Systems Engineer II, Endpoint

• Manage our Mac and Windows fleets end-to-end
• Craft a frictionless device lifecycle from unboxing to disposition
• Implement and manage robust security policies in line with strict HIPAA standards
• Manage the endpoint components of our enterprise AI security strategy
• Manage the way we patch endpoint vulnerabilities in line with our committed SLAs
• Engineer processes to do the things above in a way that minimizes employee friction and workflow disruption
• Mentor colleagues to develop their endpoint skills & capabilities
• Eliminate root causes of IT support tickets and manual IT toil
• Contribute meaningfully in helping us build AI-first IT operations
• Develop monitoring, observability, and reporting capabilities
• Communicate proactively and clearly with employees and business partners, ensuring alignment and transparency around our plans and the trade-offs we’re making

We need this role to work across both Mac and Windows ecosystems. Applicants should have top quartile expertise in at least one ecosystem.

As a member of a growing and highly dynamic team, candidates must be ready and excited to take on significant responsibility, embrace ambiguity, and help define what world-class IT Security capabilities look like at WHOOP.

This role will collaborate closely with Security, Risk & Compliance, Software and Hardware Engineering, Business Systems, IT, and more. This is a high-impact role with a broad scope, and we have a mountain of work to accomplish. We want to attract someone who is motivated by the challenge and energized to solve tricky problems with the best tools available., * Proven experience working on 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 MDMs
• Experience managing large fleets of computers and other corporate-owned devices
• Experience contributing to large-scale implementations and/or migrations of critical IT systems
• Experience developing AI solutions to improve productivity or employee experience
• 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, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company’s long-term growth and success.

The U.S. base salary range for this full-time position is $125,000-$175,000. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job-related skills, experience, performance, and relevant education or training.

In addition to the base salary, the successful candidate will also receive benefits and a generous equity package.

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