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  • Writer's pictureJay Judas

Tier One Interview: Kari Gillenwater

In our latest Tier One Interview, our CEO, Jay Judas, spoke with Kari Gillenwater of Gillenwater Consulting Group, a leading facilitator of collaboration in the HNW life insurance industry. The two discuss how Kari came to the industry, the many benefits of study groups, what the life insurance industry can do better to attract and retain women, and share travel and restaurant tips. Read the interview in full below.

JAY: Preparing for this interview was challenging because I had a tough time cutting down the number of topics to cover. You have a unique position in the upper echelon of the life insurance industry and what I mean by that is that you are able to observe quite a bit – people, trends, technology, strategy and a whole lot more. I came to know you because, honestly, if you operate in the high net worth space of our industry, it would be impossible not to….you’re everywhere! I began to see you every few weeks at producer group meetings, at Forum 400, at AALU (now Finseca) and at broker-dealer events. Start by filling us in on your company, Gillenwater Consulting Group, and your role there.

KARI: Jay, I was elated when you asked if you could interview me for the Tier One series. But then I became a little nervous, too, so let’s see how this goes!

I think the easiest way to describe Gillenwater Consulting Group and the role I play for my clients is that I am the "sparkplug" my clients plug in to help their advisors connect, collaborate and cultivate relationships to help advisors drive revenue and grow their practices.

Over the years my clients have ranged from dozens of individual advisors and their teams, to a wide range of field marketing and industry organizations. In addition, I coach advisors on business development, accountability and creating strategic alliances to increase their bottom line.

What “brought me to the dance” was developing and managing advisor-centric study groups and conferences. The McGehee Group was my first study group and where it all started. A few years later, I was referred to the Lion Street producer group, based in Austin, to help them create a network of internal study groups they call Growth Groups. I have also been engaged to create and run study groups and conferences for FIG, FFR, C2P, Simplicity Financial, The Pinnacle Study Group, The Center for Tax Strategies and Resources, AALU, and the Forum400, just to name a few.

Interacting with all of these incredible organizations for the past 15 years has allowed me to work with and learn from hundreds of successful advisors and the leadership from all of these organizations. It has given me incredible insight into the needs and challenges advisors face, as well as those of the organizations that support them.

JAY: You didn’t enter the life insurance industry until 15 years ago so I’m curious about your upbringing and the path which led you to where you are today. I’m especially interested to learn how you ended up settling in Little Rock.

KARI: In 1980, my family moved to Little Rock, Arkansas from Winston-Salem, NC when I was in seventh grade. My father had just taken a job with Target Stores and was tasked with bringing the very first Target to Arkansas. Naturally, this caused quite a stir since Arkansas is the home of Sam Walton and Walmart. My dad also oversaw the building and operation of the first distribution center for Target Stores in the state.

My parents loved to entertain and they did it with a passion. I think a lot of what I do is a reflection of what I learned from my parents; their love of bringing people together, entertaining, the importance of focusing on the small details to make people feel at home so they can connect and have a good time.

I have always been an extrovert with a creative bent. I have a BA in Journalism and Advertising/PR from the University of Arkansas at Fayetteville. Throughout my career, I have been a media buyer, graphic designer, pharmaceutical sales person and special event director for a large health system. In 2005, I entered the insurance world when Frank McGehee, a larger-than-life insurance advisor hired me as his Director of Marketing. Little did I know at the time he would play such a pivotal role in my life, and be the impetus for one day starting my own company.

A founding member of NFP/Partners, Frank, loved collaborating with other advisors and many came to him for his brilliant ideas and to do joint business. Frank also loved to travel and entertain, so he decided to combine them all and start a study group. In a wildly competitive industry, it was a unique concept to bring highly successful insurance advisors together to share best practices and work collaboratively. By the time I met Frank, the group had grown to 30 members, and part of my new role was to manage the study group.

I jumped right in and orchestrated their Fall Advisors Conference in Vegas. This was my first introduction to a professional study group, and I was hooked! I loved the energy and watching everyone come together to learn and share ideas. It was everything I loved all rolled in to one great event.

Tragically, two weeks later, Frank died of a massive heart attack in the office at the age of 56. We were all shocked and devastated. I had worked for him for less than a year, and just like that, he was gone. It was a huge loss for all who knew him. Shortly after his death, the members of the study group renamed the group, The McGehee Study Group in his honor and named me Executive Director ad infinitum to ensure Frank’s legacy. Frank’s death truly changed my life and set me on my path to start my own company.

Over the years, I continued working with the McGehee Group and began doing business planning, marketing and business development for many of the member firms. After working closely with some of the best in the business - Rod Sager, John Smith, Jim Hebets, and Simon Singer- I decided it was time to “go big or go home” and I officially started Gillenwater Consulting Group.

