Jacquelyn ‘Jackie’ Hoyt of Hillsboro Title Company: “You can keep doing what you are doing, but you need to make a change if you don’t want it to kill you”

“You can keep doing what you are doing, but you need to make a change if you don’t want it to kill you.” These words let me know that I had to let go of some long-held beliefs. As a part of our series about women who are shaking things up in their industry, I […]

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“You can keep doing what you are doing, but you need to make a change if you don’t want it to kill you.” These words let me know that I had to let go of some long-held beliefs.


As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Jacquelyn “Jackie” Hoyt.

Jacquelyn “Jackie” Hoyt is the CEO of Hillsboro Title Company, a Missouri-based full-service residential, commercial, and construction disbursement title company. Her career arc illuminates an impressive track record of persistent professional growth and entrepreneurial spirit.

Jackie started at Hillsboro Title Company as a bookkeeping clerk, worked her way up to CFO, and then the position of COO. In 2012, she purchased the assets of Hillsboro Title Company, becoming both owner and CEO. Prior to her employment at Hillsboro Title Company, Jackie was an accountant at a CPA firm while working at, and eventually owning, a music store. With her propensity for numbers and her business savvy, Jackie nurtures and sustains continued growth in both herself and her business endeavors. Her strong commitment to employees and clients caused Hillsboro Title Company to flourish, and under Jackie’s leadership, the company expanded from five to eight locations.

Jackie actively donates her time and resources to a wide range of community events, causes, and organizations. Through multiple donation drives held at Hillsboro Title Company, she has supported Jefferson County Rescue Mission, Connections to Success, and Missouri Alliance for Children and Families, among others. Hillsboro Title Company is a frequent sponsor of local fundraising events, and their Washington Closing Office is a designated location for SafeKids, a program that offers safe places for youths in need of them.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I began by choosing a course of study that would assure job security. I attended the University of Missouri St. Louis and received a Bachelor of Science in Business Administration with an area of concentration in accounting. After graduation I worked for a pre-recorded music wholesaler in accounts payable and as a buyer. Simultaneously, I owned a small, pre-recorded music retail store. My next few years were spent working for a CPA as a staff accountant. After a particularly grueling tax season in 1998, I decided to accept a part-time position in the bookkeeping department of Hillsboro Title Company, and the rest is history! That job turned into a full-time position as Administrative Assistant to the CEO, and from there I worked my way up to CFO and later COO.

In June of 2012, at the age of 56, I left my safe, predictable life behind and purchased the assets of a troubled Hillsboro Title Company. As a newly minted CEO, I began operating the company with the intent of creating a business that was noteworthy in an industry where the product of title insurance does not have many distinguishing or fascinating characteristics. I told myself that with a reduced debt service, a little time, a good business plan, and a recovering economy, we would soon be on a trajectory towards economic health. However, one day after I signed the ownership papers, we lost a major customer worth ten percent of our business. On top of that, I inherited a staff that was overworked, fearful of additional layoffs, and had not received a raise in six years. Needless to say, I had my work cut out for me.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

One of my favorite quotes is “Well behaved women seldom make history.” Since day one I have applied this mentality to my leadership strategy. Conforming to a stereotype has never been fun, nor does it create room for new ideas. My goal for Hillsboro Title Company has always been the same; make a traditionally bland and clinical industry more approachable and less difficult to navigate for all involved. People told me I was crazy when I expressed the desire to make title insurance more personable and directly connected to the consumer, but we take pride in those values. Our disruption comes in the form of constant ripples that slowly change the status quo while building a strong business. For example, while many in the industry are motivated by financial gains and status, we aim to make a positive lasting impact on the communities where we operate. One way we do that is by volunteering our time and offering up financial support for civic initiatives.

Can you share a story about the funniest mistake you made when you were first starting?

I was in survival mode. Absolutely NOTHING was funny.

Can you tell us what lesson you learned from that? I learned that humor can be a bridge through hard times, and I never should have given up that positive outlook.

We all need a little help along the journey. Who have been some of your mentors?

  1. My three predecessors at Hillsboro Title Company
  2. David Corsaut, who brokered my purchase transaction and became my initial business management coach
  3. Erin Joy, a coach and consultant for female entrepreneurs who continues to influence my journey in a positive way

Can you share a story about how they made an impact?

  • My predecessors each had characteristics that led them to their own successes. They gave me a forty-year history to learn from and choose the very best strategies that work for me.
  • David Corsaut taught me to view myself differently. I needed self-confidence; he taught me to acknowledge my strengths. We were once in the board room of an important St. Louis based business. I was the only female in the room. I looked at him and remarked that I didn’t feel as though I belonged among that group of men. He quickly helped me to size up the room. That was the last time I was intimidated by a group of men. I acknowledge talent, I respect knowledge, but I am not fearful anymore.
  • Erin Joy taught me to walk into the future I imagined. In my time with her as a guide, I learned that there are always choices and techniques for success. Erin showed us we could execute on ideas that others viewed as outlandish. I learned that being OK with disruptive behavior could be a real strength.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good?

If one is causing a disruption for the right reasons — a greater business or organizational good — then it can be positive and is certainly necessary. On the other hand, when people cause disruptions for the wrong reasons, that can be detrimental to the organization. Disruption of any kind is exhausting; it involves plenty of organizational energy. When disruption is focused and for the greater good, it is rewarding for everyone.

When do we say the converse, that a system or structure has ‘withstood the test of time’?

A system or structure is good when it reflects our human values, when it makes us feel secure and respected.

Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’?

Disruption is positive when it’s a change that accomplishes a positive purpose for employees and customers. It is the antithesis of “We have always done it that way” thinking. Disruption is not positive when it puts expediency ahead of values.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  • “Fail fast and cheap.” That is, don’t be afraid to fail, but minimize the effects as much as possible.
  • “You can keep doing what you are doing, but you need to make a change if you don’t want it to kill you.” These words let me know that I had to let go of some long-held beliefs.
  • “Be careful of the things you volunteer to do.” At the beginning of my ownership of Hillsboro Title, my energy level was high, and I wanted to be involved in every good idea. I grossly underestimated the amount of energy it would take to make a troubled company prosperous.

We are sure you aren’t done. How are you going to shake things up next?

I’ll never reject a good idea just because it involves change.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

We need to do more homework to perfect the style in our approach. In an industry that is predominantly male, the men have an established method of communication that is learned from their male mentors. A “woman disruptor” needs to do a great deal of preparation (I did it through coaches) if she is to pitch a disruptive proposal effectively.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

“Radical Forgiveness” by Colin Tipping. There is no specific story about the concept of radical forgiveness. It is an acceptance of a way of living that can influence me every day in how I react and understand others.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

This question reminds me of another book called “The Phantom Tollbooth” by Norton Juster. It contains a chapter about perspective. Should I have the platform, I would like to inspire a movement and forum where we all try to understand the perspective of others and what their experiences have been that have created their individual viewpoints.

Can you please give us your favorite “Life Lesson Quote”?

From my mother: “Just because you say I’m stupid, doesn’t make me stupid”.

Can you share how that was relevant to you in your life?

In business and in life, it is impossible to please everyone (trite, but true). These words serve to remind me that a disagreement does not diminish my capacity to accomplish.

How can our readers follow you online?

You can find me on LinkedIn! Hillsboro Title Company also has a Facebook page and an Instagram profile to keep our clients and friends updated on what we are doing and informed about industry news. Our company website is www.hillsborotitle.com .

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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