Deanna Sheridan | General Counsel, Vice President, & Corporate Secretary at Spartan Race

Authentic Leadership | Psychological Safety | COVID Benefits | Unconventional Path to GC | Best Career Decision | Nimble as a GC | Girls Rock Boston | ONCE | Dance Parties


I interviewed Deanna Sheridan | General Counsel, Vice President, & Corporate Secretary of Spartan Race on Friday, February 5th, 2021.

We started the episode with Deanna sharing how she began to focus on diversity, equity, & inclusion initiatives at Spartan along with how COVID created opportunities for DE&I.  We discussed the Tough Mudder acquisition and the unique integration process that COVID allowed Spartan Race. She shared a personal story of living authentically. She also shared her unconventional path to becoming a GC after beginning as a paralegal. She shared about speaking the language of a business leader and what she’s learned through coaching and through working with Spartan’s Founder CEO, Joe de Sena. She shared Spartan Race’s origin story and how it’s evolved over the last 10-20 years. And we ended with her sharing some passion projects of hers and the books she’s currently reading.

Here are some highlights of my interview with Deanna Sheridan:

Inclusion meant allowing psychological safety for everyone to be who they are and be authentic within an organization. That creates a better community and better thought processes for the organization.

We quickly realized as an organization, it’s not enough to have some tokenization with black and brown athletes on our website. It really has to start from the beginning.  

Throughout the course of my career, not intentionally, I had developed this split appearance. I realized I couldn’t speak authentically as a leader within the organization if I wasn’t authentic about who I was in all facets of my life.

The biggest impact on my career at Spartan was hiring a coach. Having Stewart in my corner allowed me to really step into my role as a leader. 

I have my pronouns in my signature block, both at work and on my personal email. It’s a simple way I can signal that I am available to be counsel or guide. 

We need folks that are underrepresented at the table. It’s not just kindness to do this for them, but it makes us all better.

Leadership means someone who can demonstrate through example how to not just live the mission for an organization, but be true to themselves at the same time.

The key interesting factor of being a GC, regardless of where it is, is the variety of work. And it’s an embarrassment of riches at Spartan with the amount of work variety I had. 

Watching kids channel creativity is just pure joy. There’s no emotional baggage that adults pick up along the way in our lives.

Links referred to in this episode:

Deanna Sheridan | LinkedIn Profile

Spartan Race | Website

Erin Sutton | LinkedIn Profile

SHE Summit | Event Website

Tough Mudder | Website

Howrey Law Firm | Wikipedia Site

Winston & Strawn | Firm Website

Ropes & Gray | Firm Website

Hinckley Allen | Firm Website

NORESCO | Company Website

Darren Braham | Former GC of Spartan Race

Joe de Sena | Spartan Race CEO & Founder

Stewart Hirsch | Strategic Relationships | Coaching

Theresa Mackinnon | Former GC of NORESCO

Hugh Merryweather | Former CFO of Spartan Race

DEKA Fit Events | Spartan Race Website

Girls Rock Campaign Boston | Website

ONCE Somerville | Website

Alexandra Carter | Ask for More: 10 Questions to Negotiate Anything

Erik Larson | The Splendid and the Vile: A Saga of Churchill, Family, and Defiance During the Blitz

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Audio Transcription 

***To Download the PDF Transcript, click here*** 

Greetings, friends. This is Chris Batz, your host of The Law Firm Leadership Podcast. In today’s episode, I spoke with the General Counsel of a rather dirty, but athletic business. We discussed being genuine and authentic in leadership, working for a founder and CEO, and creating a psychologically safe culture for underrepresented employees and so much more.

If you haven’t already, please subscribe to this podcast and leave a review on iTunes. We interview corporate defense law firm leaders, partners, general counsel, and legal consultants.

You’re listening to Episode 52 of The Law Firm Leadership Podcast.

Chris:  Welcome to The Law Firm Leadership Podcast. I’m your host, Chris Batz, with The Lion Group.

