Being Open and Vulnerable as a CEO
A conversation with Beck Sydow, CEO, StickerGiant
This week I spoke with Beck Sydow, CEO of StickerGiant, a company that prints custom stickers and labels fast. We talked about their career trajectory, how their background as a mindfulness teacher helps them as a leader and what it was like to come out as non-binary while CEO.
This interview has been lightly edited for length and clarity.
We’ve known each other got over a decade. We met just after I moved to Boulder. We met at a job seekers seminar luncheon.
It was a job seekers group that met every week. And, I had been coming and you were there for the first time, and our eyes kind of locked across the room and we were like, "Oh yeah. There’s my friend.”
I don't know if I ever went again.
I think we might have both ditched on that one together and we started having coffee and having our own little group, which was super fun. And to be honest, I've been in some job search groups over the years and, yeah, it's rare to find a kindred spirit there. So I'm glad that we discovered each other all those years ago.
Me too. Before we talk about your journey or your story, can you tell us a little bit about your work background?
I got an early start on my career in college, the summer of my junior year in college. I got a job at UPS and I stayed for over 10 years and had a good career in Virginia. I went from loading tractor-trailers to being in management. Then I took the first UPS buyout, which was in the early '90s. That was a radical thing to do. I had thought I had my whole life planned and I had a retirement plan to stop working at 45 and I could retire from UPS. There's a lot that went into that decision. I really think some people thought my mental health was off at the time, but I took the buyout and I did everything I could do to not work a formal job as long as I could.
I made almost two and a half years. I worked with a paint contractor for a while. Lots of fun stories there. I worked with a landscape contractor. I did a couple of professional contract gigs and then I was like, "Oh gosh, I'm going to have to get back to a career." I landed in transportation again, still in Richmond, Virginia. I had a contact center background and I took a job as the contact center director at Overnight Transportation, which eventually became UPS Freight and stayed there for six and a half years. While I was there, I got a master's degree from George Washington University, in organizational and human development.
I started to have an experience of all of this external success didn't actually feel so successful inside. While I was in graduate school, I started working with a mindful awareness and meditation teacher in Richmond and worked with that teacher for over six years. That was a really, for my career and for me personally, that was a real pivotal decision I made. As more awareness personal came and I ended up leaving Overnight before it transitioned into UPS Freight and left that career to move to Boulder to get a second master's degree in contemplative psychotherapy at Naropa University, which for listeners that don't know is the only Buddhist inspired university in North America. So again, the influence of that teacher and really aligning my inside and my outside played a role in that decision.
I moved myself to Boulder — another really big and radical change - but I didn't know it at the time. I thought I'd be out here for three years and moved back to Richmond. I loved my life there. All my friends told me, pretty quickly they knew I wasn't coming back, which is actually what happened. So after I got out of graduate school which was a three-year program, I set up private practice as a therapist, I worked in public health and mental health to make some money and explore, putting that career together. I pretty quickly figured out that while I chased a dream to become a therapist that just wasn't me. I was complimenting my therapy practice with executive coaching as well, so I could still stay close to the business world. I made another really big shift and decided to go back to the business world.
In 2008, as things were crashing, I got a job in a time-sensitive, time-critical transportation company, and then got laid off after about six months and helping save them about $750,000 in that time. So great experience. From there I worked in a startup with a sustainable, eco-fabric model in the uniform and apparel industry, and that company ran out of money. So I was one of the last two people to help close the company there.
You were closing the door on the company.
Yes. It was literally me and the controller that would show up every day and help with the liquidation and things of that nature. Another job search, I think that's right when we met was when that job had ended. And then through that job search, I ended up in technology here in Colorado, again in Longmont with a company that does technology in the 911 data and telecommunications industry. I was there for five years, then got laid off.
What was your role there?
I was a Director of Operations. And I was in the mobility division. It was a ton of fun. I learned an awful lot. I fell in love with agile methods while I was working there and got really acquainted with something called Open Agile, which is an open-source learning community, and used those approaches on operations teams, which is where agile is not often used, had some great success, just had a ton of fun, learned a lot. Another job search launched. That's when I landed at StickerGiant and now I'm in manufacturing. We are a quick-turn manufacturer of custom promotional stickers and product labels. We're in Longmont, Colorado.
