Head of Enterprise AI Security Sales — Remote

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

Benefits offered by this job

401k matching

28 days annual leave

Health, dental, and vision coverage

Catered lunches (Pittsburgh office)

Flexible work arrangements

Job summary

Gray Swan AI is seeking a VP of Sales to build and lead a best‑in‑class enterprise sales organization. You will own the numbers, build pipeline, and drive scalable growth while hands‑on in early deals and shaping the team, processes, and systems for the next growth phase.

You will lead a remote US team with a focus on enterprise customers, complex six- to seven-figure deals, and strong alignment with Marketing, Partnerships, and GTM operations to accelerate ARR growth.

Qualifications

• 10+ years of B2B SaaS enterprise sales experience.
• 3+ years leading sales teams.
• Hands-on enterprise selling with six- or seven-figure deals.

Responsibilities

• Own new ARR and bookings target; drive revenue growth.
• Lead and scale the sales team; build plan for growth 12–18 months.
• Structure territories; manage pipeline with Marketing and Partners.

Skills

Enterprise sales

Sales leadership

B2B SaaS

Forecasting

CRM (HubSpot)

Tools

HubSpot CRM

Job description

Gray Swan AI is seeking a VP of Sales to build and lead a best‑in‑class enterprise sales organization. You will own the numbers, build pipeline, and drive scalable growth while hands‑on in early deals and shaping the team, processes, and systems for the next growth phase.

You will lead a remote US team with a focus on enterprise customers, complex six- to seven-figure deals, and strong alignment with Marketing, Partnerships, and GTM operations to accelerate ARR growth.