Proven Professionals: Helping You Form a Path to Success

A professional provider who has your back is worth their weight in gold. Here are some of our area’s top experts, from financial and insurance advisors to law firms that will be in your corner when you need them.

When the right partners are available, good teamwork makes the difference in attaining the success you seek each day.

In your personal and business finances, you’re drafting a team that includes attorneys, investment advisors, insurance advisors and certified public accountants (CPAs) all focused on helping you attain your important goals. Together, these talented professionals can guide you through the maze of complex decisions you’ll need to make – especially in these unusual times.

We’ve sought out the region’s most trusted experts – the kind whose work is sure to align with your objectives and whose philosophies are sure to align with your values. Together, these talented professionals can guide you through the maze of your business and personal needs.

The key to your financial success is coalescing all of your Proven Professionals around your personal mission. This is your strategy to command, and these dedicated professionals are your team to engage.

We hope and trust you’ll find the Proven Professionals you’re about to meet can provide invaluable and unmatched assistance to the success of your mission … on both the personal and business fronts.

Prairie Trust

Waukesha: N16W23321 Stone Ridge Dr., (262) 522-7400
Madison: 4600 American Pkwy., Ste. 204, (608) 535-3040,

Prairie Trust, a division of Waukesha State Bank, is a trust services provider with unrivaled expertise in trust administration.

They serve clients throughout the U.S. and are privately owned, giving them the independence and freedom to do the right thing for the right reason.

In addition, Prairie Trust works closely with other financial professionals, including attorneys and financial advisors. The advisor-friendly business model means they regularly support financial advisors as they nurture and grow relationships with clients.

Prairie Trust’s expertise is demonstrated by its ability to handle difficult situations, including special needs trusts, trusts subject to family friction (even with active litigation), and estate settlements with complex requirements.

The team includes attorneys, Certified Financial Planners, Certified Trust and Fiduciary Advisors, licensed Certified Public Accountants, MBAs and more. Just as importantly, because direct personal contact never goes out of style, Prairie Trust’s approach is responsive, active and accessible.

Stillman Bank, Trust & Wealth Management

608 W. Blackhawk Dr., Byron, IL, (815) 234-5626
8492 E. State St., Rockford, IL, (815) 332-8100
1445 IL Rt. 2, Oregon, IL, (815) 732-7956
5250 Bridge St., Roscoe, IL, (815) 623-1800
455 W. IL Rt. 38, Rochelle, IL, (815) 562-7071
101 E. Main St., Stillman Valley, IL, (815) 645-2266

Serving the community since 1882, Stillman Bank has spent 140 years forging a stable financial institution that is dedicated to the customers and communities it serves.

With six full-service office locations throughout Ogle and Winnebago counties, it still remains locally owned and headquartered right here in the Rock River Valley. While the banking industry has transformed since Stillman Bank’s founding, its guiding principles have always remained steadfast. Stillman Bank has been cultivated through a long and continuing tradition of integrity, community involvement and leadership that builds value for its customers, communities and shareholders, all of which are important to the bank’s success.

Stillman Trust & Wealth Management offers a full range of trust and investment services to individuals and businesses. Managing personal assets or a company’s assets in today’s financial marketplace requires knowledge and expertise. Stillman Bank provides comprehensive and creative solutions to individuals interested in building and preserving their wealth through Trust Administration, Retirement & Estate Planning, and Investment Management services. Stillman Bank’s advisors work with their customers to determine long-term and short-term goals to develop a strategy that is customized to every unique situation. They take pride in offering clients innovative financial solutions to build and protect their assets. For more information or to arrange a no-obligation, complimentary consultation, contact them at any of their six locations. Trust administrators regularly visit all offices, so appointments can be made for any location or time.

In addition to the products and services it offers, Stillman Bank provides support to numerous community organizations with monetary donations, resources and volunteer hours. As your neighbors, their employees are truly living, working and investing in the betterment of their local communities.

Benning Group, LLC

50 W. Douglas St., Ste. 300, Freeport, IL, (815) 235-3157
6815 Weaver Road, Ste. 300, Rockford, IL, (815) 316-2375
1809 10th St., Monroe, WI, (608) 325-5035

Benning Group, LLC (BG) is a full-service traditional CPA firm with offices in northern Illinois (Freeport and Rockford) and southern Wisconsin (Monroe). BG’s origins date back to its predecessor in 1987. Original partners Don Benning, CPA, and Curt Kleckler, CPA, had worked together in the 1980s at a national accounting firm and teamed up to form a multi-office, local firm. Though BG’s name has changed over time, our commitment to providing quality, professional services has not changed since inception.