It's so interesting how many industries you've been in and it's probably really encouraging for people who are a little earlier in their career just to hear the shifts and changes you've made and have been able to successfully make throughout your career.
Yeah. And I didn't know that starting out. It's so important to have a plan and work that plan, but to be really flexible, I'm so grateful that I learned how to listen to my insides too, around that connect point. I think culturally, we're really taught to chase all the external validations of our success and how we feel about ourselves. So I tell people often I've retired several times already, I've had some breaks away from the hot, heavy grind of working in a business environment. I'm really attracted to hyper-growth and fast-growth companies and situations. So yeah, I've been able to have some time away and I think that's refreshed me often, whether it was my choice or a company closing or a couple of layoffs that I've had, and I'm so grateful for the journey that has unfolded.
Well, and you bring so much too, into your leadership roles. You started at StickerGiant as the COO. Can you tell us a little bit more about how long you were in the role and where was the company at when you came into it?
Yeah. Toward the end of 2017. When I started at the end of November, I was employee number 47. We are 140 folks now. We refer to each other as Giants. So if I say Giants you'll know what I mean. So that was a little over four years ago. So started as the COO. At that time, our founder was using Entrepreneurial Operating System (EOS) and there's a complimentary book to it called Rocket Fuel. And so I came in as the integrator. So that's how got started.
(NOTE: Like all frameworks, there are upsides and downsides to them. It’s a whole other conversation about EOS/RocketFuel specifically around gaps within DEIB&A and ineffectiveness for scaling fast growth).
How long were you in the COO role and how did the move into CEO come about?
Three years as COO, a little bit more. It was a natural progression over time to CEO. I've been able to leverage my background in technology, and certainly contact centers. We're an eCommerce company. So we do live chat and live phone calls. So a lot of that played in and then just leadership talent, certainly having an Agile background and some Lean background didn't hurt at all. And yeah, that's how we got started. So over time as I got involved in things, as the company continued to grow, which we've grown quite an awful lot, it really was a real natural progression into the CEO role.
There's a lot of perception that the COO is the second in charge and the successor to the CEO. When I was a COO, I was not interested in the CEO job. I think it's a hard job despite the prestige that surrounds it. It’s not something I ever wanted. Were you expecting to become CEO? Was that the understanding?
No, not at all. If someone had told me I'd be COO of a thriving business, a number of years ago, I'd have been like, "Really what?" And if they'd said, "You'll be CEO," I would have been even more sort of like, puppy, dog head turned sideways, like, "Really?" I think it's about following breadcrumbs and paths that are laid out. When I saw the job posted for the COO, I got really interested in it and it was a long interview process even for that, it was around eight months, which we laugh about now. But yeah, I'm just so grateful that the right time, right place happened for me. And that I ended up being a place where I could really use all the depth of my talent and experience. So, all that said, I had no idea I would end up as the CEO, but it was just the way the cards played out.
It was the same for me. I never expected to be a COO. When I was asked, I said, "Me?" I looked around, "Are you talking to me?" I had to think about that. I hadn't perceived myself that way. It's like how we think about our identity and what we're capable of. I had never perceived myself in a C-suite role ever.
Yeah, yeah, yeah. I totally get you, totally get it. Yeah.
So now you're the CEO of StickerGiant. What are some of the biggest challenges you've faced?
Well in the last couple of years, undoubtedly, all leaders are facing what COVID-19 has done. COVID-19 has shined a really bright light on areas in our companies and business that were difficult before and made them even more so. In some ways, it just brought out the more difficult nature of things. Having enough people to keep up with demand, keeping a workforce happy and healthy, all of those things. So certainly that was a pretty big factor the last couple of years, and of course, hyper-growth and scaling a company brings with it, its challenges and opportunities.
