VP of Sales

Gray Swan AI

9h•$225,000 - $250,000

About The Position

Gray Swan is hiring a VP of Sales to build and lead its enterprise sales organization and drive predictable, scalable growth. This is a hands-on build role: the VP will personally lead strategic deals while developing the team, processes, and systems needed for the company’s next stage of growth. The role owns new ARR and bookings, pipeline development, forecasting, sales-team growth, and sales operations, while partnering across the broader go-to-market organization.

Requirements

10+ years of B2B SaaS enterprise sales experience, including 3+ years leading sales teams.
Record of hitting or exceeding targets at an early-stage company; ideally, experience growing ARR from roughly $1–5M to $20M+.
Hands-on enterprise selling experience, including personally closing complex six- or seven-figure deals involving long sales cycles, technical evaluations, and procurement and security reviews.
Experience building sales processes, forecasting, compensation plans, and a CRM-driven operating rhythm.
Strong network across security and AI buyers, channel partners, and sales talent, with a focus on North America.
Comfort with ambiguity and enthusiasm for building rather than only managing an established sales organization.
Ability to communicate clearly with leadership and cross-functional peers, supported by data.

Nice To Haves

Experience as an early sales leader at a security startup that later scaled from early stage to an exit.
Familiarity with AI security and safety and the rapidly evolving AI landscape.

Responsibilities

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.
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 accountable to them.
Manage existing sellers and build a plan for how the team should grow over the next 12–18 months.
Partner with recruiting to source and close high-performing account executives.
Define territories, quotas, and compensation plans.
Partner with GTM operations to create onboarding, enablement, and coaching programs that help new representatives become productive quickly.
Build a high-performance, accountable, and inclusive sales culture.
Refine and improve the sales process and methodology, ensuring it is documented, repeatable, and scalable.
Work with GTM operations to refine and automate dashboards and forecasting.
Refine ICP and segmentation based on win/loss and other data.
Feed field insights back to Product and Marketing to shape the roadmap and positioning.

Benefits

401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health coverage
Dental coverage
Vision coverage
Catered lunches at the Pittsburgh office
Flexible work arrangements
Meaningful equity participation
Competitive compensation package with base salary targeted to $225,000–$250,000 plus commission ($450,000–$500,000 OTE)
Opportunity for outsized earnings driven by high inbound interest and large deal sizes