AI Customer Education Lead

ABOUT BROCCOLI AI At Broccoli, we're building AI teammates for the people who build and maintain our world. We partner with plumbing, HVAC, and electrical contractors, the hardworking businesses that keep homes and communities running, and replace fragmented software and repetitive manual work with AI that actually gets the job done. Our AI teammates answer phones, book appointments, follow up with customers, recover missed revenue, and help contractors deliver exceptional customer experiences, all while integrating seamlessly with platforms like ServiceTitan. Before we wrote a single line of code, we visited more than 140 contractors to understand how these businesses truly operate. That firsthand experience shaped everything we've built. Today: - Hundreds of contractors rely on Broccoli every day. - We've grown to $15M+ ARR in under two years. - We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry. - We're backed by Khosla Ventures and Y Combinator. We're still just getting started. THE ROLE The hardest part of bringing AI into a contractor's operations isn't the software — it's getting the people at the desk and in the field confident enough to trust it and use it well. This role owns that. It's a two-sided job, and both sides run on AI. You'll teach our customers how to use a product that is itself AI-native — and you'll use AI to build the training, spot where customers get stuck, and generate documentation faster than a traditional education team ever could. It's a foundational, build-from-scratch role: instead of following a playbook, you'll write it. There's no dedicated owner today — just early proof (a handful of job aids, a few videos, some onboarding notes) and a lot of open space. You'll be the first person to own customer education end-to-end: build on what exists, then decide what it becomes. You're not tied to any one format — video, in-product guidance, live sessions, interactive walkthroughs, or something no one's tried yet — whatever gets customers confident. The goal is simple: every customer goes live and gets value from Broccoli without needing a person in the room for every step. WHAT YOU'LL DO - Own customer education end to end and build it into a scalable system. - Design the framework and roadmap for the education system. - Teach the people who work with Broccoli day to day how to get the most out of an AI-native product — choosing the formats that fit each audience, from job aids to video to in-product guidance and beyond. - Use AI to build the material: draft lessons, produce docs, and analyze friction faster than a traditional team could. - Design education around the key moments customers interact with Broccoli, so adoption feels natural and low-friction from day one. - Meet customers where they are: connect what they already do to how Broccoli helps, so getting started feels obvious, not intimidating. - Build a certification program that turns proficiency into something measurable. WHAT WE'RE LOOKING FOR - 4+ years building training, education, or instructional content that real people used to adopt a tool. - Built education or training programs from the ground up — not just run someone else's. - Can produce, not just plan — you can ship a job aid, a video, or a walkthrough yourself without a big team behind you. - Turn messy, real-world workflows into clear, confidence-building lessons. - AI-native — you use Claude and other AI tools daily to build training, analyze friction, and move faster than a traditional team could. - Opinionated about formats and tools, and curious enough to try approaches others haven't. - Comfortable being the first and only owner of a function, deciding what matters and what waits. - Comfortable getting fluent in a trade-heavy customer base fast — our customers are plumbers, HVAC techs, and electricians, and you'll need to speak their language. BONUS POINTS - Experience in home ser…