Women’s History Month: HacWare CEO On Becoming A Leader, Blocking Out The Noise

‘I try to turn off all that noise where they’re telling me it’s going to be hard and there’s only a small percentage of women and minorities to have done this. I block out all that noise because I feel there may be some messages there that if I had taken them in, I may believe it and I may not move forward with trying to trailblaze,’ says Tiffany Ricks, CEO of HacWare.

Tiffany Ricks, CEO of HacWare

Tiffany Ricks had no one to look up to in technology when she was in school. No one looked like her, so she didn’t believe a career as a woman in tech was achievable.

“If we have someone that we can look at and say, ‘Well, they have done well at it. If they can do it, then there’s a shot that I can do it.’ … It’s super important for us to have representation,” Ricks told CRN. “For me, it’s important because I didn’t have it. I went into a lot of areas where I was always second guessing myself because I would say, ‘I don’t see any women in this space and I don’t see any Black women in this space. How am I going to be successful here?’”

Ricks, a Black woman, is the founder and CEO of New York-based cybersecurity training vendor HacWare. She comes with more than 15 years of experience in the software development industry and about 10 years of cybersecurity experience. She also has led software teams for one of the largest defense contractors and Fortune 100 companies.

And as a woman, she finds that she’s always having to prove herself.

“I had a call recently, it was with anothercybersecurity company and we were thinking about doing a strategic partnership,” she said. “We spent a lot of time talking about who I am, my background, and it just seemed like I had to spend a lot of time validating why I am here.”

In the 2022 State of the Women Of The Channel survey conducted by CRN parent The Channel Company that included nearly 500 participants, 45 percent of female respondents said that they want to pursue a C-level position and most are women under 30 years of age. It’s a percentage that’s climbed drastically.

“That has gone up over 10 points over time,” said Lisa MacKenzie, founding partner of The Channel Company during the Women Of The Channel 2022 East event in New York City in December. “As long as we’ve been doing this study, that number has been about 30 [pecent] to 35 percent of women wanting to pursue C-level positions.”

Still, only 17 percent of women said there were enough women at the C-level and board positions within their organizations, compared with 46 percent of men surveyed who felt there were enough women in the same positions. But the responsibility of a leadership role is worth the effort, according to 66 percent of female respondents.

“If I can do it, I know for sure there’s so many other women who can get into cybersecurity or be in a leadership position,” Ricks said.

CRN spoke with Ricks about her experience as a woman, and a woman of color, heading a company in the tech industry, how she handles bias and what women can do to help younger generations of women get started in a technology career.

As a woman-owned business in a male-dominated industry, how important is it for you to show women, and women of color, that they can be in a leadership position?

It’s super helpful if we have a picture of what a path looks like. It’s really helpful for us to move into territories that may be a little nontypical. If we have someone that we can look at and say, ‘Well, they have done well at it. If they can do it, then there’s a shot that I can do it.’ … It’s super important for us to have representation. For me, it’s important because I didn’t have it. I went into a lot of areas where I was always second guessing myself because I would say, ‘I don’t see any women in this space and I don’t see any Black women in this space. How am I going to be successful here?’

I made the decision where I put myself out there. I’m an introvert—I would prefer to be behind the scenes or just coding and not really be out there, but I made the conscious decision that I wanted to give people a visual of what they can do in this space. If I can do it, I know for sure there’s so many other women who can get into cybersecurity or be in a leadership position. I am not the standard leader. I embrace that; I try my best to not be the status quo leader. We have enough of those. We need to lead in a way that is authentic to ourselves, which will be authentic to our team … and that will be great for business and the channel in general.

As a woman and a woman of color, have you ever been told ‘No’ in the tech space or that it was going to be harder for you? Have you ever had a setback in this industry because you are a woman?

Absolutely. I think that’s maybe why I am the way that I am. I have been told, at every step of the journey, that it’s going to be hard and it’s going to be challenging. Starting out in college I’ve always been the only one in every room. For projects, many [classmates] didn’t want to work with me because I think there was a perception that, ‘She just isn’t as intelligent as us, or she got here because of affirmative action. She’s really not that good.’

