Head of AI Success

About Broccoli AI

AI-native operating system for home service businesses

The role

This is **not a traditional Head of Customer Success role** (and previous experience leading customer success is a plus, but not required).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. Your goals are to **maximize customer happiness, product usage, and NDR.** You'll own:* 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 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### **How you operate****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### **Your background*** 8+ years of strategy, product, or operations experience (e.g., product manager, engagement manager, consultant, founder, etc.)* Strong interpersonal and relationship-building skills* Experience developing new AI solutions in fast-moving, ambiguous environments* Bonus: * Knowledge of Customer Success processes, systems, and best practices * Experience at a high-growth startup environment * Background in computer science or AI product management