How Taking Calculated Risks Benefits Women in Tech

Following Gayle Keller’s keynote on “Sustainable Empowerment: Taking Calculated Risks in Your Career,” the Women in Tech session at Summit North America 2022 involved a panel discussion. Cathy Richards-Ingram from Avalara, Jennifer Harris from TMC, and Ann D’Emilio from Vertex shared their experiences and advice as women in the technology field.

The panel answered questions such as:

1. When did you decide to take a risk in your career, and what did that look like for you?
2. How can women take risks and further promote themselves?
3. How did you fail forward in your career?
4. What does it mean to be an ally for women in the workplace?
5. As a woman, how can you foster community and relationships in the workplace?
6. What is a top initiative or trend that you see on the horizon for 2023 when it comes to closing the gender gap in technology?

Cathy Richards-Ingram: Pivoting Your Career and Fostering Community

Cathy Richards-Ingram is the audio-video engineer at Avalara. With a background in dance and working in non-profit organizations, Cathy is a perfect example of what it means to take a risk in your career.

Cathy had a goal to continue dancing and pursue theater. However, after freelancing, she recognized a need for stability; so, she took a leap toward a different goal. Cathy worked in different roles for several years before landing on something that she enjoyed and was secure. Another risk was deciding to leave New York after realizing she needed a change. So, she was looking for jobs that would give her an opportunity to move. When she landed her role at Avalara, that enabled her to move to Seattle. Initially, she was doubtful that she could do it on her own but had the support of family and friends that enabled her to start over and kick off her career as a woman in tech.

Cathy wouldn’t be where she is today if she didn’t recognize what she wanted and needed, pivoted, and taken a risk. Now, she’s able to foster community and support other women in her field as the Women of Avalara co-chair. Cathy encourages others to create a space that enables people to feel comfortable being themselves. She recommends that companies “allow space for big events to small things like a Zoom meeting where women can come together to talk and share.”

When Cathy first joined Avalara, she was on a team of six men who she didn’t know and didn’t understand their conversations; it made her feel lonely and as if she didn’t truly understand her job. This motivated her to strive to grow, understand, and find community. A year later, she became the co-chair for Women of Avalara. She encourages these spaces because it enables the people within a company to foster not only professional but also personal relationships which often leads to having a community of allies. By having this community of women to connect with, Cathy has been able to have meaningful conversations, grow more in her career, and become more confident in her role.

Jennifer Harris: Advocating for Authenticity and Being an Ally

Jennifer Harris is the president and CEO of Technology Management Concepts (TMC), one of the few solely female Microsoft partners. She’s passionate about advocating for allyship and having a team that reflects authenticity.

When you take a risk, it doesn’t always have immediate benefits. Jennifer explained how she started a business in a laundry room several years ago — before she even realized that she was a woman in tech. She encourages women to learn to be uncomfortable waiting in whatever that “laundry room” is for them because risks take time. “You have to sit with the uncomfortable, know that you’re the best for the job, and be confident,” she shares.

We have to work better together, explains Jennifer. We’re better when we take risks, when we’re uncomfortable, and when we have each other for support. This applies to both men and women supporting each other. When Jennifer was in starting off in the laundry room, her support system included her partner, her husband, and her family. Now, she has many women as well as a team that works for her who she describes as being so supportive every day.

By having that support system rallying behind her, Jennifer recognizes how important allyship is. She highlights how women must be allies for other women – taking moments to lift each other up, notice if someone is struggling, and identify when a workplace or situation might be toxic. She encourages women to not be afraid to speak up and speak out. While it’s very much appreciated —and still necessary — for men to support women, it is very impactful for women to support other women.

Ann D’Emilio: Breaking Comfort Zones and Finding Your Support System

Ann D’Emilio is a channel sales manager at Vertex. In addition to her passion for women in tech, she has deep roots in nurturing and developing relationships.

Although her background is in marketing, Ann decided to take a calculated risk when she saw an opportunity to get into sales. Because the role was with the company she was already working for, Ann felt like that added a sense of security. She explained that she had an ally encouraging her, reminding her that she brings a lot to the table and is already knowledgeable about sales. After taking the risk two and a half years ago, Ann reports, “It’s the happiest I have been in a job in a really long time . . . The challenge is to really get out of my comfort zone.”

Making the leap to sales enabled Ann to break out of her comfort zone. While she did know much about sales, there was still more to learn as she stepped into this new role. Of course, at first, leaving your comfort zone is . . . well . . . uncomfortable. But once you break out of that comfort zone, you might just stumble upon your “happiest I have been” opportunity.

Ann encouraged attendees to know who is in their support systems. Your allies are in your network. She recommends taking advantage of opportunities to connect with others in your network because you never know when you’re going to meet someone who will be your ally. Further, you never know when you’re going to need those allies in your corner. Ann elaborated on how she now has a different perspective each time she makes a connection because she recognizes the importance of having a support system.

Final Thoughts

As a young woman in tech, it was incredibly inspiring for me to connect with this panel of women. In preparation for the Women in Tech session, I was able to have conversations with the panelists and I am grateful to have such empowering women in my network. It was encouraging to hear their perspectives and stories. Their advocacy is paving the way for generations of women, opening doors and expanding opportunities for future women in tech.

Article written by Sara Cordova and reshared from How Taking Calculated Risks Benefits Women in Tech (accelerationeconomy.com)