14 New York Women Spill Their Tips For Career Domination

Illustrated by Anna Sudit.
Like many other female accomplishments, breaking professional boundaries and rising to the top (particularly when it's least expected) should not only be praised, but be celebrated. Especially when the obstacles women are forced to overcome don't just encompass interview woes and scary bosses — they include wage gaps and gender bias, particularly in industries (such as finance, tech, and engineering) that are still skewed so heavily towards men.

These 14 New York female powerhouses in particular have taken male-dominated industries by the reins and proven that anything guys can do, women can do better. They've risen to the top of their respective fields, kicking gender stereotypes in the workplace to the curb and seriously inspiring us along the way. Want to know just how they've beat the odds? Ahead, they dish on overcoming their field's difficulties, becoming majorly successful, and defeating their industry at its own game.
1 of 14
Illustrated by Alena Jaffe.
"Culturally, most women of color are expected to 'stay in their lane,' and this is especially true in the science and tech fields. We are taught to be very careful and measured regarding what we claim to be possible, and our bravado is limited to only what we can prove without even a modicum of doubt. The problem, of course, with this is that true innovation doesn't start with a proven concept, but rather a passionate idea — a vision that only you can see.

"This does not mean we do not have innovative — sometimes radical — visions of what the future might hold. However, this cultural myopia in the science and tech fields does mean that we rarely speak these ideas out loud, and when we do, the ideas are often viewed as smaller in potential reach or impact, because the idea of a woman — [not to mention,] a woman of color — doing something that big and that powerful just seems impossible.

"I deal in energy. Playful, individualized, democratic energy for all. And while my first product may be relatively focused, my dreams of what is possible are bigger than most are comfortable imagining. Honestly, it took me a while to get comfortable imagining it as well. But I found that the best way to get over this is to start saying what you believe out loud, and saying it a lot. Start with yourself — in the mirror — then your family and closest friends. Even if they laugh, just keep saying it. Before you know it, you will begin to speak your dreams into existence."

— Jessica O. Matthews, Founder and CEO, Uncharted Play, Inc.
2 of 14
Illustrated by Alena Jaffe.
"The most difficult aspect of working in [the tech] industry is the subtle bias that happens every day, unconsciously by both men and women, to discount our achievements and ambitions. For example, when we tell VC investors that we're the first tech company going after an untapped $21 billion market and the goal is to dominate it, somehow the perception is still that we're building a 'lifestyle business for working moms.' This is not what we're doing and not what we're saying, but that's what they perceive.

"We overcome it by doing a better job building our business with fewer resources and less money than our male counterparts. The best compliment I ever received from an investor was, 'Whoa, you did what you said you were going to do.' Damn straight. You have to kill them with competence. ​The only way to convert the people who don't believe in you is to do an amazing job and succeed in spite of them."

— Jules Miller, Co-founder, Hire an Esquire
3 of 14
Illustrated by Alena Jaffe.
“The most difficult thing about being a female tech entrepreneur is that there is a disconnect between your female identity as you are socialized and perceived, and the persona you are aiming to project professionally. That is an illness of society and not your fault as a woman, but it is still a problem for you.

The truth is, the male identity is much more strongly associated in our collective minds with power, which is essential to project as a tech entrepreneur. When you are starting something from nothing, it's not only about building. It's also about influencing people to take a risk on you and put their eggs in your basket. It is more straightforward for a man to project this power, because it is consistent with people's expectations and even what he is supposed to do in personal life. For a woman, it is more complicated.

“Every woman handles this differently. I think in the '90s, women handled it by acting more like a man. Now, there is a trend towards demanding that the market be more fair, and I think that's a good thing for women in the long run. However, people's subconscious minds are not going to change overnight, so you have to be careful. You have to ask yourself, what is best for my company?

Ultimately, you are part of a team, and when your team wins, you win — if you're working with the right people. So in my mind, that is the most important choice. In a high-performing team that has been working together for a long enough time, there is a professional intimacy that supercedes persona. Your team will eventually figure out what you are capable of, regardless of if you are wearing a skirt or pants, or if you have a low or high voice, or if you have short or long hair. So what I do is only work with people who I can trust to be fair in the long term. I have been very lucky with the people I have worked with. The most important career advice I have received is that you only ever win as a team.”

— Lauren Talbot
, Co-founder and Chief Data Officer, advisorCONNECT
4 of 14
Illustrated by Alena Jaffe.
"Sometimes, people will hold your judgment and analysis to a higher bar, as shown by the 'Men are judged on future potential, women are judged on past performance' axiom. The only way to overcome this is to demonstrate and communicate a track record of success and carry yourself with confidence."

