strong technical foundation — you have depth in backend systems and APIs, and you're conversant across the full stack. Familiarity with TypeScript, Rust, Postgres, Redis, and AWS is a strong plus.
Architectural thinker — you've designed and scaled distributed systems and know how to make the right tradeoffs between speed and rigor.
Startup experience — you've worked at a seed-to-Series B company and understand what it means to build in a resource-constrained, fast-moving environment.
Operator mindset — you bring structure and clarity without bureaucracy, and you know how to keep a small team moving fast.

Nice To Haves

Familiarity with TypeScript, Rust, Postgres, Redis, and AWS is a strong plus.

Responsibilities

Lead and grow the engineering team — recruit, mentor, and develop engineers across all levels, building a culture of craft, accountability, and velocity.
Own the technical roadmap — partner with founders and product to define priorities, make architectural decisions, and ensure engineering investments align with company goals.
Set engineering standards — establish best practices for code quality, system design, incident response, and on-call culture.
Drive delivery — keep the team focused and unblocked, managing execution across sprints, projects, and longer-horizon initiatives.
Architect for scale — lead the design of our HSA/FSA payment infrastructure, APIs, and checkout experiences to handle growing merchant and transaction volume.
Engage cross-functionally — work closely with customers, sales, and operations to translate real-world needs into engineering priorities.
Stay hands-on — roll up your sleeves when it counts; you're comfortable contributing directly to the codebase when needed.