Thriving As A Woman In a Male-Dominated Industry: Jennifer Cyphers of Pynwheel On The Five Things You Need To Thrive and Succeed as a Woman In a Male Dominated Industry

An Interview With Ming Zhao

Balance — Once you have mastered freeing up your time, you’ll also have more downtime to refresh and recharge your brain. Take advantage of it. Exercise. Spend as much time as you can doing what you love, that is unrelated to work. Prioritize it. Make it more important than work. This will make you a better worker, a better friend, a better spouse, a better parent, and a better person.

In the United States in 2022, fields such as Aircraft piloting, Agriculture, Architecture, Construction, Finance, and Information technology, are still male-dominated industries. For a woman who is working in a male-dominated environment, what exactly does it take to thrive and succeed? In this interview series, we are talking to successful women who work in a Male-Dominated Industry who can share their stories and experiences about navigating work and life as strong women in a male-dominated industry. As a part of this series, we had the distinct pleasure of interviewing Jennifer Cox Cyphers

Jennifer Cox Cyphers is the founder and CEO of Pynwheel Inc., a software company focused on tech-enabled real estate tours and on-site sales. Prior to starting Pynwheel, she was the founder and co-owner of Engrain, a digital agency, and helped to get various start-ups off the ground including ApartmentList, Vast.com, and SafeRent. She serves as a member of the Philanthropy Council and the Board of Alumni Equity & Inclusion and Honors Committees for Lewis and Clark College and is the founder of The RBG Society.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up in a middleclass family near Denver. We are a very female-centric family. My mom was raised with her sister by their mother and their great-aunt. After my parents got divorced, my sister and I lived primarily with our mother. She had been a traditional stay at home mom prior to her divorce, and her going back to work was a difficult transition for all of us. It was probably good for her, because it gave her a sense of independence, but she had to work around our school schedules and keep us on a tight budget.

When I was young, I was classified as gifted & talented. Like a lot of GT kids, I excelled in school until I didn’t. By my junior year in high school, I was not getting good grades. I absolutely loved learning, but I missed a lot of class and didn’t stay on top of my homework. I participated in DECA and worked part-time, both of which I loved. I will forever be grateful to Lewis & Clark College for recognizing the disparity between my grades and my test scores and admitting me! I loved my time in college. It was challenging because I worked a lot and had to transfer in and out of different schools to try to stretch my tuition money, but I was in heaven. The only problem was that it was very difficult for me to choose what I wanted to focus on. I wanted to major in every subject!

Can you tell us the story about what led you to this particular career path?

When I graduated from college, I was torn between wanting to go into advertising or going to medical school to pursue a career in neurology or psychiatry. I ended up doing a couple of years in an ad agency and then going back to school to finish up my pre-med requirements. During that time, I took a temporary position at a tech company doing data entry to pay my rent while I was in school. The company ended up hiring me full-time and promoting me pretty quickly. That company happened to be under the direction of a female CEO, who was my role model. I am very grateful that I had the opportunity to work under her and watch her lead. I also learned a lot about marketing technology for multifamily properties while I was there, which took me on a different career path — away from medicine. After several years of learning that industry, I found myself spending a lot of time thinking of ways to make things better. What I landed on was that we do a good job of using marketing technology to help people find listings of homes, but then when they actually want to see it, the technology falls away and they are back to phone calls and emails and meeting with a live agent. It just seemed like there was a more efficient way for people to tour residential properties.

Can you share the most interesting story that happened to you since you began your career?

