IT Operations Lead

About Us

• 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.
  
  

What You’ll Do

• 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.
  
  

What You’ll Bring

• 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.
  
  

Even better…

• 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.
  
  

Our values

• Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
• Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
• Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
• Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
• Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
  
  

What We Offer

We want our benefits to reflect our values and offer the following to full-time employees:

• 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
  
  

These benefits are further detailed in Sierra's policies and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

Be you, with us

We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.