Strategist, Agent Development - Travel, Transportation and Hospitality

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.

Sierra was co-founded by Bret Taylor and Clay Bavor who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs.

About the Travel, Transportation and Hospitality team

• The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are pioneers in the travel space and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us not only to deliver exceptional customer experiences, but also to drive meaningful growth for their businesses.

• Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint.

• We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard for what it means to go beyond your role, and help build the travel industry of the future.

What you’ll do

As an Agent Strategist , 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 . 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:

• Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.

• Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.

• Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.

• Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.

• Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.

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.

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 technical counterparts.

• You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.

• A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.

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

• Lunch, as well as delicious snacks and coffee to keep you energized when working onsite

• 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description.

Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at View email address on jobs.ashbyhq.com. Requests are handled confidentially and do not affect your candidacy.

We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.