So working through that, having a good leadership team, building on the culture that was here, and understanding that when you're growing, your culture is going to need to continue to evolve, which is really hard in some ways. StickerGiant has been around for 20 years. So the evolution of what's happened prior to the last handful of years was all about pivoting to scale, to where we are today. Then also last year we had a change in ownership structure. So just to pile on a little bit more on to the complicated nature of navigating change for this company. It's been an important time to provide leadership.
Were the COO or the CEO roles different than you thought they might be? Were there some things that surprised you or that were different than you thought they might be?
Oh, of course. Yeah. The funny thing is when I took the job in technology (911 data and telecommunications), I accepted that job and had no idea what the job was going to be. It was like that job just fell out of the sky, that was so amazing. I'm just grateful that I had the talent and skill to meet the needs of that role. The same was true here at StickerGiant. I didn't have a real clear idea about the role. I read the book Rocket Fuel before I started. I knew I would be supporting the founder/owner/CEO at the time, but I really had no idea what that looked like.
I think that it goes back to being a mindful awareness and meditation practitioner and how all of that training and the practices are about being able to be in uncomfortable situations and developing the skills needed to navigate uncertainty. So I don't know that I actually needed to know. Taking both those roles were pretty big risks - around the not knowing. Truth is, I didn't really have the traditional qualifications on paper, what might look like all the talent needed, but certainly it all worked out. It all comes back to leadership capabilities over and over.
Leaders face discomfort and ambiguity every day and especially in the last two years. Do you feel like being a mindful awareness meditation teacher has helped you deal with uncertainty and ambiguity easier?
Oh, absolutely. And I think you have to have a lot of good business acumen to be in a role like COO or CEO. But I almost feel like, with every passing day, you have to understand the human condition too. Because it's the compliment of how you're using business acumen and tried and true business philosophies and frameworks to help a company move forward. But it's the people that are doing all that. So having leadership and mindful awareness skillsets, I think, it's more critical now than ever. And it has a lot to do with empathy too. And being able to be compassionate and empathetic, all while at the same time holding people accountable to a role that they've accepted and that we need them to do really well in to help the company continue to thrive. So there's this balancing act. Right?
My experience is that we tend to think of leadership as that business acumen and expertise 80%. I think it’s 50% business acumen and 50% working with humans and the dynamic nature of groups and organizations.
Yeah, I do too. I think the thing that sits between both of them, that relates to both of them, is to have a passion around learning and to be able to learn really quickly. So I came into a uniform and apparel company. I had no background in that. I came into transportation early, I learned a lot, but then I went to time credit transportation, which is something really quite different. And then into manufacturing and technology. But I've always said to folks that I'm working with, "I'm looking to you to influence me and help me learn this business. And along the way, I'm hoping that you learn something from me too."
So having that sense of shared learning. I do learn rather quickly the concepts and the business strategies, but all along the way, my deep wish is that people being around me also are learning things about leadership and organizational design/structure and all of those types of things. So it becomes that connective tissue, if you will, between a leader that might not know the industry or the business that they’ve come into, and in a humble way, that says, "I'm going to have a lot to learn," but in the end, you're actually able to offer a lot at the same time.
I think a lot of times leaders come in and think, "I have to be the expert. I have to know all of the answers. I have to be tough and strong and direct." It's not that you don't need to be those things, but there's so much about being open to learning and growing from your team and from other things. We get stuck in a binary of either you're an expert and you have nothing to learn or you have everything to learn, you're not an expert and have nothing to offer.
Yes. Yes. It's that sense of humility and humbleness of being able to put yourself in situations where you're going to have to trust people around you to get you up to speed quickly, and people are going to be looking at you as the leader. Like, "Are you really going to get us on a path here?"
We encourage leaders to be human and specifically to be vulnerable. But that can feel hard. And I know that you have strived to be your whole self as a CEO and I think that means being vulnerable. Can you tell me what that's been like for you and how you've gone about that?
