Principal DevOps Engineer

Principal DevOps Engineer

Remote - United States

About the Principal DevOps Engineer at Headspace:

Our mission at Headspace is to provide every person access to lifelong mental health support. As a Principal DevOps Engineer, your leadership will be essential in helping us make the mission matter by guaranteeing a secure, reliable, and highly scalable platform for over 65 million users worldwide. You will be expected to own the outcome as you lead the charge in defining and refining our cloud strategies, driving technical excellence, and ensuring our infrastructure is efficient and poised for growth. We embrace the principle of iterate to great; you will continuously leverage cutting-edge technologies to simplify and optimize our cloud solutions, accelerating our ability to deliver innovative features and a better experience for our members. Join us and use your expertise to build a world where we can all care for our minds.

You will support our efforts to bring innovative features to life, leverage cutting-edge technologies, and ensure our platform's reliability and scalability for over 65 million users. A big goal needs talented leadership, so come join us and give your career a sense of purpose!

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

What you will bring:

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 directly

Preferred Skills:

• Experience with healthcare

Location: This role is open to candidates across the US. Candidates must permanently reside in the US full-time.

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $162,000-$225,000 + equity + benefits.

For candidates based in San Francisco, New York City, or Seattle, a separate salary range of $[premium min to premium mid] applies, consistent with our location-based compensation philosophy.

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate's location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training. Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We're proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process.

About Headspace:

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that's effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren't just what we believe, they're how we work, grow, and make an impact together. We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They're our shared commitment to building a more connected, human-centered team—one that's redefining how mental health care supports people today and for generations to come.

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

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

Headspace participates in the E-Verify Program.

Privacy Statement:

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails