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.
John Przybylski
AuditRate Consultant | Property & Casualty
With over 15 years of consulting experience within the Insurance industry, John is a subject matter expert in Workers’ Compensation and General Liability premium overcharges. As an AuditRate Consultant at the firm, he serves as the main point of contact for AuditRate, a proprietary solution designed to help employers discover and recover workers’ compensation and general liability overcharges. John is primarily responsible for leading full life cycle audits on workers’ compensation and general liability audits, as well as promoting AuditRate as an effective tool for producers to use during prospecting. As a part of the AuditRate team, John has an in-depth knowledge of the factors that drive premiums, which allows him to aid clients in challenging overpaid premium. John has achieved and maintained a record of uncovering overcharges on 40% of all contingency engagements.
Prior to working at the firm, John held various audit and consulting positions for companies such as Nationwide/ Harleysville Insurance Co., Zurich NA, and HUB International.
Outside of work, John resides in Huntley, IL and currently sits on the Huntley Youth Football League Board of Directors.
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.
Resources
EXPERT EDUCATION
Events and Webinars
Employee Benefits
HIPAA Privacy and Security Overview
Join our compliance experts for an overview of HIPAA’s Privacy and Security Rules. During this webinar, we'll review the different types of entities subject to HIPAA, take an in-depth look at protected health information (PHI), individual rights under HIPAA and what to do when there is a breach of PHI.
April 11, 2025 at 01:00 pm CT | Virtual
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Employee Benefits
Balancing Cost and Care: Could a Captive solution be the right fit for you?
In this session, our experts will discuss how Captive solutions work and what you need to consider for your own group’s needs.
April 17, 2025 at 01:00 pm CT | Virtual
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Wealth Services
State of the Markets
Join us as we unveil the factors that drive the nation's financial pulse and how they may impact your personal finances.
April 23, 2025 at 12:00 pm CT | Virtual
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THOUGHT LEADERSHIP
Insights
Wealth Services
Weekly Market Update
Stocks fell broadly last week as domestic and foreign markets reacted to the White House’s tariffs.
April 7, 2025
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Property and Casualty
Improving Transportation Fleet Safety Through Gamification
The COVID-19 pandemic pushed companies to find creative ways to engage employees as isolation hit an all-time high. Many turned to gamification — the application game mechanics such as points, badges and leaderboards to everyday tasks — to reconnect with staff and improve retention, especially around key initiatives like safety. It’s a concept so suitable for the transportation industry, it could have been conceived with truckers and other commercial auto drivers in mind.
April 7, 2025
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Employee Benefits
Webinar: Is Captive Insurance the Right Solution for Your Business?
Join Alera Group on Thursday, April 17, for "Balancing Cost and Care: Could a Captive solution be the right fit for you?", a webinar on self-insuring to reduce group Medical Insurance costs and other business expense. Our experts will discuss how Captive solutions work and what you need to consider for your own group’s needs.
April 3, 2025
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Wealth Services
Weekly Market Update
Stocks moved lower last week as investors swung from exuberance to disappointment on news over tariffs and inflation.
March 31, 2025
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