Today, I have the pleasure of speaking with Deanna Sheridan, General Counsel, Vice President, and Corporate Secretary of Spartan Race in Boston. Deanna joined Spartan Race in 2016 and quickly transitioned to leading the legal team in 2017, as Spartan evolved from a sporting event startup to a global lifestyle brand. Prior to Spartan, Deanna was in-house at NORESCO, one of the largest US energy services construction companies. She was also a corporate and private equity associate at Ropes & Gray. As a key advisor to Spartan’s leadership team, Deanna led the development of the company’s crisis communication protocol and is the executive co-sponsor of the Diversity, Equity & Inclusion committee. She’s also a member of USA 500 Clubs, the Women’s General Counsel Network, the Women’s Bar Association of Massachusetts, and the Massachusetts LGBTQ Bar Association in Women’s and Sports Entertainment. She volunteers with Girls Rock Campaign Boston, a nonprofit that promotes community self-expression and self-confidence building among girls and youth of marginalized genders. Deanna received her law degree from Boston University School of Law and undergrad from Wellesley College.

Welcome, Deanna to The Law Firm Leadership Podcast. It’s great to have you on the show

Deanna: Thanks, Chris. I’m happy to be here. I’m looking forward to our conversation.

Psychological Safety 

Chris: Let’s begin this conversation with your initiatives around diversity, equity, and inclusion.

Deanna: I was really interested in creating some community or affinity groups when I first arrived at Spartan in 2016. Initially, I found that it was really challenging while I was creating space for myself, getting definition around my role, and really was an aspiring leader in the organization to be able to have much influence or impact on that. So, it took me a little while to do more than have some outings for various affinity groups and create a little bit more structure around our diversity and inclusion goals. It was really in 2019 when I attended the SHE Summit in New York, which was organized by Claudia Chan. I was going with a friend and really was excited to attend, but I was blown away by the thought leadership at that conference. It introduced a lot of ideas to me about what diversity and inclusion looked like that I hadn’t thought of before. They’ve become pretty common discussion topics now in 2020 and 2021. At the time, a lot of the ideas around inclusion meant allowing psychological safety for everyone to feel free to be who they are and be authentic within an organization. That creates a better community and better thought processes for the organization. This was really foundational for me and going back to Spartan, I was saying, “Okay, we need to start focusing on what our goals are around this.” So, I with my colleague, Erin Sutton, who’s our VP of People Operations are co-sponsors of the Diversity, Equity, and Inclusion team at Spartan. Unfortunately, we didn’t get a whole lot of momentum initially, but that changed in 2020 when things became a focus for so many companies after the George Floyd murder and the Black Lives Matter protests. It became apparent that every company had to decide for themselves what their goals were and what their mission was around diversity and inclusion. That’s when we were able to really refocus our efforts on creating those goals for the organization and having more of a conversation around that.

Covid created DE&I Opportunities

Chris: Deanna, how did the furloughs and layoffs Spartan was forced to do affect your approach to diversity and inclusion when thinking about re-hiring?

Deanna: To fully, understand, it’s important to share that part of the challenge for us to build those goals organically in 2019, was that we were really, in 1000mph mode at the tail end of that year. We were focusing on how to make 2020 the biggest year ever for Spartan events. When COVID hit, just like so many other organizations across the country and across the world, we had to focus on survival mode for the company. It was crisis containment as we were canceling events and trying to figure out the short-term, the long-term focus on compliance and safety measures, as well as actual day-to-day operations and cash flow concerns. Our revenue took a big hit, because, suddenly, we weren’t operating events anymore. It was the primary focus in Q1 and Q2 of 2020. Unfortunately, we were forced to furlough and lay off so many employees in late 2020. It allowed us to take a look at the organization and acknowledge that it was a terrible place to be in, but it also was the opportunity for us to look at and begin our diversity goals. This is when we actually start from scratch and begin our inclusion goals.  We focus on performance reviews, and how those will be conducted differently, and our hiring practices and how will we conduct those differently. It’s been challenging, just like it would be for any organization, no matter what stage or how big an organization is. When you’re running lean, like we are, it has to be top of mind as one other goal that we’re bringing into the revenue planning, the cash planning, and the other operational objectives.

Diversity Across an Organization 

Chris: Deanna, you mentioned the need for diversity, especially in terms of the Pro Team athletes and even coaches hired by Spartan. Can you speak to the challenge of diversity within a strong athletic organization?

