# AI Outcomes Associate

> UpSmith · Dallas, United States · Full-time · Posted 2026-04-23

**Salary:** USD 86,000–96,000

**Workplace:** on_site

## Description

### About UpSmith

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 Role

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 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.

### What You’ll Own

### AI Outcomes & Customer Impact

-   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

### Product & Feedback Loop

-   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

### What Success Looks Like (6–12 Months)

-   Customers expand usage because the configuration, deployment, and ongoing maintenance/support of **AI agents measurably drive revenue at clients**
-   Agent deployments become **faster, more repeatable, and less bespoke**
-   Product and engineering velocity increases due to **high-signal field feedback**
-   You are trusted internally to own some customer outcomes with minimal oversight

### Our Values (Non-Negotiable)

-   **Mission first.** Deliver magic for the builders we serve.
-   **Speed wins.** Execute efficiently with bias to action.
-   **Be an owner.** Raise the bar and take pride in the work.
-   **Choose greatness.** We perform best when we play to our superpowers. We hold a high standard for the bets we make

These are not slogans. This role lives or dies by them.

### Why This Role Matters

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.

## Requirements

### What You Must Have

### Core Capabilities

-   Strong analytical and systems thinking skills
-   Comfort working across **codebases, tooling, product, and customer conversations**
-   Ability to operate in ambiguity and make sound judgment calls quickly
-   Bias toward action with a high bar for quality

### Technical Fluency

-   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**

### Customer & Ownership Mindset

-   You take responsibility when things don’t work
-   You care deeply about real-world impact, not demos
-   You are comfortable telling hard truths—to customers and teammates

### Logistics

-   Willingness to travel frequently to customer sites
-   Comfortable operating in high-growth, high-expectation environments

### Bonus (Not Required, but Powerful)

-   Management consulting, product ops, or startup experience
-   Strong SQL & data visualization skills
-   Prior experience deploying AI or automations into production environments
-   Familiarity with skilled trades, home services, or operationally complex businesses
-   Working knowledge of APIs, data pipelines, and production constraints

## Apply

[Apply at UpSmith](https://apply.workable.com/upsmith-1/j/87364CEA88/apply)

---
Powered by [Workable](https://www.workable.com)