Forging the Path to CEO for More Women – with Carey Jenkins

Sometimes an unconventional path leads us to where we are meant to be. We never know how our education, skills, experiences, and past jobs will align to equip us for what lies ahead. 

Carey Jenkins had an unconventional path to becoming CEO of Substantial, a Seattle-based digital product studio that works with companies like Amazon, Mercedes-Benz, and the Wall Street Journal. In 2012, Carey joined the Client Services team and just six short years later, became its CEO. As the sixth female employee and first mother hired by Substantial, Cary is proud that Substantial has grown the female employee base to 37% overall and 40% on its leadership team. She’s committed to empowering other women to seize more leadership opportunities. In this episode, Carey shares what it means to be CEO material as a woman, the art of proactive goal-setting, and how she balances motherhood and being a CEO. 

The long journey

From her small town roots in Louisiana, Carey went to study theater in Manhattan and follow her dream of becoming an actress. Through jobs as a waitress, bartender, barista, and realtor, she became disillusioned with acting. After partying for a while, Carey pursued journalism in grad school in Montana. She picked Jane magazine to work for, called the publishing house, and secured a job as a floater. Soon after, Carey became the assistant to the editor – what she thought would be her dream job. Carey saw what it takes to put out a magazine from an administrative standpoint, and even though it was a formative experience in shaping her life, she became disillusioned again with the magazine publishing process. Then came career crisis #2 and a pivot into the world of digital products and web presence.

Choosing product over marketing

Carey chose to focus on the world of digital products and not the marketing aspect. Why? She loved the “give and take” between the user, the experience, and the cycle of investment. With a product, you want a relationship with the customer because you want them coming back. Carey loved the interesting interplay that didn’t happen in marketing and advertising, but she felt a void not to be involved in the technology part of product development. She pursued jobs in this area, found Substantial, and was hired as their 26th employee and given the task of building the client services experience. She says her first six months on the job were an everyday learning experience of new things. 

Finding her CEO superpower

A daily challenge that Carey is still working on is figuring out how to bring out the superpowers of her team members and highlighting those to bring out the best in each team member. “It takes actual work to figure out what kind of leader I want to be.” Carey calls storytelling (from her theater training) and communication her superpowers. 

A model for female leadership

Not many people can say they work for a company that’s a model for female leadership, but Carey is proud of Substantial’s equity and diversity. It’s an ongoing work in progress, but one specific challenge is the pipeline of technology and engineering that is still heavily skewed toward white males. It’s much easier to achieve balance in client services, executive leadership, and design teams than it is in engineering. 

More empathy

Having more women in leadership positions means a natural affinity exists for empathy and emotional attunement. The benefit from that affinity is the connection between empathy and building better business relationships and better products for clients. This empathy doesn’t just affect client relationships, but also each team member. It takes empathy and emotional intelligence to understand what clients are up against in their businesses and help them solve those challenges. Carey explains that anyone can build a digital product, but empathy is essential in the client relationship.

Navigating tension

A big part of Carey’s job as CEO is to navigate the tension that is inherent in leadership teams. She has seen the needs and objectives of both the delivery and sales team and has been able to fit people in who can achieve balance, even though it’s impossible to eliminate all the tension. Carey explains why sales and delivery teams need different approaches to the song and dance necessary to find a good fit in client relationships. 

Why it’s not a balance

Carey says of her roles as CEO and mother, “It’s not a balanced relationship.” She has a phenomenal partner in her husband, who has been willing to be the primary parent to their daughter. She says he is joyful, supportive, and doesn’t complain. Carey realizes that she has a core mission as the leader of Substantial and that certain things have to take a backseat for a time. She is deliberately open with her daughter about the demands of her job, and her husband is intentional about helping her steal precious moments of motherhood whenever she can.

Being a woman in the boardroom

For Carey, being a female CEO in the boardroom isn’t an issue, since Substantial is a privately-held company. She and the founder/owner have a relationship built on mutual respect with a lot of love underneath, and he shows his support and absolute faith in her. They may not always agree, but it’s a much different relationship than having to navigate the boardroom.

Highlights of this episode:

  • 13:45 – Why Carey focuses on digital products
  • 16:45 – How she found Substantial to be “ultra-agile”
  • 20:30 – Finding your CEO superpowers
  • 23:33 – Substantial’s female employee base
  • 26:20 – The difference between men and women in competition and empathy
  • 31:21 – Navigating tension as a CEO
  • 34:17 – Balancing motherhood and being a CEO
  • 36:52 – Navigating the boardroom as a woman
  • 38:13 – Fem Five

Resources Mentioned:

The Fem Five:

1. Favorite book to recommend for women?

  • This is Marketing: You Can’t Be Seen Until You Learn to See by Seth Godin and Come As You Are: The Surprising New Science That Will Transform Your Sex Life by Emily Nagoski, Ph.D.

2. Favorite self-care hack?

  • “Getting off social media and taking real vacations without checking email.”

3. Best piece of advice and who gave it to you?

  • “There is always a third way!”

4. Female CEO or thought leader you’re into right now?

5. One piece of advice you’d give your five years younger self?

  • “Motherhood changes you, and you won’t know how, but it will change you for the better.”

Last Time on The NextFem Podcast

Building Inclusion Into Your Business – with Chiara Condi


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