Justin McDermott, VP of IT Strategy and Special Projects, Wintrust Financial


There is no better feeling than the “Ah-ha” moment when you solve a puzzle. Strategy has drawn me into a remarkable career path. What better job than to have the opportunity to solve puzzles every day, leading into progressively larger puzzles for the grand finale “Ah ha” moment. My friends would say, and I would agree, that I am an inquisitive person. I’ve taken those skills and used them in my professional life to do root cause and critical path analysis, helping me shape and develop solutions that are flexible and agile but have continuity and a north star to follow. At the same time, I love learning new things, how things work, and history. I take what I’ve learned and continuously apply that to situations, asking, “What if?”. This is all great in theory, but if you cannot communicate it, it’s just idea’s in one person’s head. I’ve spent a great deal of time refining my soft skills to help share in plain language and helping people understand topics using the target audience’s language. The Rosetta Stone of IT language to Business language.

I spent most of my early career in the United States Army stationed in Germany. I deployed to support US Central Command doing network administration and satellite communications. Afterward, I moved on to finishing out School at DePaul and spent some time advocating on the Illinois Board of Higher Education. After school, I entered the corporate world focusing on Network Security and expanded out into Security Architecture and then into IT management, culminating in IT Strategy and thought leadership.



David Swierzynski, Vice President of Business Solutions Architecture, Gallagher Bassett Services


David Swierzynski is an accomplished Senior IT Executive with 28+ years of Insurance expertise in the areas of Finance, Managed Care, Banking, and E-commerce Portfolios.


David is currently the Vice President of Business Solutions Architecture at Gallagher Bassett Services in Rolling Meadows, IL. He has held several key Leadership roles throughout his career and has been responsible and accountable for several Organizations within Gallagher Bassett. Some key positions include the Vice President of Application Development and Maintenance, where Dave guided and lead several Development Teams that primarily focused on Claim payments, Banking, International Banking, Managed Care, E-bill processing, and dotcom development. David also held the position of Vice President of Business Analysis where he guided and lead the Business Analysts to create an environment that standardized Business Requirements documents, created requirements traceability matrixes, and created a Business Analysis Center of Excellence for the Organization. David later took over the Quality Assurance Organization as well as the Vice President of Quality Assurance and Testing. David’s leadership created an environment that cultivated comprehensive testing solutions along with modernized automated testing scripts and the development of regression test case scenario libraries. These key items directly contributed to a reduction in defect density and an increase in defect free software deployment.


After establishing the foundation for these Organizations, David became the Vice President of IT Portfolio Management. Under David’s direction and guidance, he established partnerships with the Business Organizations that were previously nonexistent. David assisted individuals and Organizations define and scope their IT Initiatives and Business Priorities by asking insightful questions, scoring intake requests, understanding requirements, and coaching Corporate alignment while building and strengthening Partnerships and Alliances throughout the Organization. David felt that this role awarded his Team and himself to be responsible and accountable for the direction of the Strategic and Tactical Initiatives while ensuring capacity bandwidth and demand constraints were aligned in the most optimal and efficient manner. David’s current role as the Vice President of Business Solutions Architecture has allowed him to have oversight on several key initiatives that allow him to draw from his vast knowledge and expertise and provide proven guidance in the implementation solutions of these Strategic goals.


David feels the three pillars of any successful Team can be defined and supported by Attitude, Communication, and Trust. If you demonstrate these traits in a positive way, your Team will take you above and beyond your wildest expectations! David was recently quoted in an article, “It’s not what you ask a person to do for you, it’s how you ask it! I have been so very fortunate and blessed to have had the opportunity to work with such amazingly dedicated professional individuals who I am honored to have as friends! ”