From Strip Club to Boardroom

Early on in my career I was asked by my boss to entertain some male clients and their male brokers. 

Little did I realize the “entertainment” meant passing out dollar bills to the men at a pre-game party at a local strip club near Fenway Park. I did my so-called job, then I quickly left the club. And soon thereafter I left the company.

Another incident, common to all too many women: I was told to meet an important client for lunch at a private club, but I couldn’t get beyond the lobby. Back then, women were barred from such clubs. One club president was quoted as saying he found the “cackling voices” of women in the dining room disturbed the members’ lunch. I learned to suggest lunch at places that welcomed women.

Today those situations are not entirely a thing of the past. The number of senior executive women in the insurance industry remains far too low. For the last two decades, I’ve been the CEO or a senior executive with the largest brokerage firms and third-party administrators in the industry, but it’s still not common to find women in such positions.

So why don’t women get the top insurance jobs more frequently?

It’s not because of a lack of trying, despite the stereotype of women dropping out mid-career. My colleague, Erin Hamrick, is founding partner of insurance executive recruiter Sterling James. She and I decided to support research at Drake University this year to look behind the numbers to find out why so few female insurance executives failed to reach the top of the corporate ladder. At first glance, the answers are not altogether clear. These days younger men and women often share the same educational backgrounds, work experience and professional skills, so we should see as many women as men in leadership positions at insurance organizations.

The issues holding women back are multifaceted. Here are three:

First: We can’t forget discrimination remains strong in the corporate suite. Too often it might be traced to lingering attitudes among the older executive leadership. A highly regarded financial services industry and community leader recently shared his perspective with me. He said he believes the glass ceiling was created by women who can’t handle the pressure. In his experience leading a big civic organization, he said, four of six top female executives who worked for him “cried all the time.”

Where was his executive leadership? Was he asking too much? Do women put so much pressure on themselves to succeed that they buckle under the stress? Something clearly was wrong. If these kinds of comments are not questioned, then executives like him will perpetuate this ridiculous stereotype. This is 2015, so let’s focus on what is productive.

Second: Probably the most common excuse for the lack of women as senior-level insurance execs is the dearth of qualified women in the industry or in the promotion pipeline. That’s certainly an excuse that’s alive and well in the high-tech industry and the engineering and science professions. Our industry has plenty of capable women who have been held back from career-advancing opportunities. As women, we must ask for opportunities and guidance. What are my strong skills? Where do those skills fit best? How do I get to the next level?

Third: Mentoring is critical to your career. The Drake study notes mentoring by men is probably the biggest factor accounting for their successful advancement within the corporate insurance culture. But the study says women are mostly mentored by other women, while men are rarely mentored by women.

Let’s be honest, at most companies the guys are at the helm, and they know the most influential (and mostly male) mentors. Often the key part of the mentoring process for men—though not so much for women—is internal sales promotion by the male executive coach/mentor to his mostly fellow male executive colleagues.

Mentors know about opportunities well in advance, and they talk. A lot. Encouraging and aggressively supporting ambition and success is an important part of the mentoring process.

Men, as Erin Hamrick points out, may well be more outwardly ambitious and promote themselves more aggressively, especially early on in their careers. So let’s take a page from their playbook. 

Here’s why women are going to take over the world—and drive revenue for your insurance company.

Women executives, in my experience, tend to have strong talents in analytics—more so than men. Yet these analytical skills may not be as valued when it comes to distinguishing executive performance within the organization early on. Women also excel at collaboration and communication. So get yourself on a priority project and take the helm to deliver on it.

For those leaders still on the fence, the 2007 Catalyst study found that Fortune 500 companies with the highest representation of female directors outperformed those with the fewest female directors by 53% in returns on equity, 42% in returns on sales, and 66% in returns on invested capital.

There are no good reasons why more women aren’t serving on corporate boards. There is no shortage of qualified women. Women know other great women, and if you seek to recruit a female executive you might have to look a little beyond the typical, mostly male network.

A female board member I know keeps a list of women qualified to become board members in her center desk drawer. She updates it regularly and is always ready to give out names and recommendations when she receives the inevitable call seeking her input on an executive search or when she hears about a board opportunity. We all should keep a list of this nature and help others get on them.

So here’s my advice to women who want to reach the top in the insurance industry: Learn how to outwit discrimination. Co-opt men and make a male senior executive your mentor. Finally, support your fellow women colleagues and encourage them to reach the top.