Opportunities from Sierra (ashby)

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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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 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. WHAT YOU'LL BRING
• 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 — you can review architecture, reason about API design, and hold your own in a technical discussion without needing an engineer to translate.
• You've shipped and owned production-grade systems at scale, with the reliability, observability, and hard tradeoffs that come with complex systems.
• A 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.
• A high quality bar and quick to learn — you sweat the details others let slide, and pick up unfamiliar tools and domains fast.
• Exceptional communication: you can explain a complex integration decision to an engineer, then explain the same decision to a VP. EVEN BETTER...
• You've worked with language models and production AI agents, and understand not just what they do but also how they work under the hood.
• You are familiar with retail or consumer business operations — order management, CX workflows, fulfillment, subscriptions, or commerce infrastructure.
• You're a builder — side projects, open source, a startup attempt, or real production code (TypeScript, Go, Python, or similar) and enjoy getting your hands dirty.
• Experience working in a dedicated, embedded model with a named enterprise account — you know what it means to be accountable for a relationship at that depth.
• MBA or equivalent business breadth — this is a product role, but you'll shape account strategy, commercial conversations, and what Sierra builds next. 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.