About UpSmithUpSmith 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 RoleThe AI Outcomes Associate sits at the intersection of:Applied AI & agent designProduct judgment & abstraction disciplineCustomer success & real-world deploymentYou 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 OwnAI Outcomes & Customer ImpactOwn the end-to-end success of AI agent deployments for our customersDefine, 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 workflowsAct as the single accountable owner for “Is this working—and why?”Work hands-on with AI agents in production: Prompting and behavior designGuardrails, fallbacks, and human-in-the-loop escalation Partner with core engineering on deeper system improvements surfaced from the fieldProduct & Feedback LoopTranslate customer reality into clear product insights and roadmap inputIdentify when problems are: Agent behavior issuesProduct abstraction issuesCustomer workflow mismatches Help decide what not to build by grounding decisions in outcomes, not hypotheticalsWhat Success Looks Like (6–12 Months)Customers expand usage because the configuration, deployment, and ongoing maintenance/support of AI agents measurably drive revenue at clientsAgent deployments become faster, more repeatable, and less bespokeProduct and engineering velocity increases due to high-signal field feedbackYou are trusted internally to own some customer outcomes with minimal oversightOur 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 makeThese are not slogans. This role lives or dies by them.Why This Role MattersUpSmith 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.RequirementsWhat You Must HaveCore CapabilitiesStrong analytical and systems thinking skillsComfort working across codebases, tooling, product, and customer conversationsAbility to operate in ambiguity and make sound judgment calls quicklyBias toward action with a high bar for qualityTechnical FluencyWorking knowledge of: LLMs and their failure modesPrompt engineeringSQL 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 systemsCustomer & Ownership MindsetYou take responsibility when things don’t workYou care deeply about real-world impact, not demosYou are comfortable telling hard truths—to customers and teammatesLogisticsWillingness to travel frequently to customer sitesComfortable operating in high-growth, high-expectation environmentsBonus (Not Required, but Powerful)Management consulting, product ops, or startup experienceStrong SQL & data visualization skillsPrior experience deploying AI or automations into production environmentsFamiliarity with skilled trades, home services, or operationally complex businessesWorking knowledge of APIs, data pipelines, and production constraints
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
