Head of AI Success
at Broccoli AI — AI-native operating system for home service businesses
What the role involves
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
- 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
About Broccoli AI
Broccoli is building the AI-native operating system for home service businesses. Running a plumbing or HVAC company is chaotic—calls, scheduling, dispatch, follow-ups, marketing. We automate all of it so contractors can focus on what they do best: serving customers. Our AI agents handle both revenue and ops—answering phones 24/7, booking jobs in real time, following up on leads, and alerting techs when emergencies hit. We’ve grown from 0 to 200+ contractors in under a year, raised an unannounced round led by a Tier 1 VC to take on one of the biggest labor automation opportunities in the country.
Full Broccoli AI profile