Cheryl Stookes, Softchoice

WOMEN IN TECH: Q&A With Cheryl Stookes, Vice President, Revenue Growth & Operations, Softchoice

The latest candidate in our series of Q&As with influential women in the technology business in Canada is Cheryl Stookes, Vice President, Revenue Growth & Operations, Softchoice.

Name: Cheryl Stookes

Job Title: Vice President, Revenue Growth & Operations, Softchoice

Years in the Industry: 17 Years

The Quote That Most Inspires You: It has to be The Man in the Arena Speech by Teddy Roosevelt. Although I like to think that in 2021 it would be called The People in the Arena!

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

What drew you to a career in the consumer and/or business technology industry?

A career in technology was never my life master plan. I went to school for political studies and had originally planned to be a lawyer. It wasn’t until my third year of university when I began to realize that law wasn’t going to be for me. In my final year of school, I interviewed with a Toronto-based technology company and knew the moment I walked into the building it was where I was meant to be.

I started my career as an inside seller, knowing nothing about sales or technology. But I was hired for talent and potential, and the company trained me for everything else. That was 17 years ago, and I have been fortunate to build a successful career in technology at Softchoice, Lenovo, SHI, and AWS. I have always been drawn to the fast pace of the technology sales industry. Every day of my career, I can help customers transform their business and lives using technology. That’s an exciting place to be.  

Have you encountered any roadblocks along the way that were related to your gender?

Absolutely. For many years, I was often the only woman in a group full of men. I was literally the token woman. More than anything, the roadblocks I experienced were more subtle microaggressions versus blatant sexism – whether it be exclusion to offsite “meetings” (golf) to being disregarded or talked over in team meetings. Sadly, for many years, I didn’t know any better and I just assumed these things were normal in the industry.

In recent years, I have become more educated on diversity, equity, and inclusion and have experienced firsthand how diverse and inclusive cultures accelerate growth, business transformation, and foster meaningful and fulfilling careers.

I have also had the opportunity to work for companies that fully embrace DE&I, which has helped open my eyes to what good looks like. It’s one of the many reasons I was so drawn to re-joining Softchoice this spring. I feel fortunate to work for an organization that is embracing DE&I at every level of the company.

What unique characteristics or perspective do you feel you bring to your organization as a woman?

I have always approached my career in a way that’s authentic and real. What you see is what you get, and I believe in providing clear communication while fostering a culture of accountability and mutual respect. In the fall of 2020, I published a short book, The Token Woman, related to my experiences as a woman in sales. One of my former employees said to me “You write the same way you talk. It was like I could hear your voice teaching me these lessons with no BS.” When in doubt, I refer to the wise words of Brene Brown, “Clear is Kind. Unclear is unkind.”

Cheryl Stookes, Softchoice

Technology is historically a male-dominated industry, yet the use of tech is fully embraced by women, and many studies even suggest that females are the primary buyers of tech in the home. What do you feel the technology industry needs to attract more women, particularly into high-level positions?

This is top-of-mind for me. I’m sure you’ve read the McKinsey study: one in four women right now is actively considering either leaving the workplace entirely, or dramatically downshifting their careers, due to the pandemic. In most households – not all but most – the majority of childcare and eldercare falls on the shoulders of women. Balancing these things is an impossible situation, in my opinion.

Something’s got to give, and unfortunately, many women are stepping back from their careers due to not having a choice, with many more women approaching their breaking points. I think it’s more important than ever to have real, honest conversations with our teams on how we can better support them, rapidly embrace flexible, hybrid/remote working, and create a culture where appropriate boundary setting is both encouraged and modeled by senior leadership.  

In terms of financial benefits, countless studies show that companies who have diverse leadership teams consistently outperform their less diverse peers. It’s in the best interest of any technology employer to attract and retain talented women to their workforce, full stop. Candidly the question needs to shift away from “why do we need more diversity?” to “how can we create a more inclusive, diverse, and employee-focused culture to attract, grow, and retain top talent to accelerate our growth?”

If you had to sum up what it is like being a woman in this male-dominated technology industry in just a few words, what would you say?

It’s the best. And what makes it so great is all the amazing women in the industry that you meet and work with along the way. Seek these women out and amplify their voices. Support each other.

Are there other women in the tech industry who inspire you?

I call these women my unicorns, as I mention in my book! This is a group of women I have had the opportunity to work with over the years, and with whom I have maintained close personal and professional connections. We support each other, inspire each other, and keep each other laughing, while not taking ourselves too seriously. I don’t know where I would be today if not for my Unicorn Village.

What are some of the misconceptions/myths about women working in the technology space that you’d like to dispel?

That we are in competition with each other. We are not.

What’s one thing you wish was done differently in the industry, and why?

If I could go back and do it all again, I wouldn’t change a thing. I believe that in our careers, there are no mistakes, only opportunities. Things will go wrong, and you will make mistakes along the way. But I firmly believe that with the right mindset, every negative situation during your career can be treated as an opportunity to learn and grow.

Are you optimistic for the future in general and for the industry?

I can’t think of a more exciting time for any industry than what’s currently happening in the world of technology. Take the example of how the pandemic changed the way we work and live. And how technology is connecting our physical with digital worlds, making it possible to work from anywhere and anytime. I believe it’s going to be interesting (and fun!) for years to come and at Softchoice, we are excited to continue enabling successful business transformation and innovation with technology.