headway - Senior Engineering Manager (Infrastructure)

• We're looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results, and enable their teams to build for technical excellence. As a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Security, and product engineering teams across the org to help shape the future of the engineering organization. • You are an infrastructure leader who is as comfortable in a postmortem as you are in a planning doc. You know how to run a team that carries a support queue while still making progress on strategic platform work. You hold the technical bar yourself and earn credibility with the team through the quality of your judgment, not your title. • 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. • You're personally hands-on with AI coding tools day to day — not just driving your team's AI adoption as a program. Every candidate goes through a hands-on AI coding interview as part of this loop • Experience owning a platform strategy and representing it to senior leadership: setting measurable goals for infrastructure work, and making the case for foundational investment in terms the business understands • Below are additional experiences we think help engineering managers succeed at Headway: • You have led a team through a significant architectural transition, such as moving from a monolith toward service isolation, or from manual to automated operations • You have experience building or governing LLM infrastructure and AI platform primitives • You have experience in healthcare or another regulated environment • We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. • Headway participates in E-Verify. To learn more, click here. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf • A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com http://findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.