Founding Enterprise Account Executive

Pylon

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.

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.