Yeah. I'll start with this, I'm dyslexic. I'm differently-abled with my neuro connectivity. So lots of years ago when I was early in my career, I used to try to hide that. I wouldn't want to go up and write on a whiteboard because I'm a terrible speller and I would be embarrassed if I misspelled something. Along the way, I started to realize, “Dang, this is going to be hard if I don’t share this, how am I going to handle this?" So I just started telling people I'm dyslexic and I spell weird. So if you sound out what I wrote up here on the whiteboard, you'll figure out what the word is or I'll just say, "Hey, somebody spell this word for me." I did it this morning with my team. I'm like, "Oh my gosh, all these words, somebody spell such and such."
And people are fine. Again, back to mindful awareness and meditation. If you don't have practices that help you stay connected to your experience and navigate when you're anxious or things are difficult, then it can get really hard. I mean, vulnerability without practices to keep a sense of safety for yourself, then you're going to make a lot of mistakes being too vulnerable or oversharing or being overly emotional at work. When people are looking for leaders to be … Well, you just can't fall apart in front of your team. I think there's probably a time for that. But people also need to see you be able to be touched by things but to also speak through your cracky voice. Which I do often. I get so touched by things.
Then the other is really around my gender identity. I'm gender non-binary. I've been in a process around that for the last 10 years. So two summers ago when George Floyd was murdered, we were working here at StickerGiant to put together the beginnings of a DEIB&A initiative. And I was working with our director of people and culture on the kickoff presentation. I was out to her at the time around being gender non-binary. During that time I said, "Oh my goodness, I'm starting to feel inauthentic here." Because I was going to kick this off around how we show up for people that are different from us, but I’m not sharing my difference. And so I think I have to come out to the organization as non-binary. And of course, she was amazing and said, "Of course you are."
How did that feel when you realized that? Were you experiencing inside as you have this realization, "I need to come out as non-binary and I'm a leader?”
Well, I'll go back in time in my '20s, when I started coming out as same-sex attracted and progressing through just being really open and out, even at work around that. Yeah. It was just one of those moments. I don't know if you've had them in your life, I'm sure you have where it was just this very reconciled moment of the truth. And that is a lot easier when you have allies around. So the director of people and culture is a tremendous ally, like yourself, being a tremendous ally to all kinds of underrepresented people. And one of the things at StickerGiant that I love and it certainly attracted me here is, I mean, we do promotional stickers and product labels on the promotional sticker side. We are helping people express their stories and we believe in self-expression. The one self-expression that we don't believe in is hate.
So we actively look to not participate in that, in the products that we make. Hate is really subtle, so that can be challenging. So I felt like I'd found a good place to work where I could come out like that, especially as a leader. I knew I'd found the right place to work when I could wear a hat to work every day, which I do probably four out of five days a week. You'll see me in a hat around here. I picked one of my favorites, Longmont versus everybody for our time together. It felt like the culmination of a lot of inner work I'd done over a long period of time.
So I think there are a couple of notes I want to make. It's important to know that when we talk about vulnerability and leaders start to think they need to be more vulnerable, they need to be ready for that. Vulnerability has become a buzzword of leadership these days. But if you're not well supported, then vulnerability is going to come across as oversharing, too emotional. And it's going to confuse people more than it's going to help them.
I think sometimes people don't have the support and they are overly emotional and it can come off as inauthentic, despite good intentions.
Absolutely. I talk a lot about humility too, but when we're using the words to describe something, rather than looking to internalize it so that it actually comes out in our presence, then we don't need the words anymore. Right? We don't need to say vulnerability and humility and these buzzwords, done well, we actually become it. But we have to have the support, we have to have mentors, we have to have great colleagues. We have to have a team around us that has support too.
And the other thing I wanted to be sure to mention is this, I'm extremely open about talking about my gender non-binary identity and not everyone is. So it's really important. And for your listeners to know we discussed talking about this ahead of time. Just because you know someone or you see someone that might look a certain way, you should absolutely check in with them about if it’s okay to ask questions or let them bring up how they identify first. Don’t assume!
