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

• 69 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

Why now

We’ve built a strong AE bench and proven PMF. The next phase is scaling managers and process — this role helps turn what works today into a repeatable, high-performing sales org.

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

• Health, dental, and vision insurance

• Fun offsites (South Korea, Hawaii)

• Monthly SPIFFs (e.g. 49ers game, oura ring)

• Unlimited PTO (take what you need)

Compensation Range: $250K - $300K