Fractional Director of IT - Retail POS

A private equity-backed multi-location retail organization is seeking an experienced technology leader to guide a critical MSP evaluation, selection, and onboarding initiative while helping define the future-state technology strategy for the business.

This individual will serve as both a hands-on technology leader and trusted advisor to executive leadership and private equity stakeholders. The role requires a unique blend of infrastructure expertise, MSP management experience, deep retail technology knowledge, and the executive presence necessary to communicate effectively with sponsors, operating partners, and portfolio company leadership teams.

The ideal candidate has successfully supported multi-location retail environments, understands retail operations and point-of-sale ecosystems, and has experience operating within private equity-backed organizations where technology initiatives are closely tied to value creation, operational improvement, scalability, and growth objectives.

• Help Lead the evaluation, selection, negotiation, and onboarding of a Managed Services Provider (MSP) and Managed Security Services Provider (MSSP).
• Assess current-state infrastructure, retail technology platforms, support operations, cybersecurity posture, and technology architecture.
• Develop a future-state technology roadmap aligned to business objectives and private equity value creation priorities.
• Act as the primary technology advisor to executive leadership and private equity stakeholders throughout the engagement.
• Build and present business cases, investment recommendations, total cost of ownership analyses, and technology modernization plans.
• Oversee infrastructure modernization efforts including endpoint strategy, hosted desktop initiatives, cloud services, networking, security, and support model improvements.
• Evaluate and provide guidance on retail technology platforms, point-of-sale systems, store infrastructure, end-user computing environments, and multi-location support models.
• Establish governance, vendor management processes, service level expectations, and operational performance metrics for selected providers.
• Ensure technology decisions support scalability, operational efficiency, risk reduction, and future growth objectives.

• 10+ years of IT leadership, infrastructure consulting, CIO, Director of IT, or technology advisory experience.
• Hands-on experience with retail technology environments, including point-of-sale (POS) platforms, store technology, end-user computing, and distributed location support models.
• Significant experience working within private equity-backed organizations and partnering directly with sponsors, operating partners, boards, and executive leadership teams.
• Proven track record leading MSP evaluations, vendor selections, outsourcing initiatives, and technology transformations.
• Strong infrastructure background including cloud services, networking, cybersecurity, end-user computing, and enterprise technology operations.
• Strong financial acumen with experience developing business cases, investment recommendations, and cost optimization strategies.
• Executive-level communication skills with the ability to influence both business and technical stakeholders.

• Previous Director of IT, CIO, Interim CIO, Fractional CIO, or Technology Advisor experience.
• Experience supporting private equity value creation initiatives, technology assessments, and operational improvement programs.
• Experience with hosted desktop, VDI, thin-client, and endpoint modernization initiatives.
• Experience presenting directly to boards, sponsors, and private equity operating partners.