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Karen Gondoly of Leostream: “Don’t be afraid to walk away”

The path to success is not always linear (and that’s OK!). From rocket scientist to pastry chef to tech CEO–I’m not sure I would have ever been able to predict this path. I’ve allowed myself to explore different interests, such as leaving jobs in tech and working in restaurants, and that has given me the […]

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The path to success is not always linear (and that’s OK!). From rocket scientist to pastry chef to tech CEO–I’m not sure I would have ever been able to predict this path. I’ve allowed myself to explore different interests, such as leaving jobs in tech and working in restaurants, and that has given me the gift of being strong and confident in what I want from my career.


As a part of my series about “Lessons From Inspirational Women in STEM and Tech”, I had the pleasure of interviewing Karen Gondoly.

Karen Gondoly is the CEO of Leostream, the category leader in enterprise remote access solutions. Karen joined Leostream from The MathWorks, Inc., a technical software company where she was a developer for the Control System Toolbox before specializing in usability. Her technical background includes roles as a software developer, GUI designer, technical writer and usability specialist. Karen holds bachelor and master of science degrees in aeronautical/astronautical engineering from the Massachusetts Institute of Technology.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

The short story is, I answered a Craigslist ad. How I got to Craigslist includes a few twists and turns.

I was fascinated by astronomy while growing up in Michigan, but as the youngest in a family of engineers, I couldn’t conceive a career path that didn’t include engineering. So, I looked for ways to marry space and engineering and discovered aerospace engineering. The problem with aerospace engineering was that, while my entire family attended the University of Detroit, that university didn’t have an aerospace engineering program. That was a bit of a dilemma until one day I got a pamphlet in the mail from MIT. I still remember the day my acceptance letter arrived in the mail.

I entered MIT with a dream of working at NASA and I actually did co-op there as an undergraduate, as well as work on my Master’s thesis at Langley. In the end, I found the red tape of government work too stifling and I’d fallen in love with Boston. So instead of moving to where the aerospace engineering jobs were, I found a company in Cambridge writing MATLAB code for control system designs, my Master’s specialty. I stayed at that company for about a year before moving to The MathWorks, the makers of MATLAB, building user interfaces for their Control System Design toolbox. I worked there for seven years, but towards the end started thinking about fulfilling another dream.

I grew up baking with my grandmother and decided to test out the idea of one day owning my own bakery. I continued at The MathWorks by day and attended culinary school to be a pastry chef at night. As part of that experience, I staged at a top Boston restaurant for a day and unexpectedly was offered a job. That was too great an opportunity to pass up. The MathWorks was gracious enough to allow me to continue to work part time while I worked at the restaurant at night. In the end, I turned being a pastry chef into a full-time job. The only problem was that I had a mortgage to pay and that doesn’t happen on the salary of a pastry chef in Boston. So, to make ends meet, I picked up contracting gigs in the tech space — documentation, QA, UI work — and that takes us to Craigslist.

One day about 13 years ago, I applied for a part-time documentation writing position at Leostream through a Craigslist ad. My interviewer realized that I could actually fill various roles that they were looking for, so they offered me a full-time role as Product Manager. And, with that, I left the world of pastry and went to Leostream. Many years and more twists and turns later, now I’m the CEO of the company.

Can you share the most interesting story that happened to you since you began at your company?

Well, there was the time I staffed the Leostream booth at VMworld during my Honeymoon. Does that count?

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The funniest mistake I’ve made at the company did not happen when I was first starting. There’s your lesson — you will never stop making mistakes. In the beginning the mistakes are mortifying, not funny. It’s only later that you make the funny ones.

What do you think makes your company stand out? Can you share a story?

I actually left Leostream for two months in 2011 in an effort to get back to my engineering roots. The work was interesting, but I missed my “Leo-team.” When they recruited me back, I was thrilled to return. We are a group of fairly disparate personalities, but we work well together, complement each other’s strengths, and accept one another’s weaknesses. Our team of disparate souls knows we’re stronger together, and that culture means that we’re oriented towards helping our customers and innovating constantly.

Another interesting experience has been the role that Leostream has had in the sudden shift to remote work. As an enterprise remote access solution, we were one of the first calls that IT managers made last March as companies went remote overnight. We helped many of our customers quickly implement a remote work solution — in organizations from Media and Entertainment to call centers to universities. We even played a “starring” role in getting some popular films and TV shows made during the pandemic, as studios have used Leostream to gain remote access to their desktops during the shutdown. It’s been a wild year but we’re looking forward to helping people navigate the new world of hybrid and remote work.

Are you working on any exciting new projects now? How do you think that will help people?

As we enter 2021, we’re helping customers continue their remote access journey. Whether that is post-production firms who recognize the power of collaboration that a remote work solution provides, or universities attracting a new student population by offering classes for students who can’t travel to campus — we see a lot of potential for our customers in the future and we are happy to be an integral part of helping them meet that vision.