Katelyn Donnelly, ‎Managing Director, Pearson Affordable Learning Fund
5 of 14
Illustrated by Alena Jaffe.
"I raised our $1 million seed round when I was nine months pregnant. For months, I struggled with the question of whether I should bring it up in meetings. How would investors react? How do you casually slip something so personal into something so professional? Would I sabotage opportunities if I didn’t tell investors and they found out later? In this image-obsessed world, would investors critique me less harshly if they knew I was pregnant and not just 40 pounds overweight? Yeah, 40. Could I really get away with wearing Supergas and maternity jeans to every meeting? What would I do when investors wanted to meet for a drink? Was it my responsibility to help pave the way for other women who will face similar challenges?

"At a certain point, my body made the decision for me. Reactions were all over the place. Some investors just wanted to talk about their children and grandchildren, while others gave me a hard time about drinking coffee or working too hard or being out in the cold. A few told me I should really take the time to stay at home with my child and worry about work later. Others just got awkwardly quiet and stared at their notebooks for the remainder of the meeting.

"Three weeks before my due date, I got an email from Nicolas Wittenborn of Point Nine Capital. He was in New York for a few days and wanted to meet. I booked an hour with him the following morning, nervous that if we scheduled it for any later that week, I may need to cancel from the delivery room.

"He walked in unfazed. We spoke about how wonderful building a family is and how great it is to have love for two babies, my company and my soon-to-be daughter. The rest of the meeting was spent in product and cohort analysis. He was able to embrace the fact that I was about to become a mom and also see that my team and I were building something incredibly special. He never doubted both could happen at the same time. When he walked out, I knew we had found the perfect partner. We had a term sheet from Point Nine for the full round in less than two weeks."

— Rachel Kaplowitz, CEO, Honey
6 of 14
Illustrated by Alena Jaffe.
“The most difficult aspect of being a woman in my field is just that: being a woman. Project management is a male-dominated industry, and the way I have overcome that is by seeing each individual at the table as a distinct person with distinct strengths that only they can bring to the group, rather than as male or female."

— Jamie Slaper, Project Manager, Levien & Company
7 of 14
Illustrated by Alena Jaffe.
"Reputation is everything. The New York City commercial real estate world is smaller than one may think, and focusing exclusively on the Brooklyn market makes it even smaller. I've learned to hold my ground, be firm on my beliefs, and that you can build quite a following with the confidence that you radiate while doing so.

"Taking into account my current situation, morning sickness (!) has definitely been a challenging part of my job. Yes, I am almost 17 weeks pregnant with my first, and I am questioning myself every day how working women do it! I just recently got over the morning-sickness phase, which no one seems to tell you is really an ‘all-day’ sickness, but I am finally starting to feel like myself again. More than ever in my career, I am learning balance and discovering that I have limits...and that it’s okay."

Melissa Warren, Partner, TerraCRG
8 of 14
Illustrated by Alena Jaffe.
"There have been times where I’ve felt like an outsider in the industry. As an economic-development professional working within the tech community (and being a woman, and not a coder), there have been times when gender bias has led to having my authority questioned — at times in obvious ways and others not so much. I’ve definitely had to teach myself over the years to talk the talk of a technologist (as best as I could!). I even enrolled in some classes at 3rd Ward back in the day to build some tech skills — skills I understood through my work to be vital to the city’s future.

"In economic development, work perceptions aren’t quite as gendered, but there, too, women are a minority. I have worked hard to establish a leadership role in these industries, and at the end of the day, providing services and tangible benefits to the technologists and entrepreneurs of New York City gains me credibility."

— Daria Siegel, Director of LMHQ, Alliance for Downtown New York
9 of 14
Illustrated by Alena Jaffe.
"My mom is one of the most intelligent and successful women I know. I look up to her in so many ways. As the Honey team has grown from four co-founders to a team of nearly 10, I’ve had to re-teach myself what it means to be a leader and a manager. And my mom has helped me so much through the process. The best piece of advice she’s given me is: 'Knowing when to raise your voice and speak is important, but knowing when to shut your mouth and listen is critical.'

"Giving myself the head space and quiet time to observe and process helps me do my best work. And quietly listening gives my team members the space to problem-solve, brainstorm, embrace their expertise, and share what’s most important to them in their role. I’m not perfect at it yet, but I’m learning and practicing all the time."

— Alison Morris, Co-founder and Director of Accounts and Customer Experience, Honey
10 of 14
Illustrated by Alena Jaffe.
"Women on Wall Street have faced various challenges over the years — ranging from the intangibles, such as team dynamics and cultural double standards, to the tangibles, such as work-life balance for women building a family. I am personally very fortunate to work at a firm that has cultivated a progressive, forward-thinking culture where women enjoy a collaborative, respectful environment far from the old-school banking 'frat club.' That said, it is hard to not notice the broader scarcity of senior female investment bankers across Wall Street today (whether a byproduct of their own choices or the system itself). As we aspire to achieve a better gender balance in the long term, women may have to work a little bit harder to prove their credibility in the short term. The best tools in my toolkit thus far have been a relentless work ethic, an effort to expand my knowledge base daily, leading with self-awareness and confidence, and never giving up. At the end of the day, being a woman on Wall Street is not a challenge for me — it’s a source of motivation.

