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