Among other things this year, we are helping companies and IT professionals manage cloud resources, which can be a big cost issue for many organizations. As a larger vision, we see our ability to connect users from anywhere in the globe–seamlessly–as supporting a better workplace overall. You can hire based on talent, not location, and collaborate with teams scattered across the globe when you have a reliable and user-friendly remote access solution. We look at the future of work not as remote, but as connected–from anywhere, to anything.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. Are you currently satisfied with the status quo regarding women in STEM? What specific changes do you think are needed to change the status quo?

As a woman in a STEM career, I’ve been fairly lucky. On occasions early in my career, a visitor would mistake me for an office manager or would look at me in disbelief when I introduced myself as the CEO. While I find gender bias in tech frustrating, early on I decided to simply do my job–and woe betide the person who tries to stop me.

That being said, I believe that representation is important. We can always add more women to STEM fields and one of the best ways to do so is to bring other female role models in the field to the forefront, whether as their educators, speakers, mentors, bosses or colleagues. Like anything else, when you see someone you relate to, it’s easier to envision yourself in their shoes.

In your opinion, what are the biggest challenges faced by women in STEM or Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

Does mansplaining count, because it’s a real thing? Generally, and I’m not nearly good enough at this myself, women shouldn’t be afraid to have a voice. Lend your opinions and ideas to a conversation, and call people out when they take your ideas as their own or talk down to you.

What are the “myths” that you would like to dispel about being a woman in STEM or Tech. Can you explain what you mean?

I think it’s actually a myth that it’s a detriment to be one of the few, or maybe only, women in the room. In fact, it gives you an immediate way to stand out. Use that exposure as an advantage.

What are your “5 Leadership Lessons I Learned From My Experience as a Woman in STEM or Tech” and why. (Please share a story or example for each.)

  1. The path to success is not always linear (and that’s OK!). From rocket scientist to pastry chef to tech CEO–I’m not sure I would have ever been able to predict this path. I’ve allowed myself to explore different interests, such as leaving jobs in tech and working in restaurants, and that has given me the gift of being strong and confident in what I want from my career.
  2. Work hard, work clean, and never assume that someone else is going to pick up what you left on the floor. These are lessons I learned growing up in the Midwest and working in restaurant kitchens, and I bring them to my role at Leostream every day. I believe they’ve helped get me where I am.
  3. Don’t be afraid to walk away. Plenty of people might have thought it was pretty insane to spend all that time getting degrees in rocket science only to decide I preferred living in Boston and working at private companies. Or to make a career switch to the unforgiving role of pastry chef in a high-end restaurant when I had a great day job. But in fact, these experiences all helped me figure out the best path forward and have allowed me the opportunity to recognize when something is the right fit for me.
  4. Speed and agility matter in tech. Leostream is tiny compared to the giants in our market, which is dominated by a few large players. I’ve learned from leading our development team that being lightweight and agile allows us to bring features to market more quickly than anyone else in our space. In any STEM industry, being able to move quickly and innovate is essential.
  5. Coat yourself in Teflon. People will tell you when they think you’re wrong. They will tell you what they think you can and cannot do. Pick through their words for what value they might bring, and let the rest roll off.

What advice would you give to other women leaders to help their team to thrive?

I think being a woman is actually an advantage as a leader. We’re typically better than men at communicating, and communication is key to a team’s success. Don’t try to be everyone’s mom, but a team that feels heard and cared for will be a highly functioning and loyal team.

What advice would you give to other women leaders about the best way to manage a large team?

See above. Communicate with your team and foster communication between them. Teams that communicate, without arguing or accusing, can accomplish anything.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Richard Gran, and I feel horribly that I haven’t spoken to him in years. He was a mentor to me while I was at The MathWorks in my 20s and gave me some of those contracting jobs while I was a pastry chef in my 30s. He’s an old school aerospace engineer, having worked on the Apollo missions. I loved listening to his stories. If I remember correctly, his name is engraved on a plaque that was left on the moon.

How have you used your success to bring goodness to the world?

I’m one of those people who feels like the biggest impact I can have is on the world closest to me. The world closest to me, right now, is my staff and customers. I want anyone who works for me to feel valued and I want them to pass that value along to everyone they work with and touch. If I can start a chain reaction of decency, empathy, and kindness then I’ll really consider myself a success.

You are a person of enormous 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. 🙂

I think what many people in the world need is actual physical movement. I haven’t mentioned my love of running, but I’m a hobbyist marathoner. I’m not saying everyone needs to run a marathon, or even run, but if you can inspire people to get outdoors and moving, that leads to better health, a love of nature, and general happiness. Of course, it’s difficult to inspire people to get outdoors if what’s outside is just plain ugly. So, my ideal movement is twofold: inspire a movement that helps take care of nature, then inspire people to get out into it.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“If you want or need to do something, stop waiting and do it now.” The pandemic taught me that hesitation leads to lost opportunity. Don’t act rashly, but if there’s no compelling reason to wait to do something then why are you waiting? The same goes for making decisions. Think decisions through, then make them

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I would have loved to talk with Katherine Johnson to hear about being a female mathematician at NASA during the moonshot days. Unfortunately, she passed away last year. I think a conversation with Barack Obama would be fascinating. He always seems so inspirational, kind, and intelligent. And, he’s had lunch with Anthony Bourdain, whom I would have picked were he still alive.

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