Deanna: The endurance community looks different depending on what the sport is, in terms of both the customers and the pro athletes, as well as the employees and the various organizations. For Spartan, it’s interesting when you look at one of our events with 1000s of people across the United States that are doing this for fun with their friends and family. Then, you compare that with what our coaches might look like, or the folks that we are actually hiring and training to integrate the pillars of what Spartans fitness goals are with their clients as well as our Pro Team athletes. We quickly realized as an organization in July and August of 2020, that it’s not enough to have tokenization with black and brown athletes on our website. It really has to start from the beginning. Similar to our review of our internal processes like hiring, inclusion, performance reviews, we had to review everything that’s customer-facing. So, we examined what the Pro Team looks like, how we were recruiting folks for the Pro Team, and how we were doing the same things at the coach level. It allowed our teams to step back and say, “Okay, maybe we’re not being as proactive as we could be in going out and reaching communities that haven’t heard of us before and recruiting in a way that we’re educating folks on what we do.” Not everybody has the funds or the capacity to go out and run an obstacle course race every weekend. The reality is we’re often looking at athletes from a lot of different athletic and sports backgrounds to become part of the Pro Team. That could be a former triathlete or former CrossFit Pro, but there also might be somebody who’s a Nordic skier, a heavy weightlifter, or in other sports fields. This allows us to take a step back and focus on getting the best athletes. We believe that an obstacle course race (OCR) athlete is incredibly well-rounded out of necessity. It’s not just strength or agility or speed. So, we should be going out and recruiting folks from all different backgrounds, whether it’s a different sports background, different ethnic background, a different religious background, etc.

We were able to put that in play a little bit in October with the Spartan Games. It’s an event that we vetted very thoroughly for COVID procedures. It was a closed set on our CEOs farm in Pittsfield, Vermont and we filmed the vast majority of it. We invited a number of pro athletes to come to the Spartan Games and face off against each other and show what these just incredibly talented and fit athletes look like. It was a great opportunity, in the midst of COVID, to focus on something that was important to us. We wouldn’t have had the time and resources to do this in the midst of a regular race season.

Acquiring & Integrating Tough Mudder

Chris: Deanna, would you share with us the highs and lows of acquiring Tough Mudder?

Deanna: Spartan is a fascinating company and one of the most interesting things that happened to us that wasn’t COVID related was acquiring Tough Mudder in early 2020. For anyone who is familiar with either brand, they were fierce competitors for over 10 years. It was really interesting to contemplate that transaction in late 2019 as we headed into 2020. When we made it a reality, it was really exciting to think about the possibilities of this new expanded brand with the newly expanded staff, and then COVID hit. There were so many challenges across the Spartan business that we had to navigate, and those impacted the Tough Mudder team, even more than they impacted the Spartan team. Their employees had been through a lot of ups and downs in the previous two years with their company’s history. Initially, integration looked really daunting, especially when COVID hit and everybody had to go into containment mode, but without a regular race season, it allowed us to integrate a lot better as a company than we would have otherwise. This is including all the nuts and bolts, systems and processes, sharing of information, and really making sure that our operations were integrated, but also that the people were integrated. If we had been in the thick of race season, with both brands operating in parallel, we would have been very independent. The lack of a race season and our efforts around integration allowed us to become much more interdependent. It was great to see that on a business level. What I loved learning about in the midst of our integration efforts was that their culture as a company was very different from Spartan’s culture. It allowed us to leverage a lot of really great things that they had done over the last year or so. That included their diversity and inclusion efforts, which was miles ahead of where Spartan was. Integrating their goals and actions has been really instructive for our team. The thing that stands out for me the most is they really wanted to make sure they were going back to their core values as a company and community is probably the number one value for Tough Mudder. It’s very important to Spartan as well, but it’s really the defining characteristic of a Tough Mudder event. I haven’t been to one yet, but I really hope I get to go to a Tough Mudder event in 2021. It’s much more of a big celebratory party. They are not timed events like the Spartan events are, so that community aspect was something that they really wanted to make sure carried through in all of their communications, both with their staff and with their customers. They had a team sit down and very carefully and strategically went through the copy on their website and took a look at how they were communicating internally and externally, including imagery. While it seems like it could be deemed low-hanging fruit, it’s a really good example of taking the first step to really be thoughtful about commitments, taking action, and putting those actions into practice. I’m really looking forward to continuing to work on those action items in 2021.

Chris: It’s awesome to hear also about the combination of two companies and you get to see just direct benefit coming from another company’s culture with the direction of where you want to go. 

