AI Trainer - Support Operations at Homebase

Hi, Future Homie! At Homebase, you’ll join a team that’s bold, fast-moving, and obsessed with helping small businesses thrive. We build with empathy, act with urgency, and take big swings that drive real-world impact. Here, every Homie shows up to raise the bar, support one another, and celebrate wins as a team. We’re not just building an app—we’re building unstoppable teams. So what do you say, are you in?  Your Impact Starts Here - We're looking for an AI Trainer – Support Operations who's excited to shape how our AI agent thinks, responds, and resolves customer issues—end to end. This role owns how our customer-facing AI agent (powered by Sierra AI) operates: how it handles conversations, routes customer needs, executes workflows, and improves over time. It sits at the intersection of AI training, support operations, and workflow design—with a strong focus on measurable outcomes like containment rate, CSAT, and resolution quality. This is not a traditional support role. It's a specialist position focused on training and optimizing a production AI agent that serves real customers at scale. If you're energized by data, fluent in AI, and motivated by turning messy problems into clean, repeatable solutions—this role is for you. What you'll own - AI Agent Training & Workflow Design - 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. Data & Performance Analysis - 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. Cross-Functional Collaboration - 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. Quality & Iteration - 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. The Foundation for Success - Required: - 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) Nice to Have: - Experience with Sierra AI, LLM prompt engineering, or similar AI agent platforms - Background in support operations, QA, or workflow automation - Familiarity with tools like Salesforce, Talkdesk, Level AI, or Ask AI - Experience defining escalation logic, containment strategies, or AI performance benchmarks 🤝  The Homie Way - These principles guide everything we do—from how we work and make decisions to how we show up for each other. - 💡 Be Customer Obsessed – Solve problems with empathy and creativity. - ⚡ Move Fast, Learn Fast – Experiment, take action, and grow every day. - 🎯 Own Your Impact – Think big, focus on what matters, and make decisions you stand behind. - 🏆 Master Your Craft – Excellence fuels impact—show up, step up, and make your mark. - 🏅 Win Together – Put goals over roles, lead with trust, and connect to our mission and each other. What We Offer - 💰 Ownership & Financial Security: Stock options + 401(k) with 4% match - 🏥 Comprehensive Healthcare: Medical, dental, and vision coverage + FSA options - ⏰ Flexible Time: Unlimited PTO (salaried) + company holidays - 👶 Family Support: Up to 12 weeks of paid parental leave (after 6 months of service) - 🛡️ Protection Plans: Life insurance + short/long-term disability coverage - 🌟 Work Your Way: Work From Anywhere Month + meeting-free weeks yearly - 🍽️ Workspace Perks: Meals provided, commuter benefits, team offsites, and Customer Days - 💼 Our Hybrid Rhythm: We believe collaboration drives impact. That’s why Monday-Thursday are our required in-office days—a time to move faster as a team, build deeper connections, make better decisions, and build together. 💜 Belonging at Homebase - We're committed to fostering a welcoming space where every Homie can be their full self. Experience comes in many forms—so if you're excited about this role, even if you don’t meet 100% of the qualifications, we encourage you to apply!  Homebase will consider qualified applicants with criminal histories in a manner consistent with the San Francisco Fair Chance Ordinance. 👋 Hey, We’re Homebase Unstoppable teams start here. Homebase is the everything app for hourly teams—built to simplify the day-to-day and superpower local businesses. With tools for scheduling, time clocks, payroll, communication, HR, and more, we help teams stay connected and in control. Today, over 100,000 small (but mighty) businesses rely on us to make work radically easier. Together, we’ve tracked over a billion hours for 2.5+ million workers—and we’re just getting started. At Homebase, we celebrate diversity and are proud to be an equal opportunity employer. We welcome all candidates and do not discriminate based on any legally protected status. If you need accommodations during the hiring process, please let us know—we’re committed to ensuring fair and equitable access for all.