In the past 30 years, the firm has added four additional partners: Jenny Blocker, CPA; Jake Thompson, CPA; Kyle Polhill, CPA; and Kyle DeMus, CPA. BG has developed a strong team of certified public accountants and supporting staff to meet the needs of a diverse group of small businesses and individuals. In September 2020, Roger Boeke, CPA, and his team at Boeke & Associates merged into BG’s Rockford office, further strengthening BG’s client base and its breadth of experience and knowledge.

Firm clients include a wide range of manufacturers, agricultural industries, retail stores, professional services, medical services, financial institutions and other entrepreneurs and their businesses. BG assists them in accomplishing their goals through various consulting services in addition to in-depth knowledge of accounting principles, software solutions and income tax laws and regulations.

Over the years, we have also developed niche practices in the financial and compliance audits of Illinois school districts as well as audits of employee retirement plans and nonprofit entities, including their related information reporting.

Because BG is a full-service CPA firm, individual tax planning and tax return preparation are a substantial part of the practice, and BG’s more than 30 professional staff members get to know clients personally while watching their families grow and needs change over the years.

Benning Group LLC takes great pride in providing top-quality services in a timely, responsive manner at a reasonable price. A “hands-on” approach in delivering client services separates BG from larger firms, while the depth of knowledge and experience sets BG apart from other local firms.

CoyleKiley Insurance Agency

810 N. Alpine Road, Rockford, IL
18 W. Blackhawk Drive, Suite 201, Byron, IL
(815) 987-2170 |

CoyleKiley Insurance is the region’s leading, locally owned, independent agency specializing in commercial and personal insurance as well as employee benefits and wealth management.

We conduct business across the United States and also handle complex international exposures. We have established relationships with over 100 of the finest “A” rated carriers available to meet the ever-changing needs of our clients.

Our aim is to simplify the insurance process for you and provide clear-cut solutions that provide value tailored to your specific needs. We are focused on building long-term relationships, in many cases becoming an extension of your business team. Your trusted advisor. Your advocate.

When you choose CoyleKiley, we not only provide traditional solutions. As your consultant, we also review your insurance and financial priorities to provide a customized plan to help take advantage of changing times and new risk protection solutions.

We believe strongly in maintaining our core values of delivering excellence, staying engaged and earning our clients’ trust every day. Our focus on culture and community engagement has encouraged individuals from both inside and outside the insurance industry to join our growing team. Very soon, we will have more than 30 people engaged to serve you.

While continually attracting new talent, we are still built on more than 65 years of industry knowledge and expertise. CoyleKiley delivers numerous experts who have been in the insurance field for more than 30 years. This provides an extremely strong foundation for all your needs and allows for the infusion of new talent to fuel legacy and growth.

Contact us today to meet your new team.

MacCloskeyKesler and Associates, LLC

308 W. State St., Ste. 200, Rockford, IL, (815) 965-2000 |

MacCloskeyKesler and Associates, LLC, is a leader in personal injury law in the Rockford area. The firm has been serving injury victims since 1998, when Kim MacCloskey founded the firm. In 2004, Phil Kesler joined Kim in his quest to handle every case like his own. The firm has grown, but the emphasis on compassionate, personal injury representation remains.

The firm has been privileged to receive numerous awards, including the “Best of the Rock River Valley” award for both law firm and personal injury lawyer, based on votes from local community members. The firm has many million-dollar and multimillion-dollar settlements and verdicts to its credit. Kim and Phil are both members of the Million Dollar Advocates Forum and the Multimillion Dollar Advocates Forum. The best reward for Kim and Phil, however, comes from helping injury victims find peace during difficult times. 

Kim and Phil credit their staff and clients for their success and awards. The staff at MacCloskeyKesler and Associates is well-trained and dedicated to providing personal attention to their clients. Much of the staff has been with the firm for over a decade, and clients routinely refer friends and family when they’ve been injured. Kim and Phil see this as the highest honor.

