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Female Founders: Brittany Greenfield of Wabbi On The Five Things You Need To Thrive & Succeed As A Woman Founder

An Interview With Candice Georgiadis

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Brittany Greenfield.

Brittany Greenfield is the founder and CEO of Wabbi, which was recently recognized as a 2021 RSA Innovation Sandbox finalist. Wabbi’s Secure DevOps platform enables application security programs to scale across Development teams, to deliver more secure code without sacrificing agility or velocity. From startups to large companies, Brittany realized early on in her career that cyber is fundamental to a modern business’ success. Brittany is a passionate leader who believes DE&I is an unquestionable must-have for today’s businesses. She is also a Member of the Board of Trustees for the Massachusetts Technology Leadership Council (MassTLC), where she works to make the tech industry accessible to individuals from underrepresented communities. As a woman leading the cybersecurity industry forward, Brittany is committed to paving the way for future generations to follow in her footsteps.

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 “backstory”? What led you to this particular career path?

I imagine my path isn’t much different from many other founders. I’ve always been a “path-less-taken” person, having designed my own major at Duke where I looked at how technology drives innovation in legacy industries (at the time I looked specifically at Biotech and Pharma). I took the same approach when I entered the workforce in “The Cloud” at a time when I had to explain to my friends I was not working for The Weather Service. This has carried through my career, as I started in technical implementation roles, before moving into the GTM side of the business with a focus (not surprisingly) on exploring new markets and coming up with plans to tackle them.

As one investor recently pointed out to me, I shouldn’t be surprised that I became a founder as I’ve been identifying problems and coming up with solutions my entire career! Founding Wabbi was really just an extension of what I’ve always done.

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

At a startup, everything is interesting! But the last two years in particular have been the most interesting as we’ve all had to adapt and change amidst a global pandemic. Good and bad, what you learn from a situation and how you grow from it is what matters most.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Becoming a founder is the only career path you take to fail 99% of the time. Whether you’re just starting out or you’re a seasoned veteran, you can’t get hung up on mistakes, all you can do is learn from them and laugh along the way. Especially starting out, you need to admit that you won’t know what you’re doing all the time. If you’re not making mistakes, you’re doing something wrong! You can’t work in a vacuum and avoid all of the potential risks, you must take chances and surround yourself with people who will learn alongside you. I’m a big believer in post mortems to discuss what we’ve done well and what we could have done better, so that we’re constantly learning and improving.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

A general lesson I’ve learned as a founder is to not be afraid of being vulnerable. I heard this bit of wisdom from two people early on, and while I initially disregarded it, it’s been immensely impactful in my development. Vulnerability is about opening up so you can leverage the people you surround yourself with. Nobody is looking for anything in return — if you’ve surrounded yourself with the right people, they’re doing it because somebody once did it for them.

Most days as a founder are difficult and you’ll need someone to talk to who has your interest and your company’s interest at heart. One of Wabbi’s first investors once said to me “I don’t know what has possessed you, but I’m infected with it!” and he’s been one of my greatest supporters. Especially in the last year, it’s important to not be afraid to lean on those that you’ve brought

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

This data frustrates me. There isn’t anything holding women (or other underrepresented groups) back from founding companies — rather there are institutional issues holding them back from succeeding at founding companies. Despite the fact that female founded and led companies are proven to have higher exits and better profitability, in the current environment female founders are facing a losing proposition by starting a company.

The pandemic was exemplary of these conditions as in the face of another record VC funding year, funding in female-founded companies decreased, which demonstrates that we still haven’t fixed the structural issues that increases in female-founder investments had cloaked over the last years. When the numbers and the environment look so discouraging, it’s no wonder women don’t want to found a company. And I don’t blame them.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

This is not just about the dollars to support more female founders, but the institutional and systemic support. We need more investors who are willing to disrupt the status quo. At Wabbi, I’ve been lucky to find these partners, and sometimes it’s also meant saying “No” to the ones that I believed were part of the problem, not the solution.

And investors aren’t just VCs — there are a lot of opportunities out there for funding, we just need to align them with today’s standards. For example, at Wabbi we’ve been awarded a SBIR, which was a great opportunity not just for funding, but also access to a new customer base. That said, the process of applying and continuing is very much based in the world of grants, which most business leaders are not familiar with. This creates a lot of fits and starts that can become distractions for the business. Similarly, while the SBA has a loan program, it is not tailored for the kinds of businesses that require technology investments ahead of revenue, which requires founders to seek out expensive capital from traditional investors early on. If we want to be a country that drives innovation across all groups and industries, we need to make sure there is equal access to the capital to do that across all sources.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

In my point of view, it’s not just about more women becoming founders, but more underrepresented groups becoming founders. There are a lot of problems out there and a lot of perspectives on how to solve them, which requires leadership from a variety of different backgrounds and experiences. We need to avoid a linear path of problem solving and that requires more minority founders. As Albert Einstein said, “We cannot solve our problems with the same thinking we used when we created them.” More diversity means better problem solving.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

Whether reading your morning paper or watching shows like Silicon Valley, the idea of founding a company has become glamorized and deified. I hate to be the bearer of bad news, but it’s not. Being a founder is the hardest work you will ever do, but it can also be the most rewarding.

