If you’re a woman, chances are you’ve been silenced and you have felt unheard.. Now more than ever, women are reaching career milestones across all industries, yet we still seem to be categorized as less than. As Chicago is growing as a tech hub, women may be the force behind it. A handful of Chicago’s most influential female leaders in the tech industry are making history in the tech world and in the books, and they gave us the inside scoop.

These extremely hard-working, dedicated and intelligent women have proven themselves on many levels. At the Women in Tech Breakfast last Friday, 100 attendees gathered for an eye-opening, and for some, career changing, event.

Put on by General Assembly, the leading source for training, staffing and career transitions, and hosted by FreeHand Hotel, this was definitely not a girl power extravaganza. The esteemed panel of speakers shared what they have learned being in a male-dominated industry regarding how they reached their level of success, advice on navigating the workplace and what the future holds for the next generation of women in tech.


Moderators and audience members asked thought-provoking questions of the tech experts during lightning talks.

What is the biggest hurdle you have faced in your career, and what did you learn from it?

Jennifer Viola, Business Intelligence professional 

“I will say first and foremost that the biggest hurdle is being a woman.”

Jennifer has been involved in the technology world for 20 years, her experience in the Data/Analytics industry. She spoke largely on the importance of not forgetting who you are as a person, as it is all too easy to become wrapped up in what others are demanding and expecting of you as your career moves along.

She explained that the company you are working for may move you toward a career path that is not right for you because they need that specific resource. While this concept is understandable from a business standpoint, how do you keep going onto what you want to do?

“My biggest piece of advice is to invest in yourself. Make sure that if you want to keep moving on a track, don’t let the company that you’re working for, as great as they may be, dictate what you want.” 

If you could give yourself advice five years ago, what would it be?

Ellen Prinzi, Founder of Olio City

Ellen has held positions with Major League Baseball in San Francisco and New York, also working as coordinator of baseball operations for the St. Louis Cardinals. During that time, she was the only woman a part of that industry. Instead of seeing that as a barrier, she used it as a strength, explaining that complaining about what you obviously cannot change is a waste of time. You don’t let that be a crutch. You go out and attack it.

The advice that she gave to her previous self, and to everyone in the room, was, “Don’t wait for the right time to pursue something because there is never ‘a right time.'” 

“Women are chief over thinkers. If you’re on the fence about starting your own company or doing something completely different, don’t over think it. If you’re going to sit around and think how scary it is to start your own company, you’re never going to do it.”

Her candid and endearing speech left the room completely quiet. She went on to tell the 20 and 30-somethings listening in that life is passing all of us by if we let it, saying that she never regrets anything she has done, but that it took her longer to actually start it.

“We all know where we want to be. I think the fun part, I guess the messy part, is trying to figure out what you’re trying to get to instead of focusing so much on the end game.”

Relating to the mindset of hard work paying off, Ellen explained that everything that’s worth fighting for is going to be hard, but it’s going to be the best ride of your life.

“Failure can be beautiful. Everyone always says you learn more when you fail than when you succeed, and that’s true.” 

How has being a woman equipped you to being a better manager?

Freehand Hotel Amelia

While tech is very male-dominated, so is hospitality. Being told twice in her career that she was hired because she “fit the look” of the hotel, Amelia made it her mission to prove those people wrong.

“Having to prove yourself forces you to work harder. My aim is to be represented by my ability, experience and potential. Companies should not be looking at gender.” 

Hoping that that representation was why she was hired, her goal is to give people, whether they are 20 years old or 50 years old, the chance that they deserve when seeking employment.

“Don’t be afraid of taking a risk. Creating opportunities for other people has taught me not to judge a book by its cover.”

What was the moment you knew you made it?

Leslie Vickery, CEO and Founder of Clear Edge Marketing & ARA Co-Founder

This no-nonsense go-getter hit home with why she is so passionate about advancing women in tech, explaining that “making it” is different for everyone, and it happens at many different stages of your career.

“Several times throughout my career in life I thought I had made it. To some people, it’s financial gain and awards, for others it’s family, and some, its acquisition. You just have to figure out what making it means for you.”

Like a lot of women, Leslie spent her life celebrating the success of others, never taking the time to celebrate her own success. She took this platform as an opportunity to do just that, telling the group her accomplishments this past year alone.

She was adopted into the UIC entrepreneurial hall of fame, was named Enterprise Women Magazine “woman of the year” and celebrated the 10-year anniversary of Clear Edge Marketing.

Building her company on a flexible model for women who want to work and also take care of their families, little did she know she had actually built that model for herself upon finding out she was pregnant at 42 (another thing that happened last year). 

When people started questioning how she was going to run a company with a baby, she didn’t let their doubts get to her.

“If you have an inner voice that’s telling you you can’t do something, shut it down. Build a network of mentors and champions, and for the love of God, be confident in yourself.”

Sometimes it’s difficult to see in yourself what other people see. The takeaway from this amazing group was clear. Find something important to you, go after it and don’t forget about yourself in the process.