- Salary
- $200 – $300/yr
- Location
- San Francisco, US
- Type
- Full-time
- Source
- Y Combinator
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
