IT Support Specialist

About this role

ABOUT US

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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

As an IT Support Specialist in New York, you'll be the hands-on, on-the-ground owner of day-to-day IT for one of our fastest-growing offices. You'll be the first person teammates turn to when something isn't working, and the person who makes sure hardware, conference rooms, and the office network simply work. This is a role for someone who thrives in execution mode and enjoys solving problems quickly and efficiently. Your responsibilities will include:

- IT Support: Serve as the first line of defense for employee IT issues in New York, with deep focus on macOS troubleshooting, application support, and network connectivity.

- Global Support Queue: Share responsibility for Sierra's global IT helpdesk queue during your regional working hours: triage new requests, resolve issues across offices, keep ownership clear, coordinate escalation, and provide clean cross-time-zone handoffs.

- Technical User Support: Support engineers and other highly technical teammates with curiosity and confidence, using logs, command-line tools, and clear written communication when appropriate.

- AI-Assisted Troubleshooting: Use approved AI tools thoughtfully to accelerate research, hypothesis generation, and documentation while protecting sensitive data and independently validating consequential recommendations.

- Hardware Management: Own the full device lifecycle locally—procurement, deployment, inventory tracking, loaner pool oversight, and device re-provisioning for offboarded users.

- AV & Conference Rooms: Keep every room meeting-ready. Maintain and troubleshoot conference room AV, proactively test rooms, and own the peripheral and accessory inventory.

- Office Build-Out & Moves: Partner with Facilities, our project managers, and AV integrators to spec, stage, and commission IT and AV for our new New York space, and support the move from our current location.

- Network & Vendor Coordination: Triage office network and connectivity issues, then drive them to resolution with our ISP, network, and building vendors.

- IT Onboarding: Set up laptops and essential software for new hires, delivering a seamless first-day experience.

- SaaS Administration: Handle routine administration in Okta, Google Workspace, and other core applications, including users and groups, app assignments, access changes, licensing, and basic audit-log review.

- IT Projects: Take on well-scoped endpoint, SaaS, access, inventory, or workplace technology projects with clear success criteria, appropriate review, testing, documentation, and rollback planning.

- Process Improvement: Look beyond the immediate ticket, respectfully challenge inefficient or fragile practices, propose practical improvements, and help implement and document better ways of working.

- IT Logistics: Support software installs, device shipments to East Coast teammates, repair and warranty coordination, and proactive hardware refresh planning.

WHAT YOU’LL BRING

- Experience: 2-5 years in hands-on IT support or systems administration, with strong macOS experience in a fast-paced or startup environment.

- Technical Proficiency: Comfort with endpoint management and MDM systems (e.g., Jamf), identity tooling (e.g., Okta), and troubleshooting across Mac hardware and software.

- SaaS Foundations: Hands-on experience with basic Okta, Google Workspace, or comparable SaaS administration and a desire to grow into broader systems ownership.

- Engineering Environment: Experience supporting engineers or other highly technical users, or clear evidence that you can communicate credibly, work from technical evidence, and learn unfamiliar systems quickly.

- Troubleshooting Judgment: A structured, hypothesis-driven approach; strong follow-through; and the judgment to recognize uncertainty, seek review, or escalate before a risky change.

- Queue Ownership: Able to manage competing requests in a shared global queue, communicate priorities, maintain accurate status, and carry issues through resolution or a clear handoff.

- Continuous Improvement: Curious about why work is done a certain way and comfortable constructively challenging the status quo with specific, practical recommendations.

- AV & Network Fluency: Practical troubleshooting of conference room AV and office networking fundamentals—Wi-Fi, DHCP, VLANs—and the judgment to know when to escalate to a vendor.

- Organization: Highly organized with a systems-oriented mindset—able to track devices, accessories, and inventory accurately across multiple offices.

- Execution Focused: Bias for action and the ability to troubleshoot, solve problems, and follow through without constant direction, while knowing when to seek review or escalate.

- Communicat

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