VP of Sales

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

About Gray Swan

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.

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.

What You’ll Do

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 territories and target accounts.
• Partner with Marketing on ICP, buyer personas, messaging, and lead‑to‑opportunity handoffs.
• Collaborate with the partner team across channel, services (SIs, MSPs), technology alliances, and cloud marketplaces (AWS, Azure, GCP).
• Set pipeline coverage targets and conversion benchmarks by stage, and hold the team to them.

Lead and scale the sales team

• Manage our existing sellers and build out a plan for how the team should grow over the next 12-18 months.
• Partner with the recruiting team to source and close very high performing new account executives.
• Define territories, quotas, and compensation plans that reward the right behavior.
• Partner with GTM operations to create onboarding, enablement, and coaching programs that get new reps productive fast.
• Build a high‑performance, accountable, and inclusive sales culture.

Mature sales operations

• Refine and consistently improve our sales process and methodology; ensure it is well‑documented, repeatable, and scalable.
• Work with GTM operations to refine and automate dashboards and forecasting.
• Refine ICP and segmentation (mid‑market vs. enterprise, priority verticals) based on win/loss and other data.
• Feed field insight back to Product and Marketing to shape the roadmap and positioning.

Who You Are

• 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.
• Demonstrated ability to clearly communicate with leadership and cross‑functional peers, backed by data.

Nice to Have

• You were an early sales leader at a security startup that went on to scale (early stage to an exit).
• Familiarity with AI security and safety and the rapidly evolving AI landscape.

You’ll Thrive Here If You:

• Want to help define how enterprise AI safety and security software is sold.
• Enjoy learning innovative, technically advanced products and explaining them clearly to customers.
• Are motivated by ownership, accountability, and upside rather than rigid structure.
• Are excited by Gray Swan’s mission to help organizations deploy AI safely and securely.

What We Offer:

A competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.

• Base salary is targeted to $225,000-250,000 + commission ($450,000 - 500,000 OTE)
• Meaningful equity participation
• Flexible location within the United States
• Opportunity for outsized earnings driven by high inbound interest and large deal sizes

Benefits:

• 401k with up to 4% matching
• 28 days annual leave (vacation + holidays)
• Health, dental, and vision coverage
• Catered lunches (Pittsburgh office)
• Flexible work arrangements

Typical Interview Process

• Application review. We read everything.
• Recruiter Screen. We learn about you; you learn about us.
• Hiring Manager Interview.
• Role related assessment
• Experience & culture interview
• Reference checks. We’ll reach out to 3-5 references that you provide.
• Offer. If it’s mutual, we move fast.