Greg Callahan

About Greg Callahan

IT Leader | Strategic Sourcing & Procurement | Project ManagementAccomplished IT leader with 38 years of experience driving large-scale technology, sourcing, and outsourcing initiatives for Fortune 500 organizations. Recognized as an Information Technology Subject Matter Expert (SME) with PMP and COP certifications, I bring deep expertise in program and project management, strategic sourcing, IT procurement, outsourcing, and category management.I have led global IT procurement teams of 15–20 professionals, managing portfolios exceeding $1 billion and delivering measurable cost savings, operational efficiencies, and business value. Trusted advisor to C-level and senior IT leadership, I have successfully executed 50+ outsourcing initiatives, aligning enterprise technology transformations with corporate roadmaps and consistently surpassing business and financial targets.With over 25 years of project management experience, I excel in building, coaching, and leading high-performing teams across industries including financial services, consumer goods, professional services and manufacturing. My strengths include analytical rigor, structured problem-solving, and the ability to balance strategic vision with execution. Adept at managing complex stakeholder environments, I thrive in high-pressure settings where clarity, collaboration, and results are paramount.

Experience

1. Principal Consultant Subject Matter Expert

   It Sourcing Experts, Llc

   Jan 2022 — Present

   Results-driven IT leader specializing in program and project management, cost optimization, and strategic sourcing of IT products and services. Proven expertise in leading complex IT initiatives, aligning technology investments with business goals, and driving operational efficiency. Adept at managing large-scale programs, optimizing IT budgets, and executing high-value outsourcing and procurement strategies. Skilled in advising CIOs and CFOs, negotiating with top-tier vendors, and ensuring IT investments deliver long-term business value. Core Expertise areas include:CIO/CFO Advisory Services:• Develop and execute cost-saving strategies across IT domains, including IT Professional Services (ITPS), Software, Infrastructure, and Telecommunications.• Optimize IT budgets to enhance financial efficiency while maintaining operational effectiveness.IT Outsourcing & Vendor Management:• Design and implement customized outsourcing strategies aligned with business goals.• Manage end-to-end outsourcing engagements, including vendor selection, contract structuring, and performance oversight.IT Sourcing, Procurement & Category Management:• Lead IT sourcing initiatives, contract negotiations, and supplier relationship management.• Develop and execute IT category management strategies for cost control and risk mitigation.• Drive competitive renewals and renegotiations to optimize existing agreements.• Negotiate high-value contracts with leading providers such as Microsoft, SAP, Oracle, and industry-specific software and services vendors.Program & Project Management:• Oversee complex IT programs and projects, ensuring alignment with business objectives, budgets, and timelines.• Manage cross-functional teams and stakeholders to drive successful project execution and deliver measurable business outcomes.• Implement governance frameworks to mitigate risks, enhance transparency, and improve decision-making.

Education

• University of Cincinnati

  Associate Degree, Computer Programming

  1988 — 1988

• University of Cincinnati

  Bachelor Science, Information Systems

  1993 — 1993