Homebase (YC W21)

AI Trainer – Support Operations

Homebase (YC W21)

full-time

Posted on:

Location Type: Hybrid

Location: Houston • Texas • United States

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Salary

💰 $56,525 - $66,500 per year

About the role

  • Build and optimize conversational journeys within Sierra AI—defining how the agent gathers context, handles branching logic, and resolves customer issues without human handoff.
  • Translate complex support workflows into structured, testable AI journeys that the agent can execute accurately and confidently.
  • Identify gaps in agent behavior through data analysis, then design, test, and iterate on solutions to close them.
  • Own the full lifecycle: identify → design → build → test → monitor → improve.
  • Analyze contact data, containment rates, and customer sentiment to identify the highest-impact areas to focus on.
  • Use tools like Sierra AI, Level AI, and Ask AI to surface trends, prioritize work, and measure the impact of every change you ship.
  • Track key metrics—containment rate, CSAT, resolution accuracy—and use them to guide decisions and communicate progress.
  • Partner with Product Managers, Engineers, and Support SMEs to scope and build AI capabilities that require backend access or new action tools.
  • Document workflows clearly in Google Docs and communicate asks to engineering and product in a way that's specific, well-reasoned, and actionable.
  • Proactively flag opportunities and surface data-backed recommendations to your manager and cross-functional partners—not just wait to be assigned work.
  • Rigorously test new journeys before they go live—catching edge cases, error states, and failure modes before customers see them.
  • Monitor live journeys post-launch and continuously refine based on real customer behavior.
  • Contribute to a culture of experimentation: form a hypothesis, build it, measure it, iterate.

Requirements

  • 2+ years of experience in AI training, support operations, conversation design, chatbot management, or a closely related role
  • Hands-on experience working with AI tools—ideally building or optimizing a customer-facing chatbot, AI agent, or automated workflow
  • Demonstrated ability to use data to identify problems, prioritize work, and measure impact
  • Strong written communication skills—a significant portion of this role is writing: journeys, documentation, workflows, and prompts
  • Comfort with cross-functional collaboration, including working with Product and Engineering teams
  • A bias for action: you don't wait for perfect information to start moving
  • Ability to work in-office Monday–Thursday at our Houston hub (non-negotiable)
Benefits
  • Stock options + 401(k) with 4% match
  • Medical, dental, and vision coverage + FSA options
  • Unlimited PTO (salaried) + company holidays
  • Up to 12 weeks of paid parental leave (after 6 months of service)
  • Life insurance + short/long-term disability coverage
  • Work From Anywhere Month + meeting-free weeks yearly
  • Meals provided, commuter benefits, team offsites, and Customer Days
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AI trainingconversation designchatbot managementdata analysisworkflow optimizationmetrics trackingtesting methodologiescustomer sentiment analysisproblem identificationimpact measurement
Soft Skills
written communicationcross-functional collaborationproactive problem-solvingaction-oriented mindsetdocumentation skillsanalytical thinkingcreativityattention to detailadaptabilityteamwork