On being a woman in tech: Be bold, be courageous!

Working at EssayJack, we have that rare opportunity to work in a tech startup led by a woman, and in a team that has more women than men. So we thought we’d take a little bit of time off this International Women’s Day to quiz our CEO Dr. Lindy Ledohowski on the dynamics of this arrangement, and whether this was an intended or unintended consequence of running a tech startup in the education world.


EssayJack (EJ): As a female entrepreneur, what has been your biggest challenge up until now?

Dr. Lindy: That there are certain ways of interacting and networking that can be very gendered. For instance, I’m in Canada at the moment, so pick up hockey games are a big thing for guys, be they investors, clients, coworkers, colleagues or whatnot. Now there are some amazing female hockey players out there, but I’m of the generation that didn’t grow up as a girl playing hockey, and so I can never participate in those sorts of activities. I think it’s the same for golfing or other non-business specific moments that are nonetheless important to one’s business.


EJ: Flip that on its head for a bit – as a female entrepreneur are there any advantages?

Dr. Lindy: Absolutely. There are a number of funds and initiatives for female-led endeavours and for me as a newbie to the entrepreneurial space, these focused types of help have been invaluable to me as I’ve worked hard to find my feet.


EJ: How have these initiatives and endeavours helped you in your journey?

Dr. Lindy: In the early days, I was a winner of a Stevie Award for Female Entrepreneur of the Year and a finalist for the Ottawa Business Women of the Year Awards “Emerging Entrepreneur” category. As well, in December 2018, I did a first trip to Silicon Valley as part of “Connection Silicon Valley” Accelerator, which connects Canadian, female-led companies with mentors, VCs, and other experts based in Silicon Valley; and just this year I have joined Ontario’s first feminist accelerator, The Fifth Wave, as well as The Big Push’s Lift-Off Program for female-led businesses. I am also an active member of the 7,700-strong Facebook group, Women Who Tech. There are other groups, both in person and online, that I am a part of that focus on women supporting women in various workplace contexts.

Each of these groups – networking in the case of the awards, mentorship and training in the case of the accelerators, and support in the case of groups and associations – offer different helpful things from practical advice and guidance to friendship. For me, the most important thing that each of these female-focused entities have offered me is the feeling of belonging. I am not alone.


EJ: Do you think the EdTech space is more welcoming to women? What about SaaS?

Dr. Lindy: EdTech is most definitely very welcoming to women. Education more broadly still tends to be very female-dominated (especially in literacy fields) than other spaces, and so I find that often I’m dealing with female teachers, department heads, district representatives, university professors, etc. whereas when I’m in SaaS-focused meetings, there isn’t that same gender balance. Very often in tech meetings around SaaS or financing, I can be the only woman in the room, which can be both bad and good, depending on the circumstance.


EJ: Have you had to adapt your leadership style to run a startup in the SaaS industry which tends to be more male-dominated?

Dr. Lindy: For me, I had to not really adjust my leadership style, but more adjust my expectations. Because I came from academia and have worked in equity and human rights spaces for the last two decades, I was very used to being taken seriously as an expert, where my gender didn’t matter. Finding myself faced with various “micro-aggressions” or discovering that some men in this industry find me “prickly” was a bit of a surprise. So I had to change some of the ways that I interact with some men in tech and finance so that I come across a little less harshly. I’m not sure that I’ve mastered it, as people still tell me: “you don’t suffer fools!”


EJ: Have there been any moments where you’ve wished you were a guy in the startup world?

Dr. Lindy: 100%! Yes! And yes again! I never thought I would say this, but I’ve seen guys get up in front of a room of people and pitch their business or idea and see a million and one holes in what they’re doing from the product to the foundational work to the financials to the vision, but they get genuine questions and engagement. I’m often baffled.


EJ: Your team consists mostly of women. How does that impact team dynamics?

Dr. Lindy: I’ve definitely made clear the importance of aiming for gender balanced teams on EssayJack. Mentorship has always been very important to me. I’ve always worked to mentor girls and women whenever I’m in a position of power (or perceived power), because I believe that I’ve been a beneficiary of help from women who have gone before me (and a few of them are early EssayJack investors and advisors), and so in whatever way that I can support, develop, and mentor women and girls in their professional lives I’ll do it. And that means that our team, as you note, has a pretty impressive gender balance – and that includes our partners, legal team, bookkeeping, accounting etc. I’m not sure exactly how this affects the team dynamics, because I’ve never headed another company with other team dynamics, but I know that our team works!


EJ: You’ve chosen to partner with a software company that also features more women than men – was that on purpose? 

Dr. Lindy: Yes, definitely. Not only do we work with a female-led company that offers us business support and a talented female legal partner in her firm, our main software partner is also not a typical “bro only” coding house. When we first started working with Rapid River Software, there were a number of alignments in terms of corporate values that we were looking for, and their commitment to diversity (including gender diversity) was one of them. Their corporate culture and how well we work with them is one of the main reasons this partnership is four years in!


EJ: Right, so it was more of a coincidence. Speaking of your software partner, they’re a small boutique firm. Was there a reason that you chose a small firm vs. a large one?

Dr. Lindy: Before we started working with Rapid River Software, we tried a number of different technical working solutions, from hiring our own coders and freelancers to working with a big, local software development office. There were a few things that we found that weren’t great in both those scenarios. When hiring your own small team – be they as staff of freelancers – you are limited to that small team’s skill set. Any weaknesses they may have become your own company’s weaknesses. Whereas with a larger company, you have the entire corporation’s expertise to bring to bear to your project. However, with a larger company working with larger clients, you can tend to get lost. With Rapid River Software, we find a nice middle ground. It’s like Goldilocks and the Three Bears, just right!


EJ: One last question – what advice do you have for fellow women who want to be entrepreneurs or contribute to the field of education in the 21st century?

Dr. Lindy: While there are challenges to doing anything – from academia to entrepreneurship – from a minoritized position and being a woman is just that, we also live in a world now where there are more opportunities than ever before, especially in the world of tech. While traditional finance is still very male dominated, tech fields with the ways that they can disrupt traditional business models – be it through remote work or non standard approaches – can offer fantastic opportunities for women and girls. So my advice? My advice is to just get out there and do it! I gave a presentation at a university last week on my transition from being a professor to being a tech CEO and afterwards a professor came up to thank me for my talk and said, “I wish I had your courage, because really that’s what your story is, a story of courage,” and so my advice to women and girls wanting to be entrepreneurs or contribute to educational goals and outcomes would be to BE BOLD, BE COURAGEOUS!


Follow Dr. Lindy on Twitter. 


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