Companies with CEOs who are women — women make up only 5 percent of people in the top C-suite position — also have a 15 percent increase in profitability over a typical firm, a study by the Harvard Business Review found in 2016.
Portland's top CEO is Monica Enand, founder of Zapproved, according to a 2017 national likeability study by Owler — and she is the only woman on the Top 25 list.
"It's very exciting and humbling. I feel really honored," Enand told the Business Tribune. "First of all, we have a city with other people on the list who are really accomplished, really bright people, innovators bringing great things to Portland."
According to the report, the top three most likeable CEOs in Portland include Zapproved's Monica Enand, Cloudability's Mat Ellis and Puppet's Sanjay Mirchandani.
"I've interacted with almost everybody on this list. I think super highly of them," said Enand, who has spent time with Ellis and Mirchandani. "To be on the list with them is pretty amazing, it feels great."
Zapproved is a Portland-based software-as-a-service provider, and its flagship product Legal Hold Pro was the first cloud-based litigation hold management software, and is now the No. 1 litigation software.
"In leadership in general, if likeability is super important to you, being a leader is probably not a good choice because you can't make everybody happy," Enand said. "You can't think of yourself and prioritize likeability as a leader, it's just not a past success."
As CEO, Enand has grown Zapproved into a leading cloud-based software provider for corporate legal, changing how they respond to litigation so they can take control of their processes, mitigate risk and reduce costs.
"Going for likeability ... doesn't cause people to follow you or respect you or want to be around you," Enand said. "Portraying confidence, competence and likability, that's what gets hard for women. Every human has biased ideas about what is likeable for a woman, and competence and likeability are hard things to combine."
The fine line women in leadership walk is why aiming for likeability is a surefire way to miss the mark: women leaders are often spoken of in terms such as bossy or aggressive, instead of confident or competent — but not Enand.
"I think likeability is critical for both (female and male CEOs) even though a person can't prioritize likeability, it turns out likeability and competence are extremely important — required for people to follow you, they have to like you and think you're competent," Enand said. "Likeability along with competence is a harder trick for women, a little bit more than both competence and likeability for men. You need to have both."
Before founding Zapproved in 2008, Enand spent more than 15 years working for blue-chip companies including Intel and IBM. Today, she is a frequent speaker in Portland's entrepreneurial community, was appointed to the Oregon Growth Board by the Governor of Oregon, and serves on the boards of the Technology Association of Oregon and Auth0. Her M.B.A. is from the University of Portland.
"Somewhere along the lines I started realizing … I am an aggressive, ambitious person and I'm proud of that about myself," Enand said. "Being that and realizing that I enjoy it when I feel like people like me, I think somewhere along the way this concept of being really deliberate and explicit about why I think things are important … I think that's something I developed over time, to balance aggressiveness of wanting people to think things are important with wanting them to understand you."
Enand describes Zapproved's workplace culture as similar to many startups: growing, trying to take on more every day, a place where people who enjoy taking on a lot of new responsibilities can stretch themselves and do things they never have before.
"Teams are best put together when you have a shared vision, shared values and then complementary — not shared — skills," Enand said. "A lot of people have different values with which they'll go about achieving a vision. People are willing to do different things to achieve a vision in a time frame."
Specifically, Enand points to her working relationship with Chris Bright, vice president of marketing.
"The things he's good at, I'm horrible at, I've gotten to a point I can't even function without him helping me on certain things, and the things I'm good at Chris is glad I'm doing," Enand said. "We really have that shared vision, we definitely have shared values. Chris is a very good writer, a very good communicator. I went to engineering school. There are lots of things in the way he knows how to communicate that I struggle with as an engineer. I have a lot of engineering background and training which sets you up differently."
Bright said Enand earns everybody's respect and that a good culture of respect at Zapproved creates a high-functioning team.
"I think there are a lot of things she brings that makes her an awesome CEO, executive and human being, which the fact that she is female is completely secondary," Bright said. "She works really hard, she leads from the front, she shows incredible integrity, she shows wisdom by involving the right people and also making sure that people know why decisions are made, and it's really about the decisions in the company, not about your quality as a person. That's an important distinction."
Enand has talked about shared values with her team, and what values go into decision-making, and talks about the why.
"What are the values when we make different choices, why did we make those, what values do we have to say it's ok if this takes longer but we're not going to try to go fast and take these risks," Enand said. "In terms of being a successful company, it takes so much more than one person, it takes a whole team pulling together and making a contribution. You think a culture is strongly led from the top, but you attract people who them complement your culture and they attract people and your culture evolved."