Ready, Set, Soar

Cofounder Milena Berry’s PowerToFly helps top companies, from tech start-ups to the Fortune 500, connect with talented women

Milena Berry grew up in Bulgaria, during the country’s final years under Communism. As a kid, she loved challenging herself. Watching a Russian TV show on Friday nights helped her learn Russian. She attended an English language high school and a German language high school, getting diplomas from both.

At age 19, she moved to the Netherlands and then to New York City, where she earned a master’s degree from the Interactive Telecommunications Program at the Tisch School of the Arts at New York University. She relished the approach of the dynamic, multidisciplinary program, which combined entrepreneurship, innovation, arts, and technology to solve challenges.

Berry’s diverse background served her well when she became CTO of Avaaz, an online community that allows people to push for change on issues ranging from corruption and poverty to the climate crisis. Her team scaled the organization’s technology to support millions of members around the world. Avaaz’s impact has earned it praise from the likes of former Vice President Al Gore, former UK Prime Minister Gordon Brown, and Salil Shetty, former secretary general of Amnesty International.

While Berry loved working in tech, she was disheartened by the dearth of women in tech jobs. So in 2014, she cofounded PowerToFly with Katharine Zaleski, whose Fortune essay “I’m Sorry to All the Moms I Worked With” spotlighted the challenges faced by working mothers.

PowerToFly helps connect companies aiming to diversify their talent pipeline with women seeking innovative jobs, especially tech roles. The organization focuses on remote and flexible jobs, which can often benefit women’s careers—especially those of marginalized women.

Milena Berry spoke to Diversity Woman about how companies can attract more women, the current transformation of workplaces, and the magic of getting in over your head.

Diveristy Woman: What did you learn during your time at Avaaz?
Milena Berry: I ran an amazing technology team for seven years and scaled the technology to a place where we were supporting 40 million members, which was really a challenge.
Frankly, when I took the job, I was probably underqualified. I didn’t know what I was getting myself into, but that’s what created the drive and hard work and the excitement. And that’s what I tell women at the beginning of their career: never take a job that you’re 100 percent qualified for, because that’s not where the growth happens. It’s part of my entrepreneurship journey and my success story to constantly push myself and stretch.

DW: What prompted the idea for PowerToFly?
MB: Everybody was talking about the plight of women in technology. I was like, “Yes, it sounds right,” but that wasn’t my story. I had three kids and an amazing career. I was working at a company changing the world. It paid me well. The company was a remote-first company, and I had flexibility. Why can’t my story be a story of hope for millions of women around the world?
At the same time, I realized that every time I had to hire, I’d get 99 percent male candidates. I had very few women on my own team, so I had experienced firsthand the diversity problem.

DW: How does PowerToFly help connect companies with women?
MB: We have a community of 275,000 women, mostly in the US. There was just no platform putting them together for companies to find them.
We found that creating the pipeline was not enough. A lot of systemic issues—how companies market themselves, and how they interview women, onboard women, and make women feel that they belong—prevented women’s numbers from growing over time. PowerToFly provides solutions on all of those fronts to really move the needle. The diversity challenge needs a multifaceted solution.
As an example, women don’t apply to jobs like men do, especially the skilled professionals or highly technical women that our clients are looking for. So employers have to start by telling stories. [Women want to know], why do I belong in your organization? Show me women who are successful in your organization. What did it take? Show me a male ally who is going speak to his commitment to diversity in the organization.

DW: What sets the PowerToFly community apart?
MB: We have achieved something special in creating a community of senior professional women [who participate in panel discussions and networking events]. It’s sometimes tough to get senior folks interested because they have a lot of responsibilities.

DW: How do your virtual hiring events work?
MB: We held over 300 virtual events in 2019. We did in-person events pre-COVID-19, then helped companies pivot to virtual hiring events.
We start the event by showing why women can belong at their organization, giving attendees the opportunity to network with the company’s executives. We target the event to the people with whom the companies want to engage. American Express, Microsoft, and Deloitte are just a few of the companies that keep coming back for more. American Express put together an event in New York City and hired five women after the event. Microsoft sometimes does five to 20 hires per event.
We have a couple of other solutions on the hiring front, like a service called dedicated sourcing. Companies can hire a recruiter from PowertoFly to work full-time on their [recruitment], and 100 percent of the people coming from that recruiter will be women and diverse candidates.

