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