Technical Program Manager, Enterprise Cloud Deployments

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.

Responsibilities

Own the end-to-end program plan for a customer's in-VPC (Bring Your Own Cloud, BYOC) deployment, translating customer requirements into a deployment plan with workstreams, owners, milestones, and dependencies; Keep customer teams (platform engineering, cloud provisioning, security, networking, model access) aligned and clear blockers before the launch date; Act as the translation layer between Sierra engineers and customer teams, defining requirements such as model access, observability, and upgrade cadence; Run the operating cadence (standups, weekly status, escalations) for leadership and working groups on both sides; Partner with Sierra's Platform and Deployed Infrastructure teams to feed customer-specific learnings back into the standard deployment offering, runbooks, and tooling; Define the TPM function at Sierra by establishing playbooks, operating rhythms, and standards

Requirements

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 follow-through; A strong technical foundation from infrastructure, platform, or complex backend programs, including working through technical dependencies with engineers and understanding how networking, permissions, and provisioning affect delivery; Technical curiosity: learning new systems quickly, asking thoughtful questions, and applying what you learn; Comfort operating inside large, complex enterprise organizations (change management, security reviews, ownership spread across many teams); Clear, structured communication with engineers and leaders; Degree in Computer Science, Engineering, or a related field, or equivalent professional experience

Nice to have

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

Benefits

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, snacks and coffee; Discretionary benefit stipend; Free alphorn lessons; Eligible full-time employees can participate in Sierra's equity plans