Head of AI Success

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

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

• 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