Founding Enterprise Account Executive

Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work – investigating, resolving, and acting on every signal across every channel that matters. Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself. We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io http://Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List https://www.enterprisetech30.com/. 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