5+ years in customer success or related field, with an emphasis on AI integration
Proven experience designing scalable systems and processes
Strong analytical skills with a focus on key metrics such as NDR and churn
Experience utilizing AI tools for workflow automation
Demonstrated success in a revenue-driven environment, focusing on expansion and upsell strategies
Responsibilities
Design and build an AI-powered customer success engine scalable from 500 to over 5,000 customers
Create scalable systems for account segmentation, health scoring, and playbooks
Analyze customer data to identify and convert revenue opportunities
Streamline onboarding processes for fast, repeatable customer integration
Automate success and support workflows leveraging AI technologies
Lead and develop high-performing teams in Success, Deployment, and Support roles
Benefits
Innovative work environment focused on AI and systems design
Opportunity to shape and build customer success strategies from the ground up
Leadership role with the potential to drive significant revenue growth
Collaborative team culture that emphasizes data-driven decision making
Flexibility to implement AI solutions that enhance customer experience
Full Job Description
Head of AI Success @ Broccoli
This is not a traditional Head of Customer Success role. 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 - with one goal: maximize customer happiness, product usage, and NDR
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 and success workflows using AI
Hire and lead teams across Success, Deployment, and Support
What we're looking for
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
