Head of AI Success

About Broccoli AI At Broccoli, we're building AI teammates for the people who build and maintain our world. We partner with plumbing, HVAC, and electrical contractors, the hardworking businesses that keep homes and communities running, and replace fragmented software and repetitive manual work with AI that actually gets the job done. Our AI teammates answer phones, book appointments, follow up with customers, recover missed revenue, and help contractors deliver exceptional customer experiences, all while integrating seamlessly with platforms like ServiceTitan. Before we wrote a single line of code, we visited more than 140 contractors to understand how these businesses truly operate. That firsthand experience shaped everything we've built. Today: Hundreds of contractors rely on Broccoli every day. We've grown to $15M+ ARR in under two years. We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry. We're backed by Khosla Ventures and Y Combinator . We're still just getting started. Head of AI Success @ Broccoli 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