Some people enjoy going where no man (or woman) has gone before.

Take, for example, Mickey Webb, Chief Operating Officer for Associated Financial Group (AFG).

“Good things happen when you’re willing to do something no one else will do,” she said in a recent interview from her office in Minnetonka, Minnesota. “In many ways, that’s been the story of my career. I’ve made it a habit to figure out what my employer needs, and then to volunteer to make it happen.”

An unconventional career

Mickey started out following a relatively traditional path – earning a B.S. in Accounting from the University of Minnesota-Duluth, with a minor in Business.

But there was always something a little different about the routes she chose. For instance, when the majority of accounting majors were following the traditional path of sitting for their CPA, Mickey chose to leverage her accounting and business acumen to work in a more collaborative type of role.

Early in her career, she found opportunities to help executives select, install and implement computerized accounting systems – long before these systems were considered staples to most companies.

And she worked for an advertising agency, handling not only its accounting but also serving as human resources and office manager.

“The ad agency helped me appreciate how many different ways there are to make a living,” she said. “There are some very intriguing businesses out there!”

That probably helps explain her next move, almost 15 years ago, to a leading Minnesota insurance and employee benefits agency. It gave her a bird’s-eye view of all kinds of enterprises, as well as the enormous range of products and services a successful business needs.

Mickey joined the firm as Accounting Manager, but soon realized that there was something amiss. “The owner was keeping all the fun accounting work to himself,” she said, adding that yes indeed, there is such a thing as “fun” accounting work.

“I talked him into leveraging my skills differently. As a result, I was promoted and moved to the insurance arm, where I did everything from managing the marketing staff to building relationships with the insurance companies whose products we offered.”

It wasn’t exactly the post you’d envision for someone with a garden-variety accounting degree. But she was enjoying her new role – so much so that, along the way, she earned her Certified Employee Benefits Specialist designation from Wharton School of Business, and her Registered Employee Benefits Consultant designation from American College.

Next stop: Associated


The agency was a great success. In 2003, it was acquired by Associated Financial Group. And by 2008, Mickey had been named its Chief Operating Officer.

Her wide-ranging experience and her mind-set that “no task is outside my ‘job description’ had groomed her perfectly for this position.

“My role is primarily industry-facing today,” she said. “But I came from heading up the services side of our business. So I have a good understanding of the risk-management solutions our clients need from us, and from the companies we represent.”

Whether or not it was an “untraditional” route she was seeking, Mickey has certainly found her way to a diverse, exciting and fast-paced career. AFG is now not only one of the largest agencies of its kind in the nation, offering just about every type of insurance you can think of; it also provides everything from property & casualty and retirement plans to HR consulting to regulatory compliance seminars and services.

That means AFG plays a critical role in the operation of literally thousands of businesses today – as well as Associated Bank’s.

A balanced life … sort of

Mickey is a self-proclaimed Type A personality. Fortunately, she’s married to a type B personality who left the world of corporate America to run his own coffee shop in Carver, Minnesota, the tiny town they call home.

It’s no surprise that, in her spare time, Type A Mickey takes care of his accounting and serves as chair of Carver’s park and recreation board. Nor is it any surprise that Carver has more parkland per capita than any other community in her area – in spite of the fact that the population has grown by more than 650% in the 16 years that they’ve lived there, from 600 to 4000.

She does take the time to relax now and then. She and her husband are spectators at hundreds of college and professional hockey games each season. They also enjoy exploring the great outdoors, particularly partaking in adventures such as kayaking into sea caves around the Apostle Islands.

But she is never away from AFG for long. Her work and future projects always beckon, and she returns to work happily.

Her advice to young women entering the field?

“Always treat your employer as your most important customer,” she said. “Figure out what this customer needs to succeed, and then offer to do it, even if it means taking the ‘non-traditional’ approach. These are the keys to opportunity and growth in virtually any business.”