Several years ago, the owner of our office space decided to renovate. While it was under construction, everyone had to work from home. I wasn’t a fan of the plan, but then it kind of worked out. I think a lot of companies went through this in 2020. We got the hang of communicating with each other remotely, and any decrease in productivity was made up for by the time we saved on commuting and having unnecessary meetings and conversations. By the time the office was ready for us to move back in, I could no longer justify the time we wasted going to an office. I lost up to 90 minutes a day of productivity on the commute and parking alone. We looked into flexible coworking space, but the consensus was that everyone wanted to try working from home full-time. The surprise benefit of the new arrangement was that we had complete flexibility. Anyone could work from anywhere. As a test, I moved to Costa Rica for a month with my family. We traveled around. We hiked, surfed, swam. We saw monkeys, tapirs, and blue jean frogs. We watched the sunset over the water every night. The next year, we went back for six weeks. I worked every morning from our AirBnB, and worked in the afternoon from the beach or wherever we were. It was an exceptional experience for my whole family. The memories will last us a lifetime, and the experience of living abroad changed my kids’ perspective on the world. I am proud that I was able to use my career path to design that lifestyle.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1. Tenacity — Without hesitation, I can say that the #1 character trait that is most instrumental to success is tenacity. I have never met a founder who hasn’t had dark moments when they couldn’t sleep and wondered why they chose to shave years off their life by starting a company. The pressure and the stress can be monumental, but if you don’t give up you have not failed. I stubbornly and persistently work through every problem, even when I want to give up.
2. Decisiveness — Another thing that all founders that I know have in common is that everyone has had to lay people off, and everyone was sick about it. I use this as an example, because it’s one that doesn’t get talked about much, and it’s tough one. It’s so important, not only to health of your company, but to the mental health of your team, to have the foresight to see the decisions that need to be made, and then make and execute those decisions. It’s very common for companies to struggle because leadership hesitated to make challenging decisions and then everyone is worse off as a result.
3. Humility — Keeping an awareness that I don’t know everything has been important to my success. When a client chooses not to work with my company, or when an employee has an issue with our processes, I listen to them with openness to learn what we can do better instead of getting defensive, and I am truly grateful to them for helping. I try to keep my ego in check so that I don’t conflate my identity and self-worth with the success of my company, which is very tempting. Letting go of the need for success is crucial to succeeding.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you help articulate a few of the biggest obstacles or challenges you’ve had to overcome while working in a male-dominated industry?

There are quite a few challenges to working as an outsider in a male-dominated industry. Here are a few that I have experienced:

1. Stereotyping

One of the reasons I am grateful to the CEO whom I worked under early in my career, is that I got to witness the abuse that she took as a female CEO. She was widely criticized for being insensitive. I believe her sharp business-mindedness was a contrast to the sexist stereotype that people expected: a woman being soft, sensitive, and indecisive. It was a good lesson to me that my sex would affect the way people regarded me in a leadership position.

2. Objectification of Women

My work environments have at times displayed objectification of women — groups going to gentlemen’s clubs at lunch time or at conferences, for example. Men would make inappropriate comments to me about my appearance, even focusing on my body. Every promotion I ever got, at least one person suggested it was because my boss “had the hots” for me. Yes, it was distracting and oppressive, but it was also just a part of my day-to-day life, so I didn’t think too much of it throughout my career. I just knew when I had my own company, that I wanted to make sure that the culture was different.

3. Credibility

On a more practical level, getting things done takes more work. When you look at the statistics, you will see that this is true. Raising money is harder. Getting responses is harder. For me, working in software development has posed its own particular challenges because it takes an unnecessarily high volume of communications to convince and remind software developers that I know what I’m talking about. It is truly on the verge of silly how condescending men in the software industry tend to be towards women. At events and in meetings with other tech founders, I find that my voice gets drowned out by my louder male counterparts.

4. Managing Emotions

Perhaps most startling to me is how highly emotional men can be in the workplace. I know that the stereotype is that women are more emotional, but this has not been my experience. It has been very challenging to work with men who shout at others when they don’t get their way or feel threatened, covertly cry in meetings, and storm out of the conference room when they feel like they’re losing control. I don’t have any patience for such a lack of decorum in the workplace, but it seems to be commonplace in a lot of male-dominated organizations. It interferes greatly with good decision-making and productivity.

5. Women Supporting Women

Lastly, I find the idea that women need to support women to be a dangerous one. On multiple occasions, men have suggested to me that I try to find a female mentor, and then implied that it’s difficult because women are competitive with one another. It’s true that my business and career mentors have been men, not women (and I am grateful to all of them). This is true mainly because there are few women at the top in my industry. The women who are at the top often got there from working harder, longer hours than their male counterparts and fighting all the issues I raised above, and more. It’s not their obligation to take me on as a protégé in addition to all the extra challenges they have to take on because of their sex. Instead of shaming women for not supporting other women, I’d rather support women by letting them off the hook. They do enough already.

Can you share a few of the things you have done to gain acceptance among your male peers and the general work community? What did your female co-workers do? Can you share some stories or examples?

This all goes back to tenacity and persistence. I spend a lot of time asking questions, doing research, and turning problems over in my head. That way, when I discuss problems or solutions with people (whether they be peers, coworkers, clients, or partners) I can be confident in my position while remaining open to other ideas. If I am not confident, I ask questions and listen. I never assume that someone else has the correct answer though — whenever necessary, I do my own research to confirm.

What do you think male-oriented organizations can do to enhance their recruiting efforts to attract more women?

