OverviewThe VP of Sales, Retail Solutions is responsible for leading and scaling Pomeroy's retail vertical, driving profitable growth across existing accounts and new logo acquisition. This leader will own a $114M business, with accountability for revenue performance, pipeline health, and expanding the 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.
Key ResponsibilitiesRevenue 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, with a focus 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
Candidate ProfileExperience- 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
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