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Sierra is a leading platform for customer-facing AI agents, working with major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is headquartered in San Francisco with offices across North America, Europe, and Asia. Co-founders include Bret Taylor (former Salesforce co-CEO, Google Maps co-creator, OpenAI Board Chair) and Clay Bavor (18-year Google veteran who led Google Labs and AR/VR initiatives).
As a Strategist in Agent Development for Financial Services, you will own the complete agent development lifecycle for Sierra's financial services customers—spanning systemically important banks, neobanks, insurers, and vertically integrated ecosystems like Rocket Companies. Your role sits at the intersection of product, technical implementation, and customer-facing strategy.
Key responsibilities:
- Own the agent development lifecycle from initial scope through conversation design, tooling, evaluation, launch, and continuous production iteration. Translate business goals into agents that measurably outperform and iterate relentlessly for real-world excellence.
- Serve as a trusted strategic advisor to enterprise leaders, sitting shoulder-to-shoulder with customer executives to understand what success means to their business and shape their AI strategy accordingly.
- Partner with customer working teams day-to-day, running working sessions, troubleshooting agents as issues arise, and making calls that keep builds on track for launch.
- Directly impact product by surfacing unmet customer needs and feeding them back to research and platform teams to shape Sierra's roadmap.
Recent example projects include: scoping and launching subscription-retention agents that outperform human agents; building commerce agents that troubleshoot devices end-to-end while personalizing recommendations; redesigning conversation flows for regulated financial services interactions; partnering with product on net-new agent architectures using live customers as design partners; and defining evaluation frameworks that drive measurable outcome improvements.
You will work with customers whose decisions impact millions of end customers and billions in economic activity, handling high-stakes moments like mortgage pre-approval decisions, fraud detection, and card replacement experiences.
REQUIREMENTS:
- Customer obsession with genuine energy for being in front of customers, understanding their business, thriving in complex organizations, and building trusted relationships.
- Clear, direct, and persuasive communication across technical and non-technical audiences.
- Strategic problem-solving ability in ambiguity, with strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt quickly.
- Technical aptitude: comfortable engaging directly with technical concepts including API documentation, data models, system architecture, and engineering tradeoffs.
- Proven track record of running multiple complex, high-visibility projects simultaneously and driving them to outcomes.
- Genuine interest in financial services and improving end-customer experience. Experience in fintech, implementations at financial institutions, working inside financial institutions, or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) is a strong plus.
STRONG PLUS:
- Hands-on experience building or deploying AI/LLM agents in production, including direct experience with evaluation frameworks, agent tooling, RAG, and prompt engineering.
- Founder, founding team member, or operator experience—ability to balance craft, ownership, and speed.
- Degree in Computer Science, Engineering, Mathematics, or related technical field (or equivalent practical experience), and/or an MBA or comparable experience at the intersection of technology and business.
