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Broccoli AIBroccoli AISan Francisco, CA

Head of AI Success

Leads post-sale AI success operations at scale, building automated systems for retention, expansion, health scoring, and support to drive NDR and customer outcomes. Requires 8+ years in strategy/product/ops, AI-native mindset, and analytical revenue focus.

200k – 300k/yr
On-site8+ YOECustomer Success

About the role

Responsibilities

  • Own everything post-sale: maximize customer happiness, product usage, and NDR.
  • Drive retention + expansion, customer outcomes (bookings, revenue, efficiency), deployment speed, and AI-first support.
  • Build AI-powered success engine that scales from 500 → 5,000+ customers.
  • Create systems for account segmentation + ownership, health scoring, expansion/upsell playbooks.
  • Turn customer data into revenue opportunities.
  • Redesign onboarding to be fast, repeatable, low-touch.
  • Automate support and success workflows using AI.
  • Hire and lead teams across Success, Deployment, and Support.

Requirements

  • 8+ years of strategy, product, or operations experience (e.g., product manager, engagement manager, consultant, founder).
  • Strong interpersonal and relationship-building skills.
  • Experience developing new AI solutions in fast-moving, ambiguous environments.
  • Systems thinker: design scalable systems, not manual processes; build health scoring, segmentation, playbooks.
  • Analytical: live in metrics (NDR, churn, expansion, usage); turn data into actions.
  • AI-native: automate workflows using tools like Claude; think leverage first.
  • Revenue-driven: see CS as revenue function; own expansion and NDR.
  • Builder mindset: create playbooks from scratch; scale messy systems.

Nice-to-Haves

  • Knowledge of Customer Success processes, systems, best practices.
  • Experience at high-growth startup.
  • Background in computer science or AI product management.

Skills

AIClaudeHealth ScoringAccount SegmentationNdrChurn AnalysisExpansion PlaybooksOnboarding AutomationCustomer Success SystemsMetrics Analysis
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