Cheryl Stookes discusses the best way to build an impactful career in sales, and it's about to get futuristic

"Be open and willing to accept feedback. Feedback is a gift, it means someone has taken the time to invest in you, and they’re giving you something - embrace it - and ask what you can learn from that." In this week's You've Got This, senior sales professional Cheryl Stookes outlines her career trajectory, what inspired her to write?The Token Woman: A Guide to Thriving as a Female Leader in Sales, and her best insights for those looking to strengthen their sales approach. Be sure to check out her answers below, along with announcing our next guest, multi-hyphenate change navigator and author April Rinne.

Victoria: "Can you share with us a bit about your professional journey?"

Cheryl: "I graduated with a degree in political science. So like every other political science graduate in the world, I thought I was going to be a lawyer, and somewhere along the line, realized it wasn’t what I wanted to do. When I finished school, I looked at a number of paths related to my degree—government, academia—and ended up taking a left turn into sales. I started my career at a company called?Softchoice?as an inside seller, knowing nothing about sales or technology, but they hired for talent and potential and?trained?for everything else. So I started out my career and for the first three months, I thought I’d have to quit every day - 'What am I doing? I went to school for something totally different' - but I stuck with it, and things started to click for me around the three-month mark. I realized I was going to be pretty good at sales, and started to embrace it. I was promoted to an account manager role, and when I was 24, I got tapped on the shoulder to take over a sales manager role, and at the time I was the youngest sales manager in the company history, and I was terrified, to be candid. There were people on the team with a lot more experience?than?myself, but I embraced it and surrounded myself with strong leaders, and I absolutely loved sales leadership. I continued to progress my career in sales leadership with Softchoice for?3.5?years, then worked at a consulting company for a year in Toronto?doing business development, then I worked at a company called SHI for five and a half years, in increasingly senior sales leadership roles. And my last two years there, I was leading all of their sales for Canada for the company.

In 2013, I actually made the decision to take a lateral move with my career —primarily for personal reasons in that I was expecting my first son and was traveling over 100 days a year, and when I wasn’t traveling, I was commuting 3-4 hours a day, so something had to give - and I went to work for a company called Lenovo where I was for a little over 4 years. I ran the public sector sales team in Canada for a number of years, and then in 2017 I moved along with my family to Raleigh, NC to take on a chief of staff role. That was exciting and terrifying —my husband quit his job, we had two young kids, and we went all-in—on this chief of staff role for the North American president. And that was a phenomenal experience, because until that point, all my experience was in sales leadership, and this role exposed me to marketing, finance, supply chain, all these other areas of business. I attribute my time in that role to being the closest thing I could have done to an MBA without paying tuition in terms of accelerating my learning.?After Lenovo,?I rejoined SHI, the company I was with previously for 5.5 years, and was based out of the US to build out the first version of their marketing?& partnerships?organization for their commercial division. This was building out an events team, comms team, a partnership organization where we ran strategic marketing campaigns and did digital campaigns with our partners. I was based in Austin, Texas, and then in 2019 SHI asked me to take back over the Canadian business.

So I went full-circle with SHI, came back to Canada doing that role?and led a major expansion, and we were on a great trajectory of growth, but in March 2020 COVID-19 hit, and like every organization the company pressed pause on the expansion in Canada to prioritize US-business, so my role was going away. For the first time in my life, at the end of May 2020, I left a job without having another one lined up—which was TERRIFYING—but I was excited, because I felt like I could take a little bit of a breath and?bet on myself in the open market.?Last spring I joined AWS leading their partner sales teams for Canada, and just this month I went 100% full circle and re-joined Softchoice as the Vice President of Marketing! It’s an incredible honor to re-join the company that gave me my very first opportunity as a member of their Senior Leadership team at such an exciting time for the company (we just went public!) and the industry."

Victoria: "With the disproportionate impact of the pandemic on the careers of women and caregivers, what insights from your book do you think are particularly timely now as we look towards the future?"

Cheryl: "On?my last day at SHI, May 30, 2020, I literally woke up in the middle of the night on June 1 and went into my home office and started writing down a few ideas. These were reflections on my own career so far, some funny stories that had happened to me, and key lessons. This started out as a personal, cathartic experience while I was thinking about what my next move was going to be, but I shared these chapters with a few women in my network, and they said 'We think there’s something here.' So I kept going, I hired an editor who helped me with a bit of copy editing, and ended up signing on with a Canadian publishing company, and the book came out in October 2020. So this started out as a very personal reflection, looking at what I’ve learned as a female leader in sales, and share that knowledge more broadly, with a goal of helping others and inspiring more women to go into sales leadership (and hopefully inspiring more men to support women in sales leadership). So that was the main motivation for me, and I’m so glad that I did it.?

