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Sierra is a customer-facing AI agent platform serving major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. Founded by Bret Taylor (former Salesforce co-CEO, Facebook CTO, Google Maps co-creator) and Clay Bavor (18-year Google veteran who led Google Labs and AR/VR initiatives), Sierra is transforming how enterprises deploy and optimize AI agents.
As a Software Engineer on the Insights team, you will build core systems that enable agent developers to understand, test, and improve their AI agents at scale. Your responsibilities include:
**Reporting & Experimentation**: Design and build systems to analyze and visualize millions of data points about agent performance. Enable developers to run A/B tests on agent behavior and make data-driven optimization decisions.
**Data Exploration**: Develop Explorer, an AI-powered tool combining conversational interfaces with intelligent clustering over agent interaction data—similar to ChatGPT but specialized for agent analytics.
**Monitoring**: Create proactive monitoring systems to detect agent defects, performance regressions, and emerging behavioral patterns.
You'll work in a high-autonomy culture where individual contributors have significant agency to drive customer impact. The role emphasizes balancing craftsmanship with competitive intensity and customer obsession. You'll be part of a primarily in-person team based in San Francisco with growing offices across North America, Europe, and Asia.
**Requirements:**
- 4+ years of hands-on experience building production products and systems
- Ability to build and ship full-stack solutions
- Bachelor's degree in Computer Science or related field, or equivalent professional experience
- Passion for working on the frontier of AI products
- High agency and motivation to drive outcomes independently
**Preferred qualifications:**
- Experience building AI-powered products
- Strong design sensibility
- Proficiency in Go and TypeScript
- Background in developer tooling, programming languages, or databases
- Technical leadership experience on projects or teams
