Recently we announced the creation of our new leadership team at PresenceLearning. It was important to me to prove that what I had accomplished at The Princeton Review could be repeated: we could build an executive team that was both exactly what the business needed in terms of talent, skills and leadership, and that was gender-balanced. Our newly formed team at PresenceLearning is 100% the right group to lead the company forward, and we are also 50% female.

It’s well documented that there are multiple benefits to having meaningful female representation in senior levels of an organization. A 2014 Gallup study found that businesses with more gender diversity produce “better financial outcomes than those dominated by one gender”. This is in large part due to the ability of a diverse organization to attract the best talent from the largest pool. Some diversity brings more diversity. A 2019 Harvard Business Review survey found that “the most talented individuals go to places that do better with diversity, and this may be what is driving diverse firms in certain contexts to outperform their peers.” Diversity of perspectives leads to more thoughtful decisions. Representation of all customer/client perspectives leads to better product-market fit. And, when those who work for and within the company feel that they can relate to their management team, it supports the development and promotion of more diverse talent at all levels of the organization.

So the research reinforces that it matters tremendously to create diversity on executive teams, as well as on boards and in investment firms. The more diversity we have among the decision makers, the more likely we will see diversity in the executive and other senior roles in the future, and the more likely that those senior leaders will cultivate a more diverse group of employees on their teams.

I believe in this research in part because in my own experience, this is how it worked for me. In the first decade of my career, I was often the only woman in the room. I worked on Wall Street for five years, then went to Harvard Business School, and then worked in M&A, all fields dominated by white men. Despite having career success, I never saw myself as being the next leader of any of the organizations I worked for, and I don’t believe they saw me that way either. I had never seen or interacted with a strong female CEO. It wasn’t until I found women in positions of power that bigger opportunities opened up for me.

Consider my path to my first CEO role, at The Princeton Review. My first C-suite role was as CFO, reporting to our CEO, Mandy Ginsberg. Mandy was the one to see my potential to be a successful executive a year earlier, and she recruited me to be on her team. She was like me in so many ways. She was also a young executive, under 40 when she took on her first CEO role. She was an MBA and a working mom with two daughters, just like me. 

We even looked alike. Early in the days after we acquired The Princeton Review, I attended the corporate holiday party for the Boston office, and Mandy couldn’t make it. About an hour in, sitting around a table chatting with a captive audience, someone called me Mandy, and I realized that everyone thought I was the CEO! They had seen both of us on video screens but never in person, and I suppose we looked similar enough that they mixed us up. 

So you can imagine, when we started talking about succession plans for the company, it was very easy for Mandy to say “I see you as the next CEO” and it was very easy for me to picture modeling myself after her.

The day I met Elizabeth Chou on my path to becoming CEO of Presence Learning.

The path to my next CEO role began with an introduction to Elizabeth Chou, a General Partner at New Markets Venture Partners. Elizabeth and I arranged to meet at an industry conference. We were exchanging those awkward texts you write when meeting someone for the first time; where you have to describe how you look and what you’re wearing to a stranger. Elizabeth wrote, “I have long straight brown hair, and I’m wearing a black and white striped dress.” I responded, “That’s weird…you could say exactly the same thing about me, including the dress!”

Funny though it was, I realize now it was also significant. Because we had a lot in common, our conversation flowed easily and was productive from the start. We each assumed that the other was worth talking to, and we got straight to the substance of talking about what kinds of companies and business models we believed in, and our approaches to leading them. We spoke energetically, well past our scheduled time together, and Elizabeth said she would be following up with a possible opportunity for me. That opportunity was with PresenceLearning, in which New Markets had a minority investment.

She then introduced me to Mia Hegazy, a Principal at Catalyst, the majority investor in PresenceLearning, and the Interim CEO leading the board’s search for a permanent CEO for PresenceLearning. When I first met Mia, I discovered that we also had a lot in common. While we weren’t wearing identical outfits, over our next few meetings we bonded over our shared passion for running, confessed our mutual guilty pleasure of watching The Bachelor, and noted how we tended to order the same thing for lunch. As with Elizabeth, because we had so much common ground and easily identified with each other, my conversations with Mia went straight to the heart of the needs of the company, my experiences and perspective, and how we saw them all fitting together.

The odds were low that I would find powerful women to connect with. Fewer than 7% of Fortune 500 CEOs are women. Less than a quarter of Fortune 500 board members are women. And three quarters of venture capital firms don’t have a single female partner. As companies, funds and boards continue to prioritize gender re-balancing, the chances that high potential women will find relatable role models is increasing. But what about all of the high potential individuals for whom it’s even harder to find representation at senior levels? There are currently only 3 CEOs in the Fortune 500 who are persons of color, and none of them are women. And 81% of venture firms don’t have a single black investor, let alone partner.

When I reflect on the ease of my path to PresenceLearning, I can’t help but compare it to the many more challenging discussions I had along the way with recruiters, board members, and investors who I didn’t have very much in common with; older white men who had a harder time envisioning me as the next CEO for the organizations they influenced. They found awkward ways to say I looked too young: “We were expecting a different in-person presence based on your resume”; too mom-like “Are you sure you want to do this while you have two young kids?”; or, in the words of one Chairman, simply: “I just don’t see you as the CEO.”  

So I’m grateful that when I found a company that I wanted to lead, two women held the influence and credibility to open the door to the opportunity. Our shared interests made it easy to quickly get comfortable with each other and get to the point of talking directly about the company, its challenges and opportunities, and what they were looking for in their next leader. And because the rest of the board respected them, they were able to propose me as a candidate, and because of the board’s own openness to women leaders (in part because they work alongside Elizabeth and Mia and are familiar with women in such roles), they evaluated me as a qualified candidate for PL and not as a young, working mom.  

While we are beginning to ask people in power to do the important, necessary work to root out their own conscious and unconscious biases, my experiences have taught me that people do still tend to hire people who are like them. But we can’t leave it only to the women to hire more women, to people of color to hire more people of color, and so on. Everyone needs to deliberately and actively seek to place more diverse representation in leadership roles.

I spent the first decade-plus of my career fighting to be seen and heard as a woman in a pool dominated by men. As I acquired more influence, I saw it as my responsibility to “pay it forward” to other women by actively managing my own hiring goals to create gender-balanced teams. But I now see that this is not enough; while I’ve created better, more gender-diverse teams, I need to recognize that I’ve done so largely by hiring people like me: white women. So I need to go a step further and actively seek to promote and recruit more people of color to lead the organizations where I have influence. I am now a gatekeeper of opportunity. I will keep working at diversifying my teams to reflect different races, ethnicities, abilities, identities, and backgrounds, to foster true inclusion and representation in my organizations. I’ve established this as a personal goal for the next phase of my career, and I encourage other leaders to do the same.