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Head of AI Success

Broccoli AI· Operations
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Hybrid (San Francisco)$200k - $300kFull-timePosted 5mo ago

About the role

AI-native operating system for home service businesses company Broccoli AI is hiring a data-driven, AI-first Head of AI Success to design and scale an automated customer success engine that drives retention, expansion, and NDR post-sale.

Responsibilities

  • Retention + Expansion
  • Customer outcomes (bookings, revenue, efficiency)
  • Deployment speed (time-to-value in days, not weeks)
  • Support (AI-first, proactive, scalable)
  • 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

Qualifications

  • 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
  • Bonus: Experience at a high-growth startup environment
  • Bonus: Background in computer science or AI product management

Skills

Required:Health scoringAccount segmentationExpansion and upsell playbooksAI workflow automation
Last updated Aug 19, 2026. Interested? Apply on the company site.
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About Broccoli AI

AI-native operating system for home service businesses

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.

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