Stellar Women co-host Mary Rechtoris and I were lucky enough to sit down with Relativity’s chief security officer, Amanda Fennell, for this episode of Stellar Women. The interview comes on the heels of Amanda’s most recent ISE North America’s People’s Choice Award win.
This episode follows Amanda’s unique career path to becoming CSO at Relativity and uncovers what makes for a successful remote employee and leader. Amanda also highlights how bringing your whole self is the most valuable asset you can bring to your team.
Chief Security Officer
Mary Rechtoris: Hey Stellar Women fans. I'm your host, Mary Rechtoris.
Mila Taylor: And I'm your co-host, Mila Taylor. Stellar Women shines a light on female leaders making their mark in tech.
MR: For this month, we're really excited to welcome Relativity’s own chief security officer, Amanda Fennell!
MT: Welcome, Amanda!
MR: Amanda, thanks for joining us.
Amanda Fennell: Absolutely. Thanks for having me.
MT: We're so excited to have you and very lucky to get on your calendar. We appreciate the time. Before we jump into questions, a piece of news came across my desk the other day, and I would be remiss if I didn't acknowledge it! I read a headline that Relativity’s CSO, Amanda Fennell, won ISE’s North America People's Choice Award. This award recognizes both information security executives and project teams for outstanding achievements and innovation.
MR: As part of Relativity, we're excited and proud of Amanda for taking home the big W! Amanda, congrats.
AF: Thanks! That is definitely a reflection of the fact that we have an amazing marketing team making sure that the information was constantly out there. And, it was a reflection of the team. So, I'm pretty excited.
MR: Awesome. Can you tell us a little bit about the award and what the award meant for you?
AF: Security is a small industry so People's Choice Awards can sometimes feel like it's a popularity contest. I think that I love people so much that, that could be part of it. The biggest thing is that we were a visible team in the industry. I think that it's not normal for such a small team or a small company to be so noticeable. [We were] smaller than the companies that we were up against. We were up against companies that have 350,000 employees and many of these are Fortune 50 companies. The award is a sign that we are on the scene and that we're doing something that's visible. I might be there, but I'm really just the person that's in the middle of the team picture. It's not about just me; it's really about the fact that we're very present in the industry.
MT: Cool. It’s great to see where the team is now, but if we take a step back, could you talk us through your path to becoming CSO at Relativity?
AF: Yeah, this is a winding path but I'm going to make it short because I think some people have heard this in some form or fashion, especially at Relativity. We talk about this a lot in our Relativity women's groups. Originally, I was an archaeologist, and you know, like all archaeologists, I went into security. It turned out that archaeology was a little more cutthroat than I was expecting. It's not really my style to have to beg for money all the time. Ironically, as an executive, that is what you do. You're definitely trying to get budget, but it wasn't my scene in that regard. So, I looked for where I could do forensics and I could also do something with job security. At the time, this was becoming a really interesting industry. Where e-discovery was really starting to take off, forensics and digital investigations were really starting to take off. So, I moved my master's program from paleoanthropology into digital investigations. Totally simple. Everyone should know that's how you go about it. I went that route and then it was it was kind of a straight line after that. I got recruited really quickly because it wasn't a common thing to have a formal education in this industry 10-15 years ago. I got recruited and did a lot of government contracting with all the agencies and the letters and the acronyms that we're used to. Then I did work with Symantec and worked with a lot of the Fortune 500 companies managing their security. Then, in a roundabout way I ended up at Zurich, which is right outside of Chicago. I have ironically worked from Chicago for five or six years now. I don't know why, but that is why my Twitter handle is @Chi_from_afar. It's a homonym—I’m not that shy, but I'm constantly going to and from Chicago. Zurich was a really short stint. When I was there, I was excited to finally get to put things into place, such as the things that I had learned and mistakes I'd seen people making along the way. I finally had a position where I could do that and I could enact some change. Within about eight months of being there, Andrew Sieja came calling. Ironically, the first time I talked to him, somebody who was a mutual friend of ours said, “Can you talk to this guy at Relativity for me?” And I said, “Sure, I'll talk to him.” I had heard of Relativity. There's very few people in any investigation backgrounds that haven't and so I had heard of Relativity. When Andrew first started talking to me about the product, I was like, “No, no, I know what your product is and does. If you want to sell to me, I have 56 business units and legal teams that you're going to have to talk to. This is not going to work.” And his response was, “Oh, I don't want to sell it to you. I want you to work for me.” My response was the typical: “I'm not a jumper, I don't want to leave my job after just eight months. I have a lot of work to do here at Zurich.” And his response was, “Why don't you just come in and just talk to some people? No commitments.” I am super reticent, but I did. I came in and I met with a lot of people intermittently throughout the teams. I was blown away that—and this is going to sound almost egotistical, but it's not—I was shocked that in every room I was in, there were people smarter than me. I just was shocked and blown away. When you feel like you're a reasonably intelligent person, that's an attractive thing. You want to be around that because that's a growth area. I looked at all these things, and I thought, “Oh my God, I would love to be working with these people every day so that I could learn more and I can grow from it.” And that is how the love affair with Relativity started for me.
