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 http://Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List https://www.enterprisetech30.com/.

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