Five Insights I learned from the No. 1 Small Commercial Insurance Carrier in the USA

Written by Orate Speaker, Simon T. Bailey


The Hartford is a 200-year-old company that continues to adapt and redefine itself in order to stay relevant. Its small commercial line of business is the No. 1 market leader that protects the livelihood of over one million small business customers. Recently, Stephanie Bush, SVP of Small Commercial Insurance for The Hartford, invited me to come and speak about my latest thinking with their sales representatives and key e-lines executives on how they could remain in the No. 1 position.

I thought I would waltz in, speak about my ideas, receive a nice check, and walk away. Instead, I learned what a $3 billion company does to stay on top. My first encounter was with Bridgeen Policarpio, Director of Sales Practices and Training for Sales Distribution, and Amy Bray, Assistant Director of Sales Practices and Training; they grilled me for almost two hours. After the initial meeting, I was not sure if I needed to give them my Social Security number or my first born. I walked away shaking my head at the thought that, if I ever got the speaking assignment, it would not be a walk in the park.

I finally received the green light to do the speaking assignment and the real work began. Their previous keynote speaker was Waldo Waldman—a personal friend, mastermind colleague, and someone instrumental in helping me land the opportunity. I contacted him to let him know that I got the nod, and he shared his insights from when he  had presented to them the prior year. He also gave me a download about the culture what makes them successful.  

The first conversation I had was with Rick Newell, Vice President of Small Commercial Sales. He told me they didn’t want a simple rah-rah session; they wanted specific actionable takeaways. With that directive, our office set out to arrange 15 separate 30- to 45-minute interviews. We invested 25 hours of preparation, time to share our best thinking in a four-hour experience. I can honestly say that after working with their small commercial division, I became a better thinker and have transferred some of my key learnings to other clients. Why reinvent the wheel?

Here are the five insights I learned from The Hartford’s small commercial insurance team:

  1. Remain Thirsty and Hungry – In my interviewing of the several internal team members, I continued to hear a recurring theme of never resting on your laurels. Past wins don’t always guarantee future success. Be intentionally paranoid and work harder than anyone in your space. Out think them and out work them.
  2. Leverage Brand Swagger – The Hartford is the only carrier to be certified three years in a row by J.D. Power and Associates. They were selected six times for being one of the world’s most ethical companies to do business with in the United States. They understand that a brand is more than the product or service offered to the agency distribution channel. A brand is an emotion, a connection, and a memory. Every touch point with the principal, agency producer, and CSR (customer service representative) reinforces the brand.
  3. Be Über-Responsive – With just three clicks on your smartphone you can have an Uber driver dispatched to your location. This quick response has caused disruption in the traditional taxicab industry. Now, there are other contenders, such as Lyft, that understand that speed is a differentiator in a noisy economy. Being responsive means unlocking your inner Madagascar so you can move it, move it. In business and in life, I believe that the fortune is in the follow-up.
  1. Shift from Busyness to Effectiveness – During my interview with The Hartford team, one of the executives said that sales reps could spend an entire week doing a ton of busy work and get nothing done. Effectiveness is having a consistent plan that is executed daily. By the end of the week, you realize that doing the right things at the right time produces the best results. Men and women who are effective manage their energy distribution, which ultimately impacts how they use their time. In fact, energy management is more important than time management. Your energy is the very essence of your being, and it allows the flow of your creativity and power.
  2. Stop Selling and Start Connecting – When a person sells, that is a transaction. However, when a person connects, they build a relationship. I believe that relationships are the currency of the future. Sales representatives are really the CEOs—chief engagement officers—of their territories, and underwriters are the CCOs—chief customer officers—of the relationships. Connectors build bridges from where the customer is to where they want to be. Sellers push products based on driving revenue goals that benefit their company first instead of the customer.

The Hartford’s small commercial insurance team is one of the most brilliant organizations that I’ve worked with to date. As its leader, Stephanie is brilliant and tough, doesn’t take any excuses and, more importantly, values the whole person.

This represents a leadershift where executives realize that, in order to grow revenue, they must grow people. In the book Firms of Endearment, R. Edward Freeman, professor of business administration, The Darden School, University of Virginia, says in the foreword, “Great business leaders channel their employees’ desires to be a part of something bigger than themselves and to be a part of making the world a better place for their children into the overall purpose of their business. Profit is an outcome.” The Hartford’s small commercial insurance leadership gets it.

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