Startups · AI

VP of Sales

Grayswan · Remote (U.S. Only) · Remote

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About Grayswan

Gray Swan provides enterprise-grade security solutions for LLMs, developed by the pioneers of AI vulnerability research. Deploy AI with confidence using just two lines of code. Backed by Madrona.

About the role

We’re hiring a VP of Sales to join our growing GTM team and help us build a best-in-class enterprise sales org that drives predictable and scalable growth. You'll own the number, build qualified pipeline, grow and lead our sales team, and be directly involved in key strategic opportunities. This is a build role. You'll be hands-on in deals early on while designing the team, process, and systems that carry us through our next iteration of growth. Found on 1752vc Careers, the job board for startup and VC roles.

What they're looking for

  • 10+ years of B2B SaaS enterprise sales experience, with 3+ years leading sales teams
  • A record of hitting or beating targets at an early-stage company, ideally growing ARR from roughly $1–5M to $20M+
  • Hands-on enterprise selling: you've personally closed complex six- or seven-figure deals with long cycles, technical evaluations, and procurement and security reviews
  • Experience building sales process, forecasting, comp plans, and a CRM-driven operating rhythm (we use HubSpot)
  • A strong network across security and AI buyers, channel partners, and sales talent, with a focus on North America
  • Comfort with ambiguity: you're energized by building, not just managing an existing machine
More about this role

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.

We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..

Learn more about how we work .

We’re hiring a VP of Sales to join our growing GTM team and help us build a best-in-class enterprise sales org that drives predictable and scalable growth. You'll own the number, build qualified pipeline, grow and lead our sales team, and be directly involved in key strategic opportunities.

This is a build role. You'll be hands-on in deals early on while designing the team, process, and systems that carry us through our next iteration of growth.

Drive revenue growth

Own new ARR and the overall bookings target.

Deliver accurate weekly and quarterly forecasts.

Personally lead and close strategic enterprise deals while the team ramps.

Partner with the broader GTM team on renewals and net revenue retention.

Build and manage qualified pipeline

Structure...

Read the full posting on Grayswan's site ↗

Sales

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