The RoleThe 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 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 enablement 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. And you'll use AI to build training, analyze where customers get stuck, and generate documentation faster than a traditional enablement team could. 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 enablement end to end and build it into a scalable system.
- Build enablement for the people who work with Broccoli day to day-choosing the formats that fit each audience, from job aids to video to in-product guidance and beyond.
- Design enablement 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, enablement, or instructional content that real people used to adopt a tool.
- Built enablement 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.
- Experience in home services (HVAC, plumbing, electrical, roofing)-e.g., you've supported teams on tools like ServiceTitan, or run operations inside one.
Bonus Points- Startup experience.
- Spanish fluency.
