Strategist, Agent Development - Retail

About this role

ABOUT US

At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.

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 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. 

ABOUT THE RETAIL TEAM

- Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.

- Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.

- Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.

WHAT YOU’LL DO

As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.

- Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.

- Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.

- Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.

- Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.

EXAMPLE PROJECTS

These are the kinds of projects that strategists on our team have worked on recently:

- Launch an order management agent for a national apparel brand — order lookup, cancellations, returns, and exchanges — then hill-climb containment and CSAT week over week.

- Partner with Product to build a shopping agent that plugs into a retailer’s existing search and recommendation systems to guide product discovery — turning the support channel into a revenue channel.

- Stand up an in-store support voice agent for a big-box or grocery retailer, answering the stock-check and store-info calls that largely go unanswered today and converting them into store visits and sales.

- Design a booking, payments, and outbound agent for a consumer services brand operating hundreds of locations.

- Help a marketplace handle order status and buyer–seller disputes at enormous scale.

- Launch outbound campaigns — cart recovery, win-back, churn saves, and subscription renewals — across voice and SMS.

WHAT YOU’LL BRING

- Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.

- Communication. Clear, direct, and persuasive across technical and non-technical audiences.

- Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.

- Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.

- Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.

- Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.

EVEN BETTER...

- Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with tec

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