So I'm grateful that I'm at a place in my life where I'm able to be really open about it because it's been really moving for me as I've been more open to hear people come up and share with me how much it means that I am open and out. They'll tell me about an adult kid that is non-binary and I'll help them think about how to be in a good relationship with their adult kid, and listen to how hard it is because they keep making a mistake and referring to their adult kid a son or a daughter - the embarrassment of that. It's like just having the ability to help folks think about new ways to think about - how do we take gender reference out? And then being really kind with people when they make mistakes. My pronouns are they, them. I just changed from they, she, which was super confusing to people, and I also just had just chest affirming surgery.
Once I did that, I was like, “she" really is not fitting for me anymore. So I went to they, them and our brain doesn't work that way. Once neuro networks connect around, he, him, she, her, it's really hard to rewire the brain on something we don't even think about. So I'm glad I can play a role in the world where... This is one way I can help people think differently to pause and really think about how they reference me when they're referring to me. And with a lot of care and kindness, just respond by saying “they” (when I’m mis-gendered), like that as opposed to getting angry and upset. I don't know, I think of the Ram Dass quote, that's quite famous, "We're all just walking each other home."
It just touches me that we're all in this together, this human condition, and we're going to screw up and we're going to forget. But what a radical thing it can be when someone's kind and says, "Yeah, no, I don't identify as a lady. So let's not refer to me that way." So yeah, I'm pretty passionate about it.
I have so many tears in my eyes. It's so beautiful what you're doing. How was that coming out within the company? Was there a plan in place? What did that support look like?
Yeah. So we were in a COVID moment. So prior to COVID we would get people physically together. We had weekly huddles where all the company would come together. This was about eight, 10 months into COVID. So we were on video, we did the DEIB&A initiative kickoff on Zoom. So it was a virtual meeting and yeah, I just said, "Hey, we're kicking this off and I want to share something with you all about myself so that I feel authentic if I don't share this I would feel very inauthentic." So I just said, "I'm gender non-binary. And I've known this for some time and it's been a big process.”
I've been out as same-sex attracted for a long time. And it would just feel so inauthentic for me to be talking about how we put together our own understanding of how to be supportive of people that are different than us by race, by any kind of identity that people have. Ethnicity, attraction, gender identity, ability. Abilities is a big one that gets overlooked. So, I had to share that part of myself.
So I just said, "I want to share this with you and I'm pretty open about talking about it." But I also remember saying, "I don't want to take up a lot of time about me." Because I think leaders make mistakes like that. Again, they just get too personal and it gets to be too much about them.
Yep and emotional. Like maybe they haven't worked through that as it seems like you have.
Yes. Well, and I think then employees will rush to take care of a leader. If you're not careful about the way that you share really personal things. So we had already planned that I would share my news and then I passed it back to Betsy, our Director of People and Culture. She took the meeting on from there and then we scheduled an AMA a week later. It was a time when anybody could show up and ask me questions about being gender non-binary. We had a great turnout and I just really lovely support and wonderful questions. So making sure that when you're doing something like that, really as a leader, when sharing personal things make sure that you've thought about the impact and how that's going to land for your employees and that you give them a chance to metabolize bite sizes, otherwise it can get super awkward.
So I felt like we had a plan and yeah, I'm super pleased with the way that happened. Then I had chest affirming surgery toward the end of this past year, in November, the week before Thanksgiving. During the time between my coming out and surgery, our company had grown a lot. We were under 100 people when I came out as non-binary and maybe 140 in November. I just made a choice to send out a Slack message to share about my surgery. I wrote this really personal Slack message saying, "If you were here at this time, you'll remember this and I just wanted to share with everybody that I'm having this surgery and it's okay to ask me about it." And I always say, and remember, if you have non-binary friends or people that you discover in your life, always make sure that they're as comfortable answering your questions as I am. So there was just this outpouring of love and support that was really wonderful. So I think over time, you have to think about different ways that you can communicate. So yeah, that's how that went.
You are very careful about what and how you communicate. When you decided to share about the chest affirming surgery, what was the primary reason?
When I'm out of pocket (away from the office), even now that we're in a hybrid work environment, it's noticed. So for me to disappear for 10 days, that's something. And I didn't want people to feel awkward, chest affirming surgery is about having your chest flattened. So it's like, "Do I say something about that? Do I not say something about that?" I didn't want there to be awkwardness. So I do give a lot of thought to communication, whether it's about something like this or any level of communication we're doing because you only get one shot to do the best job possible.
