What are the responsibilities and job description for the Head of AI Success position at Broccoli AI?
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:
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
Systems thinker
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
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)
- 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
Systems thinker
- You design scalable systems, not manual processes
- You’ve built (or can build) health scoring, segmentation, and playbooks
- You live in metrics: NDR, churn, expansion, usage
- You turn messy data into clear actions
- You instinctively automate workflows using tools like Claude
- You think leverage first, headcount last
- You see CS as a revenue function, not support
- You’re comfortable owning expansion and NDR
- You want to create the playbook, not inherit one
- You’ve scaled or want to scale messy systems into machines
- Best-in-class NDR (expansion becomes predictable)
- Faster deployments, lower support load
- Clear, repeatable expansion engine
- A lean, high-leverage team powered by AI
Salary : $200,000 - $300,000