Deanna: It’s a testament to both companies, cultures, and the leaders of both organizations that they’ve been able to weather so much because Spartan had very different challenges in 2019 than Tough Mudder did before we acquired them. The fact that both companies are still standing and are poised, God willing, with vaccination rollouts and things improving across the globe, to come out on top again is enormous. We’re in an industry that’s been heavily impacted by COVID compared to some other industries, so it’s pretty great that we’re still here. We’ve got this incredible team that’s still willing to roll up sleeves and get back to racing again.

Living Authentically 

Chris: Let’s transition. You shared a story with me that I felt would be really powerful for our listeners in tandem with the initiative that you and Erin are doing at Spartan. I’ll let you take it from here.

Deanna: I have to go back to what I’d like to talk about before I talk about the moment. I’m bisexual and have identified as bisexual since I was 16. There are a lot of discussions about what that means versus pansexual. It comes down to a personal definition. For me, bisexual means someone who is attracted to people of their own gender as well as other genders. For background, I am married to a cisgender straight man. Throughout the course of my career, not intentionally, I had developed this split appearance. With friends and family, I was out and it was a part of my identity that I talked about. I identify as part of the LGBTQ community. In a professional context, it never came up. I never actively avoided it, but there is such a thing as bisexual privilege for those folks that are in a seemingly heterosexual relationship, who can “pass as straight.” I was learning more and more about myself and was learning more about focusing on diversity and inclusion within the organization. I realized I couldn’t speak authentically as a leader within the organization if I wasn’t authentic about who I was in all facets of my life. It was something that I’d been working on in terms of figuring out when the right time would be to address that within the organization and how to come out to other folks that I’ve worked with over the years. During COVID, the conversations within the organization around diversity and inclusion raised the issue. I’d been thinking about this for some time, and we were talking about the company goals one morning in a leadership meeting. It was all of the VPs in the company and our C-suite. Somebody made a comment that we’re already an inclusive company and diverse, especially when you look at our race events with people that come from all over. It was an opportunity for education. On one hand, I struggle with whether I should have personalized it, but I felt like using myself as an anecdote was the perfect way to educate. I said, “Well, that’s actually completely not true. Here’s why I haven’t felt the psychological safety of being free to come out as bisexual within the organization, and inclusivity means creating that space. We have a lot of work to do if I’m on the leadership team and a leader of the organization, and I haven’t felt safe to come out until now. I know it must be much more challenging for other folks that have even less privilege than I do.” 

It was a big moment. It was probably a much bigger moment for me than it was for the organization. You could hear a pin drop afterward, and there was a long silence. Then, someone led into the next subject, and it wasn’t addressed directly on the call.  We dove right back into the conversation. Afterward, I was very happy to get direct communications from at least six or seven of my colleagues saying they were so glad that I could be myself and be authentic. They were really glad that I shared that. That moment allowed me to make a similar statement on LinkedIn, and really be 100% out. LinkedIn was far less scary because the folks that I was seeing on a daily basis in the workplace felt like a much more challenging environment for me than coming out on the internet. It was really the last step for me. It hasn’t really been discussed much since then, but I think that’s okay. It’s really been helpful to feel 100% free to speak authentically, both as myself, as a member of the Spartan community, and as a leader within the organization.

Chris: Deanna, thank you for just being so genuine. It’s a beautiful example of how you embrace your approach to life, which is being genuine. Thank you for sharing that.

Deanna: It was definitely an imperative for me. If I had to do things over, maybe the timing would be different, but I don’t think the message would have been any different. I was ready to have that conversation with everyone, and it’s made a difference for other folks. I have my pronouns in my signature block, both at work and on my personal email. It’s a simple way I can signal that I am available to be counsel or guide. I’m an example of somebody that can lead tough conversations within the organization and outside of the organization. So, I’m happy to be there as a resource for everyone else who struggles with that.

It takes Diversity to Strengthen an Organization

Chris: Deanna, if we had a room full of women and underrepresented attorneys, what advice would you give them right now?

