IT Operations Lead

Sierra • San Francisco, CA

2d

About The Position

At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, France, Singapore, and Japan. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

Requirements

• Proven experience leading IT support or helpdesk teams in a fast-scaling, multi-office environment.
• Strong troubleshooting skills across macOS endpoints, hardware, SaaS, and fundamentals like networking, printers, and AV.
• Practical ITSM expertise—configuring ticket queues, workflows, SLAs, and built-in automations to streamline service delivery.
• Deep customer empathy with clear communication and documentation habits that build trust across technical and non-technical audiences.
• Experience managing MSPs or vendor partners and driving accountability through clear metrics and reviews.
• Bachelor’s degree or equivalent professional experience in Information Technology, Computer Science, or a related field.

Nice To Haves

• Certifications or equivalent experience (e.g., ITIL Foundations, Jamf, Okta).
• Background in scaling global IT support or building distributed coverage models.
• Experience developing support playbooks, KCS knowledge programs, or IT onboarding improvements in a fast-growth environment.

Responsibilities

• Lead global end-user support operations, providing a consistent, high-quality employee experience across offices and remote teams.
• Serve as a player-coach—working tickets directly while mentoring others, refining processes, and building scalable support routines.
• Partner with GRC, security, and engineering teams to align on device, identity, and SaaS management standards.
• Oversee onboarding and device offboarding, ensuring timely laptop retrievals, Jamf wipes/reassignments, and accurate asset records.
• Manage vendor and MSP relationships with clear SLOs, documentation, and service reviews to extend coverage globally.
• Use a concise scorecard (CSAT, response/resolution SLOs, backlog health, and knowledge quality) to guide coaching and continuous improvement.
• Build workflows and leverage automation and AI agents to optimize ITSM.

Benefits

• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Life Insurance and Disability Benefits
• Retirement Plan (e.g. 401K, pension) with Sierra match
• Parental Leave
• Fertility and family building benefits through Carrot
• Lunch, as well as delicious snacks and coffee to keep you energized
• Discretionary Benefit Stipend giving people the ability to spend where it matters most
• Free alphorn lessons

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 251-500 employees