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Salary
$230k – $390k per year
Location
In office (San Francisco)
Seniority
Middle · 3+ years exp
Employment
Full-Time
Overview
Company
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Profile match
Sierra, formerly known as Sierra Trading Post, is a major American off-price retailer operated by The TJX Companies. The company offers a wide selection of discounted activewear, outdoor recreation gear, footwear, apparel, and home goods from top name brands.

About us

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 Family. 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.

About the role

We’re looking for a Product Manager for Ghostwriter: the agent-building agent.

Ghostwriter transforms how software is built. Instead of navigating tools, users simply describe what they want, and Ghostwriter creates and deploys fully functional AI agents across channels like chat, voice, and email.

As PM for Ghostwriter, you will define how humans interact with software in the agent era. You’ll own the end-to-end product experience-from prompt → agent → outcome-and help scale Sierra to thousands of customers.

This is a zero-to-one and one-to-many role at the same time.

What you'll do

  • Define how AI augments agent development - shape the workflows by which CX teams and developers draft journeys, run simulations, analyze conversations, and improve agents using natural language.

  • Balance autonomy and control - design the right human-in-the-loop patterns (approval flows, change review, workspace isolation) so customers trust Ghostwriter to make meaningful changes to their agents.

  • Partner deeply with AI/ML and platform engineering - collaborate on model selection, harness engineering, execution architecture, and evaluation/testing infrastructure.

  • Be the voice of the agent builder - deeply understand the pain points of CX managers, agent developers, and technical teams configuring journeys, integrations, and simulations.

What you'll bring

  • 3+ years of product management experience, with meaningful time working with large language models directly.

  • Experience shipping AI products at the frontier - you deeply understand frontier model capabilities and limitations, evaluation challenges, and the unique UX considerations of non-deterministic systems.

  • Track record of 0→1 product development - you've taken an early-stage product and driven it to broad adoption; comfortable with high ambiguity and rapid iteration.

  • Strong technical depth - ability to engage meaningfully with engineers on architecture decisions (e.g., harness design and engineering, workspace isolation, API design).

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.

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