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 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

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.