Deanna: There are so many best practices and thought practices that we have to put into place and strategize in order to get influence with slightly less power. It’s so crucial to get that through community. Community is really the only way to be able to make big strides forward. A  perfect practice that comes to mind is the amplification method that the women in Obama’s White House wrote about. They actively agreed with each other and had a social contract where if one woman in a conversation raised an idea or put a thought out there, the other woman would amplify that message.  They would say, “That’s a great point that Charlene makes, we should do X, Y, and Z. She really thought this through so let’s refer to this strategy as we’re putting this together.” It’s unfortunate that it takes that level of strategizing before getting into regular everyday conversations and communications throughout the organization. But it’s so key and so necessary to have those conversations with each other. The key component for anyone within an organization (not just leaders) is recognizing that we should be doing that for anybody that has less privileged than we do. This extends beyond just other women in the organization. It really extends to physical abilities. There are times that within Spartan, for example, we get into conversations where there may be a very strategic sort of maverick approach to solving a problem. We’re just going to dash this out the door and get it done. But there may be a smaller group of people that have a much more thoughtful, collaborative approach to problem-solving. None of them are bad, and none of them are unilaterally good. It takes diversity to really strengthen an organization and recognizing that we need folks that are underrepresented at the table. It’s not just a kindness to do this for them. It makes us all better if we’re engaging in these social contracts with each other in order to bring the underrepresented people to the table.

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The Unconventional Path to GC

Chris: Deanna, would you share your non-linear journey to becoming General Counsel? 

Deanna: If we start from the beginning, that might take a while. I started off as a paralegal, which doesn’t sound so nonlinear. But, wait for it. I began at Howery in Washington, DC, which at the time was Howery and Simon. Many folks may not even know what it is, since it’s been a good decade since it’s been gone. It was a huge antitrust firm back in the 80s, and I thought I had arrived. This was like my first job out of college. I was there for about two years and then switched to a senior paralegal position at Winston & Strawn in the construction litigation practice. The litigation foundation was incredible for the rest of my career, and not just from a substantive perspective, but really understanding the challenges of having to sleep on the floor of your office, or midnight deadlines to get to the printer. For some reason that didn’t scare me away from going to law school. 

Chris: Did you know you were going to go to law school before or after becoming a paralegal?

Deanna: Being a paralegal was a trial run for me. My father was a construction litigator, and he had a very interesting career path where he’d been in the Corps of Engineers and the US Army for 20 years and then went to Catholic University night school for law school, and got his law degree in his 40s. So, I had this fantastic example of, figuring out your own path that doesn’t have to match others’ paths. When I graduated, he was very gung ho for me to go to law school. I thought it sounded interesting, but I wasn’t sure if it was his idea or if it was my idea. So, I thought I’ll do this paralegal thing for a couple of years, make some money, and it’ll look good on my resume for when I go to grad school, even if it’s not law school. In between working for Howery and then Winston & Strawn, I took an unconventional path. When I left Howery, I wasn’t ready to go to law school. I had a strong economics background in undergrad. I decided to go to the University of Heidelberg to get my degree in economics because it’s free there and I spoke German. Once I arrived, I knew I had made a huge mistake. So for one semester, I learned economics, accounting, and financial documents in German. I really missed being in a law firm setting. I missed the level of conversation and the intellectual challenges. I missed the day-to-day, the frenetic deadlines, and all those sorts of things. I quickly made my way back to the US, got a job at Winston & Strawn, and then started studying for the LSAT right away. It was one of the best mistakes I’ve ever made because it allowed me to quickly identify what my real goal was.

Chris: I love that you had to go to Germany for you to realize that.

Deanna: Unfortunately, I spent a lot of what I had made in my job at Howery, but it was great because I felt grounded in my first year of law school. I could see that a lot of my friends and colleagues were struggling, especially those folks that had gone straight through from college to law school. It really helped me crystallize what my career goals were.

Chris: So, you graduate from law school, and you went to a couple of different employers. Give us a really quick jaunt from graduating to Ropes & Gray.

