Founding Enterprise Account Executive

Pylon•San Francisco, CA

3d•Onsite

About The Position

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

Responsibilities

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