Head of AI Success

About Broccoli AI

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
Head of AI Success @ Broccoli

What You’ll Own

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

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

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

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

Compensation Range

$200K - $300K

Equal Opportunity Employer

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