MacCloskeyKesler and Associates continues to grow and succeed. Despite its success, its dedication to providing experienced representation and personal attention to each case remains the same. With this in mind, MacCloskeyKesler and Associates only handles personal injury cases and does not represent insurance companies. Because of the firm’s reputation, most cases settle without trial or without even the need to file a lawsuit. 

The team is willing to meet with clients by phone, video conference or in-person, as desired.
If you have been a victim of someone else’s negligence, contact MacCloskeyKesler and Associates for a free consultation at (815) 965-2000.

Rockford Community Bank

1825 N. Perryville Road | Rockford, IL | (815) 523-1425 |

When Rockford Community Bank first opened its doors in January 2022, located at 1825 N. Perryville Road in Rockford, it was so well received that the full-service retail bank is now planning a new location in Machesney Park, Ill., and additional locations in Rockford.

What sets Rockford Community Bank apart is the focus it places on the second word in its name: Community. Customers will notice this when they attend an in-bank ice cream social, a family cookout, a visit from Chicago Cubs Hall of Famer Andre Dawson, or a chance for children to meet special guests such as the Easter Bunny or Santa Claus during the holidays.

At this full-service community bank, customers have access to a variety of services including personal accounts, mortgages, investments and trust services. These services include: no ATM fees (even while using other banks’ ATMs), free coin counting, Cubs and Sox checking and free online/mobile banking.

Rockford Community Bank is a public space, where no appointments are necessary. A community room on site offers a place for seminars or groups that need a place to gather. The bank sponsors a variety of events, including free document shred days, blood drives, Dinner on the Dock at Prairie Street Brewing Co. and Donation Days at Anderson Gardens, an evening where visitors to the gardens pay a donation in lieu of admission. Team members also volunteer to serve on a number of boards including the Rockford Chamber of Commerce, Shelter Care Ministries, Rockford Park District Foundation Board, Belvidere School Board, YMCA of Rock River Valley, Crusader Community Health Foundation, Rockford Local Development Corp., and many more.

The bank is also developing partnerships with area schools, so that young people become more financially fluent as they journey into adulthood. Free training seminars are regularly held, at the bank and throughout the community, to help customers from all walks of life learn about financial literacy, identity protection, trusts, estates, and building or rebuilding credit.

The retail banking team membes who greet visitors at Rockford Community Bank are the same people you wave to on a jog through the park or a trip to the supermarket. They are proud members, not just of Rockford Community Bank, but of Rockford itself.

Law Offices of Canfield, McKenna and Lawson

1111 S. Alpine Road, Ste. 704, Rockford, IL | (815) 968-7200 | [email protected]

Robert E. Canfield has more than 40 years of experience in the general practice of law. Andrea McKenna has more than 10 years of legal experience in the general practice of the law and focuses mostly on family law. Maureen Lawson has more than 19 years of legal experience in juvenile and family court.

Canfield, McKenna, Lawson and their associates are persuasive in the courtroom. They’ve been providing Rockford-area residents with expert legal service that comes from more than 100 years of combined legal experience.

They can handle your family law, small business, probate, estate planning, wills and trusts, estate planning and general practice law. They have all the right qualifications, but you may be looking for something more.

You’re probably looking for someone who understands that your divorce is not just about separating property and accounts but about your life being turned upside down. You’re looking for someone who can see that you would do anything for your kids and that you won’t play games when it comes to their best interest.

You’re probably looking for someone who understands that your small business is more than just business. It’s personal and you want to protect all of the blood, sweat and tears you’ve poured in over the years.

You’re looking for someone who understands what it’s like to worry about what will happen when it’s your time to pass on and how to provide for the loved ones you leave behind.

The attorneys of the Law Offices of Canfield, McKenna and Lawson looks at the law and facts, and how they affect clients. Chances are, if you need an attorney you are going through a tough stage of life. That’s why Canfield, McKenna and Lawson make it their mission to help clients achieve their goals and understand every step in the process. Their attorneys and staff are compassionate, knowledgeable, patient and understanding. But, they’re also fiercely protective of their clients’ interests and won’t back down when the time comes to fight.

Trust between a client and attorney is absolutely essential to good representation. And, they also understand just how expensive legal proceedings can be, so in some circumstances, they offer payment plans to help their clients afford representation.

They also offer meetings face-to-face, over the phone or virtually by Zoom.

Because this legal team understands their clients’ needs and has spent years demonstrating their success at representing clients, people come back again and again when they encounter a need for legal help.

