Senior Head Of Engineering; Remote

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Head Of Engineering - REMOTE. In this role, you will have a significant impact on shaping the future of healthcare payments technology. By leading a talented engineering team, you will establish best practices and ensure the development of reliable and cutting-edge systems. You will partner directly with founders, define engineering priorities, and create a culture of accountability.

This position offers an opportunity to drive growth and execute architectural visions that align with the company's goals, influencing both the technical roadmap and team dynamics.

• 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.

• 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 have 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 Type Script, 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.

• Define the engineering function at a company with a clear wedge in a $150B+ market.
• Work directly with founders on the highest‑leverage technical and product decisions.
• 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.

We appreciate your interest and wish you the best!