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.
CompanySeries B, $51M raised
Backed by a16z, BCV, General Catalyst, Y Combinator
90+ employees
Offices in San Francisco and New York City
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
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
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
Salesforce
Scratchpad
Amplemarket
Salesfinity
🏥 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
Skills Required
- 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
What We Do
Pylon is the modern alternative to Zendesk, optimized for B2B. We bring together everything a post-sales teams team needs including a ticketing system, B2B omnichannel integrations (Slack Connect, Microsoft Teams), modern chat widget, knowledge base, AI support bot, account management, customer marketing, and more.
