Hybrid AI Trainer – Support Operations

at Homebase (YC W21)

• Job title: AI Trainer – Support Operations
• Job type: Full Time
• Experience level: Junior, Mid level
• Salary: $56,525 - $66,500 per year
• Degree requirement: Bachelor's Degree
• Location requirements: Hybrid, Houston, United States

About the role

• AI Trainer shaping AI agent strategy for customer interactions at Homebase. Focus on training, optimizing, and analyzing performance for AI solutions.

Responsibilities

• 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