Broccoli AI

Head of AI Success

Broccoli AI

San Francisco6+ yearsFull-timePosted May 18, 2026

Job description

This is not a traditional Head of Customer Success role (and previous experience leading customer success is a plus, but not required).

We’re not hiring someone to just manage relationships or coach people. 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.

What you’ll own

Everything post-sale. 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:
  • 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 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

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

Your 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