IT Support Specialist

About us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. 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 a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Sierra was co-founded by Bret Taylor and Clay Bavor who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs.

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.

• Communication: Friendly, clear communicator who can help teammates quickly and patiently—whether they're in-office or remote.

• Work model: This role is based in our New York office, with in-office work Monday through Thursday and remote work on Fridays.

Even better…

• Experience supporting an office build-out, relocation, or new-site commissioning from the IT and AV side.

• Familiarity with Zoom Rooms and hardware such as Neat, Logitech, or Poly.

• Past experience with Apple Business Manager or zero-touch deployment tools.

• Passion for documentation, process improvement, and enabling others to solve simple issues themselves.

• Change-Control Exposure: Familiarity with version control, peer review, staged rollout, rollback planning, infrastructure or configuration as code, or other disciplined change practices.

• Automation: Experience using APIs, scripts, Terraform, or similar tools to make routine administration safer and more repeatable.

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 dependent on country of employment

• Parental leave

• Fertility and family building benefits

• Lunch, as well as delicious snacks and coffee to keep you energized when working onsite

• 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, may vary by region and employment type, 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 through the link on this page even if your experience doesn't precisely match the job description.

Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy.

We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.