About this role
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 → millions in ARR in under a year
- We’re trusted by both single-location operators and large multi-location groups
- Raised $25M+ from Khosla Ventures and YC
Head of AI Success @ Broccoli
This is not a traditional Head of Customer Success role .
We’re not hiring someone to just manage relationships or coach people. We’re hiring someone deeply analytical, systems-driven, and AI-native — someone who can design and build a machine that drives retention and expansion at scale, not manage it manually.
What you’ll own
Everything post-sale — with one goal: maximize customer happiness, product usage, and NDR
- Retention + Expansion
- Customer outcomes (bookings, revenue, efficiency)
- Deployment speed (time-to-value in days, not weeks)
- Support (AI-first, proactive, scalable)
What you’ll do
- Build the AI-powered success engine that scales from 500 → 5,000+ customers
- Create systems for:
Account segmentation + ownership
- Health scoring
- Expansion and upsell playbooks
- Turn customer data into revenue opportunities
- Redesign onboarding to be fast, repeatable, and low-touch
- Automate support and success workflows using AI
- Hire and lead teams across Success, Deployment, and Support
What we’re looking for
Systems thinker
- You design scalable systems, not manual processes
- You’ve built (or can build) health scoring, segmentation, and playbooks
Analytical
- You live in metrics: NDR, churn, expansion, usage
- You turn messy data into clear actions
AI-native
- You instinctively automate workflows using tools like Claude
- You think leverage first, headcount last
Revenue-driven
- You see CS as a revenue function , not support
- You’re comfortable owning expansion and NDR
Builder
- You want to create the playbook, not inherit one
- You’ve scaled or want to scale messy systems into machines
What success looks like
- Best-in-class NDR (expansion becomes predictable)
- Faster deployments, lower support load
- Clear, repeatable expansion engine
- A lean, high-leverage team powered by AI