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 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.

What you'll do

As Sierra’s founding Infrastructure Technical Program Manager, 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 takes customers from deployment planning to agents live in production, and continue to support the upgrades and expansion that follow.

• 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.
• Drive execution across many customer teams (platform engineering, cloud provisioning, security, networking, model access, observability) and build alignment across customer teams, establish clear commitments, and find creative ways to resolve blockers and keep deployments moving.
• 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 for the deployment (standups, weekly status, escalations) so leadership on both sides always knows what's blocked, who owns it, and what it means for the launch date.
• 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.
• Technical curiosity and slope: ability to learn new systems quickly, ask thoughtful questions, build context, and apply learnings.
• Comfort operating inside large, complex enterprise organizations (change management, security reviews, ownership spread across many teams) with persistence and resourcefulness.
• Clear, structured communication: make complex technical topics, program status, and decisions understandable to engineers and leaders.
• 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.