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
Ben May, CIC, CBC
Senior Benefits Consultant | Employee Benefits
Ben May is a Senior Benefits Consultant with the firm. He focuses primarily on small- and mid-sized businesses. Ben’s expertise centers around the design, funding, communication, administration, and compliance of employee benefit programs. Ben focuses on making clients comfortable, and he takes the time to learn and understand their unique business to meet their challenges effectively. This approach allows Ben to create a first-class benefits program to provide outside-the-box solutions that solve these challenges.
Ben has extensive experience in the employee benefits industry, including a previous role as the Director of Sales in the Benefits Division with Hallberg Commercial and Group Health.
Outside of work, Ben is an athletic board member at St. Pius X School and volunteers as a coach for soccer, basketball and baseball. Ben currently resides in Lombard, IL with wife, Julie, and children Riley, Haley, Colin and Jack. He enjoys coaching his kids and staying active playing basketball, softball, and soccer.
Education: BA, Finance and Accounting, Illinois State University.
Certifications: CIC, CBC
Marcus B. Newman, RHU, CBC
Vice President, Employee Benefits
Since joining the firm in 1997, Marcus has focused on serving small businesses. He is responsible for more than 200 privately held businesses, medical practices, and physicians. Marcus provides expert and objective guidance with respect to group insurance benefits of all kinds, 401(k) and other salary deferral plans, pension and profit-sharing plans, deferred compensation plans, executive benefits, and a wide variety of investments for closely held business owners.
Marcus is an annual qualifier for the Million Dollar Round Table. He is the youngest firm advisor ever elected to the Executive Board of the Chicago Chapter of the National Association of Insurance and Financial Advisors.
Before joining the firm, Marcus spent several years working with teenagers as a social worker. Marcus is the Founder and President of Array Education, Inc., an organization committed to the prevention of teenage substance abuse and addiction through a wide variety of programs that help young people make responsible, informed decisions about drugs and alcohol.
Marcus lives in Deerfield, Illinois with his wife and three daughters. He spends considerable time with his family and is a fitness enthusiast. Marcus is an avid reader and a patron of the theater.
Education: B.A., Philosophy, Northeastern Illinois University
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
Resources
EXPERT EDUCATION
Events and Webinars
Employee Benefits
Preparing for Open Enrollment: How to Engage and Educate Your Employees on Their Total Benefits Package
In this session, our experts will share guidance on setting yourself up for success during Open Enrollment.
August 21, 2025 at 01:00 pm CT | Virtual
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Employee Benefits
Q3 2025 Quarterly Compliance Webinar
Alera Group's quarterly employee benefits compliance roundup will help you stay current on the latest national regulatory developments impacting employers.
September 9, 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.
October 22, 2025 at 12:00 pm CT | Virtual
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THOUGHT LEADERSHIP
Insights
Property and Casualty
Alera Group’s 2025 Property and Casualty Market Update
Alera Group’s 2025 Property and Casualty Market Update, designed as a bridge between Alera Group’s annual Market Outlooks — provides insight into pricing, coverage availability, market capacity and underwriting trends for the balance of 2025.
August 1, 2025
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Wealth Services
The Hidden Cost of Sitting on Cash
Holding cash might feel safe — but it could be quietly costing you. Learn how to find the right balance between flexibility and growth, so your money keeps working as hard as you do.
July 28, 2025
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Wealth Services
Tuition, Travel, Retirement — Can You Plan for It All?
You’re juggling college savings, retirement planning, and living fully today. Here’s how a personalized plan can help you balance it all — without losing momentum or peace of mind.
July 28, 2025
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What Does Wealth Mean to Your Family?
Wealth is more than a number — it’s what you’re able to do with it. Discover how aligning your financial strategy with your family’s values can lead to greater clarity, connection, and purpose.
July 28, 2025
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