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
Rosemary O'Brien, CPCU, ARM
Senior Risk Management Consultant | Property & Casualty
Rosemary O’Brien is a Senior Risk Management Consultant at the firm. She focuses on the asset protection needs of high net worth individuals and families, representing the elite carriers in the property and casualty insurance industry.
Rose has more than 35 years of industry experience, specializing for the past 30 years in developing customized personal insurance programs for affluent and high net worth individuals. Her experience includes working for large global insurance brokers in the areas of management, business development and service. She started her own boutique personal lines agency which was subsequently acquired by the firm.
Known for her remarkable ability to cultivate strong, meaningful professional relationships, Rose is differentiated by her extraordinary communication skills, collaborative, needs-based approach and industry knowledge. She currently holds insurance producer licenses in 45 states.
Education: B.S., Education/Math, University of Wisconsin.
Certifications: CPCU, ARM
Jill Olshefke
Director of Select Accounts | Employee Benefits
Jill leads the administrative processes of the Select Accounts team, which manages employee benefits for small group employers (1-100 lives). Focusing on quality assurance and scalability, she ensures an excellent client experience by creating efficient processes and procedures for this high-volume team.
Jill Olshefke has been with the firm since 2011. She previously worked at Northern Suburban Special Education District where she managed and scheduled substitute teachers.
An avid dog lover (Roxie, Pitbull/Staffie mix and Zeus, German Shepherd), Jill enjoys live music (and following her son’s band, Ax and the Hatchetmen), reading and painting.
Education: B.A., Albion College; Master of Education in Educational Psychology, National Louis University
- VUCA Leadership, Cornell University, May 2022
- Leadership Agility, Cornell University, May 2022
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.
Resources
EXPERT EDUCATION
Events and Webinars
Employee Benefits
2025 Healthcare and Employee Benefits Benchmarking Report: How Does Your Benefits Program Stack Up?
In this session, our experts will dive into the results of our annual, market-leading benchmarking survey.
June 26, 2025 at 01:00 pm CT | Virtual
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Employee Benefits
Dynamic Data: Strategies for Success
Join us for this session, as our experts will share how to utilize your organization’s data to create advanced and innovative strategies for success.
July 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.
July 23, 2025 at 12:00 pm CT | Virtual
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THOUGHT LEADERSHIP
Insights
Wealth Services
Protecting Your Business from the Loss of a Key Person
The unexpected loss of a key team member can disrupt operations and impact your bottom line. Explore how key person insurance can help your business stay resilient and maintain continuity during a critical transition.
May 20, 2025
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Wealth Services
Weekly Market Update
Stocks roared higher last week, powered by upbeat trade news and tame inflation reports.
May 19, 2025
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Agencies Push Pause Button on Enforcement of MHPAEA 2024 Final Rule
On May 15, 2025, the Department of Labor, Department of Health and Human Services, and the Treasury Department (collectively, the “Agencies”) released a statement regarding the Agencies’ recent request for abeyance of a lawsuit filed by the ERISA Industry Committee (“ERIC”) in the U.S. District Court for the District of Columbia that challenged certain aspects of Mental Health Parity and Addiction Equity Act (MHPAEA) Final Rule (“2024 Final Rule”) relating to nonquantitative treatment limitation comparative analyses (“NQTL analyses”).
May 16, 2025
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Wealth Services
The Practical Value of Insuring Against Life’s Risks
Unexpected events can derail even the best-laid financial plans, yet many people remain underinsured. This article explores how the right coverage can help protect your income and support your long-term goals.
May 16, 2025
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