Deanna: Well, Ropes & Gray was part of that nonlinear process at the beginning of my career, and a lot of it was me going to law school at the wrong time because of the impact of the economy at that time. As a paralegal, I gained experience in a regulatory practice and then in a litigation practice. In law school, I couldn’t really identify which path I wanted to take, but I suspected I wanted to do transactional law. In my second and third years, I took all the litigation classes to hedge my bets, and I kept doing really well, much to my chagrin. When I graduated, I thought I would go work for a corporate transactional practice. This was in 2003, and then the dot-com bubble burst. I remember waking up for an exam one morning in December of 2002 and listening to a radio interview with a bunch of lawyers in the Boston area. They were talking about places that had closed their doors, and what poor law students were going to do with the impact the economy had on the legal industry. I was concerned about how I was going to get a corporate job in that environment. Litigation came to the rescue, and I began at Hinckley Allen for about two years, handling one massive arbitration during that time. That was a pivotal experience for me, but it was very clear that I wanted to be in a transactional practice. By the time I got to Ropes, I had paid off a few student loans, but I was in awe of finally arriving. Then, the economy tanked in 2008, and I was laid off as were so many other associates at that time. Thankfully, I was able to really quickly find an in-house position and began at NORESCO in January 2010. That was probably the first time in my entire career where I felt like this is it, in-house is where I belong. My husband couldn’t shut me up. I would come home and just talk and talk about the cool contracts I worked on that day. It was not a linear path by any stretch of the imagination, but I’m a better GC for it at Spartan, especially because of the construction background, the litigation background, and also the transactional practices that I was involved in. It’s all been fantastic expertise for me to fall back on.

Chris: How did your transition to Spartan occur?

Deanna: At the time I started at Spartan, the GC was Darren Braham. Darren and I worked with each other at Ropes as young associates on a lot of the same projects. We kept in touch over the years, and he’d been at Spartan for a few years. I was so jealous because it sounded like so much fun. I’m a runner and I was so fascinated by the race and the concept, and the ability to marry my personal interests. Darren called me when I was coincidentally looking for my next opportunity in 2016. He was looking for an Assistant General Counsel and asked if I was interested. I immediately said yes and went through a whirlwind interview process, including a four-minute interview with Joe de Sena. Then, I was brought aboard.

Best Career Decision Made 

Chris: How do you see yourself as a female legal executive in today’s environment?

Deanna: it’s hard for me to articulate how being a woman impacts it. I’ve always been a woman and I’ve always identified as a woman. My journey has allowed me to really identify how to create my own education for myself as a leader. My interests in diversity and inclusion, specifically, really highlighted what is important for me to become the leader that I’ve always wanted to become. Going to the SHE Summit and absorbing information on what it means to use my influence in a particular organization was pivotal for me. Whether I’m a volunteer within a nonprofit organization or within my role at Spartan, I think about what I can do in order to provide better counsel and be a resource.  I don’t know if I would have arrived at the same conclusions if I wasn’t a woman, but because of my identity and my past experiences, that has been huge. The biggest impact on my career at Spartan was hiring a coach. When I was up for the GC position, it was a pretty drawn-out process and interviewing cycle. There were some questions that were openly discussed about if I had the executive presence or leadership skills necessary to really step up into the role. I thought I did, but I didn’t know how to work on them or articulate them. So, I hired a coach, Stewart Hirsch from Strategic Relationships, and it was one of the best professional decisions I’ve ever made. He’s not only my coach but now he’s become a very dear friend and collaborator. Through working with Stewart, I was able to identify my communication challenges, my strengths, and what I bring to the table. That has allowed me to really step into my role as a leader and I don’t think I would have been able to identify all of those with the speed that I was able to if I hadn’t had Stewart in my corner. I’ve had so many other folks that have been really influential for me and have been there as sponsors and mentors to me and I like to think of it as building a personal board of directors. It’s a group of people in my life that I go to for advice. Every person who steps into the GC role has the substantive law under their belt already at that point, otherwise, they wouldn’t be there. When I got the GC position at Spartan, it highlighted the fact that this was the first time in my career that I wasn’t reporting to an attorney. I didn’t speak the same language anymore, but I thought I did. Joe de Sena, our CEO, is the face of the brand. He lives the brand. He’s fast, he’s intense. He moves at a million miles an hour, and if you don’t get to the point in 30 seconds, you’ve lost him. I would start in with the analysis on something, and it was apparent that I’d lost him as my audience. I had to consciously focus on building my skill of communication as a leader. I had to start with the conclusion and then go into the analysis if he wants to hear about it, but probably not. Little things like that add up over time.

Chris: Any other mentors you have a shout-out for who have influenced your leadership?

Deanna: Oh, so many people. Theresa Mackinnon was instrumental. She is the former General Counsel of NORESCO who went to Carrier Corporation, the parent corporation at the time, and is now at Otis Elevators. She was a huge influence on me. Hugh Merryweather, the former CFO of Spartan Race, and I still stay in touch and he was really helpful for me in that transition period between Assistant General Counsel and General Counsel at Spartan.

