VP of Sales

Gray Swan

. Own new ARR and the overall bookings target .

Posted 10/31/2026full-timeRemote • United StatesLead💰 $225,000 - $250,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive B2B SaaS enterprise sales expertise, with a proven track record of leading sales teams and closing complex deals. Capable of building scalable sales processes, managing high-performance teams, and leveraging data for strategic decision-making.

Highest-signal resume keywords

B2B SaaS Enterprise Sales ExperienceSales Team LeadershipComplex Deal ClosingSales Process DevelopmentHubSpot Proficiency

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales ForecastingCompensation Plan DesignPipeline ManagementSales Methodology ImprovementData-Driven Decision Making

Soft Skills

Communication with LeadershipCollaboration with Cross-Functional TeamsComfort with AmbiguityTeam BuildingCoaching and Enablement

Tools & Technologies

HubSpotCRM SystemsDashboards Automation

Industry Keywords

Enterprise SalesARR GrowthSecurity Startup ExperienceAI Security and SafetyNorth America Market Focus

Tech Stack

Tools & technologies

AWSAzureCloudGoogle Cloud Platform

About the role

Key responsibilities & impact

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 partner teams across channel, services, technology alliances, and cloud marketplaces including AWS, Azure, and GCP
Set pipeline coverage targets and conversion benchmarks by stage
Manage existing sellers and plan team growth over the next 12–18 months
Recruit and close high-performing account executives
Define territories, quotas, and compensation plans
Create onboarding, enablement, and coaching programs with GTM operations
Build a high-performance, accountable, and inclusive sales culture
Improve and document scalable sales processes and methodology
Refine and automate dashboards and forecasting
Refine ICP and segmentation using win/loss and other data
Feed field insight back to Product and Marketing to shape roadmap and positioning

Requirements

What you’ll need

10+ years of B2B SaaS enterprise sales experience, with 3+ years leading sales teams
Record of hitting or beating targets at an early-stage company, ideally growing ARR from roughly $1–5M to $20M+
Hands-on enterprise selling experience, including personally closing 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
Experience with HubSpot
Strong network across security and AI buyers, channel partners, and sales talent, with a focus on North America
Comfort with ambiguity and building new sales functions
Ability to clearly communicate with leadership and cross-functional peers, backed by data
Familiarity with AI security and safety and the rapidly evolving AI landscape (nice to have)
Early sales leadership experience at a security startup that scaled from early stage to an exit (nice to have)

Benefits

Comp & perks

Meaningful equity participation
Flexible location within the United States
Opportunity for outsized earnings driven by high inbound interest and large deal sizes
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements