Pylon
Head of Customer Success
$250K–$300K
San Francisco · Director · Full-time · Posted Sep 11, 2026
- Experience
- 5+ years in post-sales, including 2+ years leading customer success organizations; experience managing managers in an organization of 15+ people.
About the job
Own and scale Pylon’s Customer Success organization, post-sales revenue, and customer adoption of agentic support and usage-based billing.
What you'll do
- Own NRR, GRR, churn, expansion targets, forecasting, and the commercial system, including renewals, pipeline reviews, and deal approvals.
- Lead customer adoption and migration to agentic support and usage-based billing, and help transform CS workflows with AI.
- Scale the CS organization across segments and offices, develop managers, and represent Pylon in the customer success community.
What they ask for
- Experience leading customer success at a company with an agentic and/or usage-based billing product.
- 5+ years in post-sales, with 2+ years leading customer success organizations, including managing managers in an org of 15+ people across segments and geographies.
- Track record of personally owning and exceeding NRR and expansion targets in B2B SaaS.
- Experience scaling a CS org through hypergrowth, multi-geo expansion, or a pricing model shift; based in San Francisco or willing to relocate.
Nice to have
- Existing public presence in the CS community, such as speaking, writing, or participating in communities like Support Driven.
- EMEA team experience.
Pay
$250K – $300K USD base salary
AI focus
Lead customer adoption of agentic support, migrate customers to usage-based billing, and apply AI agents and agentic workflows to transform customer success internally and in the product.
Model-written summary · the original posting is authoritative