VP of Sales
This is the employer's own posting, not a copy on a job board.
What we know
Is it still open?
Confirmed still open
Last checked 2d ago — checked against the employer's own applicant tracking system, which is the company answering directly.
We re-read the employer's own applicant tracking system and the posting was still there. That is the company answering directly.
How old is it?
Posted 2d ago
The date the source published, not the day we noticed it (2026-10-31). Last seen at its source 8h ago.
We have tracked this listing since 31 Oct 2026 (2 days). The employer's own board has carried it every time we have read it, most recently 8 hours ago.
Is it remote?
Remote (U.S. Only)
That is the location the employer filed this posting under. Quoted as written — we do not re-word the source's own location.
Who may apply?
United States
The description states no restriction of its own. This is the source's own tag.
Pay
$225k–250k/yr
Read out of the job description by us, not from a structured field. Shown in the posting's own currency and period; we never convert.
Skills named in the ad
Recognised terms only, from a fixed vocabulary — this is what CV matching compares against.
Carried by 1 source
-
Ashby employer's own board first seen 2d ago · last seen 8h ago
The listing
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..
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.