Pylon is a Series B, AI-native B2B SaaS 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.
Series B, $51M raised
Backed by a16z, BCV, General Catalyst, Y Combinator
69 employees
Offices in San Francisco and New York City
Own full-cycle sales for large, complex B2B accounts
Source a portion of your own pipeline through strategic outbound
Sell to post-sales, support, and success leaders at larger organizations
Lead multi-threaded discovery, exec-level conversations, and longer sales cycles
Run proof-of-value trials and close six-figure+ ARR deals
4+ years of SaaS sales experience
Experience closing $100-500k+ ARR deals
Proven ability to sell into competitive, incumbent-heavy markets
Strong discovery, deal orchestration, and executive presence
Based in SF or NYC and willing to work in-person
Experience selling support, success, or customer-facing platforms
Familiarity with AI-driven or data-heavy products
Experience helping build an enterprise motion at a growth-stage company
Salesforce
Scratchpad
Amplemarket
Salesfinity
Health, dental, and vision insurance
Fun offsites (South Korea, Hawaii)
Monthly SPIFFs (e.g. 49ers game, oura ring)
Unlimited PTO (take what you need)
Fast career growth (all leaders have been internally promoted)
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