Passion and Success – Jennifer Didier, a CEO with Passion

Enterprising Women 2Jennifer Didier, a CEO with passion, is recognized for her entrepreneurial skills and business success.

It was in the days before Netflix and YouTube. A time when at home movie entertainment meant renting VHS tapes from a local store… and it was in one of those where Jennifer Didier’s entrepreneurial career was launched. The technology has since changed but Jennifer’s passion and drive to deliver client focused solutions has only grown just as has the company she started twenty years.

Jennifer Didier is the CEO of Directions Training, a global training company based in Chicago. Jennifer has recently been recognized as one the Class of 2016 Champions by Enterprising Women Magazine. This is a prestigious award used to recognize top women entrepreneurs from around the globe.

“These “Champions” excel in a variety of ways –through fast business growth, community leadership, or as outstanding role models and mentors in their communities”

– Monica Smiley, Publisher/CEO, Enterprising Women Magazine

Entrepreneurship in the Early Days

When asked about her start as an entrepreneur, Jennifer explains, “I knew very early on that I would run my own business, I just didn’t realize that it would be technology based, even though I always loved innovation and computers.”

Walking into her local video store while in high school, Jennifer was struck by a problem facing store owners: cataloguing the inventory of videos available for customers to rent. New titles were added frequently and the list would need changing. Keeping the list up-to-date grew more and more challenging and time consuming.

Armed with her PC and technical skills, Jennifer seized the opportunity and offered to create a master video list and regular updates for a monthly subscription fee. Jennifer would go on to expand her first business offering to 12 more stores.

The Birth of a New Venture with Global Reach

So how did Jennifer go from her early high school venture to running a global training company? In 1985, Jennifer worked for a typical computer company selling hardware and software. Wanting to spend more time at home once her daughter was born, she had planned to take a leave. Her quick-thinking boss had another idea and suggested to Jennifer that she could continue to work and help train clients in the evenings and on weekends. Jennifer started training clients and the light bulb went off when she realized how much she loved imparting information and helping people learn new skills. Opening a small training center was the next stop on Jennifer entrepreneurial path.

Laughing, she recalls that period of time, “I was young and naïve and I thought that having my own business would give me more time to spend with my children and family. Suddenly I had demand for my training services and my customers were my bosses. It required an adjustment to my original thinking but it was so exciting, I couldn’t stop and just found a way to make it work.”

Meeting the Challenges of Business Growth

Building a company focused on long term customer solutions that has achieved double digit growth year after year does not come without its challenges. Jennifer highlights the approaches she has taken to meet these challenges and what she had learned to garner her success:

  • Growing a Company Comes with a Lot of Risk and Investment. “You have to quantify that risk and build the right mitigation plans. Investing, the right way, for growth is a delicate balance that you have to constantly pay attention to”, Jennifer points out.
  • Manage by Data. According to Jennifer, “I’m naturally optimistic and earlier on, I made a lot of decisions because they simply felt right. When you scale the business, however, you need to work more with the data and not rely so heavily on gut instinct.”
  • Give It 24 Hours. Jennifer admits that it took a while to learn this one. She came to realize not to make decisions too quickly because the perspective on something can change drastically with a step back and a bit of time to reflect.
  • Engage the Right Support. Jennifer has worked with coaches and other advisers to help her grow her business at different points in time and that investment has paid off. On the topic of mentors, while she did not have a single individual she worked with, she became adept at the concept of “micro-mentoring” and learning in-the-moment from whomever was willing to share thoughts and experiences.
  • Stay Positive. Jennifer makes it a point to surround herself with positive people, “It’s best for dealing with the setbacks and challenges that are inevitable in business. You just have to keep going. Negativity can be contagious so I keep my distance.” She is also grateful for the support of her wonderful family, friends, and professional network.
  • Be Confident. Working in the more male-dominated technology industry, Jennifer points to simply staying confident and focused as one of the most important things women can do, “I think the biggest success comes from holding yourself with confidence and speaking to the point”. Jennifer advises that ego and any concerns about how one might be perceived be set aside. As would be expected of any professional, women in the industry should bring the best they have to offer to the fore and do it succinctly, with confidence.

Key Piece of Advice: It Is All About Passion

When asked what advice she would give others about starting a business or embarking on their careers, Jennifer has this to say:

“A business runs on passion. I love building solutions and discovering that “a-ha” moment with customers. It’s not about the money, the bottom line is what happens when you do everything else right and find the excitement in what you do. You have to look deep in your heart. If it’s someone else’s idea and not something you are truly passionate about, you won’t be successful.” 

Jennifer’s passion for business accompanies her dedication to advancing women in technology. In addition to her role as global chair for IAMCP’s Women in Technology (WIT) community, Jennifer is also involved with the Chicago chapter which supports the Young Women’s Leadership Charter School, an allgirls public school that emphasizes math, science, and technology. She is also a board member of the Illinois Institute of Technology and the Illinois Technology Foundation. She donates thousands of dollars in scholarships for students at the Foundation’s annual Fifty for the Future® event which honors high school students looking to pursue careers in the information technology field.

More Great Advice: A Blended Balance 

How does Jennifer balance active community involvement, a thriving business, friends and family? “It’s difficult, but I’ve learned to blend it. Life doesn’t fit neatly into time slots. I’ll respond to an email from a friend during the day, work on a project in the evening or tend to a personal matter if I need to during a week day morning while taking care of some business on the weekend. Integration is the key. Give yourself permission to blend and don’t be too hard on yourself.”


Enterprising Women of the Year Champions will be recognized at the 14th Annual Enterprising Women of the Year Awards Celebration & Conference, Sunday, February 28 to Tuesday, March 1 at The RitzCarlton Coconut Grove in Miami, Florida.

Congratulations Jennifer and thank you for contributing your passion and talents to IAMCP and IAMCP WIT!

Leave a Reply