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.

Company

• Series B, $51M raised

• Backed by a16z, BCV, General Catalyst, Y Combinator

• 100+ employees

• Offices in San Francisco and New York City

Pylon is looking for a Sales Manager to own our net-new business motion: managing a team of 6-10 Account Executives selling into commercial and mid-market segmentations, generating pipeline alongside a dedicated BDR team running in and outbound, and building the playbook for how we win bigger, more complex deals.

You'd join as only the second sales manager in the org, reporting directly to our Head of Sales. With a strong AE bench and proven product-market fit already in place, this role has real latitude to define how we sell upmarket rather than inherit someone else's playbook.

What You'll Do 📌

• Manage and coach a team of 6-10 Account Executives focused exclusively on net new business — no renewals, no expansion, just new logos.

• Own the commercial and mid-market motion: your team sells into growing, higher-velocity accounts where deal size and complexity are stepping up, and the muscle we build now sets the standard for how Pylon sells at this level.

• Generate pipeline alongside your team. You'll have a team of BDRs running in and outbound to fuel the funnel, but we expect you and your AEs to be builders who create their own opportunities too, not just closers waiting on leads.

• Drive consistent execution across inbound and outbound motions, and partner with the BDR org on targeting, handoff quality, and lead flow.

• Help build, document, and scale our commercial and mid-market sales playbook. We have a foundation that works; we need someone who can turn it into a repeatable system as deal size and complexity go up.

• Lead deal reviews, pipeline inspection, and forecasting. You'll know the state of every meaningful deal in your pipeline at all times.

• Recruit and hire AEs as the team grows. You're building the bench, not just managing the one you inherit.

• Partner closely with our Head of Sales to shape segmentation, quotas, and process for the commercial and mid-market segment.

Who You Are 💼

• 2+ years managing SaaS AEs, required.

• Experience scaling a team beyond the "early reps" phase and selling into commercial or mid-market accounts.

• Strong coaching instincts and operational rigor — you can look at a deal or a rep's pipeline and know exactly what needs to change.

• Experience managing teams selling $10k-$100k+ ARR deals.

• Experience in competitive, incumbent-heavy markets.

• Familiarity with AI-driven or technical products.

• Comfortable operating in ambiguity and building processes from scratch; we're not looking for someone who needs a fully paved road.

• Track record of hitting team quota through disciplined pipeline management, not just individual heroics.

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