Head of AI Success

Broccoli AI • San Francisco, CA

3d

About The Position

Broccoli AI is building the AI operating system for home service businesses, working with plumbing, HVAC, and electrical contractors to replace fragmented tools and manual workflows with AI agents. Their AI assistants handle phone calls, book jobs, follow up with customers, and drive revenue, fully integrated into systems like ServiceTitan. The company started by understanding contractors' needs through direct engagement, which shaped their product. Currently, hundreds of contractors use Broccoli for their front office, and the company has grown from $0 to millions in ARR in under a year, trusted by both single-location and multi-location groups. They have raised over $25M from Khosla Ventures and YC. The Head of AI Success role is not a traditional customer success position; it seeks an analytical, systems-driven, and AI-native individual to design and build a scalable machine for retention and expansion, rather than managing it manually.

Requirements

• Design scalable systems, not manual processes
• Built (or can build) health scoring, segmentation, and playbooks
• Live in metrics: NDR, churn, expansion, usage
• Turn messy data into clear actions
• Instinctively automate workflows using tools like Claude
• Think leverage first, headcount last
• See CS as a revenue function, not support
• Comfortable owning expansion and NDR
• Want to create the playbook, not inherit one
• Scaled or want to scale messy systems into machines

Responsibilities

• Own everything post-sale with the goal to maximize customer happiness, product usage, and NDR
• Own Retention + Expansion
• Own Customer outcomes (bookings, revenue, efficiency)
• Own Deployment speed (time-to-value in days, not weeks)
• Own Support (AI-first, proactive, scalable)
• Build the AI-powered success engine that scales from 500 to 5,000+ customers
• Create systems for Account segmentation + ownership
• Create systems for Health scoring
• Create systems for 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 This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 1-10 employees