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.
CompanySeries B, $51M raised
Backed by a16z, BCV, General Catalyst, Y Combinator
70+ employees
Sales team: 11 AEs, 6 SDRs
Offices in San Francisco and New York City
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
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
Sold into competitive markets
Experience selling to Support, Success, or Post-Sales teams
Familiarity with AI-driven products
Salesforce
Scratchpad
Salesbricks
🏥 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
Top Skills
What We Do
Pylon is the modern alternative to Zendesk, optimized for B2B.
We bring together everything a post-sales teams team needs including a ticketing system, B2B omnichannel integrations (Slack Connect, Microsoft Teams), modern chat widget, knowledge base, AI support bot, account management, customer marketing, and more.