Whatever that might look like in the moment, as a leader to communicate effectively really means that people connect with it on varying levels. And you have to have a sense of broad up appeal. As we've grown at StickerGiant, we have 140 very diverse folks that work here. We have people of faith, people of different political persuasions. So my goal, as a leader and in my personal life is to hold this tension and middle ground between all kinds of people. Now, I grew up in a fundamental Christian home. My dad was a fundamental Christian minister. I went to a Christian school, I graduated from a fundamental Christian college in Virginia. So I understand folks that have that mindset and the framework and I'm able to hang out there. So I've made big choices in my life with my family to stay connected with them.
I was with both my parents when they passed. And as we say, as meditation and mindful awareness practitioners, it was a lot of fruitful, organic matter to work with to stay connected with my family. I didn't tell them that I was same-sex attracted until I was about 40. I'd moved to Boulder before I actually came out. So that was a big deal for more than 15 years that I stayed connected to my family. So I think the gift of that is … look, I'm not trying to change anybody's mind or their heart. I’m just learning to grow into my own integrity. I'm just going to show up as me. And I think in conscious leadership, one of the concepts there is strong back, open heart. So we have to work on both. We can't just be muscle-y in our back and not work on our heart. We just can't be gooey in our heart without having some structure and some strength to us. So it's again, that careful balance of both.
That articulates very much how I see the balance of leadership and what leaders have to navigate because there are dangers to open heart being too open and gooey and not no boundaries, or lack of strength. The latter is as hard on the team as being too strong.
Agree. I often think about it this way. When I was in graduate school at Naropa, my freshman year, I took a Tai Chi class. And I go back to this again and again - if you think about Tai Chi masters, there's this sense of when the series begins, it's all about sinking in, you aren't leaning too forward or leaning too backward. But constantly working to sink in and find your center as a leader is the work because you have to be malleable. If you get too rigid as a leader, that's not going to work. And to your point, you get too boundary-less and that’s not good either. You know, like, let's just self-organized, that's also going to cause harm. So yeah, those are just some of the concepts that I lean on pretty regularly.
Is there anything about your journey, that we haven't talked about that you think is important to share or that you want other leaders to know?
Yeah, I think pulling it all together. We talk so much about culture in our companies. And one of the things that attracted me to StickerGiant was an emphasis on culture. And you think about the impacts at COVID-19 and hybrid work and how we've had to change the impact to workplace culture just that a pandemic has had alone. So I just think it's really important that we know that culture is always evolving and that’d just the nature of culture. I think of Ari Weinzweig, Zingerman's Co-Owner and Founding Partner in Ann Arbor, Michigan. He's a prophetic writer and business philosopher, and he talks about companies as ecosystems. It’s so important that we think as leaders of the outside influences that impact the ecosystems, which certainly there have been a lot of outside influences. And the inside influences with every employee that you hire is bringing something into the ecosystem and understanding that as a leader, the seat you hold is adding a significant something to the ecosystem.
Ari also writes a lot and he has something called the 12 Natural Laws of Business and 12 isn't enough. So he is adding to them. The 13th law is, "Everything's out of control, all we have are varying levels of influence." And that's humbling. We can't control our cultures. And as soon as leaders start thinking that we can control things, we might get tricked into doing some manipulative things. One of the things I say often is if I want to influence you, then I have to be influenceable, or my influence will be outsized. And it won't work. So certainly at StickerGiant, we have been challenged with our culture, and it has changed a lot with an ownership change, with COVID, with fast growth.
But I am dedicated to the endeavor, of continuing to allow it to evolve and know that it is like sand running through our hands. And really appealing to our Giants here that I can't do it myself. I will play my role. I come to work every day, 110% ready, but I can't do it on my own. I certainly hold a big responsibility to our culture but part of that is the humility that's all out of control.
What else to read
The 15 Commitments of Conscious Leadership
The Culture Code
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