Strategist, Agent Development - Flagship Deployment
About this role
The team builds a leading platform for customer-facing AI agents, transforming how major global brands serve customers and grow their businesses. This strategist role leads end-to-end deployments for large and strategic enterprise accounts, sitting at the intersection of product development, agent building, and direct customer engagement. Responsibilities include managing the agent development life cycle, advising enterprise leaders, and collaborating closely with engineering and product groups to translate complex business problems into high-performing AI solutions. Ideal candidates possess strong technical aptitude combined with deep customer empathy, comfortable navigating enterprise complexity while driving measurable business value and financial success.
What you will do
- Lead the end-to-end deployment lifecycle for large enterprise customers, taking AI agents from initial scope and conversation design through to production launch and continuous iteration.
- Serve as a trusted strategic advisor to enterprise leaders, understanding their business goals and shaping the AI strategy required to achieve them.
- Manage cross-functional teams across engineering, product, procurement, and compliance to steer technical discussions and resolve enterprise complexity.
- Directly impact product development by surfacing unmet customer needs and feeding insights back to research and platform teams.
- Oversee internal resourcing requirements and drive financial success by optimizing value exchange and managing costs over time.
- Partner with the sales team on commercial strategy to identify opportunities, align resources, and close new business within deployments.
What you need
- Bring 10 or more years of relevant experience driving results in high-stakes situations within an enterprise customer-facing role.
- Demonstrate a genuine energy for being in front of customers, understanding their needs, and building trusted relationships.
- Communicate clearly, directly, and persuasively across both technical and non-technical audiences.
- Apply strong analytical and critical-thinking skills to solve strategic problems in ambiguous environments.
- Engage comfortably with technical concepts such as API documentation, data models, system architecture, and engineering tradeoffs.
- Maintain a track record of running multiple complex, high-visibility projects simultaneously and driving them to successful outcomes.
Nice to have
- Experience running a company, business unit, or forward deployed team with general management accountability.
- Hands-on experience building or deploying AI and LLM agents in production using eval frameworks, agent tooling, RAG, and prompt engineering.
- A degree in Computer Science, Engineering, Mathematics, a related technical field, or an MBA.
Benefits
- Offers Equity
Skills and tech stack
Questions candidates ask
What is the work location policy for this role?
Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
What is the compensation range for this position?
The salary ranges from $200K to $290K with offers of equity included.
What kind of customers will this strategist work with?
The strategist leads deployments for some of the world's biggest brands and Fortune 100 companies, including organizations like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank.