[Remote] Principal DevOps Engineer

Note: The job is a remote job and is open to candidates in USA. Headspace is committed to providing lifelong mental health support and is seeking a Principal DevOps Engineer to lead the development of a secure and scalable platform for over 65 million users. The role involves defining cloud strategies, ensuring operational excellence, and mentoring engineering teams to enhance the developer experience.

Responsibilities

• 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

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 directly
• Experience with healthcare

Benefits

• Equity
• Benefits
• Stock awards
• Comprehensive healthcare coverage
• Monthly wellness stipend
• Retirement savings match
• Lifetime Headspace membership
• Generous parental leave

Company Overview