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Systems Engineer II, Endpoint

Job in Boston, Suffolk County, Massachusetts, 02297, USA
Listing for: WHOOP
Full Time position
Listed on 2026-10-23
Job specializations:
  • IT/Tech
    Cybersecurity, Systems Engineer, IT Support, Systems Administrator
Job Description & How to Apply Below
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.

WHOOP is building a deeply technical IT organization and is looking to add a Systems Engineer II focused on endpoint engineering. As WHOOP evolves from a consumer tech company into a personal health company, it is mission-critical to secure our fleet of endpoints while also enabling a frictionless employee experience. Doing both of those things well requires deep technical expertise, creativity, and a remarkably high bar for the quality of experience you’ll push onto your colleagues.

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 s 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.

RESPONSIBILITIES:

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 SLAsEngineer 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

QUALIFICATIONS:

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 MDMsExperience 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 environmentA 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…
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