I take that as a challenge to show you that I am really good at my career and I’m a student of my craft. I take it almost as a chip on my shoulder where I know in every area of growth it is not going to be easy. There is going to be a point where I am going to have to prove myself, and that’s just what comes with the territory. I try to learn from previous individuals before me who went down these paths and they had to trailblaze and be trailblazers. I’ve been watching a lot of documentaries and one of the things that I see then, that I kind of see now, is there’s this talk that they tell women entrepreneurs and minority-owned entrepreneurs that it’s going to be very hard for you to grow and scale your company or it’s going to be very hard for you if you want to raise capital.

The way that I think about that is maybe that’s something that you’re trying to tell me so I won’t move forward and tackle this challenge. I try to turn off all that noise where they’re telling me it’s going to be hard and there’s only a small percentage of women and minorities to have done this. I block out all that noise because I feel there may be some messages there that if I had taken them in, I may believe it and I may not move forward with trying to trailblaze. So I look at it as that’s a message, but it’s not for me. I’m not going to receive it. I have a bigger mission of why I’m here and who I’m trying to educate to trailblaze their own path. Sometimes I have to block out the noise, and many women have to block out the noise.

You said you experienced this in college, but do you still experience it today?

Absolutely, they still give me pause. I can tell you where it happens. It happens when you are trying to get access to capital. It’s relationship-based. [When it comes to] your resources, it’s better to have a relationship with them and know them. For me and for many other women and Black people, we aren’t in those circles. It is a challenge and a journey to get into those circles and build those relationships where people will give us access to capital. They just don’t know me and they haven’t invested in any diverse companies before. That is a big hurdle for them to try to jump over and do something new.

The other area where I see a challenge is when we’re doing strategic relationships. HacWare is not just me, we have employees throughout the United States. Many times before a deal comes to me, they’re doing business with my teammates and then I come in at the end. I know sometimes they haven’t done research on who leads HacWare so there’s a little bit of, ‘Oh. Who are you? Are you the CEO?’

I had a call recently, it was with another cybersecurity company and we were thinking about doing a strategic partnership. We spent a lot of time talking about who I am, my background, and it just seemed like I had to spend a lot of time validating why I am here. Before we had the meeting, they met with that majority of my team members and they were excited, they understood the vision. But we spent so much time when I was on the call to understand who I am, what part I play in this company and what my background is. It was a little bit more than just the normal introductions, we spent quite a bit of time, and that was something that was a little bit frustrating. I have to sort of check myself because I don’t know how we’re going to have a strategic relationship if I have to combat your bias, I have to prove that I am a subject matter expert and that I should be on this call. So it’s a little bit of a challenge.

So you have to sell yourself because their bias is at the forefront of their mind. Is that what you're saying?

I think so, and it’s hard for me to try to assume because it’s not blatant. I would prefer that, actually, because I’m very transparent. For me, I can read and understand where we stand if I knew exactly what was going on. It could be that I’m perceiving that because there’s a lot of questions and there’s just a lot of digging. I’m always wondering is this the norm or is this something that is happening because they see that I am a Black woman in tech and this is something that they don’t typically see.

As a woman of color in a leadership position, do you do any outreach to children in STEM or any other programs to show them they can be a leader like you?

Yes, and that is a passion of mine because technology is something that really saved my life. It helped me see differently how people live, see different parts of the world and think in different ways. It really opened me up. I do a lot of teaching. I used to be a part of Black Girls CODE and I was going to after-school programs and teaching young students how coding can be fun, how I got introduced to it through video gaming and how they can take their passion for games and start creating things.

In April we’re doing a hack-a-thon with university students and allowing them to use their educational background to think about how they can solve a problem around phishing, human risks and vulnerability. This gives them the ability to build their confidence and see that they can do these things. That’s a big, big mission of mine—to keep inspiring the young generation to get into tech because there is a huge gap. Many believe that it isn’t for them because in movies they portray people in technology as someone who is awkward and unfriendly and even sometimes borderline psychotic. They portray people in tech in this way where a lot of people are like, ‘I’m not like this. So that’s not the world for me.’

One of the things that I like about myself is that I can relate and nerd out with my friends who are super, super techie, but also my friends who love pop culture. I can relate to them and still be able to be in technology. It’s not this thing that is just for one group. It’s an opportunity for more to get into it.