Vice President of Sales

Position Summary

VSSTAVSSTA is seeking an executive builder to design, lead, and scale a predictable commercial revenue engine. This is a highly hands-on leadership role responsible for transforming a successful early-stage sales organization into a disciplined, repeatable, data-driven revenue operation capable of supporting the company's next phase of growth.

About the Role

This role is best suited for leaders who have personally built commercial organizations and not simply inherited mature sales teams. Key areas of ownership include:

• Build structure and accountability across the sales organization
• Drive consistent pipeline generation and forecast accuracy
• Scale a repeatable, metrics-driven sales motion
• Partner closely with Marketing and Partnerships to maximize demand generation

Success in Year One

• Establish a disciplined sales operating cadence with weekly pipeline inspections and accurate forecasting
• Improve pipeline conversion rates and sales velocity
• Implement a repeatable sales methodology and coaching framework
• Build and develop a high-performing SDR and Account Executive organization
• Successfully integrate partner-generated opportunities into the direct sales process
• Recruit, develop, and retain top-performing sales talent
• Deliver executive-level KPI visibility and predictable revenue performance

Why This Role Is Critical — And Unique

• VSSTA is transitioning from early-stage growth to scalable revenue execution
• The company has strong market demand and a differentiated offering but requires a sales leader to build pipeline discipline, develop a high-performing team, and create a scalable foundation for continued growth
• This role offers the opportunity to build and scale a revenue organization at a critical inflection point, influence executive-level decisions, and participate meaningfully in the next phase of value creation within a PE-backed environment

Key Responsibilities

• Revenue Builder
• Design and build a commercial operating system that creates predictable pipeline generation, disciplined execution, accurate forecasting, and repeatable revenue growth
• Set the bookings strategy and execution rhythm required to deliver consistent growth across new business channels
• Create visibility into pipeline health, conversion trends, and revenue risks, using data to drive corrective action quickly
• Establish a culture of accountability in which the team manages to outcomes, not activity alone
• Pipeline & Forecast Management
• Own forecast accuracy and pipeline coverage, with clear inspection routines and proactive risk management
• Implement disciplined CRM usage, opportunity qualification, and forecast methodology across the sales organization
• Run rigorous deal reviews and weekly inspection processes to improve visibility, conversion, and close predictability
• Create a culture of inspection where pipeline quality and deal progression are reviewed continuously — not just reported
• Player-Coach Leadership
• Lead from the front by actively participating in strategic opportunities, coaching live deals, and demonstrating the sales behaviors expected throughout the organization
• Coach sellers in real time on qualification, customer conversations, negotiation strategy, and closing execution — with focus on transactional SMB buyer dynamics
• Maintain credibility with customers, partners, and the internal team by staying close to the market and active deals
• Team Builder & Developer
• Recruit, onboard, and develop high-performing sales talent with clear expectations for pipeline, conversion, and bookings
• Train reps with a structured, repeatable sales methodology — focusing on skill-building and individual growth, not just quota enforcement
• Define performance standards, identify top talent, and act decisively on underperformance
• Develop future sales leaders through structured coaching, career development, and succession planning
• Process & Operations
• Design and continuously improve the commercial operating rhythm, including pipeline inspections, forecasting cadence, KPI reviews, and cross-functional execution
• Ensure sales infrastructure, reporting, and workflows support data-driven decision-making and execution
• Accountability & Ownership
• Own new business revenue performance through disciplined execution, transparent communication, and relentless accountability
• Address misses directly, diagnose root causes, and implement corrective actions without deflecting responsibility
• Market & Commercial Leadership
• Bring strong market understanding and translate customer insights into scalable commercial strategy
• Provide structured feedback on pricing, packaging, and competitive positioning
• Partner & Direct Channel Execution
• Lead a dual-engine go-to-market model integrating direct sales execution with partner-sourced pipeline
• Build a scalable motion that turns partner demand into measurable revenue contribution

Ideal Candidate Profile

• Proven experience building and scaling B2B revenue organizations in growth-stage or small company environments
• Hands-on experience in transactional sales — driving volume, velocity, and rep productivity in SMB-facing markets
• Experience in B2B SaaS, automotive technology, and/or selling into collision repair environments
• Demonstrated success training and developing sales reps with a structured sales methodology
• Proven success as a quota-carrying sales leader (player-coach)
• Experience with forecast rigor, pipeline discipline, and accountability frameworks
• Experience managing both direct sales and partner/channel-driven revenue models
• Strong CRM discipline and data-driven management approach (HubSpot preferred)
• Comfortable in a private equity-backed, high-accountability environment
• Employment stability — a track record of meaningful tenure in prior roles

CORE LEADERSHIP TRAITS

• Hands-on, player-coach leadership style
• Strong coaching and team development capability — focused on building skills, not just managing numbers
• Operational mindset with a focus on building repeatable systems
• Biased toward execution, accountability, and measurable results
• Ability to apply big-company sales discipline to a smaller, entrepreneurial environment
• Naturally curious, decisive, and thrives where leaders build rather than inherit

Location & Travel

This role is fully remote within the United States. Regular travel is required for customer engagements, field sales support, partner development, and industry events.

Compensation & Opportunity

• Competitive executive compensation with a target OTE of $250,000+ (base salary plus variable — not solely base)
• Significant upside tied directly to revenue growth and company performance
• Opportunity to play a meaningful role in scaling a high-growth, PE-backed business at a critical stage of expansion

Why Join VSSTA

If you're energized by building organizations, coaching teams, creating commercial discipline, and helping transform an emerging market leader into a predictable revenue engine, we'd welcome the opportunity to speak with you. Apply via LinkedIn, the Greybull Stewardship website, or send your resume to jennifer@greybullstewardship.com.