Head of Customer Success

pylon-labs; San Francisco (CA); Hybrid; USD 220,000 - 320,000; Full time

Job summary

Pylon seeks a Head of Customer Success to own how post-sales works and scale it across SF, NYC, and London. You’ll inherit a 15+ person CS team, forecast results, and drive renewal, expansion, and customer migrations to agentic workflows. You’ll shape strategy for AI-driven CS and represent Pylon in the CS community.

You’ll lead a strategic, hands-on team that partners with product, sales, and support to ensure durable growth and high NRR across our 1,600+ customers.

Qualifications

• Experience leading customer success at a company with agentic or usage-based billing.
• Proven ability to scale a CS organization across multiple offices.
• Track record of owning NRR, GRR, and expansion targets at scale.

Responsibilities

• Own NRR, GRR, and churn; forecast weekly and present to the board.
• Own expansion numbers; lead cross-sell and upsell as a core part of the role.
• Run the commercial system: goal setting, pipeline reviews, renewals, and compensation design.
• Lead the Agentic Motion; drive deployment and usage of agentic CS across customers.
• Shape how AI changes the CS role and implement it internally.
• Scale the Org: hire and develop managers; segment design for Enterprise, Mid-Market, and Scaled.
• Manage Sales-to-CS relationship and post-sales customer expectations.
• Run CS as Customer Zero; dogfooding and champion programs with PMs.
• Be Pylon’s voice in the CS community through speaking, writing, podcasts.

Skills

Leadership

Forecasting

Strategic thinking

People management

Job description

Pylon is the only agentic support platform, purpose-built for B2B companies.

For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work, investigating, resolving, and acting on every signal across every channel that matters.

Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself.

We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List.

ABOUT THE ROLE

Pylon is looking for a Head of Customer Success to own how post-sales works at Pylon, and to scale it, not rebuild it.

You’ll inherit a Customer Success organization that works: 159% NRR, quarterly expansion goals at scale, and a 15+ person team across SF, NYC, and London with team leads already in place. The systems run. Your job is to scale the team, from team leads to a management layer, and from strong quarters to a durable machine, all while leading Pylon’s biggest bet: making agentic support the way our 1,600+ customers work.

This is one of the most strategic seats we’ll fill this year. Our customers are support and CS leaders themselves, so they look to us for how other companies use Pylon to run support and success, and how we do it internally. You’ll sit at the forefront of the next generation of CS, with real room to become a thought leader in the community.

WHAT YOU’LL DO

• Own the Number Own NRR, GRR, and churn. Post-sales revenue is yours, forecast weekly and presented to the board.
• Own the expansion number Own the expansion number. Cross-sell and upsell are not handed off to someone else, they’re a core part of how you run the org, and you’re directly accountable for hitting the quarterly expansion goal.
• Run the commercial system quarterly goal setting (bottoms-up and top-down), pipeline reviews, renewal and save motions, deal approvals, and comp/SPIFF design tied to the company’s bets.
• Lead the Agentic Motion Drive Agentic Support deployment and usage across the customer base, the company’s top priority, run through your team. Own the customer migration motion to agentic, usage-based billing: drive adoption of the usage-based product, guide customers through the transition, and land successful migrations. This isn’t ownership of pricing strategy itself, it’s ownership of how customers actually get there.
• Have a strong point of view on how AI changes the customer success role and be able to implement that transformation internally as well as help carry it through to our product.
• Scale the Org Grow the team across three offices: hire and develop managers (two team leads are already ready for that step), own segment design across Enterprise, Mid-Market, and Scaled, book economics, and capacity planning.
• Own the Sales to CS relationship qualification criteria, deal review, and customer expectations post sales.
• Run CS as Customer Zero Lead the dogfooding and Championship programs, where CSM DRIs master a Pylon workflow with the PM and champion it to the team. Use Pylon every day for your own workflows. Your hands‑on usage directly shapes what we build next.
• Be Pylon’s Voice in the CS Community Represent Pylon externally through speaking, writing, podcasts, and the communities where support leaders compare notes. The person who runs CS at Pylon should be a name our buyers know.

WHAT MAKES YOU A GREAT FIT

You move fluidly between altitudes: building the board deck in the morning, hopping on an escalation call to save a renewal in the afternoon, and hosting a CS leader dinner in the evening. Equally strategic and hands on.

You’ve owned the number, not just the relationship. NRR, GRR, expansion targets: personally accountable, at scale, with a track record of hitting them.

You’ve led leaders. You get as much energy developing a manager as closing a deal, and you know the difference between running 50 people and running 50 people well.

You inherit well. You get energy from scaling systems that already work, and you earn the right to change them by understanding them first.

A 1,600+ account base energizes you. Our customers range from four figures to six figures, and we’re building a CS org to support all of them.

You want the stage. You already speak, write, or build in public about how customer success should work, or you’ve been waiting for the company and platform that makes it worth doing.

You’re AI native. You use agents in your own workflow, you can demo ours credibly to a skeptical CCO, and you have a real point of view on what agentic CS looks like.

WHAT YOU’LL BRING

Experience leading customer success at a company with an agentic and/or usage-based billin