What does it take to step into the shoes of a founder and lead a company in its next chapter of growth? In this episode of One of One, join host Darren Gold as he sits down with Silvija Martincevic, CEO of Deputy, a leading global workforce management company. You’ll follow Silvija’s journey from her early years growing up in Croatia to her senior executive roles at companies like Groupon and Affirm and her eventual transition to becoming the CEO of Deputy. Silvija shares her philosophy of integrating high care with high performance, the importance of adaptability as a leader, and the challenges and triumphs of leading a global company. You’ll also hear about her personal life, family integration, and the lessons learned from being on the boards of Lemonade and Kiva. Through this insightful conversation, you can expect to gain valuable perspectives on leading with empathy, driving innovation, and the importance of continuous personal transformation.
Timestamped Overview
00:00 Deputy’s Global Enterprise Journey
06:08 From MBA Student to Groupon Leader
07:31 Scaling Success: From 1 to 100
11:53 Transitioning Leadership: Becoming a Founder
14:29 Empathy and Leadership in Management
18:01 “Transformative Leadership Through Self-Adaptation”
23:56 “Creating Thriving Workplaces”
27:17 Balancing Communication in Meetings
29:10 Leadership Pace and Communication
32:02 Tech for Good: Kiva & Lemonade
36:04 Work-Life Integration & Family Dynamics
41:23 “AI Revolutionizing Business Innovation”
44:09 Embrace Change and Growth
46:44 “Inspiring Leadership and Transformation”
Full Transcript
Darren [00:00:02]:
Hi everyone. Welcome back to another episode of one of one. I’m your host, Darren Gold, CEO of the Trium Group. My guest today is Silvija Martinevich, CEO of Deputy, a leading global workforce management company. In our conversation, we explore Silvija’s extraordinary career, starting with her early years growing up in Croatia to becoming a senior executive at companies like Groupon and Affirm. Before joining Deputy, we talk about the transition of being a longtime number two to becoming a successful first time CEO. Her philosophy of leading with both high care and high performance, and her experience of serving on the boards of Lemonade and Kiva while being CEO. This was a really fun conversation. I know you’ll enjoy it. Hi Silvija. It’s so good to see you and I’m so looking forward to this conversation and really thank you for being here.
Silvija [00:01:07]:
Thank you so much. It’s wonderful to be here with you.
Darren [00:01:09]:
Thanks. Yeah. Well, we have a lot of ground to cover, I’m sure. But I wanted to start with this special company that you’re leading, Deputy. And you’re rocking a very cool Deputy T shirt right now. For those of you that are watching, you can see that. And those, those of you that are listening, I want you to imagine it. But it’s a special company. You’ve been now leading it for a couple years. I think February will be two years joining as CEO. But can you tell us a little bit about who Deputy is for those that may not know or may want to know more?
Silvija [00:01:38]:
Of course. It’s a really, really special company that’s transforming the future of work for the community of workers that tend to be underserved, deskless workers, workers that work on their feet, from nurses that work in elderly care centers to retail workers to hospitality workers. And we do that today across 100 countries serving 40,000 small and mid sized businesses. And we provide those mid sized businesses and small businesses with software to manage that deskless workforce. And for end users, our workers, we give them the technology to be more engaged, more productive at work and happier at work. And at the end of the day, really what our technology is enabling is for those workers that oftentimes are invisible to give them dignity at work.
Darren [00:02:33]:
Founded in Australia, I believe, but global right now. What’s it been like to lead a company that’s both founded in Australia and has a global footprint? What are the challenges of that or what? Bring that to life if you could.
Silvija [00:02:46]:
Yeah, so it’s a company that was founded in Australia and I am running it from San Francisco. We have employees across Sydney, Melbourne, London and all over Us, we have customers that are all over the world and the origin of the company actually is really, really special. For those of you that work in the tech industry, you probably have noticed that a lot of really wonderful HR tech companies came from Australia. And the reason for it is that Australia has some of the most complex and highly regulated labor markets. And for that reason, software penetrated the labor force in Australia much earlier than the rest of the world. So Deputy was founded. We just had our 16th birthday. I joke internally that we are a teenager that is ready to become an adult company. And yeah, it’s been really a wonderful journey. Over the last two years. I make multiple trips around the world. Sf, Sydney, Sydney, London, London, sf. I do that a few times a year. But it’s been fun. It’s been crazy. Just as for many CEOs that are leading global companies, it’s an interesting time.
Darren [00:04:05]:
And this is your first role as CEO. You’ve been in it for two years. I want to get into those two years in a moment, but I’d like to go back in time and have you walk us through your professional journey to get to this moment where you were considered and hired and started in the role and maybe if you could bring to life because you’ve been at some great companies. I think you ran all of international Groupon, Chief Commercial Officer at a firm which is another great company. You had an investment career. What were the lessons learned or capabilities you built or things you discovered about yourself that you were good at along the way that gave you the confidence to believe you’d be a CEO and do it well?
