Introduction
Cheryl Stookes is the author of The Token Woman: A Guide to Thriving as a Female Leader in Sales, co-host of The Catalyst podcast, and the Vice President of Revenue Growth & Marketing at Softchoice. Throughout her distinguished career, she has given much of her time to advocacy. She is an advisor to The WIT Network (Women in Technology) and a frequent speaker at industry events. In our newest Unapologetic Voices article, Cheryl describes how her commitment to helping women and minority professionals evolved throughout the COVID-19 pandemic.
Harpreet: What would you say was the most significant challenge of your professional career, and how did you overcome it?
Cheryl: It was in May 2020 when my job was eliminated. We were in the early stages of Covid with two young children. Our boys at the time were five and three. We were homeschooling as Ontario schools were shut down. It was a rough time. It’s hard not to take a role elimination personally. I went through all the emotions; however, I went quickly from upset to thinking: Wow, what a gift. I had worked for the company for eight and a half years. I’d done seven different jobs in two countries. I learned so many things. In that time, I built a strong brand and reputation in the industry both in Canada and the US. And, I thought, this is an opportunity to bet on myself in the open market. One day after my job went away, I started writing. And in October 2020, I published The Token Woman: A Guide to Thriving as a Female Leader in Sales. The book started as a personal project. But I shared some early writing with some trusted women in my network, and they said, “Cheryl, you need to publish this. This is good”. I’m glad I listened! The book has done well and has opened many doors for me with speaking opportunities. The book fueled my writing itch; since then, I have published several articles. So, losing my job amid a global pandemic with so much uncertainty was the best thing to accelerate my career. It also accelerated doing more of what I’m passionate about: my work around diversity, equity, and inclusion, specifically women in technology and sales.
Harpreet: So, I would love to hear what kept you going, from feeling angry after losing your job. How did that transition happen?
Cheryl: Well, it was a quick transition for me. Some of me experienced a bit of relief after losing my job. It was a challenging culture as a working mom, and I don’t think I fully realized its impact on my mental and physical health. The pause gave me time to catch my breath. I also knew the organization, and my experience there didn’t define me. What defined me was how I showed up every day in my role at work, at home, and in the broader community.
Harpreet: You’ve mentioned a couple of times how you’ve found exceptional value in fostering relationships. Would you have something to say about building networks and reaping their benefits?
Cheryl: Regardless of your job title, where you are in your career, or your experience, your most significant currency is your reputation and brand. And in the relationships that you build and nurture. I’ve been very intentional with staying connected to people throughout my career, particularly strong women. I have a term that I like to call The Unicorn Village. The Unicorns are all the fantastic women in my network. We support one another. We amplify one another. We raise each other, laugh, share memes, and celebrate our successes. We put each other’s names forward for opportunities. I invest in meaningful relationships because it won’t matter my title or how much money I make. What is the impact that I have had on the lives of others? What positive change did I contribute to? That’s what matters.
Harpreet: How have you experienced your commitment changing and evolving towards helping other women in your circle throughout the years?
Cheryl: I would say it has always been important to me and that it accelerated since the pandemic. Every day since, I wake up just as fired up and want to make real, meaningful change in the industry but, more broadly, ensure the workforce gets better for women, people of color, and marginalized communities. And hopefully within my generation, but certainly for my niece’s generation and beyond. I wrote a book about what it’s like being the only woman for many years in sales leadership. Telling those real stories, speaking up openly about my own experiences, being vulnerable in public places, like LinkedIn, and speaking about my experiences with Long Covid and what that meant for my journey. I’m an active member of The WIT Network and am currently mentoring over a dozen women in the industry. Spending time with other women is what fuels my soul.
Harpreet: As you reflect on your career, what’s the most enduring part of your identity?
Cheryl: I think it’s interesting because, for so many years of my career, I was “the only,” I was the first female director with sixteen male peers. I was the only Canadian. I was the only one on the team whose spouse worked full-time. Subconscious Assimilation is the term I use to describe this career period. I didn’t feel comfortable showing up as my authentic self. I would even dress a certain way and try to fit in with the guys. It was exhausting. Over the years and a few more women on the team, things started to shift for me, and I felt more comfortable being who I was at work. And then, I began leaning into my diversity as a superpower. That, too, had its downsides, as I suddenly felt like the company mascot for diversity, equality, and inclusion. These days, I’m very intentional about supporting and developing the women in my life. The Unicorn Village is strong whether they are a friend, peer, direct report, in a different area of the company, or broader industry.
Harpreet: I’m quite interested in understanding how you managed to create some distance from those challenges after facing difficulties in fitting into the dominant culture. Did you rely on self-reflection, seek support from others, or employ other strategies?
Cheryl: For me, it was just hard learning and the toll it took on my mental and physical health. I think there was a direct correlation between our challenges with infertility and how much I pushed myself for years to fit into a structure that wasn’t built for me. I would say, the first significant shift for me was when our oldest son was born in terms of asking myself what type of example, I wanted to set for him. I was also very fortunate when I worked for Lenovo to go through a women-in-leadership executive development program. And I started to build a lot of relationships with folks in that program, I still am very close with several of them. And then that just became more and more core to who I was and something that became increasingly important to me.
Then, the ultimate kicker for me was during COVID-19 when we quickly saw decades of gender progress and parity reverse seemingly overnight. One in four women were forced to leave the workforce or significantly downshift their career during that time. And we have not remotely recovered. And now, DE&I initiatives go on the back burner for many organizations. I am frustrated that we are back here. But I am motivated more than ever to make a meaningful and lasting change.
Harpreet: So finally, what does “unapologetically Cheryl” look like? What does it mean to you, and how do you embody it personally and professionally?
Cheryl: Being unapologetically me means I am who I am. I know who I am. It’s not for everybody and I’m okay with that. I would say your past does not define your future. Every day is an opportunity to do something new. And there’s so much opportunity right now for women to think differently. I believe we will have unprecedented female-led entrepreneurialism in the coming years. More women like you will build successful new ventures blaze new trails, and fuel global economic prosperity. I believe the future is bright.
Cheryl’s book, "The Token Woman: A Guide to Thriving as a Female Leader in Sales," is available on Amazon.
ALLOW YOURSELF A MOMENT TO REFLECT
Now that you’ve finished the article, please feel free to answer these three questions. If you keep a personal log or journal, they may be specifically helpful as writing prompts!
What have I done for my local communities lately, my struggling peers, or those within a minority who may feel alienated?
Have I shared my story yet? What experiences in my life could be helpful to share with others? Through what difficulties have I struggled and prevailed?
When I’m stressed and upset, do I remember to reorient myself by asking, "What is most important to me as a human being? What matters most to me in my life?’’
