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Salary
$180k – $390k per year
Location
In office (San Francisco, New York)
Seniority
Staff · 10+ years exp
Employment
Full-Time
Overview
Company
Impact
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 Financial Services team

  • Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.

  • Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.

  • Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.

What you'll do

  • Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.

  • Engage with customers: In the role, you will engage with all levels of our customers’ businesses:

    • Discover and assess their requirements.

    • Prepare and present demonstrations of Sierra’s agent.

    • Address and overcome technical challenges in the business process by working with technical counterparts.

    • Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.

    • Become trusted advisors and drive strategic technical strategies for our customers.

  • Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.

What you'll bring

  • 5-10+ years experience in product development of highly technical products.

  • Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.

  • Experience in financial services, such as banking, fintech, lending, payments, insurance, mortgages, or wealth management.

  • A track record of taking products from ambiguous customer problems through launch and meaningful scale.

  • Strong technical fluency and the ability to reason about APIs, data flows, system architecture, AI systems, integrations, and failure modes.

  • Exceptional product judgment, including the ability to balance customer needs, speed, reliability, risk, and long-term platform leverage.

  • Experience working directly with enterprise customers and communicating effectively with both executives and deeply technical teams.

  • A builder mindset: you prototype, investigate, and work hands-on rather than relying solely on process.

  • Clear, structured communication, with the ability to explain complex technical and AI concepts to diverse audiences and create alignment in fast-moving, ambiguous environments.

  • Degree in a technical or related field, or equivalent professional experience.

Even better...

  • AI-related experience (experience with product development for AI agents a plus).

  • Some coding experience with React, Typescript, and Go.

  • MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).

  • Past roles that interface with end customers to influence software development.

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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