About Us
Our History
Since 1975, GCG Financial, LLC, has been a trusted partner for our clients. Our mission has been to enhance the financial security of the businesses and families we serve through exceptional employee benefits, risk management, and wealth management solutions.
In 2017, GCG Financial and 23 other like- minded, entrepreneurial firms came together to form Alera Group. Since then, Alera Group has grown to become the 11th largest independent insurance and financial services firm in the nation with over 4,000 employees, 180 firms, and thousands of clients across the country.
In 2022, we officially began embracing the Alera Group brand. What remains consistent is holding our clients at the core of our business; we focus on bringing personalized solutions, expanding our capabilities, and deepening our resources nationally.
Our Team
Trusted. Smart. Passionate.
Our team has a sincere commitment to the long- term success of our clients. With an emphasis on collaboration and teamwork, we create unique solutions that fit the distinct needs of each client. We are passionate about doing what is right for every client, driven by the highest standards of professionalism, ethics, integrity, character, fairness, trust, and confidence.
Our Presence
Our clients benefit from the expertise and resources of a large national firm, while still maintaining the advantages of local service and relationships. We leverage powerful relationships, industry experience, and resources with the goal of supporting our clients’ business strategies and elevating the experience of working with us.
Above all, our firm believes in empowering people – our clients, our team, and the individuals in the communities where we live and work.
We are headquartered in Deerfield, IL, with offices throughout Illinois and Colorado, along with more than 150 Alera Group locations across the country. Wherever you are, we can meet your needs.
Investment advisory services offered through Alera Investment Advisors, LLC. Securities offered through Osaic Wealth, Inc. member FINRA/SIPC. Osaic Wealth is separately owned and other entities and/or marketing names, products or services referenced here are independent of Osaic Wealth.
Meet Our Team
Kyle Orr
Senior Benefits Consultant | Employee Benefits
Since Kyle joined the firm in 2013, he has worked with a variety of clients, ranging from manufacturing corporations to law firms. He believes that all industries can offer thorough yet affordable employee benefits packages when working with a broker whose goal is to meet the needs of their clients.
Kyle has specialized in serving the mid-market segment and works with clients across the country. He has developed considerable expertise in working with multi-locations companies and those growing through acquisition, specifically organizations working with PEOs (Professional Employer Organization). Kyle has 18 years of experience working in the PEO world and has strategic partnerships to help ensure his clients are receiving the best service and price available.
A graduate of the University of Illinois and originally from Buffalo Hart, IL, Kyle has lived in Denver, CO since 2010.
He enjoys basketball, hiking, staying fit, and spending time with his dog Norman. Kyle is also an active member of the development committee for Denver Kids. Denver Kids is a local non-profit assisting at risk youth in the Denver Public School system and providing them with a path to graduation and advanced degrees.
Education: B.A., Ornamental Horticulture, University of Illinois in Champaign-Urbana.
Jesse Pleuss, MBA, CBC
Vice President, Employee Benefits
Jesse Pleuss joined Alera Group in 2005 and works extensively with Corporations, School Districts and not- for-profit, in areas of strategic and innovative management of their employee benefits. Consulting and advising organizations in the evaluation, implementation and communication of their employee benefit plans is his expertise. He focuses on employee communication by leveraging resources and proprietary tools to help employees make better healthcare decisions.
Jesse’s goal is to make sure his clients are receiving thoughtful, expert advice and the tools they need to address increasing costs and regulatory and compliance law risks. With more than 25 years of healthcare experience, Jesse helps his clients build both short and long-term objectives in a unique “play-book process”. A member of the Alera Advanced Healthcare Strategy Impact Group, Jesse keeps his skills sharp. He continues to lead both his clients and cohorts in implementing some of the most innovative health plans in the country.
Jesse began his career as a District Sales Manager for American Medical Security that specialized in small group health plans, where he consistently led the nation in new business development and retention. Later he worked with PPO network company Private Healthcare Systems (PHCS), where he partnered with large national employers, insurance carriers and third-party administrators. Jesse has a very deep understanding of the many facets in healthcare services, which bodes well for his client’s in representing their interests.
