Head of AI Success

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.

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.

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.