The Corridor’s largest privately held companies: TrueNorth Companies

The TrueNorth team pictured at a company outing. CREDIT TRUENORTH
The TrueNorth team pictured at a company outing. CREDIT TRUENORTH

After tripling its revenue and personnel in the last decade, TrueNorth Companies is focusing on its next stage with its “Secure the Future” initiative.

President and Chief Revenue Officer Trent Tillman said the company does not plan to sell or become publicly traded. To ensure those goals are met, he and CEO Jason Smith are preparing the company for future generations’ leadership.

“The original founders were passionate about setting up the firm for succession from within and we’ve perpetuated out five of the six founders,” he said. “Now, around 60 people have equity in the firm and it’s our responsibility to do that again … The Secure the Future initiative is a reinforcement of our core commitment that we’re not going to sell to anyone.”

TrueNorth Companies began when six Iowans merged three insurance companies in 2001 to create the largest financial services firm at the time in Eastern Iowa. One of its founding principles was to remain in the state and not sell to a Wall Street firm.

One of the main reasons for this continued ideology today is because of the company’s interactions with the community.  

“We focus on reinvestment in Cedar Rapids or Iowa City, Des Moines, Denver or Chicago where we have brick and mortar,” he said. “It’s an element of the business and it’s important to the community and our colleagues. If we shift ownership or equity to a third party, the new employer is going to treat people differently. So there’s an element of stability in being privately owned.”

When TrueNorth was profiled in Largest Privately Held in 2020, one of the company’s main focuses was “perpetuation from within.” Protecting employees’ energy and keeping them confident is a tried and true approach for the company. 

Mr. Tillman has worked for the company since 2003 and was initially presented with a path to leadership and partial company ownership. He said it was one of the reasons he, and many other employees, continue to work for the company.

“During the first conversation we ever had, they laid out a map of presenting a private company who was willing to teach me and if I worked hard, I would earn the opportunity to become an owner here,” Mr. Tillman said. “Right out of the chute, that attracted me as this is an entrepreneurial firm with an entrepreneurial path for me sitting inside of it. We still present those opportunities and we have the ability to be a career company for those interested.”

The company is also keeping most of its employees on a hybrid schedule following the COVID-19 pandemic. 

TrueNorth already had the infrastructure to ensure smooth transitions after the 2008 flood, which eased one of the largest, universal business struggles in recent history for the company. 

“We’ve been very fortunate through it (COVID) because we were already structured in a way that we could go remote almost overnight,” he said. “… Our workforce, we have 240 people here in Cedar Rapids but at 550 colleagues we have brick and mortar shops in Des Moines, Denver and Chicago. We also have roughly 75 people who are kind of scattered throughout the U.S. remotely. They work from home because we’ve had this approach of recruiting talent where they exist. Since we had that, once COVID hit we were okay from a structural perspective.”

He said hybrid options offer the flexibility needed for teams within the company to thrive. 

As the business continues to grow and plan for the future, Mr. Tillman said TrueNorth Companies remains focused on building up its community. 

“Our firm, our purpose, at its core is to create value,” he said. “We like to describe ourselves as, we’re really good problem solvers who happen to also sell insurance. That applies to individuals and to the business. We’re very focused on the folks who we work with and understanding them and then ultimately help them shape solutions. We also use that approach in dealing with issues in our community. We’re looking to provide support everywhere we can.”

TrueNorth Companies details:

2022 Revenue: $1.283 B

Established: 2001

Top Executive: Jason Smith, CEO

This article was originally published in the CBJ’s Largest Privately Held Companies magazine.

In 2023, this magazine celebrated its tenth anniversary, after a three-year hiatus due to the pandemic. It featured a look back through the last decade and a glimpse into the future of the Corridor’s biggest, and most impactful, companies. Through in-depth interviews and people-focussed articles, the magazine explored how these industry titans have supported and inspired their communities through hardship and prosperity, and how they plan to continue their involvement for years to come.