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Sierra is the leading platform for customer-facing AI agents, serving major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company was founded by Bret Taylor (former co-CEO of Salesforce, CTO of Facebook, Google Maps co-creator) and Clay Bavor (18 years at Google, led Google Labs and Project Starline).
As an Agent Strategist on a Flagship Deployment, you will lead end-to-end deployments for Sierra's largest and most strategic customers. You own how Sierra's AI agents come to life, managing scaled deployments and new proofs of concept within the same account. You sit at the intersection of product, agent building, and customer-facing work, staying close to both the technology and the people you build for.
Key responsibilities include:
- Own the Agent Development Life Cycle: take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production. Translate business goals into agents that outperform and tune relentlessly until optimal in the real world.
- Serve as trusted strategic advisor to enterprise leaders, sitting shoulder-to-shoulder with customer executives to understand what success means to their business and shape AI strategy accordingly.
- Partner with customer working teams and executives day-to-day, overseeing overall program management while ensuring ongoing executive alignment on long-term roadmap.
- Navigate enterprise complexity with cross-functional teams (engineering and product). Every big technical discussion is also a negotiation — you'll read implications in real time, hold your ground, and steer toward the right outcome. Work across business units, procurement, compliance, and senior executives.
- Directly impact product by surfacing unmet needs from customer work and feeding them back to research and platform to shape Sierra's direction.
- Manage internal resourcing requirements to ensure your deployment is appropriately resourced today and into the future.
- Drive financial success for both customer and Sierra: optimize value exchange, drive revenue upside for Sierra, and manage cost to serve, improving margins.
- Partner with Sales on commercial strategy, identifying opportunities, aligning resources, and closing new business within the deployment.
Recent example projects include: planning and executing on-site business reviews at Fortune 100 companies with Sierra cofounders; managing portfolios of agents across customer deployments as they scale nationally; building relationships throughout customer organizations to unlock high trust and new ARR; standing up agents for commerce customers that troubleshoot devices end-to-end and personalize recommendations; partnering with product on net-new capabilities using live customers as design partners; and defining evaluation and quality bars for new agents to drive measurable outcome lifts week over week.
REQUIREMENTS:
- 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 account. You know what it means to be accountable for a relationship at that depth.
- 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 design discussions.
- Ownership and delivery: track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
PREFERRED QUALIFICATIONS:
- Experience running a company, business unit, forward deployed team, or comparable general management of business initiatives requiring technical aptitude, strategic leadership, operational excellence, and financial outcome accountability.
- Experience building or deploying AI/LLM agents in production — hands-on with tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
- 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.
