System Administrator, Boston at WHOOP in Boston, MA

Summary: WHOOP is on a mission to unlock human performance, empowering members to perform at a higher level through a deeper understanding of their bodies and daily lives. They are seeking a System Administrator to join their technical IT organization, responsible for executing against the IT roadmap and improving employee experience through automation and self-service capabilities. Responsibilities: - Configure systems, implement new features, and troubleshoot issues across our IT environment - Provide expert management of third-party applications we rely on - Harden our 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 HelpDesk automation - 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 - Assist our IT Support team with escalations, coaching, and mentorship Required Qualifications: - Proven experience working on innovative systems and processes from the ground up - Programming skills to enable automation and custom solutions - Hands-on administration experience with cloud infrastructure (AWS/GCP) - Strong knowledge of Mac & Windows operating systems, identity management, and corporate security best practices - Experience managing large fleets of corporate computing devices - Experience working on large-scale implementations and/or migrations of critical IT systems - Experience working on AI projects, 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 Required Skills: Cloud infrastructure (AWS/GCP), Programming skills for automation, Mac & Windows OS knowledge Important Skills: Identity management, Corporate security best practices, Large-scale IT implementations Nice-to-Have Skills: judgment in prioritization, Employee-first mindset, communication skills, work independently Benefits: Meaningful equity, Benefits, Generous equity package