Find out why these clients believe in Canfield, McKenna and Lawson by making an appointment today.

Charles Schwab

801 N. Perryville Road, Rockford, IL, (815) 209-0055,

At Charles Schwab, we believe in the power of investing to help individuals create a better tomorrow.

We have a history of challenging status quo in our industry, innovating in ways that benefit investors, advisors and employers who serve them, and championing our clients’ goals with passion and integrity.

Schwab’s independent branch in Rockford opened in 2013 and has since been offering local residents access to a range of investing and wealth management guidance, products and services.
The branch is led by independent branch leader Mark Gerard, a financial services professional with 25 years of experience in financial planning and portfolio design.

Clients can also meet with financial consultant Bill Osborne, a 40-year veteran of the investment management industry, for financial planning discussion and personalized portfolio consultations.

James E. Meason Law Office

113 W. Main St., Rockton, IL | (815) 624-6517 | | [email protected]

James E. Meason opened his Rockton, Ill., office in 1997 after working as a federal attorney in Washington, D.C., and practicing environmental law with a major national Chicago-based firm. 

He also served 28 years in Naval Intelligence, retiring in 2016 after a tour in Afghanistan. But for more than two decades Meason’s true focus has been family and business law, estate planning and real estate for clients in Winnebago, Stephenson, Boone and McHenry counties.

When it comes to estate planning, Meason emphasizes “the big six” areas that need to be in a family’s action plan: will, revocable trust, property power of attorney, health care power of attorney, living will and appointment of agent. These areas ensure that your desires are followed during your lifetime and after your death.

Wills designate who gets your possessions upon your death. Revocable trusts are like a “fancy will” that help to avoid probate for your family. A living will states your end-of-life health care treatment decisions.

Power of attorney, in both property and health care matters, designates a family member or friend to manage your affairs if you can’t.

Appointment of agent authorizes one to make your final arrangements, including details such as cremation, burial and organ donation.

To avoid mistakes in planning your estate, contact Jim.

Edward Jones/Mike Donnelly

2406 Charles St., Ste. 1-A, Rockford, IL, (815) 398-7759,

As an Edward Jones financial advisor, I believe it’s important to understand what you’re working toward before you invest your money. It’s also important to understand the level of risk you’re comfortable accepting when investing, so we can balance it with the steps necessary to reach your long-term goals.

Whether you’re planning for retirement, saving for college for children or grandchildren, or just trying to protect the financial future of the ones you care for the most, we can work together to develop specific strategies to help you achieve your goals. We can also monitor your progress to help make sure you stay on track or determine if any adjustments need to be made. Throughout it all, we’re dedicated to providing you top-notch client service.

Thousands of people working with advanced technology support our office so we can help ensure you receive the most current and comprehensive guidance. In addition, we welcome the opportunity to work with your attorney, accountant and other trusted professionals to deliver a comprehensive strategy that leverages everyone’s expertise.

Working together, we can help you develop a complete, tailored strategy to help you achieve your financial goals.

Flanders Insurance Agency

1947 N. Lyford Road, Rockford, (815) 226-1444,

Flanders Insurance Agency has been serving the surrounding community since 1927. It’s an independent agency that offers competitive coverage for both commercial and personal clients. The agency offers a full spectrum of coverage for its clients, including auto, homeowner, health, flood, life and business insurance plans, as well as umbrella policies that offer robust liability coverage. Many of the top-rated companies that Flanders Insurance works with are trusted brands that have been named to the Ward’s Top 50, an industry list that annually names the top-performing insurance agencies in the United States.

“We’re licensed in multiple states,” says Owen Costanza, owner of Flanders Insurance Agency. “We work with trusted companies like Auto Owners, Travelers, The Hartford, Chub and Progressive.”
Costanza, who has 28 years of industry experience, took the helm in 2010 and has continued to honor the company’s community-driven roots.

“We love to sponsor Little League teams and youth sports,” says Costanza. “We also support local Girl Scout organizations and school initiatives. We have a whole wall full of photos in our office.”
Flanders Insurance Agency’s wide variety of insurance options, trusted carriers and personalized service continue to make the company a trusted fixture in the Rockford region.

“You never know how important insurance can be until you need it,” says Costanza. “We have real, local and licensed agents who handle your claim.”