IT transformation success starts with expert guidance from both sides of the table.
Windsor Group is a strategic IT advisory firm that specializes in aligning organizations with optimal vendor solutions. Drawing from our dual perspective, having sat on both sides of the table as clients and service providers, our team collaborates closely with IT leaders to define opportunities for cost reduction, service enhancement, and long-term strategic growth. From roadmap to partner selection, we support IT leaders through complex IT sourcing decisions with clear insights utilizing our competitive co-design approach.
Strategic IT decisions start with the right partner at the table.
Windsor Group empowers IT leaders to make smarter technology decisions through advisory services grounded in real-world experience. With a perspective shaped by time on both sides of the table—client and provider—we help organizations define priorities, evaluate partners, and chart a clear course for long-term success. Our co-design approach brings clarity, alignment, and lasting impact to every IT transformation.
Strategic IT decisions start with the right partner at the table.
Windsor Group empowers IT leaders to make smarter technology decisions through advisory services grounded in real-world experience. With a perspective shaped by time on both sides of the table—client and provider—we help organizations define priorities, evaluate partners, and chart a clear course for long-term success. Our co-design approach brings clarity, alignment, and lasting impact to every IT transformation.
IT transformation success starts with expert guidance from both sides of the table.
Windsor Group is a strategic IT advisory firm that specializes in aligning organizations with optimal vendor solutions. Drawing from our dual perspective, having sat on both sides of the table as clients and service providers, our team collaborates closely with IT leaders to define opportunities for cost reduction, service enhancement, and long-term strategic growth. From roadmap to partner selection, we support IT leaders through complex IT sourcing decisions with clear insights utilizing our competitive co-design approach.
We Optimize IT Operations to Address Business Challenges
By bringing our dual perspective to every engagement, we deliver powerful advantages:
From Managed Services to Hybrid Infrastructure and Business Process solutions, we create actionable roadmaps that simultaneously reduce operational costs and increase business value. We align IT initiatives with business goals, modeling outcomes before execution to reduce risk and improve impact.
We translate IT budgets and inventories into clear insights, creating customized dashboards that empower IT leaders to make confident, evidence-based decisions aligned with broader organizational objectives. Our business-first, technology-smart approach ensures smarter technology investments that support both immediate needs and long-term goals.
Our experts model the impact of potential changes before implementation, identifying scenarios that minimize disruption while maximizing ROI through optimal vendor partnerships. This helps strengthen vendor performance, providing insight and clarity to your improvement plans.
With our dual-perspective approach, extensive track record, and rigorous methodology, we actively reduce the uncertainties associated with vendor selection, ensuring cultural and operational alignment. We advocate for a strong selection process supported by a governance model that easily adapts to change.
Beyond typical IT advisory teams, Windsor Group offers something fundamentally different: collaboration, culture, and fit. Our ability to see beyond surface-level requirements is the essential connection between business strategy and technology execution. With this methodology, we bridge organizational silos, align stakeholders, and create technology partnerships that evolve with your business.
We adapt to our clients’ needs—whether they require a rapid assessment, a deep-dive financial analysis, or full-scale vendor negotiations.
We prioritize both strategic and cultural alignment in vendor selection, resulting in partnerships with greater stability, adaptability, and long-term value. We work with your IT teams and service providers, not over them, ensuring stakeholder buy-in and scalable solutions.
Windsor Group is comprised of seasoned IT executives (former CIOs, CTOs, and senior IT leaders) who remain hands-on from initial strategy through implementation, ensuring expert guidance at every step.
Our recommendations come from rigorous analysis, creating IT solutions that deliver measurable improvements today while supporting your evolution tomorrow.
Whether you’re dissatisfied with your current IT partnerships, looking to reduce operations costs to fund innovation, or considering external partnerships for the first time, our process keeps you in control.
We objectively assess your existing relationships, help negotiate improvements, and guide you through change when necessary.
For organizations to engage in external partnerships, we set clear expectations and careful cultural matching to ensure successful transitions.
We help shift your IT budget from operations to innovation while improving overall service quality and strategic alignment.
“Windsor Group delivered an exceptional new approach to IT vendor selection. Our goal was to reduce infrastructure costs to fund innovation projects. Windsor did a thorough assessment and suggested five managed services providers. With their help, we designed potential solutions and assessed culture fit. We ended up with a great solution at a great price, thanks to the seasoned advisors at Windsor Group.”
“We partnered with Windsor because they were transparent, technically knowledgeable, and thorough. They assessed both our IT environment and financials, helped us evaluate options beyond just switching vendors, and ultimately recommended providers that best fit our needs. From start to finish, they were responsive and supportive throughout the process”
“We worked with Windsor Group for two key engagements, and they really went above and beyond each time. They were hand-in-hand throughout the whole process, ensuring we obtained the best deal for our requirements. It can be challenging to structure a vendor agreement, but they had someone with us the whole time to make it as easy as possible. The team provides on-hand advice without charging additional fees for every interaction, which, as a client, really makes a big difference. We would never have found the service providers that we have in place now if it weren’t for Windsor Group.”
For over 40 years, our strategic IT advisory firm has transformed IT operations for Fortune 1000 organizations across all industries. From Insurance to Manufacturing and Energy & Resources, we co-create solutions that deliver both immediate cost reduction and long-term strategic advantage through our competitive co-design approach. Everything we do relates to your strategic goals, and our job is to ensure it works for your business, culture, and future.
Contact our advisory team today to schedule a no-obligation consultation and discover how our unique approach can help you reduce costs, enhance service quality, and create sustainable IT partnerships.
©Copyright 2025, All Rights Reserved.
©Copyright 2025, All Rights Reserved.