Women in Insurance: Kelly Lennon, Vice President, Commercial Risk Advisor, USI Insurance

Women in Insurance - November 3 2020

In this interview series, we profile women who are shaping the future of insurance. This week, we’re pleased to profile Kelly Lennon, Vice President, Commercial Risk Advisor, USI Insurance, a leading property & casualty, employee benefit, personal risk and retirement brokerage firm serving more than 150,000 clients nationwide.

Kelly, tell us about your path to insurance. What attracted you to the profession?

It happened quite by happenstance. I was coming off a career in kids marketing with a taxing daily commute, so I was looking for something closer to home. Despite having no insurance experience, I applied for an account management job for a travel insurance TPA. Fortunately, they were intentionally seeking outsiders, and I was hired to manage several travel supplier accounts (mainly cruise lines). It was such a positive experience and gave me a real respect for the insurance industry. I learned that, contrary to popular belief, insurance carriers were not looking to deny claims but were truly looking to make insureds whole. After that, I entered the property and casualty space with a national wholesaler, and I started in my current position as a property and casualty broker with a national organization, smack dab in the middle of the COVID-19 pandemic.

What do you find most fulfilling about the work you do?  

Having a direct impact on helping people prosper! As those of us in the industry know, it’s pretty much what insurance is all about.

The insurance industry is in the midst of massive change. What do you think the insurance business will look like in five years?

I think technology will continue to improve the processes, not disrupt it. Insureds will always need experienced Risk Advisors, Agents, and Brokers. Big data and technology will continue to enhance how we do it.

If you had to pick one technology trend that will fundamentally transform insurance over the next 5-10 years, what would it be?

I would say Artificial Intelligence because it’s going to continue to drive emerging risks (like autonomous vehicles). Our industry will continue to develop products and programs to protect insureds and the general public.

The insurance industry faces a recruitment challenge with millennials choosing professions they deem to be more progressive, challenging and fun. What can insurers do to entice new talent?

If we look at industries that attract the most millennials (e.g., technology), let us ask ourselves why the appeal and then replicate those incentives. Do you offer a competitive compensation package? Are you flexible around remote work? Are you socially conscious? Is the board diverse? Etc.

According to a 2017 study, just 12 percent of insurance companies’ top corporate officers are women. Why do you think there are so few women in senior leadership roles in the insurance industry?

In general, I think it is a combination of unconscious bias and stereotypes. Companies may not consider women when filling positions of leadership and when they do, they do not view them the same way. The same trait in a man and a woman are perceived differently. For a man, a certain trait may make him promotable, but for a woman possessing the same trait, she is perceived as being too aggressive.

What can insurance companies do to ensure that women not only stay in the profession but advance in their careers?

There needs to be a defined initiative for the company and training for all employees. But not just “check this box” training. Instead, they need to examine if and where biases occur and how it can be addressed in all areas from hiring to promotions.

What recommendations do you have for young female professionals entering into the insurance on how to find a mentor and develop the relationship?

I would say find someone (male or female) whom you admire and learn all you can about them. Use them as your inspiration. Then reach out to women in leadership roles at companies you are interested in and join network groups such as Lean In.

Does your firm have initiatives in place to encourage gender parity and diversity?

Yes! We have an initiative in place called I’m With U. “I” represents the individual action we each take. “With” is how we bring people together, not apart. And “U” for understanding, uncovering, uplifting, upholding, unblinking, and unifying. I am thrilled to be a part of the I’m With U team!

What positive changes have you seen since you began in your career?

We have come a long way from when I started my career until now. Women are more educated, hold more positions of leadership, and are more likely to become entrepreneurs. But it’s still not enough! When Ruth Bader Ginsberg was asked when there will be enough women on the Supreme Court, she (famously) replied, “When there are nine.” 

What advice would you give the next generation of women considering a career in insurance?

Learn about the industry. Talk to your own agents or brokers to see what they like and dislike. Find someone in the industry (LinkedIn is a great resource for that) and interview them. And whatever they decide, learn about the ERA, suffragettes, and women like Ruth Bader Ginsberg and recognize and respect all of the hard work that went into earning women “a seat at the table.”

IMG_8630 - Kelly Lennon

Kelly Lennon is a Vice President, Risk Advisor at USI Insurance Services, a leading local and national insurance brokerage and consulting firm. Kelly is part of the Property & Casualty practice, and her main function is to help companies in the technology sector manage their risks.


Kelly was an early adopter of social selling in the insurance space. As part of her social media efforts, she has created and posted more than 50 one-minute insurance videos from “Guess the Insurance Acronym” to “Have you Hugged an ACORD Form Today.” She is a content contributor for InsuranceNerds, served as a featured panelist on Argo Group’s “Post, Share, Follow: Grow Your business with Social Media” webinar, and was featured in the January 2020 issue of Big I magazine and the April 2020 edition of  Business Insurance America magazine.  


Kelly grew up in the New York City borough of Queens and now lives on the north shore of Long Island, New York. You can find Kelly online at LinkedIn, YouTube, and Twitter.

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