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Name: Flagship Strategic Services LLC
Address: Deer Park, IL, 60010, US
Telephone: (888) 578-3088

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MSP SERVICES

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
Deer Park, 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. We were 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

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
CIO/CTO Management
Enterprise IT Strategic Transformation
Enterprise Infrastructure Transformation
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
Transformation Readiness Assessment
Transformation Design and Program Leadership & Rescue and Recovery
AI and IT Strategy Advisory
Fractional CIO and Strategic Leadership

Our Brands include:

Microsoft
Intermedia
Barracuda
Fortinet
Google
Citrix
Dell
HP
Comcast
Infrascale

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@flagshipis.com

SERVING MID-MARKET AND ENTERPRISE CLIENTS NATIONWIDE

Where To Find Us

Our Hours

Holiday Hours May Vary. Please Call For Details.

Monday: Available by Appointment — Contact Us to Schedule
Tuesday: Available by Appointment — Contact Us to Schedule
Wednesday: Available by Appointment — Contact Us to Schedule
Thursday: Available by Appointment — Contact Us to Schedule
Friday: Available by Appointment — Contact Us to Schedule
Saturday: Available by Appointment — Contact Us to Schedule
Sunday: Available by Appointment — Contact Us to Schedule

News

On 7/13/2026 this was posted:
⚡ Powering IT Transformation in Energy Engineering
Flagship Strategic Services LLC delivered a headquarters IT transformation for Sargent & Lundy, a globally recognized engineering firm in power generation and energy.
🔹 Total engagement value: $500,000
Supporting mission-critical infrastructure with forward-thinking solutions.
Image suggestion: Power plant, engineering team, or energy infrastructure visuals.
Expires 7/12/2027

On 7/6/2026 this was posted:
⚖️ Transforming Technology for Legal Excellence
Flagship Strategic Services LLC completed a technology readiness assessment and headquarters network transformation for Seyfarth Shaw LLP, a leading Chicago-based international law firm.
📊 Total engagement value: $750,000
Delivering scalable, future-ready IT solutions.
Image suggestion: Corporate law office interior or skyline view of Chicago with office setting.
Expires 7/5/2027

On 6/29/2026 this was posted:
💼 Long-Term Financial Technology Leadership
Flagship Strategic Services LLC continues to support Old Second Bancorp with ongoing IT transformation and advisory services.
💡 Annual engagement value: ~$1.5M
🤝 Trusted partnership spanning 15+ years
Driving innovation and stability in financial services technology.
Expires 6/28/2027

Info

Industries & Awards

FAQ

Managed IT Services

For organizations that need experienced, reliable technology operations support on an ongoing basis — Flagship Strategic Services provides managed services that reflect the same operational discipline and accountability we bring to every transformation engagement.

Our managed services practice is a natural complement to our transformation work. We manage what we scope. We scope what we can deliver. Service levels, response times, and deliverables are defined clearly before any engagement begins.

24/7 Security Operations and Cybersecurity Assurance

Continuous monitoring, threat detection, and response for organizations where security cannot wait for business hours. Services include vulnerability scanning and patch management, endpoint detection and response, email security and spam filtering, and backup and disaster recovery testing.

For organizations operating in regulated environments — Flagship configures and maintains IT environments to support HIPAA, SOC2, and PCI-DSS compliance requirements. Formal certification and compliance auditing is performed by qualified independent third-party vendors. Flagship implements and applies any remediation items identified through the certification process to the supported environment.

24/7 Network Operations and Server Management

Around-the-clock monitoring and management of your network infrastructure, servers, and data center environment. Services include cloud infrastructure management across Azure and AWS environments, virtualization and storage management, business continuity planning, proactive maintenance, and rapid response to alerts. Disaster recovery support ensures continuity when it matters most.

24/7 Help Desk and Workstation Management

End-user support and workstation management for organizations that need reliable, responsive technical assistance at any hour. Services include mobile device management, software licensing management, and onboarding and offboarding support. We resolve issues quickly, manage devices proactively, and keep your workforce productive.

Service Level Agreements

All Flagship Strategic Services managed services engagements are governed by clearly defined Service Level Agreements established and documented before services begin.
SLAs define response and resolution time commitments by issue severity — critical, high, medium, and low priority. Staffing and resources are allocated based on contracted SLA levels. Clients receive the response capability they have contracted and budgeted for.

Escalation to a higher service level is available through contract amendment. Flagship does not commit to response capabilities beyond what has been contracted and staffed for each specific engagement.
Monthly performance reporting against defined SLA metrics is provided as standard.

All Managed Services

All managed services engagements are scoped carefully at the outset with clearly defined service levels, response times, and deliverables. New requirements are handled as separate nested engagements protecting the original scope and fee structure.