Strategist, Agent Development - Travel, Transportation and Hospitality

Sierra • San Francisco, CA

8d • $200,000 - $290,000 • Onsite

About The Position

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands 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. Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce 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.

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 frontiers 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 to not only deliver standout customer experiences, driving stronger growth in their business.
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 on what it means to go beyond your role, and help build the travel industry of the future.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Associate degree