Head of AI Success

broccoli · Remote

Experience: lead

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 the largest PE-backed roll-ups Raised

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5M+ from Khosla Ventures and YC 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 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 predicta

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