Head of AI Success @ BroccoliThis 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 ownEverything 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 forSystems 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
