Deployed Infrastructure Engineer

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 a Forward Deployed Infrastructure Engineer at Sierra, and a founding member of this function, you will own the end-to-end lifecycle of customer deployments, while helping define how Sierra’s AI platform is deployed and operated across enterprise environments. You'll work directly with enterprise customers to architect, deploy, upgrade, and manage Sierra's AI platform infrastructure — ensuring every deployment meets their security, compliance, and operational requirements. In addition, you’ll establish the standards, tooling, and processes that make deployments scalable and repeatable, and partner cross-functionally with Engineering, Product, Sales, and Customer Success. This role will define how Sierra scales some of its most complex customer engagements.

• Own deployment architecture conversations and execution — designing and implementing deployment strategies across customer environments, including VPC configuration, permissioning, networking, and infrastructure provisioning.

• Manage the full infrastructure lifecycle for some of Sierra’s most critical customers: initial deployment, ongoing upgrades, scaling, and incident support.

• Develop and maintain deployment runbooks, upgrade procedures, and automation tooling to make operations repeatable and reliable.

• Partner with engineering teams to ensure Sierra's platform is deployable and operable across diverse customer requirements.

• Work with customers' platform engineering, security, and DevOps teams to navigate their infrastructure constraints and compliance requirements.

• Collaborate with Sales and Customer Success to scope infrastructure requirements during pre-sales and onboarding, translating customer needs into concrete deployment plans.

What you'll bring

• 4+ years of experience in infrastructure, DevOps, platform engineering, or solutions architecture roles — with significant time spent on customer-facing deployment work.

• Deep experience with AWS services, Terraform, container orchestration, and cloud networking (VPCs, IAM, DNS, load balancing).

• Track record of managing deployments in customer-owned cloud environments, including navigating security reviews, compliance requirements, and change management processes.

• Ability to navigate ambiguity with enterprise stakeholders — from platform engineers to CISOs — and turn infrastructure conversations into actionable deployment plans.

• Strong operational instincts: you think about upgrades, rollbacks, monitoring, and failure modes from the start, not as an afterthought.

• Comfortable working in a fast-moving environment and collaborating across engineering, product, and go-to-market teams.

• Degree in Computer Science or a related field, or equivalent professional experience.

Even better…

• Hands-on experience with Go services, GraphQL APIs, or LLM infrastructure in production environments.

• Past experience at an early-stage company where you built deployment operations, playbooks, and tooling.

• Familiarity with observability and incident management in distributed systems (Prometheus, Grafana, Datadog, or similar).

• Experience with CI/CD pipeline design, deployment automation, or infrastructure self-service tooling for enterprise customers.

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 [email protected]. 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.