MR: Amanda, where are you working from?
AF: Today I'm at home in Princeton, New Jersey. Originally when I was starting at Relativity, I lived in Buffalo. Now I'm in New Jersey and we are moving to New Orleans in a couple months.
MR: I just got back from New Orleans this past week.
AF: I am excited. When it first came up that New Orleans was where we'd be moving, I thought: “Hey, that's a really weird town and they like to party. I think that's a good fit for me!”
MR: Definitely. Being the leader of the security team, how do you lead that team from afar?
AF: I got asked that question during the interview process. A lot of the people at Relativity would ask me “How do you plan to do this?” At the time, there really weren't a lot of remote leaders, and there certainly weren't any remote executives. I didn't have the best tangible answer. But, what I can tell you is that remote leaders tend to be very people-focused. Over the years, you tend to pick up your tips and tricks for how to be very present for your team, even when you are not there. I've probably worked remotely 15 years now in this industry from whatever job I was at. I've always been remote. I've learned some things that you do in terms of having a consistent cadence with your direct reports and complete accessibility on all of the channels that work best for them. Some people prefer texting, some prefer Slack, etc. [It’s about being] accommodating and being really being people-focused whenever I'm talking with any of the people on the team. I just actually ended a skip level with somebody. I do one-on-ones with every single person on our team, and there are 55 people. So, I rotate a lot. It's about being really engaged and present. More than anything, it's being super focused so that you know how the employee experience is going for them. It's not just about the deliverable. It's not just about what you're doing for me or for the team. It's about how your experience is here. When I consider leadership, I'm very focused on the servant leadership idea. I almost feel like I'm elected into the position and I'm hoping that I'm lucky enough to be here for another year. I think that's the biggest difference for a lot of remote people: you have to be super focused on just the people. The process and the technology can come and go, but the people have to be really happy and engaged.
MR: A big part of this podcast is elevating women in legal tech, which are predominantly very male industries. Mila and I did a little research about what the security landscape is like and I found a study from Executive Women's Forum that found 11 percent of cybersecurity workers across the globe are women. Being a female leader in this space, why do you think it is important that the field is diverse?
AF: Diversity has been a really big topic for a few years now and it's getting more and more in the news. I think that people are losing sight of what the purpose of it was. The terminology has become so common that it's kind of like world peace. When somebody says “world peace,” you don't actually think about the fact that world peace would be some amazing thing and let's talk about it. Diversity is the same way; we've lost the value of the word. We're not focusing on what diversity and inclusion means. I believe that behind all of this, it's just a proven fact with the data, that you will have more success as a team whenever you have different inputs and thoughts that people are bringing to the table to try to solve complex problems. I don't think it's just women. There are a number of different areas that you could focus on. I'm very focused that every single person has something diverse about them. For me in security, I needed some people on my team that had a government background. So, I needed some veterans with a process-oriented background. That more militant government style of thinking is awesome in cybersecurity. So, I needed that and that was diversity. We had a team of all people that were really focused on application security. So, I needed government people, or I needed somebody who had zero experience but was a fresh set of eyes. They had just completed their education. Diversity brings a lot of help to complex problem-solving—being innovative and outside the box. If you have everybody that thinks the same, you're going to end up with the same resolutions you've always had and obviously that's not working.
MR: I think that's super important. Diversity, of course, is gender, ethnicity, religion, all that stuff—but it also is background. If everyone comes from the same work experience or industry, you're all going to have the same solutions to a problem, which is not always effective.
