VP of Sales, Retail Solutions

About the Role

Lead and scale Pomeroy’s retail vertical, driving profitable growth across existing accounts and new logo acquisition. Own a $114M business with accountability for revenue performance, pipeline health, and expanding adoption of higher-value services including Managed Services, Advisory & Consulting Services (ACS), and Smart Desk. This is a build-while-running role—inheriting an established team while elevating performance, strengthening sales discipline, and expanding beyond transactional selling into strategic, outcome-based solutions.

Responsibilities

• Revenue Leadership
  • Own and deliver $114M revenue target across the retail vertical
  • Drive a 70/30 balance of existing account growth and net new logo acquisition
  • Lead the shift toward higher-value offerings with a 25%+ attach rate across Managed Services, ACS, and Smart Desk
  • Ensure consistent pipeline coverage of 3–4x quota to support predictable growth
• Team Leadership & Performance
  • Lead a team of 8 sellers (growing to ~10), with full accountability for performance, hiring, and development
  • Execute a “rebuild while running” strategy—upgrade talent, elevate expectations, and drive accountability
  • Establish a high-performance culture grounded in pipeline creation, activity discipline, win rates, and deal quality
  • Conduct 90-day performance assessments and take decisive action where needed
• Go-To-Market & Vertical Strategy
  • Own and execute the retail vertical strategy, focusing on enterprise and mid-market accounts, particularly within grocery and large retail segments
  • Drive both named account growth and net new prospecting
  • Partner with Marketing to lead account-based marketing (ABM) and targeted pipeline generation efforts
  • Build industry presence through events, partnerships, and vertical plays
• Customer & Deal Leadership
  • Act as an executive sponsor across key accounts
  • Lead deal strategy, pricing, and solution shaping to maximize margin and long-term value
  • Expand relationships beyond product and professional services into strategic, multi-year service engagements
• Cross-Functional Alignment
  • Partner closely with Services leadership to improve alignment and drive growth in services-led solutions
  • Leverage shared Solution Architects and dedicated product resources to build differentiated solutions
  • Collaborate with Sales, Marketing, and Delivery to ensure alignment across the full customer lifecycle

What Success Looks Like

• Predictable, scalable growth with strong pipeline coverage (3–4x)
• Measurable expansion of Managed Services, ACS, and Smart Desk across the retail base
• Improved win rates and larger, more strategic deal sizes
• Upgraded team performance with clear accountability and consistent execution
• Strong alignment across Sales, Services, and Marketing

Requirements

• Bachelor’s degree required
• 10-15+ years of proven sales leadership experience in IT services and solutions, with deep exposure to the retail vertical (preferably grocery)
• Track record of leading enterprise and mid-market teams
• Demonstrated success in:
  • Growing and protecting existing revenue
  • Winning new logos
  • Expanding into higher-value, services-led engagements

Leadership Characteristics

• Builder mindset—comfortable transforming teams while delivering results
• Strong operator—drives pipeline discipline, forecasting rigor, and execution cadence
• Commercial leader—skilled in deal shaping, pricing, and complex negotiations
• Customer-first mindset with ability to engage at the executive level

Non-Negotiables

• Ability to:
  • Protect and grow the existing base
  • Prospect and win new business
  • Expand and cross-sell strategic services beyond transactional deals
• Experience building or upgrading teams in a performance-driven environment
• Strong hunting orientation combined with strategic account leadership