Product Manager, Agent Development - Flagship Deployment

Sierra•San Francisco, CA

11d•$180,000 - $390,000•Onsite

About The Position

This role is dedicated to one of Sierra's largest and most strategic customers — a company running AI agents at massive scale across millions of customer interactions. You'll be the product owner embedded within a dedicated team, responsible for the full quality and evolution of production AI agents across chat and beyond. Own the agent, end to end. You own what the agent does (workflows, decisions, escalation logic), how it works (architecture, data flows, APIs, integrations), and how it feels to users (clarity, trust, edge cases, failures at scale). It takes equal parts product sense, technical depth, and taste. Drive quality and outcomes. You're not done when the agent ships. You own the customer experience end to end — running evaluations, digging into failures, identifying the highest leverage experience improvements, and working with engineers to ship them. You define what "great" looks like and hold the bar. Push the platform forward. The bar on a flagship account is as high as it gets — huge volume, complex workflows, and demanding quality and performance requirements. It’s also one of the best places at Sierra to do 0→1 platform work — hard problems regularly drive new platform capabilities, and you'll partner closely with our Platform team to build them. Navigate enterprise complexity. At this scale, every big technical discussion is also a negotiation — you'll need to read the implications in real time, hold your ground, and steer toward the right outcome. Expect to work across business units, procurement, compliance, and senior execs. Invent what’s next. Beyond making today's agent great, you'll imagine experiences the customer hasn't asked for yet — then partner with their teams to scope, design, and ship them.

Requirements

5–8+ years of experience building highly technical products, with at least 2–3 years as a Senior PM or above (or equivalent demonstrated scope and ownership).
Engineering background or equivalent technical depth — ability to review architecture, reason about API design, and participate in technical discussions.
Shipped and owned production-grade systems at scale, with experience in reliability, observability, and handling hard tradeoffs in complex systems.
Track record of operating as a trusted technical partner to enterprise customers, managing ambiguity and competing priorities, influencing without authority, and knowing when to push back.
High quality bar and quick to learn — attention to detail and ability to pick up unfamiliar tools and domains quickly.
Exceptional communication skills — ability to explain complex decisions to both engineers and VPs.

Nice To Haves

Experience with language models and production AI agents, understanding their functionality and underlying mechanisms.
Familiarity with retail or consumer business operations (order management, CX workflows, fulfillment, subscriptions, or commerce infrastructure).
Experience as a builder (side projects, open source, startup attempts, or production code in TypeScript, Go, Python, or similar).
Experience working in a dedicated, embedded model with a named enterprise account.
MBA or equivalent business breadth, with experience shaping account strategy, commercial conversations, and product development.

Responsibilities

Own the agent, end to end (workflows, decisions, escalation logic, architecture, data flows, APIs, integrations, user experience).
Drive quality and outcomes by running evaluations, analyzing failures, identifying improvements, and working with engineers to implement them.
Push the platform forward by identifying and driving new platform capabilities based on the needs of a flagship account.
Navigate enterprise complexity by working across business units, procurement, compliance, and senior executives.
Invent and ship new experiences that the customer has not yet requested.