Jesse received his bachelor’s degree in Marketing from St. Mary’s University of Minnesota where he also participated at collegiate level in both hockey and soccer. He later received his MBA from Elmhurst College and is a Charter Benefits Consultant (CBC). Jesse is active in many charities and service organizations including Park Ridge Rotary, St. Paul of the Cross Men’s Club and Rawhide Boys Ranch of Wisconsin,
Jesse lives in Park Ridge, Illinois with his wife Patty. They have two children, Declan and Maizie. Away from work Jesse enjoys going to his children’s sporting events, playing hockey and family time in Wisconsin.
Shelly Rabin
Senior Benefits Consultant | Employee Benefits
Shelly Rabin is a Senior Benefits Consultant at the firm with over 30 years of experience writing and servicing small group benefits, individual medical plans, and Medicare supplement plans. Among other things, her responsibilities include serving as the first point of contact for small group account specialists with complex issues, working with her team to troubleshoot challenges and identify solutions, and managing a book of small group accounts.
Shelly received her Bachelor of Arts in Communications with a specialty in interpersonal communication from The University of Wisconsin- Madison.
Brent Rosen, CBC
Senior Partner, Benefits Consulting | Employee Benefits
Brent Rosen is a Senior Partner of Benefits Consulting. Since joining the firm, Brent has specialized in serving the mid-market segment and works with clients across the country. Brent supports multiple middle-market private equity firms as they work to achieve economies of scale and deliver value to their portfolio companies with respect to benefit plan enhancements, cost savings, and acquisition due-diligence.
Brent has developed considerable expertise in working with multi-location companies, and those growing through acquisition. Brent also functions as the Co-Managing Broker for the firm’s Veterinary Employee Benefits Practice and has served proudly as the American Animal Hospital Association’s (AAHA) preferred provider for employee benefits since 2009.
In addition to group medical and ancillary lines of insurance, Brent also works to provide expert and objective guidance with respect to 401(k) and other salary-deferral plans, pension and profit-sharing plans, deferred-compensation plans, and executive benefits. Brent has also earned the Chartered Benefits Consultant (CBC) designation, provided by the National Association of Alternative Benefits Consultants, which demonstrates his expertise in Consumer-Driven Health Plans.
Brent provides a unique strategic perspective to employee benefits with a focus on long-term sustainability of his clients’ plans. Brent’s practice is built on a foundation of education and believes his focus on educating his clients’ employees and their benefit administrators has been a key factor in his success.
Brent is a graduate of Indiana University and spent a semester abroad in Florence, Italy. Originally from Cleveland, Ohio, Brent has lived in Chicago since 2002. He enjoys playing guitar, exercising, reading, cooking, and is an enthusiastic world traveler. Brent is also an active member of the firm’s Hardly Riders Team and participates annually in a nationwide charitable ride that raises money for research for rare cancers.
Education: B.S. Finance, Kelley School of Business, Indiana University
Investment advisory services offered through Alera Investment Advisors, LLC. Securities offered through Osaic Wealth, Inc. member FINRA/SIPC. Osaic Wealth is separately owned and other entities and/or marketing names, products or services referenced here are independent of Osaic Wealth.
Resources
EXPERT EDUCATION
Events and Webinars
Employee Benefits
Navigating Medicare: Educational Webinar
The knowledgeable team at Alera Group is here to help you navigate your Medicare options to ensure you feel confident in your post-65 healthcare coverage.
November 12, 2025 at 12:00 pm CT | Virtual
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THOUGHT LEADERSHIP
Insights
Employee Benefits
Legal Alert: Agencies Clarify How Certain Fertility Benefits May be Treated as Excepted Benefits
This alert is of interest to all employers that offer fertility benefits or may be interested in offering fertility benefits in the future.
November 4, 2025
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Property and Casualty
Top 5 Insurance Surprises Businesses Face in Q4 — and How to Prevent Them
As year-end approaches, many organizations focus on closing out financials and planning for the year ahead. It’s also the time when insurance programs often reveal unexpected challenges, some avoidable, others the result of shifting market conditions or overlooked details.
October 30, 2025
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Employee Benefits
Legal Alert: IRS Adjusts Health Flexible Spending Account and Other Benefit Limits for 2026
This alert is of interest to all employers that sponsor health FSAs and qualified transit plans, among others.
October 10, 2025
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2025 Leave Report: Insights to Guide 2026 Leave Planning
Explore Alera Group’s 2025 Leave Report. Benchmark PTO, parental leave, and holiday policies to strengthen employee retention and recruitment as you plan for 2026 and beyond.
October 1, 2025
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