Fast forward to today, I am proud to say, in January of 2020, I entered into an exclusive client relationship with the Lion Street producer group, and while I still work with The McGehee Group and some other industry organizations, the Lion Street universe is where I spend most of my time managing their growth groups and working on building resources and programs to support their advisors.

JAY: I want you to talk more about study groups, or growth groups as they are increasingly called. You are the undisputed expert in forming these groups and organizing their gatherings in a way that the unique educational needs of the individual members are satisfied. How do you form study groups and what are the benefits?

KARI: While I don’t necessarily view myself as an expert, I have dedicated the last 15 years to leading and facilitating growth for advisors through study groups. By nature I am a natural connector. I love bringing people together and watching people interact and collaborate.

My website is which stands for Gillenwater Consulting Group where I specialize in helping advisors with the three C’s: Connecting, Collaborating and Cultivating Relationships with each other and their clients.

If you are familiar with StrengthsFinder 2.0 assessment– my top five strengths are Strategic, Maximizer, Individualization, Communication and WOO (Winning over others quickly). I think one of the reasons I have been so successful with study groups is that I get to use my biggest strengths every day.

I am intrigued with the unique qualities of each person and love figuring out how people who are different can work together productively. In my career, I have worked with over thirty different study or mastermind groups and not one of them was remotely the same. In my experience, there is no exact science in forming a study group, but I have learned some things that contribute to the overall success of a group.

So many things have to be considered when putting a group together. First and foremost, they must be aligned with the purpose of the group. Some groups want to mix business with fun, others are very serious and only want to discuss business and not cross over into personal matters. It is very important to understand what the groups’ purpose is and to understand the group boundaries from the very start and create a structure that fits that unique group.

In working with elite-insurance advisors, finding a diverse balance of personalities, ages, regionality, market size, focus of practice as well as personal hobbies and interests all lead to a healthy group dynamic. For example, if you have too many Alpha personalities in the group, it can stifle productivity and leave some members feeling frustrated.

Study groups are much like children. They all have their unique personalities, needs, interests and idiosyncrasies. I think that is why I love working with them and my advisors so much – each group is so different which makes every day interesting and I never stop learning.

JAY: Your enthusiasm about study groups is infectious. What part about your work with these groups do you enjoy most?

KARI: My favorite thing about creating and working with study groups is bringing a diverse group of people and personalities together and watching them grow not only individually, but collectively. These small groups are also critical to keeping a company culture intact. As a company grows bigger, the culture that started the company can get lost. These small groups serve as the backbone of the company culture and make sure that no matter how large the company gets the underlying culture remains intact.

This industry can also be very isolating, so it is very gratifying to know that I play an important part by facilitating the creation of relationships that lead to better outcomes both personally and professionally for my advisors. Watching the sparks fly as people connect and share ideas is like a sport to me.

JAY: Notably, just because the life insurance industry has embraced growth groups, doesn’t mean they aren’t beneficial for other industries. Where else do you see them fitting?

KARI: The focus and goal of any study, mastermind or growth group is to use the combined brainpower and experience of the group members to elevate, educate and help everyone. I don’t know of any industry or field that would not benefit from bringing people together to share their skills, experience and knowledge.

In the business world Dan Sullivan’s Strategic Coach program, Young President’s Organization (YPO) and Vistage, just to name a few, are all great examples of bringing business people from different industries to benefit from mastermind or the study group concept.

As I researched to learn more about study groups, I discovered that even Albert Einstein was in a study group. In October of 1927 the world's most notable physicists met to discuss the newly formulated quantum theory at the Fifth Solvay International Conference. Albert Einstein, Marie Curit and Niels Bohr were members and 17 of the 29 attendees were, or became, Nobel Prize winners.

JAY: As a master networker and someone whose work involves bringing people together, I can imagine you have had to make some adjustments due to the COVID-19 pandemic. How are you staying connected with your clients and, especially with your growth groups, what are you doing to keep them connected and sharing?

KARI: Thankfully we had incorporated Zoom into most of our study groups long before the pandemic hit. What did change immediately was the urgency and frequency of our calls.

Most of my groups have quarterly calls and meet in person around conferences several times a year. Once Covid-19 hit, a lot of my groups started doing calls every two weeks or monthly, so the number of calls I was on skyrocketed. The first six months I practically lived on Zoom. But I am so thankful we had those groups – it made it so much easier for us to stay connected.

Before COVID-19, I traveled 60-70% of the time going to conferences, retreats and meetings where I saw hundreds of people a month. I began to develop a reputation for taking pictures with everyone at my events and posting them on LinkedIn. People started commenting on how much they enjoyed seeing my pictures, and over the years I developed a following and people began asking me to take pictures so I would post them. I miss not being able to do that now.

