SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Pylon is an agentic support platform built for B2B companies, enabling human-AI collaboration on customer work across all channels. The company is backed by a16z, BCV, General Catalyst, and Y Combinator, with 1,600+ customers including Linear, Cognition, Modal Labs, and Incident.io.
As Head of Customer Success, you will own the entire post-sales function and scale it from a strong foundation. You'll inherit a 15+ person team across San Francisco, New York, and London with team leads already in place, currently delivering 159% NRR and hitting quarterly expansion goals.
Key responsibilities include:
**Own the Number**: Directly accountable for NRR, GRR, and churn metrics. Own expansion revenue through cross-sell and upsell, not as a handoff but as a core organizational function. Run the commercial system including quarterly goal setting, pipeline reviews, renewal and save motions, deal approvals, and compensation design.
**Lead the Agentic Motion**: Drive agentic support deployment and usage across the customer base as the company's top priority. Own the customer migration motion to usage-based billing, guiding customers through adoption and successful transitions. Develop and implement a strong point of view on how AI transforms the customer success role, both internally and for customers.
**Scale the Org**: Grow the team across three geographies by hiring and developing managers (two team leads are ready for promotion). Own segment design across Enterprise, Mid-Market, and Scaled segments, including book economics and capacity planning. Own the Sales-to-CS relationship, including qualification criteria and customer expectations.
**Run CS as Customer Zero**: Lead dogfooding and championship programs where CSMs master Pylon workflows. Use Pylon daily in your own workflows to directly shape product development.
**Be Pylon's Voice**: Represent Pylon externally through speaking, writing, podcasts, and community engagement where support leaders connect.
You'll move fluidly between strategic (board decks) and tactical (renewal escalations) work. You'll inherit and scale systems that already work, earning the right to change them through deep understanding. You'll work with a 1,600+ account base ranging from four-figure to six-figure customers.
**Requirements**:
- Experience leading customer success at a company with an agentic and/or usage-based billing product; you've lived through this exact shift before and understand variable consumption models
- 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 an inflection point (hypergrowth, multi-geo expansion, or pricing model shift)
- Based in San Francisco or willing to relocate, with genuine enthusiasm for in-person work
- Nice to have: existing public presence in the CS community (speaking, writing, or communities like Support Driven) and EMEA team experience
- AI native: you use agents in your own workflow, can demo credibly to skeptical buyers, and have a real point of view on agentic CS