Being True to Yourself

Chris: Deanna, how do you define leadership?

Deanna: Leadership means someone who can demonstrate through example how to not just live the mission for an organization, but be true to themselves at the same time. To be able to articulate it and break that down and bring other folks along and try to meet them where they’re at is also a part of it. This whole journey at Spartan for the last four and a half years has allowed me to see more and more clearly how to do that on a daily basis. The flavor is a little bit different for each organization and each individual but I think those are the key components. 

Becoming Nimble as a GC 

Chris: How has working for Joe de Sena, the CEO of Spartan, made you a better attorney and executive?

Deanna: I’ll start by confirming the underlying assumption. Joe has challenged me incredibly, in ways that I would not have been challenged if I was working for somebody that was more similar to me. I move a lot faster now and I don’t get caught up in the analysis nearly as much as I used to. Some of that is organic growth for a lot of leaders as they move into a legal executive position, but working with Joe sped up that process a lot for me. I mentioned the previous anecdote about learning how to communicate more succinctly with him and really drive with identifying the solution first and caring less about demonstrating the analysis. It’s helped in other ways as well, where I can hone in on what the underlying concern is better, or ask questions, if I don’t know, as opposed to assuming. Coming from a Big Law background, there are times that as young associates, you get this nice, neat package, and it’s very academic. You solve a problem, or you offer solutions and then they get sent off to the client, and you never see them again. It’s so different when you’re in the trenches with the business, especially when you’re communicating on a day-to-day basis with the C-suite. There have been so many times where he and I absolutely do not agree on a solution or an outcome for something. I’ve learned to recognize when I really want to stand my ground and speak up with why I don’t think this is the best decision for the business. But, he’s the founder, CEO, and the majority shareholder so, ultimately, it is his decision. Recognizing that has allowed me to become a better attorney because previously I was so tuned into the hypotheticals, the what-ifs, and the risks. When I first took the position I wasn’t taking a step back to think about what he wanted or what he needed out of the conversation. He has a strong personality, and because he moves fast and wants the organization to move twice as fast, that’s allowed me to become more nimble.

Spartan’s Origin Story

Chris: Deanna, so we’re going to do this a little bit backward, but would you explain to my listeners a little history of Spartan Race? 

Deanna: About 20 years ago, Joe started various endurance events on his farm, and that was the kernel that Spartan Race was born out of. One that’s pretty infamous is called the Death Race. The Death Race is this absolutely brutal endurance event and you don’t know when it ends. It’s Joe having unlimited reign to tell participants to do whatever he wants to do for days on end, and see how they hold up. I’m really glad that it evolved into Spartan Race. Spartan Race was a way for Joe to identify while there were folks that were nuts enough to sign up for torture and loved it, for most human beings it was scary. So they decided to figure out a way to scale it down and create something that allows people to challenge themselves, push themselves forward, get a little gritty, and get in touch with themselves in a way that they probably don’t feel on a daily basis. But they had to make it doable and make it scalable where someone can train for a month and still be able to do it. That’s how Spartan Race was born in 2010 in Vermont on Joe’s farm and it grew from there.

The Spartan Community & Lifestyle 

Chris: You guys are a lot more than a race now, correct?

Deanna: Yeah, we’re so much more. It was really focused on the obstacle course race events through about 2016. When I arrived, we were starting to build out other products and services at that time. It’s been rapid-fire since then. Initially, the growth was focused on territory and finding third-party partners and other countries to operate on a franchise basis. We’re currently in more than 43 countries now which is amazing. Before COVID hit, we had about 250 events a year around the globe, so there was a race happening every single weekend somewhere in the world. Which is really exciting, but also exhausting. 

It’s really become a lifestyle and a community for so many of our fans and customers that we’ve had to focus on how to help someone identify as a Spartan 365 days a year. We do that with training, nutritional products, and supplements and with additional events like Spartan Trail, which is trail running or mountain biking. We have a race product called DEKA and DEKA Fit events are held at gyms and it’s almost like an indoor decathlon where you’re doing circuits of groups of exercises. It allows different types of consumers to access the brand in other ways and is for the folks that aren’t only interested in obstacle course racing. I often feel like I’m the GC of five different companies because we’re also focused on media opportunities. We have an incredible media team that does a lot of our own content. We have nutritional products, training services, and we’re launching a membership program soon. The key interesting factor of being a GC, regardless of where it is, is the variety of work. And it’s an embarrassment of riches at Spartan with so much variety. 

