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
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Series B, $51M raised
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Backed by a16z, BCV, General Catalyst, Y Combinator
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100+ employees
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Offices in San Francisco and New York City
The Role
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Manage and coach a team of 6-10 Account Executives
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Help build, document, and scale our sales playbooks (commercial and upmarket)
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Drive consistent execution across inbound and outbound motions
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Partner closely with leadership to refine segmentation, quotas, and process
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Lead deal reviews, pipeline inspection, forecasting, and performance management
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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
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2+ years managing SaaS AEs
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Experience scaling a team beyond the “early reps” phase
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Strong coaching instincts and operational rigor
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Comfortable operating in ambiguity and building process from scratch
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Based in SF or NYC and willing to work in-person
Nice to Haves
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Experience managing teams selling $10k–$100k+ ARR deals
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Experience in competitive, incumbent-heavy markets
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Familiarity with AI-driven or technical products
Sales Stack
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Salesforce
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Scratchpad
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Salesbricks
Benefits
🏥 Fully covered medical, dental, and vision insurance for employees