Scaled Customer Success Manager
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 Customer Success Manager, Scaled to own how our scaled CS motion works, not just run it. You'll diagnose where our volume actually comes from, decide what's worth fixing, and build the systems and playbooks that let us support hundreds of customers well without needing hundreds of CSMs to do it.
Half your time goes into that strategic work: diagnosing, prioritizing based on impact and lift, and project managing fixes from idea to shipped outcome, partnering closely with CS Ops, Product, and Engineering. The other half goes into running the motion yourself, owning onboarding, adoption, and renewal/upsell for your own book of business, because you can't redesign a system you don't run. We're looking for someone who thinks like an internal consultant: diagnose the problem, build the plan, then get your hands dirty running it.
What You'll Do
Build the Machine (50%)
Diagnose CS volume actually comes from: patterns, root causes, and the handful of issues driving most of the noise.
Prioritize what to fix based on impact and effort, and make the call on what's actually worth building.
Turn what you learn on the ground into playbook improvements. As we scale the team, you'll help define what "great" actually looks like.
Project manage the fix end to end, from first idea to shipped, measurable outcome, partnering with CS Ops, Product, and Engineering to design the tooling and workflows this motion needs to keep scaling.
Build the systems and metrics that tell you whether it worked, and keep improving from there.
Run the Motion (50%)
Manage a high-volume portfolio (500+ low touch customers) within our Scaled CS team, ensuring every customer, regardless of size, gets a high-quality, responsive experience.
Own the full customer lifecycle for your book of business, from post-onboarding stabilization through renewal, hosting calls and managing inbound communication across Slack, email, and Pylon.
Monitor product usage and customer signals to catch churn risk early and spot expansion opportunities. You're accountable for the health of your segment and for flagging which accounts are ready for deeper partnership.
Use Pylon every day for your own workflows. Your hands-on usage directly shapes what we build next.
What Makes You a Great Fit
You think in systems, not tickets. Diagnosing why 30% of volume is one issue, and deciding what to build in response, is the job, not a side project.
You move fluidly between altitudes: working a single customer's issue in the morning, redesigning the system behind hundreds of similar issues in the afternoon.
You believe you can't fix what you don't run. You want to be in the queue and on the calls, close enough to the work to know what's actually broken.
You're rigorous with projects. You can take a fix from idea to shipped outcome without someone managing you through it.
You're never satisfied. If you've solved the same problem twice, you're already building the fix so you don't solve it a third time.
You get more energy from impact at scale. A change that helps hundreds of customers excites you more than a single great save.
You know how to get things done through people who don't report to you.
What You’ll Bring
Based in San Francisco or willing to relocate, with real enthusiasm for working in person.
Comfortable interacting with customers daily over chat and video.
Strong analytical thinking: able to deeply understand a customer's use case and recommend thoughtful, strategic solutions.
Highly organized and process-oriented, capable of managing a high-volume workload without things slipping.
Genuine curiosity about the product, interested in exploring its nuances and designing more efficient workflows.
Bonus: experience building or analyzing dashboards in modern analytics tools.
Why This Role
Own a real, measurable system, not just a book of accounts.
A high-leverage seat: your fixes compound across hundreds of accounts, not one.
Join a well-funded, high-growth company, backed by a16z, BCV, General Catalyst, and Y Combinator, and featured on the Enterprise Tech 30 list.
Our perks
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
More about Pylon
Funding: Series B led by a16z and BCV ($51M total raised)
Founders: Advith Chelikani, Robert Eng, and Marty Kausas
Team: Currently 100+ and growing!