Headspace
Principal DevOps Engineer
Remote Principal DevOps Engineer role with clear candidate location fit.
PostedJun 7, 2026
Eligible countries1 accepted country
Seniority signalSenior
Work settingRemote
Accepted candidate locations
USA
Role overview
Principal DevOps Engineer
Requirements and responsibilities
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What you will do:
- Define the long-term technical vision for our cloud platform, advising leadership on architectural strategy, investment priorities, and systemic risk
- Set organizational standards for cloud reliability, observability, and operational excellence, including SLO/SLI frameworks, incident management practices, and the platform tooling that underpins them
- Serve as the senior solutions engineering authority for partner teams: translating cross-functional requirements into platform strategy and driving prioritization of developer experience investments
- Own the developer experience roadmap, identifying and closing systemic gaps in self-service infrastructure, CI/CD workflows, and operational visibility across engineering
- Proactively surface systemic risks in our AWS infrastructure, IaC practices, and delivery pipelines, and drive organizational action before issues become incidents
- Translate complex infrastructure risk and platform strategy into clear, business-aligned narratives for Director-level and executive stakeholders to drive resourcing and prioritization decisions
- Mentor Staff (T4) and Senior (T3) engineers and model the culture of engineering rigor, documentation, and cross-functional accountability expected across the organization
Required Skills:
- Bachelor’s Degree in Computer Science, Engineering, or equivalent
- 8+ years of cloud platform or infrastructure engineering experience with demonstrated org-level technical impact
- Expert AWS knowledge across compute (EC2, ECS, Lambda), networking (VPCs, Transit Gateway, Route 53, CloudFront), data (RDS, S3), and security (IAM, Secrets Manager, Systems Manager), with a track record of high-stakes architectural decisions
- Deep expertise in cloud reliability and operational excellence: SLO/SLI design, centralized observability, alerting strategy, and incident lifecycle management at production scale
- Expert-level Terraform and IaC platform leadership: organizational module strategy, policy-as-code, and self-service provisioning standards that scale across teams with varying infrastructure maturity
- Proven solutions engineering partner and developer experience advocate: working across teams to discover needs, set priorities, and ship platform capabilities that reduce toil and improve engineering velocity
- Executive-level communicator: able to translate infrastructure risk and platform strategy into business-aligned narratives for Director and VP audiences, and drive alignment without formal authority
- Track record of mentoring Staff and Senior engineers, setting org-wide engineering standards, and building a culture of technical accountability and documentation rigor
- Ability to translate business goals and organizational risk into multi-year platform roadmaps, sequencing initiatives by strategic impact and building the case for long-horizon technical investment
- Experience setting CI/CD governance models and delivery philosophy at an organizational level, defining the standards and self-service patterns that teams build on, not owning pipeline implementation directl
Preferred Skills:
- Experience with healthcare
Why You’ll Love Working Here:
- A mission that matters—with impact you can see and feel
- A culture that’s collaborative, inclusive, and grounded in our values
- The chance to shape what mental health care looks like next
- Competitive pay and benefits that support your whole self
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