management
Posted Apr 23Head of AI Success
at Broccoli AI
San Francisco, United StatesOn-site
Requirements
- 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.
- 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 This is not a traditional Head of Customer Success role (and previous
- experience leading customer success is a plus, but not required).
- 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.
- 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
- 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 details
- We started by going door-to-door, meeting 100+ contractors, and understanding how these businesses actually run.
- We’re not hiring someone to just manage relationships or coach people.
- Your goals are to maximize customer happiness, product usage, and NDR.
- experience (e.g., product manager, engagement manager, consultant, founder, etc.) - Strong interpersonal and relationship-building skills -