Agent Development Strategist - Flagship

Salary: $211,000 - 251,000 per year Requirements:

• We want someone with 10+ years of relevant experience delivering results in high-stakes enterprise customer-facing roles, ideally in a dedicated embedded model with a named enterprise account.
• We value a genuine customer-first mindset and strong motivation to work directly with customers, understand their business, and build trusted relationships.
• We look for clear, direct, and persuasive communication across both technical and non-technical audiences.
• We need strong analytical and critical-thinking ability to solve complex problems, identify risks early, and adapt quickly in ambiguous situations.
• We expect comfort working with technical concepts, including API documentation, data models, system architecture, and engineering tradeoffs.
• We want a track record of owning and delivering multiple complex, high-visibility projects at the same time.
• It is even better if you have led a company, business unit, forward-deployed team, or comparable general-management initiatives with technical, strategic, operational, and financial accountability.
• It is a plus if you have built or deployed AI/LLM agents in production and worked hands-on with eval frameworks, agent tooling, RAG, and prompt engineering.
• It is also a plus if you hold a degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience, and/or an MBA or similar experience at the intersection of technology and business.

• We own the end-to-end Agent Development Life Cycle, from initial scoping through conversation design, tooling, evaluation, launch, and continuous production iteration.
• We translate business goals into agents that outperform and continuously refine them to achieve the best possible real-world results.
• We act as trusted strategic advisors to enterprise leaders, understanding what success means for their business and helping shape the AI strategy to get there.
• We partner day to day with customer working teams and executives, managing the overall program and maintaining alignment on the long-term roadmap.
• We navigate enterprise complexity by working closely with engineering, product, business units, procurement, compliance, and senior executives.
• We surface unmet customer needs and feed them back to research and platform teams to influence the product direction.
• We manage internal resourcing so the deployment is properly supported now and in the future.
• We drive financial success for both the customer and Sierra by optimizing value exchange, supporting revenue growth, and reducing cost to serve over time.
• We partner with Sales on commercial strategy and help close new business opportunities within the deployment by identifying opportunities and aligning resources.

• AI
• AI Agents
• API
• Embedded
• Support
• LLM
• RAG
• CTO
• Salesforce
• VR

More:

We are Sierra, the leading platform for customer-facing AI agents, and we work with many of the worlds biggest brands, including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank, to transform customer service and business growth. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. Our culture is shaped by our values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family. We were founded by Bret Taylor and Clay Bavor, and we offer a full-time benefits package that includes flexible unlimited PTO, medical, dental, and vision coverage, life and disability insurance, a retirement plan depending on country, parental leave, fertility and family-building support through Carrot, lunch, snacks, coffee, a discretionary benefit stipend, and free alphorn lessons. We also offer equity participation for eligible full-time employees, subject to plan terms and policies.

last updated 39 week of 2026