AF: I think that is one thing people miss. The area I focus on more than anything is probably socioeconomic and it's from my own experience. I come from a background with very little money, and I had no exposure to technology at an early age. When Relativity launched Relativity Fellows, I jumped right in, and asked, “How do I get involved? What can I do?” I've already been working with Year Up for a long time, but I'm really focused on getting technology into the hands of people earlier. I want to give them work experience that they wouldn't normally be able to get because of socioeconomic reasons.
MR: Amanda for our listeners who may not be aware—what is Relativity Fellows? Mike Gamson talked about it at Relativity Fest earlier this year.
AF: This is a program that will allow us to get more exposure and involvement for people that wouldn’t normally have opportunities. In the legal tech industry, we want to bring people in who are from backgrounds that wouldn't normally have exposure or experience to something like Relativity. We're trying to give them this opportunity and make sure that they would be placed into a job at the end of their internship with us.
MT: Question on the tangent of diversity. This is kind of off topic, but I'm currently reading a book by Ali Wong, the stand-up comedian. She says that she always gets asked the question: “What's it like to be an Asian American woman in stand-up comedy?” She hates the question because she hates being bound to an Asian American and a woman because she feels like she's so much more than just those things. At the same time, she feels this responsibility to represent Asian Americans and females in stand-up comedy. I wanted to get your thoughts because we're asking a lot of female-centric questions. Does that question invigorate or excite you? Where do you fall on that?
AF: That's amazing that you would ask that question. That is exactly how I feel. Exactly. I feel an obligation to hold the mantle and make sure that I'm using my role for something that's helpful, especially for my fellow women in this industry. There are so many times in an interview that I always get talked about or asked about this. It makes me feel like people devalue the fact that I'm good at my job. I'm not in my job because I'm a woman. I'm in my job because I'm good at it. Sometimes my identity gets a little bit messy because I'm a chief security officer. Yes, I'm female, but I'm a CSO. That's my identity. So that's part one. I agree and I love that idea from her. That’s exactly how I feel. The second part about it is this obligation of wanting to do something. Like I said, it's not just about being female. It's about being there for people and underprivileged youth. It's being there for people who can't get their foot in the door. I have a lot of compassion for a lot of different areas based on my life experience, but also just in general. I think that that's a cool way to look at it.
MT: Yeah, I actually just read it last night and thought that would be an interesting question. Another big area of the podcast we like to talk about is mentorship, because Mary and I have both had really positive experiences with mentors. We've been really lucky in the industry. Can you tell us a bit about your experience either being a mentor or mentee?
AF: This is a topic that also comes up a lot, and I have not the normal answer with this. I didn't have any really strong mentor in the industry. When I was first getting involved, I certainly had people who were a little bit like allies and people who I worked closely with. It was more so the people you work super close with over time and you become a high functioning team and you move on in your careers and you stay in touch. But, they weren't mentors, and I wasn't a mentor to someone else. In more recent years, I've definitely been focusing a lot on sponsorship as opposed to a mentor-mentee relationship. There's a reticence for a lot of women, or anyone to ask someone to be a mentor. There's this weird vacuum that happens at this level of leadership that everyone assumes that you're completely busy and that you have no time on your calendar so you would just say no. So, people don't ask. As you can definitely have referenced from your statistics, women don't like to ask. They don't want to bother anybody, so I don't actually get asked a lot. Aside from maybe two times in my career, I have never had someone outrightly say: “Could you be my legitimate/outright mentor?” The answer is always yes, of course. I will always make time for somebody who has a growth mindset. But there is a caveat. I always caveat this. There are a lot of questions we get asked about being a woman in cybersecurity and so on. All I can tell you is that my experience is not the same as everyone else's. I can tell you what works for me, but it might not and most probably won't work for you. I don't suffer from not speaking up. I'm always very vocal whenever I feel like I have something to say. I don't suffer from a shortage of confidence when I feel like I know the topic. These are areas that some women struggle with a lot and I don't. For the mentor and mentee relationship, I believe you must own where your strengths are and my strength is in sponsorship and being an ally. I am really good at advocating for people to get an opportunity and I believe that people should be put in positions where they can stretch their wings and fly. The worst they can do is fail. But you know, it's like Rocky: It's not about how hard you can hit. It's about how hard you can get hit and still get up and keep going.
MR: Cool. Amanda, I have a question because I feel the same as you. I'm very vocal and loud and confident and I've talked to other women in the industry. Maybe you haven't experienced this, but I think sometimes those qualities can be not perceived as positively as if a male had those qualities. Or, it’s perceived that you're being too pushy or too direct. Have you ever dealt with that throughout your career?
