Strategist, Agent Development - Flagship Deployment

Sierra · San Francisco, CA; New York, NY

  • Senior
  • Full-time
  • $200,000 – $290,000
  • Posted 2026-09-18
  • Confirmed live on 25 September 2026

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Job description

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.

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.

WHAT YOU’LL DO

As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai on a Flagship Deployment, you’ll lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You own how Sierra's AI agents come to life, often managing scaled deployments as well as new proofs of concept within the same account. 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 and executives day to day. Oversee overall program management while ensuring ongoing executive alignment on the long term roadmap.

- Navigate enterprise complexity with cross-functional teams (engineering and product). At this scale, every big technical discussion is also a negotiation — you'll need to read the implications in real time, hold your ground, and steer toward the right outcome. Expect to work across business units, procurement, compliance, and senior execs.

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

- Manage internal resourcing requirements. Ensure that your deployment is appropriately resourced today and into the future

- Drive financial success for both the customer and Sierra. Ensure value exchange is optimized, drive revenue upside for Sierra, and work internally to manage down cost to serve over time, improving margins.

- Partner with Sales on commercial strategy. You are a key player in closing new business within the deployment by identifying opportunities, aligning resources, and

EXAMPLE PROJECTS

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

- Plan, organize, and execute on-site business reviews onsite at a Fortune 100 company with Sierra cofounders in attendance

- Manage a portfolio of agents across a customer deployment as they scale nationally, to new use cases, and grow in technical complexity

- Build relationships throughout the customer’s organization, unlocking high trust, social capital, and ultimately new ARR

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

- 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 https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.

WHAT YOU’LL BRING

- Proven track record: 10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role, ideally in a dedicated, embedded model with a named enterprise a

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