One thing I have started to do is reach out and personally call one or two of my advisors every day just to reach out and see how they are. I learn so much about what is working and what is not, as well as their challenges and wins and it really helps me focus on connecting them with other advisors and creating solutions to help them. It makes me happy to learn that many of them have received similar phones from you, too, Jay!

I am also big on sending “happies” which are little small gifts and hand-written notes. If someone was particularly helpful or going through a rough time, I always try to send them a note. I also use an app called TouchNote that allows you to put a picture on a postcard with a personalized note and mail it right from your phone. I think it's more important than ever to do all we can to stay connected and show people we are there for them.

JAY: As I mentioned earlier, you get to observe a lot of things in our industry because of your level of access. You and I had a lengthy conversation the other day about the diversity challenges that are being addressed more slowly than in other parts of financial services. You said this has always confounded you because women are a perfect fit for the life insurance industry. Tell us why that is and then go ahead and unload about what changes you would like to see. (laughing) I’ve been waiting for this part and promise to edit out any profanity!

KARI: Wow – how much time do you have?

First, I think women are a natural fit for this industry because they are instinctively more inclined to nurture and relate to others empathetically, so they bring a dynamic to the client relationship this is often missed by a male-only team.

Being one of few women in our industry, it is a huge source of frustration for me. We are constantly asking ourselves where can we find more women? More often women become financial advisors because companies like Edward Jones and Wells Fargo and others have a structure that supports them and trains them – we don’t have that in the insurance industry.

It is no secret that the insurance industry is described by some as PMS – Pale, Male and Stale. The life insurance industry has not evolved to accurately reflect the people that it serves, and I feel strongly that if we don’t create opportunities for a younger and more diverse cross-section of candidates our industry is in peril.

JAY: What changes would you like to see to improve the situation?

KARI: While I don’t have all the answers, I believe some of the key changes that need to happen are:

We have to do a better job of educating and promoting our industry. As an industry, we have done a horrible job of positively positioning the role of an insurance advisor. There is a negative connotation of insurance sales. Most people do not understand the value that we bring as an industry and the important financial vehicle insurance truly is. We need to do a better job of educating the public and we can do that with education. By creating an educational pathway to our industry through high schools and colleges. We need to work more closely with our educational system and reach a broader ethnicity earlier so they will know enough to consider it as a potential occupation.

We have to change the way we pay advisors so more people see it as a viable career path. The traditional pay structure of “eat what you kill” is outdated and no longer makes selling insurance an attractive occupational choice for people looking to start a career.I am excited to see more firms adopt a tier system that provides a pathway for young producers to work their way up and earn more as they learn more.I think the more we can do this, the faster we can open up the market to not only attract younger people entering the workforce, but also women who are re-entering the workforce and those that have retired and are looking for their next chapter or second career.

We have to find a way to provide uniform training to those that come in to the business. Great salespeople seldom make great trainers.They want to kill it – not teach it. As a result, most producers who come into the business have no formal training and are left to just learn it on their own as they shadow a producer. That may have worked 30 years ago, but with technology and the rate of change, we have to shorten the trajectory of someone learning the business. So much time and money is wasted on young producers who fail or give up because they didn’t have adequate training and support. The career shops are becoming fewer and fewer and although they have been successful at training the basic blocking and tackling of insurance sales, those that leave the career system and join individual firms have to be re-trained in many ways and there can still be a long way to success.

And finally – we need to find a way for advisors looking to exit and/or monetize their businesses to partner with younger advisors sooner. Firms need to be proactive, rather than reactive, and integrate younger advisors into their firms sooner. This will allow the younger advisors to learn from the experienced advisors and be better prepared to take over the business and service clients successfully when the time comes to make the transition.

If we can begin making inroads into several of these areas I believe we can start attracting more people to our industry so that it is more reflective of the people we serve.

JAY: You are an excellent example of time management because not only are you running a growing company and normally traveling around the country, you have an expanding family. In addition to your husband, Spence, and your sons, Trey and Ryan, you have step-children and step-grandchildren. Introduce us to everyone and talk about how you spend your family time.

KARI: I am so lucky. Very few husbands would be as understanding and supportive of all the travel that I normally do for my job. I have to say that has been the one bright spot of this pandemic, I have gotten to see my family so much more. I think I am finally getting used to not living out of a suitcase!

I am blessed with two amazing sons, Trey, 24, and Ryan, 20, who are the light of my life. I am so proud of both of them. My devoted and very patient - have you met me? - husband, Spence, is a very successful defense attorney and probably one of the smartest and kindest people I know. He is my rock and my biggest fan, and I hit the lottery when I met and married him 10 years ago.

