Pylon is a Series B, AI-native B2B company building the next generation of customer support.

Legacy platforms like Zendesk and Salesforce Service Cloud were built around tickets. Pylon is built around accounts, real-time collaboration, and AI-driven customer intelligence.

This is a massive market with incumbents that weren’t built for AI-first workflows.

Company

Series B, $51M raised
Backed by a16z, BCV, General Catalyst, Y Combinator
90+ employees
Offices in San Francisco and New York City

The Role

Manage and coach a team of 6-10 Account Executives
Help build, document, and scale our sales playbooks (commercial and upmarket)
Drive consistent execution across inbound and outbound motions
Partner closely with leadership to refine segmentation, quotas, and process
Lead deal reviews, pipeline inspection, forecasting, and performance management
Recruit AEs

Why now

We’ve built a strong AE bench and proven PMF. The next phase is scaling managers and process — this role helps turn what works today into a repeatable, high-performing sales org.

Requirements

2+ years managing SaaS AEs
Experience scaling a team beyond the “early reps” phase
Strong coaching instincts and operational rigor
Comfortable operating in ambiguity and building process from scratch
Based in SF or NYC and willing to work in-person

Nice to Haves

Experience managing teams selling $10k–$100k+ ARR deals
Experience in competitive, incumbent-heavy markets
Familiarity with AI-driven or technical products

Sales Stack

Salesforce
Scratchpad
Salesbricks

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

Sales Manager