← All roles

Head of Customer Success

Pylon· Success
Apply on company site
San Francisco$250k - $300kFull-timePosted 1mo ago

About the role

Senior leadership role responsible for scaling and owning post-sales CS at Pylon, directing NRR/GRR growth, expanding ARR, and driving the agentic support strategy across multiple geographies.

Responsibilities

  • Own NRR, GRR, and churn. Post-sales revenue is yours, forecast weekly and presented to the board.
  • Own the expansion number. Cross-sell and upsell are not handed off and are core to the role.
  • Run the commercial system: quarterly goal setting (bottoms-up and top-down), pipeline reviews, renewal and save motions, deal approvals, and comp/SPIFF design.
  • Drive Agentic Support deployment and usage across the customer base.
  • Own the customer migration motion to agentic, usage-based billing: drive adoption and guide successful migrations.
  • Have a strong point of view on how AI changes the CS role, and implement that transformation internally and in product.
  • Grow the team across three offices (SF, NYC, London): hire and develop managers, own segment design, book economics, and capacity planning.
  • Own the Sales to CS relationship: qualification criteria, deal review, and customer post-sales expectations.
  • Lead the dogfooding and Championship programs, where CSM DRIs master a Pylon workflow with the PM.
  • Use Pylon daily for own workflows to shape future development.
  • Represent Pylon externally through speaking, writing, podcasts, and CS communities.

Qualifications

  • 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
  • Experience leading CS at a company with agentic and/or usage-based billing products
  • Track record of personally owning and exceeding NRR and expansion targets in B2B SaaS
  • Experience scaling a CS org through inflection points: hypergrowth, multi-geo expansion, or pricing model shifts
  • Based in San Francisco or willing to relocate
  • Nice to have: public CS community presence (speaking, writing) and EMEA team experience

Skills

Required:Strategic leadership and governancePeople leadershipAgentic/usage-based product knowledge

Benefits

  • Fully covered medical, dental, and vision insurance for employees
  • 401(k) retirement plan
  • Commuter benefits
  • Parental leave
  • 14 company holidays + unlimited PTO
  • Annual offsite
  • Lunch, dinner, and snacks at the office
  • Fitness stipend
Last updated Sep 17, 2026. Interested? Apply on the company site.
Pylon logo

About Pylon

The only customer support platform built for B2B.

Pylon is the modern alternative to Zendesk, Intercom, Freshdesk, and Salesforce Service Cloud. We help B2B companies track customer support issues across common B2B channels including shared Slack channels (Slack Connect), Microsoft Teams, email, in-app chat, ticket forms, Slack community, and more. Hundreds of fast-growing YC companies of all sizes like Vellum, Hightouch, and Deel are customers. Learn more at usepylon.com

AI supportB2B support platformticketingchatknowledge baseAI agentsaccount intelligence
Company profileWebsite

More open roles at Pylon