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 designed for AI-first workflows.

Company

Series B, $51M raised
Backed by a16z, BCV, General Catalyst, Y Combinator
90 employees
Sales team: 11 AEs, 6 SDRs
Offices in San Francisco and New York City

The Role

Own full-cycle sales for inbound and outbound opportunities
Source a portion of your own pipeline via outbound
Sell to B2B tech companies (<500 employees), with exposure to larger accounts over time
Run discovery, demos, trials (1–2 weeks), and close

Requirements

2+ years of SaaS sales experience
Experience selling $10k–$100k ARR deals
Comfortable with outbound prospecting
Able to sell differentiated, technical products
Based in SF or NYC and willing to work in-person

Nice to Haves

Sold into competitive markets
Experience selling to Support, Success, or Post-Sales teams
Familiarity with AI-driven 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

Account Executive