# Senior Engineering Manager (Infrastructure) at Headway

- Company: Headway
- What the company does: Backed by Accel, a16z and GV.
- Company website: https://headway.co/
- Type: Startups
- Level: Senior
- Location: Remote
- Work setup: Remote
- Pay: $265K to $332K base salary per year (USD)
- Posted: 2026-10-17
- Apply by: 2026-12-01
- Apply: https://jobs.ashbyhq.com/headway/91137d3f-1546-4f26-949b-4c079990f5cf?utm_source=1752vc&utm_medium=careers
- Page: https://www.1752.vc/careers/jobs/headway-senior-engineering-manager-infrastructure-2/

## About the role

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, and incident response, while hiring and growing a high-performance team shipping at AI-accelerated velocity. Found on 1752vc Careers, the job board for startup and VC roles.

## What they're looking for

- 5-7+ years of experience 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
- You've personally led the shift from "infra team owns everything" to a self-serve platform other engineers build on themselves — not just inherited or operated a system where that transition had already happened
- Experience managing the interface between a platform team and the product engineering teams that depend on it, including setting ownership boundaries and building self-serve tooling
- Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once
- Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement

Tags: All Cost Centers

Source: 1752vc Careers, https://www.1752.vc/careers/jobs/headway-senior-engineering-manager-infrastructure-2/