Head of AI Success

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

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

Additional information

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