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 Broccoli is an equal-opportunity employer and complies with all applicable federal, state, and local fair employment practice laws.