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