Founding Enterprise Account Executive

Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work – investigating, resolving, and acting on every signal across every channel that matters.

Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself.

We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List.

The Role

• Be Pylon's founding enterprise AE, building and owning our enterprise motion from the ground up.

• Own full-cycle sales for large, complex B2B accounts — from multi-threaded discovery through executive-level negotiation and close.

• Source a meaningful share of your own pipeline through strategic outbound. This is a build-and-sell role: you're not waiting on a BDR team to hit your number.

• Sell to post-sales, support, and success leaders at larger organizations, running proof-of-value trials that close six-figure+ ARR deals.

• Define what "enterprise" means at Pylon — the playbook, positioning, and process other AEs will follow as the motion scales.

• As the segment proves out, help shape how we hire and build our first enterprise sales team. You're not filling a seat here, you're building it.

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

• 4+ years of full-cycle SaaS sales experience, with a track record of closing $100k-$500k+ ARR deals.

• Proven ability to sell into competitive, incumbent-heavy markets against entrenched vendors.

• Strong multi-threaded discovery, deal orchestration, and executive presence — comfortable running a room of VPs and above.

• Genuinely comfortable with outbound — you build pipeline, you don't just work what's handed to you.

• Based in SF or NYC and willing to work in-person.

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