Customer Enablement Lead

About Broccoli AI
Broccoli AI is building the AI operating system for home service businesses.
We work with plumbing, HVAC, and electrical contractors, the people who keep homes running, and we replace fragmented tools and manual workflows with AI agents that actually do the work.
Our AI assistants answer phones, book jobs, follow up with customers, and drive revenue, fully integrated into systems like ServiceTitan.
We started by going door-to-door, meeting 100+ contractors, and understanding how these businesses actually run. That shaped everything we've built. Today:
Hundreds of contractors use Broccoli to run their front office
We've grown from $0 to millions in ARR in under a year
We're trusted by both single-location operators and the largest PE-backed roll-ups
Raised $25M+ from Khosla Ventures and YC
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 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.

Experience
6+ years

Work arrangement
No