1. Recruit Changemakers — It is intimidating to anyone to feel like the odd one out in any given situation. The only way to overcome it is to first embrace the people who are the least unnerved in uncomfortable situations, and have them help you to create a culture for others like them. If a male-oriented organization is interested in attracting more women, they need to start by finding women who are not only good at their jobs, but who can help act as a force of change. Then, they need to ask a lot of questions and listen to the answers without judgement.
2. Ask Questions in the Right Way — The challenge in this, of course, is that a person in that situation may have the tendency to give the “right” answer because they already feel vulnerable. So it’s extremely important to ask questions in a positive way that does not open the door to complaining. In your effort to empower a changemaker, don’t set them up to be a troublemaker. A good question to ask is, “If we were to bring in more female employees, what changes could we make that would make them feel more comfortable and help them to be successful?”
3. Don’t Separate — Generally, I think it’s important to steer clear of dividing sexes by implementing women’s groups within your organization. Nothing makes people feel more like outcasts than by suggesting that they should mix with their own kind.
4. Don’t Let People Interrupt — This is the simplest and most straight-forward of all the advice I can give: Do not let people talk over or interrupt their peers. Make it a habit to insist that others let people finish what they are saying. Don’t let loud voices drown out quiet voices, and don’t let people filibuster.

Ok thank you for all of that. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman In a Male-Dominated Industry?” (Please share a story or example for each.)

1. Free Time — This was a hard one for me to learn, and so important. The best thing that you can do to improve your chances of success is to take on less. If you compare ambitious men to ambitious women, this is where you will see the starkest difference. Work on removing things from your to do list, and keep yourself from adding more. Don’t join that committee because you’re a go-getter. Don’t whip up something to take to your friend’s for dinner. Don’t spend all day Sunday cleaning your house. Don’t volunteer to put together a report for your client that they are perfectly capable of doing themselves. You should constantly be looking for ways to do less. Only do the most important things. Erase the things at the bottom of the list. If someone asks you to do something that really needs to be done, do it as soon as possible in the least amount of time possible. This will free up your brain so that you can more effectively solve problems. You’ll have time to think things through, and you’ll have the capacity to recognize priorities that you may not notice when you are stressed and busy.
2. Balance — Once you have mastered freeing up your time, you’ll also have more downtime to refresh and recharge your brain. Take advantage of it. Exercise. Spend as much time as you can doing what you love, that is unrelated to work. Prioritize it. Make it more important than work. This will make you a better worker, a better friend, a better spouse, a better parent, and a better person.
3. Patience — When I started working in a male-dominated industry, I was completely unaware of how it would impact my career. It was frustrating to encounter so many obstacles along the way. It requires patience to work in such conditions. Change takes time. People are unaware of their own biases. Leaders are unaware of cultural complications. Women, generally, have to put in more time than their male counterparts to achieve the same end. None of this is right. However, it is true, and understanding that will help women to thrive and succeed in male-dominated industries.
4. Determination — Notwithstanding the above, it’s also important to keep your drive. It requires a certain amount of dogged ferocity to push yourself forward in a male-dominated industry. Do not back down.
5. Know-How — Finally, it’s important to feel like you’re the smartest person in the room. Some of this will come with experience. Until then, ask questions, do research, and find out everything you can about a subject. That will make you feel confident in situations where you’re surrounded by people who are subconsciously challenging your credibility. Again, it’s not fair to expect women to know more than their male counterparts to gain the same amount of respect. However, one would be naïve not to expect it.

If you had a close woman friend who came to you with a choice of entering a field that is male-dominated or female-dominated, what would you advise her? Would you advise a woman friend to start a career in a field or industry that’s traditionally been mostly men? Can you explain what you mean?

I would advise any woman who wanted to enter a male-dominated field to do just that. To quote Justice Ruth Bader Ginsburg, “Women belong in all places where decisions are being made.” It is worth the challenges to be a part of affecting change. The female perspective is valuable, and it will make the world a better place to have more women involved in male-dominated industries. Aside from that, no woman should let the narrative of sexism determine their career path.

Have you seen things change for women working in male-dominated industries, over the past ten years? How do you anticipate that it might improve in the future? Can you please explain what you mean?

It is exciting for me to see more women involved in the tech industry. In my experience, I have always been the only woman on my team, and I think this is changing. However, I do not think that the intolerance of sexism in the workplace has improved. Sexism is pervasive in our society. Both men and women openly participate in perpetuating the stereotypes and expectations laid upon women. With the political and social schism of our time, we’re slipping backwards in many regards. It’s such a deep part of our history, I am not optimistic that we’ll be able to counteract those slippages with large strides forward in a short time. We should not put the social change on the shoulders of women. However, as more and more women break themselves free from taking on the extra pressures associated with their sex, we will see change.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

The person whom I would most like to meet is Kathleen King. I am fascinated by her story of success with Tate’s Cookies after surviving a business catastrophe. I have so many questions for her about specific decisions that she made in her second act.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.