Senior IT Systems Engineer

At WHOOP, we're on a mission to unlock human performance. WHOOP empowers members to perform at a higher level through a deeper understanding of their bodies and daily lives.

WHOOP is building a deeply technical IT organization and is looking to add Senior Systems Engineers. These are critical roles that will design and build the foundation for innovative, scalable IT operations. These roles will own and evolve our IT systems, processes, and infrastructure - driving progress across employee experience, identity & access management, automation & self‑service, endpoint engineering, corporate security, compliance readiness, and more.

As an early member of a small but fast‑growing team, candidates must be ready and excited to take on significant responsibility, embrace ambiguity, and help define what world‑class IT capabilities look like at WHOOP.

This role will collaborate closely with company leadership, Security functions, Risk & Compliance, IT Support, Business Systems, and more.

This is a high‑impact role with a broad scope, and we have a mountain of work to accomplish. We don’t expect superhuman results from one individual - but we do want to attract someone who is motivated by the challenge, energized to solve technical problems, and ready to make an outsized impact.

• Serve as the technical owner of a portion of our IT systems and infrastructure
• Ensure we get maximum value from the best third‑party applications
• Engineer business processes and technology to optimize employee experience and strengthen corporate security posture
• Execute against an IT roadmap and deliver results
• Eliminate root causes of IT support tickets and manual IT work through automation and process engineering
• Build automation and self‑service capabilities to remove employee friction and enhance corporate efficiency
• Contribute meaningfully in helping us build AI‑first IT operations; our aspirations stretch far beyond Help Desk agents
• Develop monitoring, observability, and reporting capabilities
• Identify and mitigate IT risks to business continuity
• Communicate proactively and clearly with employees and business partners, ensuring alignment and transparency around our plans and the trade‑offs we’re making

• Proven experience designing and building technically innovative systems and processes from the ground up
• Strong engineering and programming skills to enable automation and custom solutions
• Hands‑on administration experience with cloud infrastructure (AWS/GCP)
• Deep knowledge of Mac & Windows operating systems, identity management, and corporate security best practices
• Experience managing large fleets of corporate computing devices
• Experience leading large‑scale implementations and/or migrations of critical IT systems
• Experience developing and deploying AI solutions, ideally driving broad usage and impact in the workplace
• Excellent communication skills, with the ability to explain technical concepts to non‑technical audiences
• Strong judgment in prioritization and solution design, balancing impact and maintenance costs
• Ability to work independently and take initiative in a rapidly changing environment
• A demonstrated employee‑first mindset, actively listening and engaging with users and making their lives better

This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.

Interested in the role, but don’t meet every qualification? We encourage you to still apply! At WHOOP, we believe there is much more to a candidate than what is written on paper, and we value character as much as experience. As we continue to build a diverse and inclusive environment, we encourage anyone who is interested in this role to apply.

WHOOP is an Equal Opportunity Employer and participates in E‑verify to determine employment eligibility.

The WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.

At WHOOP, we view total compensation as the combination of base salary, equity,…