It’s also not about sitting in a garage head down trying to create the perfect product, but getting out there and talking to people. You have to stay ahead of a lot of moving pieces constantly : market dynamics, what’s top of mind for customers and employees, what could put you out of business. It also means knowing when you need to bring others in to build out your team. You might try, but you can’t do it all yourself and you shouldn’t! Good founders may have swiss army knife capabilities, but great founders know how to hire to fill the gaps.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

“Founder” is an abstract concept. Everyone has the opportunity to be a founder, it doesn’t necessarily have to be a founder of the next unicorn. It’s a mindset, not a specific job: it could be being the founder of an initiative within an existing business or the founder of a local mentoring program. At the end of the day, Founders want to start something new and are willing to take risks. If you don’t want to investigate problems and go through a lot of trial and error to come up with a solution, then being a Founder isn’t for you.

Ok super. 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 Founder?” (Please share a story or example for each.)

  1. You don’t know what you don’t know. People like to talk about a “growth mindset,” which is important, but I think as a founder you need to be thinking with a “lesson mindset.” That is, thinking about what you can learn from every situation, good or bad, to continue improving and growing, and asking for help when you need it.
  2. You can’t do everything. Founders tend to have a knack for being a swiss army knife, but that doesn’t mean you don’t have a specialty. Your time as a founder is the most precious thing you have. Of course at the start, to be capital efficient you need to leverage that special jack-of-all-trades skill, but as you grow the company, hire for your holes so you can keep your time and attention where you can make the biggest impact. This may feel like the scariest and most selfish approach because you think you should do it to save a buck just because you are capable of the task, but it’ll be the biggest ROI of any investment you make.
  3. Work with the people who are going to push you. Sometimes this might mean pushing your buttons, but it’s not malicious. People who push you are going to make you think in different ways and even more importantly, they’re only pushing you because they know you can take it and it’s going to make the company better at the end of the day.
  4. Being a founder is a 24/7 job…but don’t work 24/7. You still have to make time for the things that are important to you, whether it’s a hobby, involvement in your community, or just time with your friends and family. There’s become a glorification that to succeed in a startup, you have to “hustle” every hour of every day. But there are no overnight successes (no matter how it may seem in the media). When it takes on average 7–10 years for a successful exit, you can’t hustle non-stop for that long and be a productive leader. You don’t see top athletes playing their sport day in and day out — they take recovery, sometimes it’s active recovery, sometimes it’s sitting on the couch. If you’re going to be a successful founder, don’t forget to still do you.
  5. Bad news always comes first. Yes, your job is to always be the biggest cheerleader for the company. No, you do not get to have a bad day. This does not mean you need to shroud your bad news in sparkles. Bad news first is not about a glass-half empty mentality, but accepting that this is a tough thing, and knowing that the people who have joined you are working WITH you to make sure there’s more good than bad. It also sets a standard for transparency and normalizes sharing the bad with the good — as a leader, you don’t want to find out on the last day of your quarter that you’re going to miss the number. Lead by example with your investors and employees, and they will reciprocate in kind.

How have you used your success to make the world a better place?

I’m still in the aspirational phase of “how to make the world a better place.” Of course, I know Wabbi has an impact that leaves the world a better place in the realm of cybersecurity and DevOps, but as an individual I often think about how I too will leave a legacy. It was one of the unexpected things that came with being a founder as the more constrained my time became, the more intentional I have become in how I spend it on the activities that would have the greatest impact.

It’s not about being a philanthropist, but rather how I dedicate my time to the communities I believe in. And for me that ranges from my alma mater to The Boston Ballet to the local Tech Community to my Shul. Startups aren’t the only thing that’s going to change the world, individuals are! Continuing to participate in and support the communities that matter to you is a great way founders can help make the world a better place, while building a successful company that will also leave its own mark.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I view wealth creation as a driver of equality. We need to find better ways to support underrepresented entrepreneurs. Wealth creation has been directly tied to not just economic growth, but also significant educational and cultural growth, which are seen as the main drivers of achieving parity. Microloans are an example of a movement that has been able to rapidly and successfully drive these changes abroad — why aren’t we looking at how we can bring these kinds of programs — and their benefits — to our own shores?

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.

Mary Barra. I once read an interview where she mentioned a car is 30,000 parts you’re putting together, and I think a startup is no different. I suspect I’d learn a lot from having a conversation with somebody who manages a team that brings together 30,000 parts 18,000 times a day. And she’s my personal J.Lo.

Thank you so much for sharing these important insights. We wish you continued success and good health!



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Candice Georgiadis

Candice Georgiadis is an active mother of three as well as a designer, founder, social media expert, and philanthropist.