Technical Program Manager, Enterprise Cloud Deployments

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. 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 As Sierra’s founding Technical Program Manager for Enterprise Cloud Deployments, you’ll help define how we bring our AI platform into the cloud environments of some of the world’s largest and most regulated enterprises. Working alongside Agent Engineers, Deployed Infrastructure Engineers, and Agent Strategists, you’ll own the programs & strategy that take customers from deployment planning to agents live in production, and continue to support the upgrades and expansion that follow. You’ll bring your technical program management expertise to enterprise AI while establishing the playbooks and ways of working that help this new function scale.

• Own the end-to-end program plan for a customer's in-VPC (Bring Your Own Cloud, BYOC) deployment. Translate customer requirements into a clear deployment plan, with clear workstreams, owners, milestones, and dependencies across Sierra and customer teams.

• Keep the customer's teams (platform engineering, cloud provisioning, security, networking, model access) aligned and moving, and clear blockers before they hit the launch date.

• Be the translation layer between our engineers and the customer's: define requirements such as model access, observability, and upgrade cadence, and turn technical discussions into actionable next steps.

• Run the operating cadence (standups, weekly status, escalations) so leadership and working groups on both sides always know where the project stands.

• Partner with Sierra's Platform and Deployed Infrastructure teams to feed customer-specific learnings back into our standard deployment offering, runbooks, and tooling, making each subsequent launch more predictable and repeatable.

• Define the TPM function at Sierra as we scale & establish the playbooks, operating rhythms, and standards that future TPMs and customer teams will build on.

WHAT YOU'LL BRING

• 4+ years in technical program management, infrastructure or platform program management, deployment or solutions engineering, or a similar role where you were accountable for delivering complex technical projects across multiple teams.

• A track record of bringing structure to complex technical programs, with strong attention to detail and the follow-through to turn plans into results.

• A strong technical foundation from infrastructure, platform, or complex backend programs. You can work through technical dependencies with engineers, understand how requirements such as networking, permissions, and provisioning affect delivery, and translate those discussions into a clear plan. You’ll deepen your knowledge of Sierra’s architecture and customer deployment environments as you ramp.

• Technical curiosity: you learn new systems quickly, ask thoughtful questions, build context, and apply what you learn to move programs forward.

• Comfort operating inside large, complex enterprise organizations (change management, security reviews, ownership spread across many teams) with the persistence and resourcefulness to keep teams aligned and deployments moving.

• Clear, structured communication: you make complex technical topics, program status, and decisions understandable to engineers and leaders, and adapt your approach to your audience.

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

EVEN BETTER…

• Hands-on engineering background (software, DevOps, SRE, or infrastructure) before moving into program or product management, or direct experience with AWS, VPCs, IAM, Kubernetes, or Terraform.

• Experience deploying software into customer-owned cloud environments (BYOC, VPC, or air-gapped), especially at banks or other regulated institutions.

• Familiarity with LLM infrastructure: model gateways, Bedrock or Azure OpenAI, observability for AI systems.

• Experience at an early-stage company where you built the program-management function from scratch.

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 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, may vary by region, 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.