# Senior Engineering Manager

**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** New York, NY, San Francisco, CA, Seattle, WA
**Role:** Engineering Management
**Salary:** $265k – $332k/yr
**Experience:** 8+ years
**Skills:** AWS, Datadog, FastAPI, Python, llm infrastructure, ai platforms, Cloud Infrastructure, deployment pipelines, Observability, database platforms, container security, secrets management, Incident Response, on-call operations, service isolation
**Posted:** 2026-08-13

> Leads Headway’s Infrastructure team, owning cloud infrastructure, deployment pipelines, LLM infrastructure, databases, observability, and incident response while hiring and developing a high-performing team. Requires substantial engineering management and software or infrastructure engineering experience, plus credibility in platform strategy, design reviews, and reliability operations.

## Job Description

## Responsibilities
- Lead the Infrastructure team within Engineering Foundations, partnering with Agentic Engineering and Eddy, Headway’s internal AI platform.
- Hire, develop, and retain engineers through senior and staff levels while running an effective on-call rotation.
- Own the infrastructure platform roadmap across cloud infrastructure, deployment pipelines, LLM infrastructure, the database layer, and observability.
- Drive a shift from reactive support toward self-service infrastructure and strategic platform work.
- Lead architectural and deployment validation efforts to reduce incident blast radius and duration.
- Define production-readiness expectations for AI workloads.
- Co-own container security and secrets management with the Security team.
- Make the platform accessible and understandable to product engineering teams.
- Set strategy and vision, establish measurable infrastructure goals, and communicate foundational investment needs to senior leadership.
- Maintain the reliability, performance, and scalability of Mamba, Headway’s FastAPI/Python monolith, and its AWS infrastructure.
- Participate in design reviews, incident response, and postmortems.

## Requirements
- 5–7+ years of experience as an Engineering Manager, including experience leading infrastructure or platform teams.
- 5+ years of experience as a Software or Infrastructure Engineer.
- Experience managing the interface between a platform team and dependent product engineering teams, including setting ownership boundaries and building self-service tooling.
- Ability to manage competing demands including support queues, strategic roadmaps, on-call rotations, and external dependencies.
- Familiarity with cloud infrastructure at scale, particularly AWS.
- Experience with observability tooling such as Datadog.
- Experience with deployment pipelines in environments where reliability is a product requirement.
- Experience owning platform strategy and representing it to senior leadership.

## Nice-to-haves
- Experience leading a significant architectural transition, such as moving from a monolith toward service isolation or from manual to automated operations.
- Experience building or governing LLM infrastructure and AI platform primitives.
- Experience in healthcare or another regulated environment.

## Compensation and Benefits
- Annual salary range: $265,200–$331,500.
- Headway is committed to providing reasonable accommodations for qualified individuals with disabilities.

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