AF: Yes. So, I spent the first half of my career not talking because I wanted to learn. I didn't know what to talk about so I would just sit there and write down things in my notebook that I didn't understand that people were talking about. I spent the beginning five years just being quiet. Then I started speaking up later, and especially when you're in a position of leadership, you're required to speak. That's why you're there. You should be giving input. I do believe that diversity is super valued at Relativity, and they asked me to speak because they want my opinion and I definitely have a different opinion from most of the people in the room. I know that there's a negative connotation for women that speak up and are confident. It's super easy for people to use terminology like arrogant or braggadocious, but if a man was like that then it would be accepted. That's true. But I just don't care. I can't be anything other than who I am and that's all I bring to the table. I've been very lucky that I've been appreciated for that over the years. Relativity is literally the most appreciation I've ever felt for being who I am. When Andrew Sieja said he was leaving for his time off at Relativity Fest, I teared up at the party. I said “I’m going to miss you bud. I feel like you're my ally in that room for crazy.” That’s how we are and normally I'll say something that's so off the spectrum and Andrew will just sit there and nod his head around and smile and say, “Yeah, Amanda. That's it. Let's do that!” So, when I said I was going to miss that, he said, “Don't stop being that. We really need that. It's great that you speak up the way that you do, and everybody really appreciates it.” That was almost my rally to keep going and be who I am. I've said this before, and I hate to say this in a recording, but I don't think Andrew knows I'm even a female. He legitimately just knows me as his CSO. And, that's it.
MT: That's awesome. It reminds me, I have a lot of close male friends and one of them said to me the other day, “You’re not a girl. You’re just my friend who has long hair.”
MR: In the security field or legal tech in general, Amanda, how can we attract more young talent? Especially from your experience—maybe from underprivileged areas that might not have access to these resources or know about the opportunities in the field?
AF: I think that's something that I look for: for companies to be active with their recruiting. It's about expanding the pool of talent for any of the areas of diversity. It's where I focus the most for security. It's not about hiring somebody because they fit into the box of what you want on your diversity [chart]. It's about getting the best talent in that pool and that's number one, which we do a lot at Relativity. I’ve really enjoyed working with our pool here and the people we put together for HR and recruiting. The next thing is about making institutional changes that are going to benefit diverse employees. I think that for STEM and for security in general, it's not super accessible to a lot of people from an introductory level. It's almost like you're either super knowledgeable about this or you don't have any experience. I think expanding that for that introductory area, which is something like Relativity Fellows, is super important. That's how we know that people could switch to the field; they could get some exposure. So, that would be number two after the talent pool: the introductory area being more accessible. Mentorship is big. But like I said, I think sponsorship availability and probably having some kind of formula there where people have some structure where this is an actual known thing is important. Then the last part, which is my favorite thing, is knowing the employee experience and being really aware of their background so your employees can be successful. I'm going to be cliché, and say, yeah, I'm a mom. I needed my work environment to be understanding of the fact that being a mother was a part of my identity and I needed the work environment to work with that. I think that the more we do that, the more we will bring in the talent, and will bring in a different diverse pool of talent in there that will enjoy the employee experience and then you have success.
MR: I think a lot of workplaces are doing that to retain top talent. People need flexible hours, whether they're a mom or if they have a sick parent or something. It’s about just knowing people will get their work done and do it well but they might need more flexibility. I think that's huge right now.
AF: I just got this question asked on Slack from somebody who recently was going to start working very remotely. She was asking how often I travel. And I told her, “Let me give you advice that I give everyone on my team. It is your job as an employee at Relativity to create the best experience for yourself. If you are good at what you do, then you will have the ability to control your experience. If you deliver and you are a rockstar, then you are the one who says I am only traveling once a month. This is what works for my family and this is what works best. If you're not great at your job, you're going to have some performance improvement plan coming, and there'll be some issues. You can't take advantage of this, but it is something that I think that people need to acknowledge. The onus is on you as an employee to say and communicate. Those one-on-ones are not for nothing; they’re for communication. Let’s have the best experience, but you have to say what good is for you.”
MR: I love that. Amanda, thanks so much for joining us today—it’s been really great having you.
MT: Thank you so much.
AF: Thanks so much for having me. This has been a lot of fun.
MR: For Stellar Woman, I'm Mary Rechtoris.
MT: I'm Mila Taylor.
Both: Signing off.