AI
At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀
We're looking for a highly skilled and experienced Senior AI Engineer to join our ClickUp Engineering team, with a focus on AI evaluations. You'll own how we measure and improve the quality of ClickUp's AI: building the eval systems that tell us how well our AI is performing, the core agent harness, and the AI that performs well on those evals. You'll work on backend systems that make AI-powered capabilities scalable, reliable, and secure, while working hands-on with LLMs to solve real user problems and drive product innovation.
Key Responsibilities
- Design, build, and own ClickUp's AI evaluation system, including golden datasets, LLM-as-judge and automated scorers, regression detection, and quality tracking across AI features.
- Build and evolve the core agent harness, and the AI that performs well on those evals, partnering closely with product and engineering to define what "great" looks like.
- Build self-improvement loops where agents modify other agents or prompts, rerun evals, and iterate automatically.
- Benchmark new models as they're released and own model selection, routing, and fallback strategies across providers (e.g., OpenAI, Anthropic, Google, open-weight), balancing quality, l