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 over 4,400 employees, 160+ locations, 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 160 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
Alera Group Spends The Week Giving Back
In the spirit of our Generous Community Giving program, Alera Group employees participated in a week of events, both in-person and virtually, for our 2023 Community Giving week.
Chicago Housing Authority Hiring Fair
Alera Group colleagues spent the day at the Chicago Housing Authority Job Fair reviewing resumes, helping with interview prep, working on communication skills, and offering general insights and advice to people just starting their professional careers. It was time well spent helping others in the community both professionally and personally.
Feed My Starving Children
The Alera Group team volunteering with Feed My Starving Children had a positive experience measuring, bagging, weighing, sealing, and packing meals for children over the course of an afternoon. Not only did they feel like they made a difference in the lives of others, but they also enjoyed using the time as a teambuilding exercise to work with colleagues outside of their department.
Lyman Woods Nature Center
Alera Group volunteers rolled up their sleeves to beautify the nature preserve by building a new fence and cleaning up the trails for the community to enjoy now that the weather has warmed up. Despite being a physically demanding morning, everyone agreed it was a rewarding experience.
Send virtual cards to patients at St. Jude
Our remote teammates were able to participate in Community Giving Week as well! They wrote dozens of encouraging notes to patients undergoing treatment for cancer and other life-threatening diseases.
The Alera Group volunteers not only gave their time and energy to make a positive impact on our communities, but unanimously agreed that they had a great time while doing it!
Alera Group’s 2023 Office 5k Raises Money for Juvenile Diabetes Research Foundation
On October 12 we laced up our sneakers as part of our Generous Community Giving initiative. This year’s annual 5k included a record number of participants who enjoyed running and walking the outdoor course at our Deerfield, Illinois headquarters as well as a step challenge for remote employees. To keep things interesting, we added a new 5k relay event consisting of teams of four colleagues for some additional friendly competition.
The proceeds of the money raised this year benefits Juvenile Diabetes Research Foundation (JDRF). Their mission is to improve lives by accelerating life-changing breakthroughs to cure, prevent, and treat type 1 diabetes (T1D).
The day was billed a success as the rain clouds held off long enough for us to support an important cause while enjoying the company of our fellow team members.
An Alera Group Care Package
Alera Group colleagues came together last month to enjoy a lunch and celebrate our shared successes in 2023. The day had a bigger purpose though, as we rolled up our sleeves to kickoff our first Generous Community Giving event in the new year with nonprofit group, Blessings in a Backpack.
Blessings in a Backpack mobilizes communities, individuals, and resources to provide food on the weekends for school-aged children across America who might otherwise go hungry. By the end of the afternoon, over 100 Alera Group colleagues had packed 500 bags! Not only was it rewarding to collaborate on a physical task together, but we were thrilled to know that our work would ensure children in our community would not go hungry that weekend.
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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