Pylon is a Series B, AI-native B2B 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

• Manage and coach a team of 6-10 Account Executives
• Help build, document, and scale our sales playbooks (commercial and upmarket)
• Drive consistent execution across inbound and outbound motions
• Partner closely with leadership to refine segmentation, quotas, and process
• Lead deal reviews, pipeline inspection, forecasting, and performance management
• Recruit AEs

Requirements

• 2+ years managing SaaS AEs
• Experience scaling a team beyond the “early reps” phase
• Strong coaching instincts and operational rigor
• Comfortable operating in ambiguity and building process from scratch
• Based in SF or NYC and willing to work in-person

Nice to Haves

• Experience managing teams selling $10k–$100k+ ARR deals
• Experience in competitive, incumbent-heavy markets
• Familiarity with AI-driven or technical products

Sales Stack

• Salesforce
• Scratchpad
• Salesbricks

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