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 the largest PE-backed roll-ups Raised $25M+ 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 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

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