I am also step-mom to Gaines, Elizabeth and Wilson, his three wonderful children. We are very proud to be “Cha-Cha”, which is my step-grandmom name, and “Pops” to three of the most precious grand-daughters that ever existed – Caroline, Catherine and Claire. Having had two brothers, two sons and working with mostly men, I was delighted to finally have some girls to dote on!

We also have two fur babies we rescued, Mocha, a 100-lb chocolate lab/mastiff mix, and Sarge, a black lab/Weimaraner mix. They are my co-workers and protectors and are a constant source of love and tail wags.

Then, I am grateful to have many close girlfriends spread out across the nation and I love to combine business with fun and stop by on my way either to or from business when I can.

Spence is a member of several law groups such as the American College and ABOTA and we love going to those meetings and traveling with his long-time friends. Every summer we enjoy going to the beach and visiting Culver, Indiana where our friends have a place on the lake.

We are also in a “Supper Club” with eight other couples and although we can’t do our monthly dinners right now, we have tried to see each other over Zoom cocktail parties, and a few social distancing get-togethers in backyards and down by the Arkansas River.

In addition to the above, I walk every day and recently started Cross Fit at the urging of my son, Trey, and his fiancé Caroline….so please pray for me! It has been fun working out with them when I am not too sore to move. I also took up painting and printmaking several years ago, and now have my own studio where I love to go and decompress on the weekends.

JAY: In law school, my Constitutional Law professor, Michael Dorf, told my section that, contrary to popular belief, there were actually stupid questions to ask, “so don’t ask them.” Unfortunately, my curiosity is overriding this wisdom and I need to know if it is a total pain to do so much traveling out of the Little Rock airport? It seems about every time I have returned home to Boston from a meeting we both attended, I would see you commenting on LinkedIn about seven hours later how you were trapped in Charlotte or Dallas or some other place in the middle of the night. What are some of your most horrific travel stories?

KARI: Oh my Gosh – isn’t it funny how a pandemic can actually make you miss flying!!!

I traditionally travel so much I started telling people my office was located on aisle 8 window seat on Southwest, which is, by far, my favorite airline to fly. Their system just makes it so much easier to board! However, I sometimes have to go on another airline for the best connections and times and this has led to my history of travel woes with American Airlines.

My biggest travel nightmare was the breaking point when I realized I couldn’t take care of all my clients and myself, too. I had booked my flight to attend an awards dinner in LA for one of my biggest clients. If you have ever flown to LA, you know there are two smaller airports, Burbank and John Wayne. Well, somehow I booked my flight on the wrong airline, and as I walked off my plane, my stomach dropped when I realized I had just landed at the wrong airport!

I was an hour away and had no idea how I was going to fight rush hour traffic and make my dinner in time. I jumped in the nearest cab and, somehow by the grace of God and a $200 cab ride later, I got to the hotel just in time to change in the bathroom and make it to the dinner on time. My client never knew! It was soon after that I hired a full-time assistant, Jillian Linder, and that has been the best investment I have ever made for my business, and my sanity.

JAY: You arrange a lot of business meals for your clients, so I know you’ll have no trouble in naming a couple of your favorite spots and dishes. Normally, I ask that no steakhouses or steaks be mentioned. You fought me on this and because you are somewhat of a hostage to your clients when it comes to eating, I'll let you break this rule.

KARI: This is actually a difficult question for me, Jay! Over a typical year, I can host over 50 dinners in almost as many cities so it is tough to say my favorites. My assistant, Jillian, helps quite a bit in researching find the local favorites which give our clients a feel for the city’s culture and cuisine.

In no particular order here are some of my favorites -

  • Best restaurant experience ever in the US - The Charleston Grill in the Belmond Charleston Hotel – 5 star in every way.

  • San Fransicso, CA – Frascoti on Green Street, The Campton Place Restaurant and Tadich Grill

  • Chicago, IL – Best Crab Claws it’s a tie - Shaw’s Crabhouse or Joe’s Seafood, Prime Steak and Stone Crab

  • NYC – The Gotham Grill and NOBU

  • Ashville, NC – The Market – creative cuisine and eclectic – amazing service, Tupalo Honey – great lunch and breakfast!

  • Las Vegas, NV – CUT is a favorite – eating there is like getting a PhD in steak.

  • Phoenix, AZ – Elements in The Sanctuary

  • Santa Rosa, Beach – Café Thirty-A

And finally my hometown favorite here in Little Rock is Café Bosa Nova, a Brazilian restaurant, and Sauced, a neighborhood restaurant where my son, Ryan, works.

Read our companion Tier One blog by clicking here.

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