Glen was initially recruited and offered a choice of several roles by Procter & Gamble, but accepted a position at Valassis Communications, a smaller company but one with large ambitions and a strong company culture. He felt he could make a larger impact there.

He worked there for 19 years, starting in sales and working his way through a variety of jobs, many of them he now sees as being highly “intrapreneurial.” If Valassis was getting into something new, something risky, he wanted to be a part of it. When the company acquired a dot-com startup during the late 90’s bubble Glen went to work for them.

Later, Valassis acquired NCH, a company that had small subsidiaries in five different countries in Europe. Glen was tapped for a role working directly with the management teams of these five, small, entrepreneurial companies to launch Valassis products in each country.

Glen returned to the U.S. in 2007. Valassis had grown into a multi-billion-dollar company, far larger and more bureaucratic. Within a year or two, he found himself missing the fast-growth experiences and the risks and rewards, of a smaller, more entrepreneurial company environment.

According to Glen, “As I looked back on my career, my greatest contributions and happiness in my role were when I was working in high-growth areas or turning around struggling business lines and clients.”

In 2009, Glen found himself across the table at an after-work happy hour with the CEO of small-cap public company, Insignia Systems, located in Minneapolis. During the conversation, the CEO asked Glen if he would like to join Insignia as the Marketing Vice-President, with the ultimate goal of eventually succeeding him in the CEO position.

At the time, Insignia was embroiled in a multi-year legal proceeding with a major competitor that was depleting the resources and focus of the company. The suit was settled in Insignia’s favor in 2011, but the company was struggling with its business model. Sales revenue had declined almost by half, down to $16M annually. The company was drowning in operating losses, losing cash each quarter.​

The CEO and Board appointed Glen to the COO role to lead a turnaround effort, which proved highly successful. Soon the company was profitable once more. Glen was handed the reins as CEO, to continue the growth trajectory, and soon annual revenues approached $26M, then $28M. It then became a takeover target and was ultimately taken control of by an activist investor with a vision for the company’s future that conflicted with Glen’s.​

Searching for his next venture, he realized how much his experience at Insignia Systems had shaped him. “I was the boss, at the top of the pyramid, with an executive team and employees all answering to me. I expected that pressure, even relished it, as part of the job. What I didn’t expect was the pressure I’d get from the other direction. Above me, was another triangle – upside down and pointing at my head – the Board of Directors and thousands of shareholders. As the CEO you feel intense pressure from both directions. No matter how good your leadership team is, you’re the one making the decisions. No one else is really feeling that same pressure. There’s no one to talk to.”

After leaving Insignia, he launched and spent the next two years as co-owner of SuiteHaus, a General Contracting and real estate investment partnership, but kept coming back to the Insignia experience. He saw an opportunity to help business leaders who were going through the same types of issues he struggled with. “I wish someone had been there to help me. That’s why I decided to start Apex North.”