DW: PowerToFly focuses on remote and flexible jobs, to benefit all women needing flexibility, including working moms, correct?
MB: Yes. I’m a mom of four and, in many ways, it’s the thing I’m most proud of in my life. I started with Avaaz when my oldest was 10 months old and then I had two more kids on the job there. Now I have four kids. My cofounder [of PowerToFly] and I were pregnant at the same time while running the company.

DW: What keeps you energized about PowerToFly?
MB: I’m a firm believer that the best way to help a society is to provide opportunities for and put income in the hands of women. Women make 80 or 90 percent of consumer decisions. We also are caretakers—of ourselves, our kids, significant others, parents, pets—so when we earn, we trickle down in the economy.
There are a lot of opportunities when it comes to the big cities, but fewer opportunities when you go inland or outside the big city zones. In certain states, there are very few opportunities, so talented people have to leave or settle for earnings that aren’t great. And then you extrapolate that to outside the US. We have been so proud to hire women in the Middle East, Latin America, Palestine, and Botswana in Africa.

DW: What have been your most challenging moments as an entrepreneur?
MB: I describe myself as having a motherly leadership style. So the moments I have suffered the most have been when we had layoffs. Having to let go of people who have done a really good job, because perhaps I hired too fast or didn’t lead the team to meet our revenue goals as fast as we could have, was very painful.

DW: Women were once told that the best way to succeed was to lead like a man. But do you think your mothering leadership style helps you in any way?
MB: That’s an interesting question, because I’m married to a trans woman and gender is definitely an interesting concept. I have a hard time categorizing male and female in that way. I think that everybody’s actually a shade of both, some people more of one or the other.
However, I do want to say—and no disrespect to Cheryl Sandberg—but her Lean In philosophy never sat well with me in that way. Because it was pushing that you’ve got to be more like the men to get a seat at the table. You’ve got to lean in and do this thing that men do. I feel it’s important for us to embrace what makes us strong and say, “Listen, I’m going to be in my circle of power. And I might be the introvert leader.” It doesn’t always have to be masculine, beating on the chest.

DW: What are you most excited about in 2020 and beyond?
MB: We want to accelerate everything we’re doing because the time is now. Obviously, the move to remote work has been fantastic. The second thing is Black Lives Matter. Many companies have renewed their commitment to DEI and are saying, “Okay, this cannot just be something we say we do. Let’s walk the walk.”
Our plans are to continue impacting the hiring, employer branding, and retention goals of companies that we’re already working with and to expand geographically. We have started our first campaigns in India, Australia, Latin America, and Europe. We’re also looking forward to scaling our content offering because our community loves it, so stay tuned. DW

Kimberly Olson is the managing editor of Diversity Woman.



Speed Round
We asked. Milena Berry answered.
Favorite app: Kindle, for reading to my toddler a few times a day.
Favorite author: I love all BrenÈ Brown’s work.
Favorite getaway: Pre-COVID, my family and I would go to Lake Chapala in Mexico every year. Ajijic is our favorite spot there as well as the hot springs in the adjacent San Juan Cosal.
Song in your head: “Say a Little Prayer” live, by Lianne La Havas
Food you can’t live without: I like to make gluten-free toast with ljutenica, a Bulgarian red pepper spread; egg; olives; and fresh parsley.  Person you most admire: Michelle Obama
Current obsession: Weekend car rides to our perfect beach spot on the Long Island sound.
Belonging you’d grab in a fire:  Our passports. The more logical choice would be phone and laptop, to work remotely.
Special talent:  Back in the day, I performed Bulgarian folk dancing.
Best gift you’ve received: My cofounder was so generous to let my family hide from COVID in her Brooklyn brownstone.
Superpower you want: Healing my family and friends
Personal style: Strong contrasting colors, like Desigual

Article By Kimberly Olson

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