W
WHOOP
Systems Engineer (Endpoint)
Skills
AI
1 month ago
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Important information
Contract type:
Permanent
Salary:
$105,000 – $145,000 / year
Location:
Boston, MA, USA
Work mode:
Onsite
Published on:
11 September 2026
What they need
- WHOOP is building a deeply technical IT organization and is looking to add a Systems Engineer focused on endpoint engineering. As WHOOP evolves from a consumer tech company into a personal health company - it is imperative 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 an early 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
- 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 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
Benefits
- Flexible Vacation: WHOOP has a flexible vacation policy that allows you to unwind, laptop-free, when you need it most.
- Focus on Family: We offer 18 weeks paid parental leave, plus an additional 2 weeks to gradually return to work.
- Get Invested: In addition to a competitive base salary and 401k, you’re eligible to receive stock options to share in the future of WHOOP.
- WHOOP +1: Everyone on the team gets a complimentary WHOOP membership—plus another membership to share with a loved one.
- Health Matters: Our competitive benefits package covers medical, dental, and vision, in addition to mental health services, life and disability insurance, and more.
- Find Your Fit: Full-time employees get $500 a year to spend on wellness in whatever way they see fit, from fitness classes and memberships, to recovery services.
- It Pays to Sleep: Our Sleep Performance Program incentivizes employees to get more sleep. Log an average sleep performance of 85% or higher for the month and get a $100 bonus.
- Location, Location, Location: You can’t beat the views from the rooftop of One Kenmore Square. Feel inspired daily as you work, enjoy free snacks and coffee, and collaborate in the heart of Boston.- A demonstrated employee-first mindset, actively listening and engaging with users and making their lives better
- Proven experience working on technically innovative systems and processes from the ground up
- Ability to work independently and take initiative in a rapidly changing environment
- 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
- Strong engineering and programming skills to enable automation and custom solutions
- Experience contributing to large-scale implementations and/or migrations of critical IT systems
- Experience managing large fleets of computers and other corporate-owned devices
- Experience developing AI solutions to improve productivity or employee experience
- Hands-on administration experience with MDMs
- 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
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