Pylon Labs

Pylon Labs

Head of Customer Success

San Francisco · Senior

Sponsorship not specifiedDetected 42 days ago
Customer Success

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odds of building a lasting career here

34Risky
Cap-exempt (no lottery)0
Sponsors this role70
Entry-level history0
PERM / green-card track0
Lottery odds40
Fits your clock70

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Files H-1B transfers

1 transfer filing in the last year, covering 1 worker. Median labor-condition decision: 7 days. An employer that already files transfers is one that can take over an existing H-1B.

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About the role

  • This is one of the most strategic seats we'll fill this year.
  • You'll sit at the forefront of the next generation of CS, with real room to become a thought leader in the community.
  • You'll inherit a Customer Success organization that works:

Responsibilities

  • Own NRR, GRR, and churn. Post-sales revenue is yours, forecast weekly and presented to the board.
  • 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.
  • 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.
  • 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.
  • 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.
  • Lead the company's biggest bet from the seat closest to customers.

Nice to have

  • Join a well funded, high growth company backed by a16z, BCV, General Catalyst, and Y Combinator, and featured on the Enterprise Tech 30 list.
  • 🍽 Lunch, dinner, and snacks at the office

Compensation

  • 🗺 Annual offsite

Benefits

  • 🏥 Fully covered medical, dental, and vision insurance for employees
  • 🏦 401(k) retirement plan
  • 🚅 Commuter benefits
  • 🌱 Parental leave
  • 🏝 14 company holidays + unlimited PTO
  • 🏇 Fitness stipend

Company info

  • 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.
  • You've owned the number, not just the relationship.
  • 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.
  • Experience leading customer success at a company with an agentic and/or usage-based billing product. You've lived through this exact shift before, helping customers understand variable consumption and tying value to real-time usage. This matters more to us than almost anything else on this list.
  • 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.
  • A track record of personally owning and exceeding NRR and expansion targets in B2B SaaS.
  • 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.
  • 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.
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This listing is sourced directly from Pylon Labs's careers page and normalized into a canonical job model.