Head of AI Success

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