[Hiring] Senior Engineering Manager @Headway

Role Description

You'll lead the Infrastructure team — one of three teams in Engineering Foundations, alongside Agentic Engineering and Eddy, Headway's internal AI platform — that every other team at Headway builds on. You'll own:

• Cloud infrastructure
• Deployment pipelines
• LLM infrastructure (gateway, multi-provider failover, per-team rate limiting)
• The database platform
• Observability
• Incident response

As AI dramatically increases code velocity across the org, our mandate is to make every change safe from the start and build systems that get safer as they get faster, working toward a model where routine infrastructure is self-serve and the team spends the majority of its time on strategic platform work.

This is a technical leadership role: you'll set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response, not through distance from the work.

What You'll Own

• An engineering team:
  • Hiring to a high bar into a growing team
  • Developing engineers through the senior and staff levels
  • Running an effective on-call rotation for a team the rest of engineering depends on
• The infrastructure platform:
  • A system every other Headway team builds on
  • A roadmap spanning cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability
• The shift from reactive to strategic:
  • Driving the team's operating model toward self-serve infrastructure
  • Allowing the team to spend more time on strategic platform work and less on routine support requests
• Blast-radius reduction:
  • Leading the architectural and deployment validation work that contains the scope and duration of incidents when they happen
• The org interface:
  • Defining production readiness expectations for AI workloads
  • Co-owning container security and secrets management with the Security team
  • Ensuring the platform is accessible and well-understood by the product engineering teams that depend on it

Principles that guide us

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself.
• Ship small, learn fast: We believe that we learn what our users need by quickly shipping and iteration.
• Everything is a product: We treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning and feel safe asking questions and discussing mistakes.

Qualifications

• 5-7+ years of engineering leadership experience, with experience leading infrastructure or platform teams.
• 5+ years of experience as a Software or Infrastructure Engineer, with enough depth to lead credibly in design reviews and incident response.
• Experience managing the interface between a platform team and the product engineering teams that depend on it.
• Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines.
• Experience owning a platform strategy and representing it to senior leadership.

Requirements

• You've personally led the shift from "infra team owns everything" to a self-serve platform.
• Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies.
• You're personally hands-on with AI coding tools day to day.

Benefits

• Headway is committed to the full inclusion of all qualified individuals.
• Reasonable accommodations for persons with disabilities during the job application or interview process.