> UpSmith · Dallas, United States · Full-time · Posted 2026-04-23
Salary: USD 86,000–96,000
Workplace: on_site
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:
You will be responsible for turning AI capability into customer-visible, revenue-driving outcomes. That means working directly with customers, AI Outcomes managers, and engineers to deploy agents, diagnose failures, refine behavior, and prove impact.
This is not a traditional CSM role.
It is a front-line, ownership-heavy role for someone who wants to see their work running in production—creating real economic value.
Own the end-to-end success of AI agent deployments for our customers
Define, track, and improve leading and lagging indicators of agent success (conversion, bookings, revenue lift, customer trust)
Diagnose failures across data, prompts, tooling, coordination logic, and customer workflows
Act as the single accountable owner for “Is this working—and why?”
Work hands-on with AI agents in production:
Prompting and behavior design
Guardrails, fallbacks, and human-in-the-loop escalation
Partner with core engineering on deeper system improvements surfaced from the field
Translate customer reality into clear product insights and roadmap input
Identify when problems are:
Agent behavior issues
Product abstraction issues
Customer workflow mismatches
Help decide what not to build by grounding decisions in outcomes, not hypotheticals
These are not slogans. This role lives or dies by them.
UpSmith is moving from “Can we build agents?” to “Can we deploy agents that win?”
This role is where that question gets answered—every day, with real customers, real revenue, and real accountability.
Working knowledge of:
LLMs and their failure modes
Prompt engineering
SQL and data visualization tools (i.e. Tableau, Retool, Metabase)
You don’t need to build solutions from scratch, but you should have the capability and reasoning to scale and help plan for the future on our current systems
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Location
Dallas, Texas
Total raised
$8.3M
Last stage
Seed
Investors
No applications, no recruiter spam. Just the intro.
A few questions to make sure this role is the right shape for you. Two minutes.
I write the intro, send it to the founder, and handle the back-and-forth.
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.