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jobSan Francisco, CA (Hybrid)$210k–$290k + equity

Software Engineer (AI Agents)

Sierra

Sierra builds conversational AI agents for enterprise customer experience — think Sonos, ADT, WeightWatchers running their support flows on Sierra's agent platform. Co-founded by Bret Taylor (ex-Salesforce co-CEO, OpenAI board chair) and Clay Bavor (ex-Google Labs). What you'd work on: the agent runtime (deterministic skills + LLM reasoning + tool use), evaluation infrastructure (every agent has to pass thousands of test scenarios before production), customer-specific fine-tuning pipelines, or the developer experience for the people who build agents on the platform. Honest fit signals: — Strong systems engineering background — Sierra agents handle real customer money/data, so reliability and observability matter as much as capability. — You've thought about LLM evals seriously. Sierra's evaluation framework is arguably their biggest moat; engineers who join expecting "just prompt the model" find the real work surprising. — You're motivated by the enterprise-AI problem space (not consumer). The customers are big, demanding, and pay seven figures. What's not a fit: anyone allergic to enterprise sales cycles influencing engineering priorities, anyone who wants pure research, or anyone who needs hard remote.
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