Head of AI Success

Role Summary

Today

• Hundreds of contractors rely on Broccoli every day.
• We've grown to $15M+ ARR in under two years.
• We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry.
• We're backed by Khosla Ventures and Y Combinator.

We're still just getting started.

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.

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

Responsibilities

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

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

Requirements

• 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.

About the Company

ABOUT BROCCOLI AI

At Broccoli, we're building AI teammates for the people who build and maintain our world.

We partner with plumbing, HVAC, and electrical contractors, the hardworking businesses that keep homes and communities running, and replace fragmented software and repetitive manual work with AI that actually gets the job done.

Our AI teammates answer phones, book appointments, follow up with customers, recover missed revenue, and help contractors deliver exceptional customer experiences, all while integrating seamlessly with platforms like ServiceTitan.

Before we wrote a single line of code, we visited more than 140 contractors to understand how these businesses truly operate. That firsthand experience shaped everything we've built.