Head of AI Success

San Francisco

**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 Compensation Range: $200K - $300K