"I have received several meaningful pieces of advice from my colleagues and friends over the years, but there is certainly one theme that stands out in particular: a willingness to take risks. I truly value being told by many: 'Don’t be afraid to make a mistake.' Whenever I have tried something new and didn’t make a mistake, I have been lucky enough to simply learn how to do something new. And whenever I have tried something new and have gone on to make a mistake (or two), I’ve learned just exactly what doesn’t work, as well. Taking risks has opened many doors for me both in my professional and personal development — and as they say, if you never try, you’ll never know."

— Aarti Kapoor, Investment Banker, Moelis & Company
11 of 14
Illustrated by Alena Jaffe.
"The hardest thing can be getting past subtle discrimination. I had a situation myself recently where I realized someone was treating me differently than they would a man. And I don’t even think they realized it.

"But the best piece of advice I received is actually 41 pieces of advice. It's only recently that I received it — and sadly, posthumously, when my dear friend and mentor, Jimmy Lee, vice chairman of J.P. Morgan bank, passed away. At the reception following his funeral, cards with his advice on how to be a great leader were passed out. They were pretty simple but worthwhile — being on time is being early; be prepared; treat everyone the same, regardless of their situation; and put clients first. I'm sharing these with my employees and my children — even my 11-year-old!"

— Alexandra Lebenthal, President and CEO, Lebenthal & Co.
12 of 14
Illustrated by Alena Jaffe.
"I began my career as a public school teacher in the Bronx. In my experience, the stereotype of teachers, particularly female teachers, is that we teach because we are kind souls who care about children. While that is of course true, teaching is too quickly overlooked as a prestigious profession.

"Elevating the teaching profession as a reputable and respected field is core to the mission of our work at Educators for Excellence (E4E). Teaching was one of the first professions open to women, and so it only makes sense that women should help blaze the trail toward higher student achievement in our country by taking on leadership roles inside and outside the classroom. I loved teaching, but also felt frustrated that for so long, teachers had been treated as subjects of change, rather than as agents of change. Too often, the voices of teachers — the majority of whom are still women — go unheard in the larger conversations taking place about our classrooms and our careers. It's time we change that.

"My mom (and best friend!) always taught me about the power of using my voice to make meaningful change. When I was in high school, my mom was a leader in the Million Mom March movement to advocate for tighter gun control. Today, she is a hospital-caregiver advocate and coach, supporting the needs of those who are taking care of loved ones during times of serious illness. Watching her practice what she preached undoubtedly influenced me when, in 2010, I co-founded E4E to give teachers an outlet for their intelligent and impactful voices to be heard in the education-policy debates affecting their students and their profession."

— Sydney Morris, Co-founder, Educators for Excellence
13 of 14
Illustrated by Alena Jaffe.
"Sometimes I find it difficult to establish myself as the authority in the classroom or in the meeting. And I think my challenges are compounded by the fact that I'm also on the younger side, which is something I still work on and struggle with from time to time. In addition to a lot of preparation on the material at hand, I just try to focus my energy on those I know respect me, whether they're students or colleagues. That, in turn, boosts my confidence, and confidence (even if it's false confidence!) makes all the difference. And regarding the very few people who may be judging me or disregarding me because I'm young or a woman or whatever other thing, ultimately those aren't the people who matter anyway.

"In my field, there is a lot of pressure to get tenure. I've been given a tremendous opportunity and have an amazing goal to strive for. But sometimes, it can be overwhelming, and you start to question whether you're doing enough or whether you're doing the right things. The best advice I've received from one of my colleagues is to just do what you believe is the right thing and that will ultimately get you to where you want to be. It's really simple, but I've found that it helps me maintain perspective and regain it when it's lost."

Shiho Kawashima, Assistant Professor of Civil Engineering and Engineering Mechanics, Columbia University
14 of 14
Illustrated by Alena Jaffe.
"Being a female in the tech industry is a very powerful thing. I actually have not encountered any setbacks as a result of being a woman — quite the opposite, in fact. I find that successful men are more likely to mentor young women in this field, as they are trying to help close the gap between male and female entrepreneurs. When embarking on the Series A for DWNLD, I was conscious of the fact that I was a 29-year-old female, and that my plans to have a family would come into play at some point in the conversation. These matters were addressed when venture capitalists asked, 'Where do you see yourself in five or 10 years?' To which I replied, 'With my baby, DWNLD.' I keep my personal life private. It’s up to me to manage, and not something that should become an issue for my business or how it runs."

— Alexandra Keating, CEO and Co-founder, dwnld.me