Founding Enterprise Account Executive

• 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