I’m sure you’ve read the McKinsey study that came out —1 in 4 women right now are actively considering either leaving the workplace entirely, or dramatically downshifting their careers, due to the pandemic. And I’m saying this to you right now hearing my five-year old son?yelling at his brother?downstairs. In most households, not all but most, the majority of childcare and eldercare falls on the shoulders of women. So balancing these things is an impossible situation in my opinion. Something’s got to give, and unfortunately women are stepping back from their careers due to not having a choice. So I think it’s more important than ever to have real, honest conversations with our teams. And employers must be as reasonable and flexible as possible with things like flexible hours.

"This is a tremendous opportunity if we want to retain women in the workforce: let’s ask where are women in particular spending their time?"

I personally saw when COVID-19 hit?it?was Zoom meeting overload. I found a lot of the meetings I was on there weren’t clear agendas, too many attendees, too many people on the call. In my own life, I’ve started to get very intentional with the meetings, setting a clear agenda, making decisions, and making sure that it HAS to be a meeting, or looking at ways to leverage other formats like email or Teams if it doesn’t have to be a meeting. Asking where people are spending their time can help you maximize the areas of greatest impact to the business and also help drive the greatest personal satisfaction. Time is finite, but it’s even more precious now when we have so many employees balancing the demands of work, family, illness, homeschool, eldercare, all in a remote way. We have to be very intentional to ensure we aren’t putting undue deliverables or meeting requirements on people, and helping manage for?OUTCOMES,?not how many hours they are sitting in front of their computer. Are they delivering on what they need to deliver? If the answer is “yes” and the work is high-quality, does it really matter if they are in front of the computer from 9-6?

"Let’s allow for more flexibility, while avoiding the danger of employees never shutting down or being able to turn off their work."

I found myself in that scenario as well, so I artificially created a commute for myself, taking my labradoodle for a walk before and after work, and that was my mental 'crossover' between the workday and family time. And then really keeping that family time. My precious time is dinner and bedtime with my kids, not having my phone in my hand at that time, and once my kids go to bed, I’ll log back on and do a few more things. Taking that time, doing a few more mental breaks, that will keep your mind and body sharp. It’s amazing what a little fresh air and exercise can do."

Victoria: "What advice would you have for those looking to start to build their career in sales?"

Cheryl: "First of all, I’ll tell you if I could go back and do it all again, I wouldn’t change a single thing. Having a career in sales has been an incredibly exciting and fulfilling place to be. You have the ability to create your own fate. Being willing to take risks and to be vulnerable and to try new things is I believe what sets aside great sales people?from?good salespeople. Be open and willing to accept feedback. Feedback is a gift, it means someone has taken the time to invest in you, and they’re giving you something—embrace it—and ask what you can learn from that. Not being afraid to put yourself in a position where it might not be natural or comfortable. I don’t think I’ve started a single job where I’ve felt natural or comfortable at the beginning, and I think that’s a good thing!

"You should always feel in over your head in the beginning, because that feeling will give you the drive, the desire, to go out and learn and embrace learning and be excellent in the job. You can always be learning, growing and developing."

And if you’re gonna go into sales, you really have to learn to not take rejection personally. Because it takes a lot of no’s to get to a yes. It can take a prospect 8 or 10 times before you get to the outcome you want. So being willing to overcome that rejection you’re gonna feel, staying confident in yourself and your message, eventually things will fall into place. The most successful sellers have persistence, professionalism, and they don’t let it get to them if they get a rejection or a no from a prospect - they just keep rolling. It’s a matter of time before you get the results you’re looking for."

Follow Cheryl on LinkedIn. ??

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Next week's guest: April Rinne

I'm looking forward to our next guest April Rinne. As a futurist, advisor, global development executive, microfinance lawyer, investor, mental health advocate, author and much more, April brings her passion for navigating flux and change to a variety of clients ranging from organizations to individuals. With that in mind, here's what I'll be asking April:

• How have you been able to combine so many of your skills and interests to build such a varied "portfolio career?"
• You recently authored FLUX: 8 Superpowers for Thriving in Constant Change which includes several ideas that may seem a contrast with adapting to a fast-paced, constantly changing environment, such as "run slower" and "get lost." Can you share how you identified these principles, and what you hope readers take away from the book?
• What advice would you have for those who are thinking about their own personal approach towards building a portfolio career, and what are some trends you're anticipating continuing to influence this environment?

Ask your questions for April in the comments below, and thank you for being a part of You've Got This.