Head of AI Success

Other

• 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
• 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.
• 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)
• 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
• Best-in-class NDR (expansion becomes predictable)
• Faster deployments, lower support load
• Clear, repeatable expansion engine
• A lean, high-leverage team powered by AI
• You design scalable systems, not manual processes
• You’ve built (or can build) health scoring, segmentation, and playbooks
• You live in metrics: NDR, churn, expansion, usage
• You turn messy data into clear actions
• You instinctively automate workflows using tools like Claude
• You think leverage first, headcount last
• You see CS as a revenue function , not support
• You’re comfortable owning expansion and NDR
• You want to create the playbook, not inherit one
• You’ve scaled or want to scale messy systems into machines
• 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.