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Flagship Strategic Services LLC
"People conceive. People believe. AI helps achieve. We do transformation. And the mission is always the people moving toward it together."
About Us
Flagship Strategic Services delivers experienced strategic leadership for IT and AI transformation initiatives across mid-market and large organizations. We serve as a true strategic partner, not a technology vendor, providing independent judgment, executive-level guidance, and program leadership to ensure complex technology investments translate into measurable business outcomes.
Our role is to help organizations bridge the gap between vision and execution—ensuring that strategy, structure, leadership alignment, and operational readiness are in place before and during transformation. We focus on reducing risk, improving decision-making, and increasing the likelihood of successful delivery in high-stakes technology initiatives.
Whether you are planning a major AI or IT transformation, or managing an initiative that requires experienced external leadership to stabilize, guide, or recover performance, Flagship Strategic Services brings the clarity, discipline, and expertise needed to move initiatives forward with confidence.
Contact us to learn how we can support your transformation journey.
Our Story
Kim Michele Flagstad
President & CEO, Flagship Strategic Services, LLC
Chicago, Illinois
Kim Michele Flagstad is a seasoned technology executive with more than 35 years of experience leading complex IT and AI transformation initiatives across financial services, manufacturing, distribution, legal, engineering, agriculture, and nonprofit sectors. Her work is grounded in a core principle: technology is rarely the hardest part of transformation. Success depends on the organizational conditions surrounding it—leadership alignment, structural readiness, and the human dynamics that ultimately determine whether a technology investment delivers on its promise.
Kim began her career in 1980 as the fifth employee of the Zenith Data Systems sales organization, prior to the emergence of the IBM PC. She went on to lead Zenith Distributing Company of Illinois to the #1 global ranking in ZDS distribution from 1983 to 1985. She later built RMI Network Services into the #1 Novell dealer worldwide, a position the company held from 1985 through 2003, earning six Novell National Support Excellence Awards and achieving Novell Platinum Dealer status. During this time, she also served on the Novell Platinum Council under the leadership of CEO Eric Schmidt.
In 2003, Kim founded Flagship Integration Services, Inc., a Microsoft Gold Partner specializing in complex, mixed operating system transformation initiatives. She also founded FIS Tracking Services, LLC, one of the first GPS race tracking companies in North America. In 2008, she established Flagship Strategic Services, LLC to provide vendor-agnostic, independent strategic advisory services for organizations seeking experienced leadership across all phases of IT transformation.
Kim holds a double major in History and Philosophy & Religion from Rollins College. She is a recipient of both the Omicron Delta Kappa Scholarship—awarded for distinguished leadership, scholarship, and service—and the Algernon Sydney Sullivan Award, one of the most prestigious honors in American higher education, recognizing exemplary character and commitment to serving others.
Her liberal arts education shaped a lifelong belief that the ability to think critically, analyze deeply, and synthesize across disciplines enables continuous learning and effective leadership. This perspective continues to inform her approach to guiding organizations through complex transformation.
Kim works remotely and throughout the Chicago metropolitan area, with selective travel for strategic engagements.
Areas Served
Lake County, IL | Cook County, IL | McHenry County, IL | Deer Park, IL | Barrington, IL | Chicago, IL | Schaumburg, IL | Elgin, IL | Lake Zurich, IL | Long Grove, IL
What We Offer
Our Specialties include:
- IT Consultant
- Computer Consultant
- 24/7 Help Desk
- 24/7 Network Operations Center
- 24/7 Security Operations Center
- Data Center Projects
Our Services include:
- 24/7 User Support
- BOIR Business Reporting
- Security Operations Center
- Exchange Email Hosting Services
- Office 365 License Management Services
- Office 365 Backup Services
- Cloud Based Backup and Disaster Recovery
- Unified Communication Services
- Mobile Device Management
- Managed Print Services
- Virtual Desktop as a Service
- CIO/CTO Management
- Enterprise IT Strategic Assessment
- Enterprise Infrastructure Assessment
- Enterprise Security Design and Process Management
- Cloud Hosting and Infrastructure Design
- Cloud Implementation and Support
- Wide Area Network Design
- Enterprise Mobile Computing Design, Implementation, and Support
- Wireless Architecture Design, Implementation, and Support
- Wiring Design, Implementation, and Support
- Project Implementation and Support
- IT or ERP Project Readiness Assessments
- IT Process Development
- IT Portfolio Management
- Project Management
Our Brands include:
Testimonials
On 4/15/2023
Joseph McGinnis
had this to say:
For more than five years, I have enjoyed the security of knowing that the Flagship Team is available to respond to my computer concerns. I have always received prompt response by knowledgeable and patient technicians who have successfully assisted with all levels of my business IT needs. I highly recommend the Flagship Team to anyone who wants sound prompt professional IT support
Testimonial written by Joseph McGinnis on this site.
On 3/28/2023
Alan C. (Chicago, IL)
had this to say:
The many years of expertise that Kim provides enables my team to focus on our business and be assured when an IT issue occurs, it will be taken care of properly.
Testimonial written by Alan C. (Chicago, IL) on this site.
On 3/28/2023
Anonymous
had this to say:
Working directly with Kim regarding our IT support, she is responsive, detailed and thorough. This results in allowing me to run my business and not have to worry about IT issues that can and will arise.
Testimonial submitted anonymously directly to this site.
On 3/22/2023
C. J. Enterprise
had this to say:
We've been working with the Flagship team for the last 12-13 years and they have always proven themselves to be conscientious, thorough, reliable and extremely responsive. I highly recommend them to anyone seeking a experienced, professional IT support team.
Testimonial written by C. J. Enterprise on this site.
On 3/19/2023
Kirsten R.
had this to say:
Flagship is a fabulous company that really cares about their customers. Responsive, timely and excellent work!
Testimonial written by Kirsten R. on this site.
Contact Us
Flagship Strategic Services LLC
Deer Park, IL 60010
Phone: (888) 578-3088
Email: transformation
Serving U.S. and international clients
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Our Hours
Holiday Hours May Vary. Please Call For Details.
Monday: 12:00 AM - 12:00 AM By Appointment Only
Tuesday: 12:00 AM - 12:00 AM By Appointment Only
Wednesday: 12:00 AM - 12:00 AM By Appointment Only
Thursday: 12:00 AM - 12:00 AM By Appointment Only
Friday: 12:00 AM - 12:00 AM By Appointment Only
Saturday: 12:00 AM - 12:00 AM By Appointment Only
Sunday: 12:00 AM - 12:00 AM By Appointment Only
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