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Head of Customer Success

Pylon

San Francisco, CA · Director

Listed on Pylon’s own careers site. You apply with them directly — we never stand between you and the employer.

What this role is

Lead and scale a 15+ person customer success organization at an AI-native SaaS platform with strong fundamentals (159% NRR, expansion goals). You'll own revenue metrics, drive adoption of agentic support across 1,600+ customers, develop managers, and build your public presence as a thought leader in how AI transforms customer success.

Our summary, not Pylon’s wording. The full posting is on their site.

What they ask for

Required

  • 5+ years in post-sales roles
  • 2+ years leading customer success organizations with 15+ people across segments and geographies
  • Experience with NRR and expansion targets in B2B SaaS
  • Track record leading customers through agentic and/or usage-based billing product transitions
  • Based in San Francisco or willing to relocate with commitment to in-person work

Nice to have

  • Existing public presence in CS community through speaking, writing, or communities like Support Driven
  • EMEA team leadership experience

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