Post-covid, businesses have started shifting the way they communicate with customers from email to chat platforms like Slack, Microsoft Teams, and Discord. At Pylon, we are building a real-time customer operations platform to help support, success, and sales teams at places like Hightouch, Merge, and Sardine scalably meet their customers where they live.

Just like how Zendesk made email scalable in a support context, Mailchimp made email scalable in a marketing context, and Salesforce & Outreach made email scalable in a sales context, Pylon is making chat scalable across customer-facing functions.

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

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

🏥 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

We’re building an event-driven workflow engine powered by conversational data and layered with intelligence to help our customers run their operations in real-time.

Our tech stack: Golang, GraphQL, React, AWS.