Daring Women Q&A: Carey Jenkins, CEO of Substantial

"We could all be better about recognizing that the world we live in is both a product of a millennia of learned behavior and a new frontier of enlightenment."

Carey Jenkins, CEO of Substantial, is unapologetic about her opinions, even if they are unpopular. The leader of the local software company shares with us how she uses her often-criticized passion to her advantage. Read about the challenges she’s faced, advice she has for women starting out in their careers and the lessons she learned from her first job in this week’s installment of our Daring Women Q&A series.

1. Tell us about the high point of your career. What do you love about your work? Describe your proudest moment.

I ended last year thinking for the first time, “What if I were CEO?” Within a couple of months, I was in talks for the role. But the hard part was still to come. I was certainly not the safest choice. I realized that if I walked away without a fight, I would regret it. So, I fought for it and I made the case for why I was the right choice. I remember leaving on a Friday feeling ecstatic because I knew, no matter what happened, I had given it everything I had. When the call came on Monday morning, I got to celebrate all over again.

What I love most about my job are the people I work with. I feel a profound sense of responsibility to them. The day we told the company I was stepping in as CEO was such a lovely moment for me. It was important to show who I am and how I want to lead in that moment, even though most of the company had known me for years. In the end, I took the opportunity to be myself, recognize their amazing contributions to the company and acknowledge how grateful I am for the opportunity to lead them. There was a tremendous amount of support in that room and even some teary eyes. I was high on that energy for days.

2. What challenges have you faced as a woman in your industry? How have you addressed them?

I feel things deeply and I don’t always filter that. I’ve been called emotional, always by men, always when I am expressing an opinion they don’t want to hear. But I try to consider all feedback an opportunity. What is positive and negative about emotions? How do I keep the passion, the deep feelings, my strong instinct, while still being an effective leader and team member? I worked on that with specificity and determination. I am now much less apologetic about expressing my point of view passionately, even when it’s an unpopular opinion.

3. Tell us about a person who has inspired or mentored you. What key lesson did you learn from them?

One of my first jobs was as an executive assistant to both the managing editor and editor-in-chief of a magazine in New York. They had very different styles and immense responsibility between them. The editor-in-chief was glamorous and the face of the magazine. She was eccentric and exacting. The managing editor was no nonsense and received none of the accolades or the perks  the editor-in-chief enjoyed, but she worked tirelessly, realizing the vision and making sure the magazine went to publish. It was a master class in navigating being the unlikable workhorse in a room full of show ponies.

I appreciated the chance to work with both of them, but if you want a mentor, you can’t beat aligning yourself with a person who is at the center of a whirlwind and knows how to get things done. Because that person will know that the key to getting things done is to delegate to you. And boom, you get very valuable experience you can take with you wherever your career takes you.

4. What advice would you give to a woman getting started in her career?

First, don’t worry so much about your path. Focus on interesting opportunities that give you the chance to work with and for great people in a variety of environments. Work hard and learn — I assure you, a path will emerge.

Second, embrace feedback even when it hurts. It took me way too long to realize that I could be true to myself and confident in my abilities while still listening to feedback from others. Take the feedback and balance it with the other data you have about yourself. Listen to the part that feels true — go toward the nugget that makes you the most uncomfortable, and then address it within yourself.

5. What can women do to improve gender equity in the workplace? What can men do?

Women should step out of their comfort zones to take on leadership opportunities. I may have been on the short list for this role, but I absolutely would not be here if I hadn’t fought for it. And fighting for it gave me an opportunity to prove what I was made of.

We could all be better about recognizing that the world we live in is both a product of a millennia of learned behavior and a new frontier of enlightenment. People are going to make mistakes navigating that world. Having the conversation, naming things, being direct and firm but compassionate is how to create a better workplace. The hardest conversations are with men who are really committed to being an ally. You want to reward their intentions and it can feel nitpicky to point out shortfalls. But no one benefits from issues swept under the rug.

6. Tell us about a favorite book/show/podcast and why/how it inspires you.

I read to my daughter at bedtime and we recently read a book called The Wild Robot and its sequel, The Wild Robot Escapes. It was engrossing and delightful and tackled complex themes for a children’s book. It’s about the wilderness and robots for sure, and had a subtle sci-fi angle that was super entertaining, but in the end, it was a powerful story about motherhood in the unlikeliest of circumstances.

I talk all day every day at my job, so I appreciate a bit of silence. But my daughter loves to listen to music and we started listening to an Australian band called Middle Kids. Their album was on constant repeat for weeks, and then the band came to town and I got to see them live. I haven’t been to a show in a while, let alone one where I knew every word to every song. It made me remember how powerful music can be in your life.

7. Where do you find support and inspiration? How important is networking and how do you expand your contacts?

I get a ton of support from my husband — he is a rock of confidence and calm and did not waver in his support of me stepping into this position. At work, I have had a professional coach for the last couple of years, and it has been invaluable.

I am not a natural at networking. I am just not comfortable at large events or with a lot of small talk. I much prefer smaller, more intimate discussions. But I paired with a person at work who was amazing at it and we created a Women in Leadership dinner series to provide an opportunity for frank and honest conversations, and that has been incredibly fulfilling and inspiring.

8. What are the most important characteristics of a good leader? What leadership traits are overrated?

I don’t think empathy can be overstated as a trait that will take you far in this world, as a leader and global citizen. I would encourage defining your core values as an individual and lead from those values. And I recommend taking the time to have a point of view and to communicate it clearly and with care, but with total openness for feedback.

One thing I wouldn’t recommend is losing your sense of curiosity and risk-taking in favor of doing things the way they have always been done.

9. What would you do differently in your career if you had a do-over.

Everything and nothing. Both of my academic areas of focus are different from where my career has taken me. It has been a winding road and I’ve made so many missteps. But I can’t say I would trade those experiences, and I know I’m better for them.

There is a little part of me that would like to be one of those people who knew where I was headed and studied all of the right things and met the right people way back when I was just starting out. I wish I was great at networking and cared more about my personal brand. Was “personal brand” even a thing when I was just starting out? Maybe, but I’m just not that person. And the person I am is doing just fine.

10. What would be the title of your autobiography?

Resting Stress Face. I get asked a couple times a week if I’m stressed, almost always when I am not stressed in the least. In my head I think this is just what 45 looks like. I’ve started saying, “Nope, it’s just my face.”

We’d love to hear from more women across all industries who are challenging the status quo. Does it sound like you? If it does, click here and fill out our questionnaire.

Daring Women Q&A responses have been edited and condensed.

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