Her Story
About Michelle
Michelle Weston is an accomplished technology executive with more than 37 years of experience leading large-scale IT modernization, digital transformation, and business strategy initiatives across both enterprise organizations and global systems integrators. Currently serving in business development at ISG (Information Services Group), she helps organizations leverage advisory services, AI-driven insights, and data analytics to optimize vendor management, strengthen governance, and reduce technology costs. Throughout her career, Michelle has held executive leadership positions including Chief Technology Officer, Chief Information Officer, and Chief Information Security Officer, delivering complex transformation programs for organizations across multiple industries.
Michelle's career began in a state government data center before advancing through leadership roles with organizations including IBM, TCS, DXC, AWS, Accenture, and now ISG. Her expertise spans cloud modernization, IT outsourcing, enterprise infrastructure, AI strategy, and technology governance. At ISG, she partners with clients to identify opportunities for operational improvement, benchmark technology investments, and achieve measurable cost savings—often ranging from 15 to 35 percent or more—through data-driven decision-making and strategic sourcing. Her customer-first approach earned her the prestigious Customer Obsession Award at AWS for successfully guiding a major client through a highly complex contract transition while building lasting executive trust.
Committed to lifelong learning, Michelle holds an associate's degree in Business Administration, a bachelor's degree in Ministry from Oceans Unite, a Project Management Certificate from George Washington University, multiple technical certifications including MCSE, and advanced certifications in infrastructure, applications, and leadership. She is passionate about helping organizations build secure, AI-ready technology foundations while mentoring teams through change and innovation. Guided by a servant leadership philosophy, Michelle is known for solving complex challenges, fostering collaboration, and creating lasting value for clients, colleagues, and the organizations she serves.
Her Interview
Ten minutes with Michelle
01What do you attribute your success to?
I attribute my success to building strong relationships and always following through on my commitments. Doing what I say I'm going to do builds trust, and trust creates opportunities. My background in customer service has also taught me the importance of understanding clients' needs and delivering an exceptional experience, which is something I genuinely enjoy.
02What’s the best career advice you’ve ever received?
The best career advice I've ever received is to never sell just to meet a number. Instead, focus on whether the solution is truly the right fit and adds real value for the client. When you lead with integrity and put the customer's needs first, the results—and the opportunities—will come back to you many times over.
03What advice would you give to young women entering your industry?
My advice to young women entering this industry is to choose a career path that aligns with your strengths and interests, whether that's technical, leadership, or sales. Be passionate about what you do, stay curious, and invest time in learning about the companies and opportunities available to you. The more prepared and knowledgeable you are, the more confident you'll be and the greater your potential for success.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges—and opportunities—in my field is ensuring that everyone is aligned on the goals they are trying to achieve before implementing a solution. Success comes from understanding the client's objectives, identifying the right strategy to meet those needs, and working together to reach a fair and mutually beneficial agreement. When there is alignment, trust, and a solution that delivers real value, everyone wins.
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