Please Meet: Helen Levinson

This week, we’re revealing our panelists one by one for the 3rd Annual Little Black Dress Night. We want you to get to know our panelists ahead of the event. Today’s reveal is Helen Levinson, the CEO of Indigo Interactive.



ChiTech: What led you into tech and entrepreneurship?
Helen Levinson: My dad was an engineer. I used to watch him build things and help him build and take things apart. I’ve always had the natural inclination of having a mechanical mind and always curious about how things worked.

I didn’t go to college right away after high school and instead got a job with the Teamster’s union automating their systems. After I realized that I really loved automation and technology, I went to school and got a my bachelor’s degree in Computer Science.

What did you learn from not going to college right away?
I learned how to handle people. I learned how to overcome challenges that you typically don’t experience when you’re a kid.

Can you tell me a memory about watching your dad build something?
We were poor growing up, and my dad used to fix T.V.’s for people on the block. He would bring parts home that he would find and he built a T.V. for us. It had a big picture tube, they looked like huge lightbulbs. He’d build the outer box and place the huge picture tubes in there, and the motherboard, and then we’d watch the T.V. that he built for us.

What shows did you watch?
Typical stuff like “The Wizard of Oz,” my dad got me hooked on “Indiana Jones,” we watched “Time Bandits,” and a lot of scifi stuff, “Star Trek,” “Star Wars,” things like that.

How did you get to building your own company?
When I started working for the Teamsters, I was in my early 20’s. I had gone through so many jobs. When I landed there, I was working in the Health and Welfare Office for Local 734 Office and I was the youngest one there. Everyone worked on a typewriter then. We were nearing to the Y2K conversion, and I convinced my manager to buy computers, and then I automated their entire paper process.

I left to start my own business selling websites. My skillset grew because I was now interacting with customers too. It started to grow quickly, and I merged my business with an ex-business partner, uniting my tech expertise with her marketing expertise. That lasted for about 10 years, and I created Indigo Interactive in 2013 with a special focus on education technology.

Did you start Indigo Interactive with any investors?
No, we are completely bootstrapped and have no investors. Being bootstrapped creates its own challenges in that the growth of the business is on a slower pace.

How did you overcome that?
We had to be really creative. We hired more people who were detailed and organized to get processes in place to make sure our projects were profitable. We’re also the leading software vendor in our market, so being able to pull in new clients and offer new solutions helped grow the business.

How do you see yourself making an impact on the company in the next two years?
We’ve come out with new models that smaller accrediting bodies can afford, so we’re expanding our reach and productizing the company, moving away from consulting. We also plan to launch products into other vertical markets like charter schools and certification bodies.

Can you give me three words you would use to describe yourself?
Tenacious, determined and methodical.

What are some of your goals, professional or personal?
From a professional standpoint, I’d really like to grow the business, be used in a larger consumer base. On a personal level, I want to go back to school and work my way up to a Doctorate degree in something technology related. I’m interested in cyber-security.

What made you want to go back to school?
I’m a lifelong learner. The moment you stop learning is the moment you end your personal growth.

What do you see as your biggest accomplishment so far?
Being able to manage and grow a business and still be a good mom.

Who are your heroes?
Outside of Wonder Woman and my mom? I’ve always admired any woman that has overcome major challenges that has become very successful. Success doesn’t always equate to making a ton of money, but overcoming any challenge where all odds are against you. It’s like being the underdog, where anyone might look at you and say “she’s never going to make it,” and then you make it with a good life and a good family. Overall, it’s all women collectively who have done great things to help others.

When you were in school, who was your favorite teacher and why?
My high school physics teacher. He had a way of teaching physics that would resonate. I couldn’t wait to be in that class everyday. He explained the laws of physics and how things worked and it was fascinating.

When you were in high school, what was your favorite album?
I have an eclectic taste in music, but I’d say the top would be “Purple Rain” by Prince.

What is something not a lot of people know about you or you wish people knew about you?
I don’t think people believe that I started out my first job at 10 years old passing out fliers door to door for 75 cents an hour. They were for a local drugstore at Montrose and Western, on the Northside of Chicago, where I grew up. When I turned 12, I convinced the owner to hire me to to do in-store merchandising. But instead he put me in the back room of the pharmacy. I had to unwrap individually wrapped aspirin samples, use a nail file to scrape off the word “sample,” and put them in a jar so he could sell them. At the time I didn’t know what I was doing, I was happy making $1.25 an hour, but later on I found out he was arrested for loansharking.

What did you spend that money on?
I used it to help my parents since my dad was out of work and my mom was pregnant with my youngest sister.

Do you have any words of wisdom for the young ladies of ChiTech?
Always ask for help when you need it. The one thing I learned early on is to surround yourself with great people who will lift you up so you can see the right path and advance. I was really lucky with people lending a hand to help me get to the next level.


About Helen Levinson:

Helen is gifted with a mind that is equal parts business woman and technical director. With two decades of entrepreneurship and her own successful EdTech firm, she provides higher education organizations with innovative tools to help automate manual tasks, increase efficiency, as well as collect and mine their student data.

Helen is a firm believer in empowering all employees to innovate and contribute to the advancement of business objectives through technology. In addition to speaking engagements and panel discussions, she is active on several school advisory boards regarding digital curricula. She is nationally recognized in the retail and education industry as a technology expert.

Helen takes great pride in working with nonprofits and charities that focus on the disadvantaged and children, particularly those that encourage young girls to pursue careers in science, technology, engineering, and mathematics (STEM). As a mother, she also enjoys collaborating and sharing advice with other entrepreneurial moms on how to strike a healthy balance between life and work. She is a Chicago born native and holds a Bachelor’s Degree in Computer Science.

Find Helen on LinkedIn


Learn more about sponsoring a table for your company at the 3rd Annual Little Black Dress Night by contacting Kelly Jones, Executive Director, at 

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