Girls Rock Campaign Boston

Chris: Deanna, let’s pivot and talk about your side hobbies or personal passions.

Deanna: Community is probably the strongest pillar that combines all of my interests. It’s what attracted me to Spartan because of this sense of community among the customers at the events as well as online, and it’s definitely why my other interests lie where they do. Girls Rock Campaign Boston is a nonprofit organization in the Boston area that I’ve been involved with for 10 years now. It’s an incredible organization. The focus is on community building and self-esteem building for girls and those of marginalized genders. The leaders of the organization do it by teaching rock music. The kids show up on day one and they don’t necessarily need to know anything about music or about the instrument that they’re about to learn. They get instrument instruction and a band coach, they form a band with other kids, and then they practice a song or they write their own song. By the end of the week, they perform it for their family and friends. The transformational process is the magic for that organization. You watch so many kids go from shy and a little unsure of themselves to rocking out onstage only one week later which is incredible.

Chris: I can’t imagine the stories that come out of that.

Deanna: Yeah, it’s really cool. Adults get involved, too. There are two kinds of volunteers. There are those that are repeat volunteers that just come back over and over again every year, and then there’s an adult workshop, as well as the ladies rock camp that helps fund the girls’ camp sessions. The organization is able to give sponsorships and scholarships to kids that otherwise wouldn’t be able to go. And for us adults that get involved, we can fulfill those childhood dreams of performing on stage with a rock band if we’ve never had that opportunity before.

ONCE & Boston’s Music Scene

Chris: Tell us about ONCE.

Deanna: ONCE is a for-profit organization that is also very community-focused here in the Boston area. It was founded by a dear friend of mine, JJ Johnson, and it started off as a food and music venue about 10 years ago. The original acronym for ONCE was One Night Culinary Event, and then it evolved from there. It very quickly became a mainstay in the music scene in Boston, specifically because of its sense of community. It’s a very safe and inclusive space. We have a small but very strong music community in Boston. Unfortunately, a lot of the independent music venues have closed over the last 10 years and ONCE became more and more important in the music scene here. I’ve been assisting JJ throughout the COVID pandemic and, unfortunately, ONCE had to close its doors on the physical space in November last year. But we have big plans, and the ONCE community will figure out how to really amplify the sense of community and get independent musicians performing again, both through the virtual venue that they have online right now and then figuring out where the new physical home is going to be.

Reading Recommendations

Chris: Deanna, what are you reading right now?

Deanna: I tend to read a lot of books at once because what I want to read on a Monday night might be different from what I read on Sunday night. Ask for More by Alexandra Carter, Alex Carter, who’s the director of the mediation clinic at Columbia Law School, is so fun. I’m halfway through it right now. I met her at the SHE Summit in 2019. She was a really dynamic speaker and it’s easy to see why her book is so engaging because her personality is so engaging. She really gets to the heart of what you need to bring to the table to have a meaningful and productive negotiation. She made what could be a very dry, academic topic a really fun, engaging, and thoughtful read. I’m about halfway through it and I’ll be sad when it’s over. I’ll probably reread it. Another book I haven’t started yet is The Splendid and the Vile by Erik Larson. For folks who know Erik Larson, he does a lot of historical lookbacks where he takes two different stories in history and sort of does this parallel path of describing certain events. This is all about Winston Churchill, so I can’t wait to get into that one. I’ll probably start it this weekend.

Dance Parties during COVID

Chris: Deanna, what makes your heart come alive?

Deanna: What makes my heart come alive? Little kids dancing. That’s part of the reason I love the Girls Rock campaign so much. Watching kids channel creativity is just pure joy. There’s no emotional baggage that adults pick up along the way in our lives. It’s not there, so kids dancing, singing, making music, or enjoying music is just one of the best things about being a human being. That’s probably one of the most fun things I enjoy with my son. He’s five and we have a lot of family dance parties in the living room, especially right now during COVID.

Chris: Deanna, it’s been an honor and a pleasure. Thank you for your time today.

Deanna: This has been really fun. Thanks so much for having me.

Thank you to everyone who listened to this episode of the law firm leadership podcast.

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