Head of Enterprise Sales – AI Security & Growth

Gray Swan AI; United States; Remote; USD 225,000 - 250,000; Full time

Benefits offered by this job

401k with matching

28 days annual leave

Health, dental, and vision

Catered lunches (Pittsburgh office)

Flexible work arrangements

Job summary

Gray Swan AI is hiring a VP of Sales to lead our growing GTM team and build a best-in-class enterprise sales organization. You’ll own the number, build a qualified pipeline, and lead our sales team through the next growth phase.

This is a hands-on build role where you’ll close strategic enterprise deals early while designing the team, processes, and systems for scalable growth. Strong preference for experience with security AI buyers in North America.

Qualifications

• 10+ years of B2B SaaS enterprise sales experience, with 3+ years leading sales teams.
• Proven track record of hitting or beating targets at an early-stage company, growing ARR.
• Hands-on enterprise selling: closed complex six- or seven-figure deals with long cycles.

Responsibilities

• Drive revenue growth through new ARR and bookings targets.
• Build and manage a qualified pipeline across territories and accounts.
• Lead and scale the sales team and define territories, quotas, and compensation plans.
• Mature sales operations and refine processes, dashboards, and forecasting.

Skills

Enterprise sales

Leadership of sales teams

Forecasting

Strategic selling

North America network

Tools

HubSpot CRM

CRM processes

Job description

Gray Swan AI is hiring a VP of Sales to lead our growing GTM team and build a best-in-class enterprise sales organization. You’ll own the number, build a qualified pipeline, and lead our sales team through the next growth phase.

This is a hands-on build role where you’ll close strategic enterprise deals early while designing the team, processes, and systems for scalable growth. Strong preference for experience with security AI buyers in North America.