AI Outcomes Associate

UpSmith builds agentic AI systems that help skilled-trades businesses win—by converting more demand into revenue without adding payroll. Our flagship platform, Jenny, deploys autonomous AI agents that engage customers, surface revenue opportunities, and execute end-to-end workflows directly inside systems like ServiceTitan.

We are entering a phase where AI capability alone is no longer the bottleneck. Rather, the bottleneck is product outcomes: deploying agents into messy, real-world environments and making them work—reliably, measurably, and at scale.

This role exists to own that problem, and associated outcomes with it.

The AI Outcomes Associate sits at the intersection of:

• Applied AI & agent design


• Product judgment & abstraction discipline


• Customer success & real-world deployment

You will be responsible for turning AI capability into cus...