Getting to know Upswing’s CRO, Christine Wyatt

It’s Women’s History Month! We at Upswing are honoring the occasion by celebrating some of the women who inspire us, starting with our very own Chief Revenue Officer, Christine Wyatt! 👏

Christine joined Upswing with 25 years of experience in servicing higher education, ranging from sales and strategy, to traditional and online teaching. However, Christine didn’t start out with her sights set on sales. Actually, Christine grew up wanting to be a writer and dreamed of going to film school for college. At the same time, she was drawn to the world of technology. Her father owned a recording studio, so, as a kid, she had the opportunity to take different electronics apart and figure out how to put them back together. Her interest in technology blossomed as access to technology exploded worldwide — game consoles, personal computers, and programming.

Tangent to her original interests in film school and technology, Christine ended up studying Radio and Television Production in college. Post graduation, she worked in the IT department at a small liberal arts college. Christine became the head of this department, where eventually, she felt she reached her ceiling and it was time to pursue something new.

At that time, a friend mentioned an edtech company with openings in the sales department and she decided to give it a chance. To Christine, her new role translated to, “I’m going to go to hundreds of schools, listen to their problems and challenges, and be super honest about how we can help them.”

Her position was remote, which was a huge transition to go from working on a college campus where she knew everyone and saw people every day, to working alone in her home and having to be an organized, disciplined, self-starter. As she put it, “As a sales person, I understood that I basically wrote my own paycheck. I learned to work smarter, not harder. I focused on the schools that I knew were the best fit. All of my efforts were spent on being super efficient, and after a while, I loved it.”

Apart from sales, Christine has a passion for supporting others toward success. She has a consulting business where she works exclusively with minority and women founders. She explained, “Seeing the gap between men and women made me really angry, and I wanted to do something.” As far as how she decides which companies or projects to work with, she shared, “I try to pick things that I think are either really interesting or really hard problems to solve, or that maybe nobody else is stepping up to solve.”

Though she has certainly seen success, Christine’s path has not been without challenges. She shared, “I have had people discount or write me off because I’m quiet, and calm, and patient. I think that’s fantastic. I always have an edge if I’m being underestimated and it’s kind of fun. But, at the same time, it’s sad, because some people think if you’re not outspoken, you’re not as successful.” She continued, “Women-led companies, or companies with women on the board perform better, but it doesn’t keep people from discriminating. People don’t feel as comfortable saying things as they did 20, 30 years ago, but if you look at the wealth, it’s still grossly uneven.”

Some of the most useful skills that Christine developed early in her career were self discipline and a propensity for efficiency. She’s learned, “The more you understand about yourself, the better. Ask yourself questions like, ‘What time of the day am I at my best?’ Understanding how your body works, how much sleep you need, what food makes you feel most energized…you have to take care of yourself so you can take care of others.”

We asked Christine what advice she would give to women interested in growing their careers. Here’s what she shared:

Take the opportunity — even if you don’t feel 100% ready

“Women in general, the best advice I could give — I took opportunities without worrying if I was qualified or at least, completely qualified. Spoiler alert: men do it all the time. Studies show that women wait longer to go after opportunities — take the opportunities given to you and figure out how to do it. I can’t tell you how many times I’ve Googled things. My philosophy, even if I don’t feel 100% confident, say yes, and I’m going to research it and do my best. Of course, you never want to apply for something you don’t know ANYTHING about, but if you’re on the trajectory, trust that you can figure it out. If you’re 100% sure you can succeed, you probably need something more challenging.”

Remember: We’re Not Competing

“I frequently see women view other women as competition. I think it’s really important to support other women, particularly if you are vastly outnumbered in your field. Find women who are peers, mentors, and create your tribe. Politely and directly support yourself and other women. We’re not always competing, and if we are, okay, let the best person win. Next time, I’ll work twice as hard. I think the better you know your own strengths, the better coach and mentor you’ll be. If you have experience in an area, be vocal about what you know. Don’t sit in a meeting and let an opportunity pass you by to be heard and bring up your idea. People avoid failure, whether subconsciously or not, but it’s a way to learn and help others.”

Be honest about efficiency and eat your frog

Eat your frog means: start your day with your biggest, most important, perhaps most overwhelming task. “It explodes open the rest of your day. Plan your work and then work the plan. If it’s not working, be flexible enough to switch it up. Be honest about how you’re spending your time. Are you being productive? Or are you just being busy? Who are you giving your time to, both personally and professionally? [Really invest] in understanding [your]self… [treat] it like a brainstorming exercise. ‘Here’s what I do well, what I need to improve on, what I’m terrible at.’”

Know how to prioritize to create balance

“Work life balance got easier for me, I’m not good at planning to the minute, but I know the most important things are that I need to get done each day. The more I invest in efficiency, the more I can leave work at work. Prepping is big. If you feel anxiety about something, sit with it and put it into action. [Productivity]’s like a mathematical equation focused on volume and conversion.”

Trust your team

“Don’t micromanage your team. Give autonomy, that’s how people grow. Know yourself really well, know your areas of improvement, and double down on the areas you’re great at. [Then,] work with people who fill your gaps. When it comes to hiring, find the best possible person you can find, set them up for success, and get out of their way. Diversify your team, and then listen to your team; I learn so much from other people just by listening and not automatically telling them what I think the answer is.”

Christine, we thank you for sharing your wisdom as we celebrate Women’s History Month, and more so, we thank you for the leadership and dedication that you bring to the Upswing team every day! 💙