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.

Company

• Series B, $51M raised

• Backed by a16z, BCV, General Catalyst, Y Combinator

• 69 employees

• Offices in San Francisco and New York City

The Role

• 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

Requirements

• 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

Nice to Haves

• 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

Sales Stack

• Salesforce

• Scratchpad

• Amplemarket

• Salesfinity

Benefits

• 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)