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
Navigating Medicare
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.
February 11, 2026 at 12:00 pm CT | Virtual
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Property and Casualty
Top Cyber Threats of 2026 – and How to Mitigate Them
Cybercriminals have a new playbook—your business could be next.
February 17, 2026 at 01:00 pm CT | Virtual
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Employee Benefits
Designing Benefits for Mid - to Late-Career Employees
In our three-part webinar series, Designing Benefits That Work – A Data-Driven, Multigenerational Focus, we’ll explore multigenerational workforce insights, debunk generational myths, share early- and late-career benefit strategies, review legal and compliance trends, and provide actionable tools and resources.
February 18, 2026 at 10:00 am CT | Virtual
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THOUGHT LEADERSHIP
Insights
Property and Casualty
AI-Powered Cyber Attacks, Why Yesterday’s Defenses Aren’t Enough.
The widespread availability of AI technology, combined with the ease of manipulating video calls, makes phone and Zoom calls susceptible to exploitation by threat actors.
February 2, 2026
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Employee Benefits
IRS Releases Guidance Related to Recent HSA Changes
The IRS recently released Notice 2026-5, which provides guidance and answers to common questions related to the expanded availability of health savings accounts (“HSA”) under the Reconciliation Act (previously named the One Big Beautiful Bill Act) passed into law earlier this year.
December 30, 2025
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Property and Casualty
Are you prepared for 2026? Property and Casualty Trends Uncovered
The sixth annual Property and Casualty Market Outlook from Alera Group sets the stage for how organizations can recalibrate their risk strategies in 2026. Built on thousands of data points — including a nationwide survey of insurance company partners and wholesale intermediaries — this report delivers actionable insights for insurance buyers, risk managers and business leaders.
December 17, 2025
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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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