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Headway

Senior Engineering Manager – Infrastructure

Headway

. Lead the Infrastructure team within Engineering Foundations .

Posted 10/17/2026full-timeRemote • United StatesSenior💰 $265,200 - $331,500 per yearWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates expertise in leading infrastructure teams, managing cloud infrastructure, and driving architectural transitions while ensuring reliability and scalability of platforms. Proficient in developing engineers and collaborating with cross-functional teams to enhance platform accessibility and performance.

Highest-signal resume keywords
Engineering Leadership ExperienceAWS Infrastructure FamiliarityAI Coding Tools ExperienceDeployment Pipeline ManagementObservability Tooling Familiarity

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Infrastructure ManagementPlatform Strategy OwnershipArchitectural Transition LeadershipIncident Response ManagementProduction-Readiness DefinitionLLM Infrastructure GovernanceSelf-Serve Platform DevelopmentDatabase Platform ManagementCloud Infrastructure OwnershipOn-Call Rotation Management
Soft Skills
Team DevelopmentStrategic Vision SettingCollaboration with Engineering Leadership
Tools & Technologies
AWSDatadogFastAPIPython
Industry Keywords
HealthcareRegulated Environment

Tech Stack

Tools & technologies
AWSCloudPython

About the role

Key responsibilities & impact
  • Lead the Infrastructure team within Engineering Foundations
  • Own cloud infrastructure, deployment pipelines, LLM infrastructure, database platform, observability, and incident response
  • Hire and develop engineers through senior and staff levels
  • Run an effective on-call rotation
  • Set team strategy and vision
  • Own the reliability, performance, and scalability of Mamba, Headway’s FastAPI/Python monolith, and its AWS infrastructure
  • Drive the transition toward self-serve infrastructure and strategic platform work
  • Lead architectural and deployment validation to reduce incident blast radius
  • 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
  • Report to the Head of Engineering Foundations
  • Collaborate with Engineering Leadership, Security, and product engineering teams

Requirements

What you’ll need
  • 5–7+ years of engineering leadership experience, including experience leading infrastructure or platform teams
  • 5+ years of experience as a Software or Infrastructure Engineer
  • Experience leading the shift from an infrastructure-owned-everything model to a self-serve platform
  • Experience managing the interface between platform and product engineering teams, including ownership boundaries and self-serve tooling
  • Ability to manage support queues, strategic roadmaps, on-call rotations, and external dependencies
  • Familiarity with AWS infrastructure at scale
  • Familiarity with Datadog or similar observability tooling
  • Familiarity with deployment pipelines at companies where reliability is a product requirement
  • Hands-on daily experience with AI coding tools
  • Successful completion of a hands-on AI coding interview
  • Experience owning platform strategy and presenting it to senior leadership
  • Experience leading significant architectural transitions
  • Experience building or governing LLM infrastructure and AI platform primitives
  • Experience in healthcare or another regulated environment is helpful

Benefits

Comp & perks
  • Robust health and wellness benefits
  • Retirement savings
  • Meaningful ownership opportunities through equity
  • Reasonable accommodations for persons with disabilities