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Sierra is building a platform for enterprises to deploy AI agents that deliver better customer experiences. As an Agent Strategist, you own the full lifecycle of AI agent development for enterprise customers—from initial scoping through conversation design, tooling, evaluation, production launch, and continuous iteration.
You'll serve as a trusted strategic advisor to enterprise leaders, sitting shoulder-to-shoulder with customers' executives to understand their business goals and shape AI strategy that drives measurable outcomes. You'll partner with customer teams day-to-day, running working sessions, troubleshooting agents, and making decisions that keep builds on track.
Your responsibilities include translating business problems into production agents, designing conversation flows for complex regulated interactions, defining quality metrics and evaluation frameworks, and directly impacting Sierra's product roadmap by surfacing unmet customer needs.
Recent projects include building subscription-retention agents for telecom/media companies, commerce troubleshooting agents with personalization, financial services agents handling complex regulated interactions, and partnering with product on new agent architectures.
You bring genuine customer obsession, clear communication across technical and non-technical audiences, strong analytical and critical-thinking skills, and technical aptitude (comfortable with APIs, data models, system architecture, and engineering tradeoffs). You have a track record of running complex, high-visibility projects and driving them to outcomes.
Financial services experience is a strong plus—familiarity with fair lending, PII handling, compliance, or prior work in fintech/financial institutions is valued. Experience building or deploying LLM agents in production, hands-on with eval frameworks, RAG, prompt engineering, and working closely with technical teams is ideal. Founder or founding-team experience, or an operator's mindset balancing craft and speed, is a bonus. A technical degree (CS, Engineering, Math) or equivalent practical experience, plus an MBA or comparable tech-business experience, strengthens your candidacy.
