Head of Enterprise Sales & Growth (Remote/US)

Gray Swan AI; Oregon; Hybrid; USD 225,000 - 250,000; Full time

Benefits offered by this job

Equity participation

Flexible US location

High earnings potential

401k with match

Health/dental/vision

Paid time off

Catered lunches

Job summary

Gray Swan AI is seeking a VP of Sales to join our growing GTM team and help build a best-in-class enterprise sales organization that drives predictable and scalable growth. You'll own the numbers, build qualified pipeline, and lead our sales team through early deals while shaping structure and processes for the next growth phase.

This role requires hands-on enterprise selling, with a track record of closing six- and seven-figure deals and expanding ARR.

Qualifications

• 10+ years in B2B SaaS enterprise sales
• Proven record closing six- to seven-figure deals
• Experience building sales processes and CRM rhythms
• Strong North America network in security/AI buyers

Responsibilities

• Drive revenue growth
• Own new ARR and the bookings target
• Deliver accurate weekly and quarterly forecasts
• Personally lead and close strategic enterprise deals
• Build and manage qualified pipeline
• Structure territories and target accounts
• Partner with Marketing on ICP, buyer personas, messaging, and lead-to-opportunity handoffs
• Collaborate with partner teams across channel and cloud marketplaces
• Lead and scale the sales team
• Mature sales operations and dashboards/forecasting

Skills

Enterprise sales leadership

Forecasting & pipeline management

CRM proficiency (HubSpot)

Strategic deal closing

Team building & coaching

North America market focus

Tools

HubSpot CRM

Job description

Gray Swan AI is seeking a VP of Sales to join our growing GTM team and help build a best-in-class enterprise sales organization that drives predictable and scalable growth. You'll own the numbers, build qualified pipeline, and lead our sales team through early deals while shaping structure and processes for the next growth phase.

This role requires hands-on enterprise selling, with a track record of closing six- and seven-figure deals and expanding ARR.