Founding Enterprise Account Executive

About this role

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 90 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 🏥 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