Silvija [00:04:46]:
That’s such a great question, Darren. TL Dr. Is there was no big plan. I didn’t really know or I didn’t admit to myself that I wanted to be CEO up until I decided to take the Deputy role. And for many, many years I was a number two in really wonderful companies. I started my career. You alluded to that in Investment Management. Early 2002. It was an exciting time to be in investment management as hedge funds were being created and I invested for many years in. I built a quant index fund. So that was my first experience as a founder and then invested in women and minority owned companies. It was really, really an incredible time. You know, during the Great Recession in 2000 when I was investing in these companies. And what I realized is that even you know, during the darkest times it passes and actually it is in those tough times, whether macroeconomic times or whatever you may be going through as a leader, that is when boldest opportunities are presented. And so during 2008, I was so incredibly fortunate to build this company that went from managing 400 million in assets to over 1.5 billion that invested in women and minority owned companies. And we invested money for city and state governments. And it was during the time when everything was declining in sort of conventional asset classes and it was an opportunity for investors to invest in underserved areas of the economy. And so that was really a wonderful career. And as luck would have it, I was getting my MBA at University of Chicago and I met one of my professors who was a co founder of Groupon, who recruited me into Groupon and effectively said, groupon is a data company and you’re a data person. I was getting my stats and econometrics degree out of University of Chicago and I grew my career for many, many years at Groupon and learnings there. I mean, it was a company that scaled so effectively globally and I was incredibly fortunate to lead a team across 14 countries from UK all the way to Japan and Australia and really learn the power of diverse teams that come from different cultures, with different perspectives, different ways to look at how Internet should be penetrating small businesses. And it was really a transformative experience. I learned at Groupon that I love to be a builder of businesses, not a maintenance manager. I also tried the founding gig. You know, zero to one is not my jam. I love to take businesses from 1 to 100 and I learned that at Groupon and then the wonderful, wonderful opportunity post Groupon was an opportunity that Max Lefchin gave me at a firm. I was the first chief commercial officer for a firm and I had an opportunity to scale a firm. Through partnerships with Shopify, with Amazon, with Walmart. We grew a firm from 100 million in revenue to over 1.3 billion in revenue. And one of the most important lessons at Affirm, we all know when Covid hit, all of us weren’t sure how the world was going to be transformed by that. And Affirm was one of the rare companies that was bold during that time. And we went public when everybody else was trying to grasp at straws of what was going to happen. It’s a really, really special company. I learned the power of bringing the smartest people together. Max is an amazing culture builder as well.
Darren [00:08:36]:
Yeah.
Silvija [00:08:36]:
And yeah. And all of those really incredible rides at Groupon and at Affirm prepared me for Deputy, which I’m so fortunate to lead today.
Darren [00:08:47]:
Yeah. As you were thinking about your next role after Affirm, it sounds like it wasn’t necessarily to be CEO. But tell. Tell us a little bit about how that came about. How did the opportunity come about for you?
Silvija [00:09:02]:
So, you know, I had mentioned for many, many years I was a number two. I’m a solid operator. I love to inspire people and lead them into battle passionately. I can be a good commander when the time needs to, but I love to do that in the background. You know, I didn’t quite. I had this vision since my early career days that CEO needs to be is made of one type. Somebody that’s comfortable with visibility, that’s a great communicator. I didn’t speak English until I was 17, so I always feel I could be a better communicator. So I had all of these visions of what CEO is, and I didn’t see myself. I certainly knew my power. I’m an amazing operator. I love to lead people, bring them together, inspire them to do the best work of their lives. But I felt I could do that in the number two position. And when I was leaving a firm, Max actually pulled me aside and he said, do not tell me that you’re gonna go and be COO again. Go be CEO.
Darren [00:10:09]:
Oh, wow. I did not know that.
Silvija [00:10:11]:
Yeah.
Darren [00:10:12]:
Okay. Cause you and I met when you were at a firm.
Silvija [00:10:14]:
That’s right.
Darren [00:10:15]:
Max has been a guest on this show, but I didn’t realize that was. Those were some of his parting comments to. They were what’s sage advice.
Silvija [00:10:23]:
It really was.
Darren [00:10:24]:
He obviously saw something in you that many now see in you.
Silvija [00:10:27]:
Yeah. And you know what? I feel that when I now look at the seat that I sit in, it is not that different than the seat that I sat in for the last 15 years. It is a privileged seat. And Deputy is absolutely the right company for me to lead because I believe in leading, both with the brain and with the heart. And in order to do my best work, I need to feel emotional connection to that work. And I always felt emotional connection to customers at Groupon, at a firm, and now at Deputy.
Darren [00:10:59]:
Yeah. So let’s talk a little bit about these two years. I do want to share something, because I can’t help myself, which is I do think there’s something really interesting about a person who’s been in this number two role moving into the CEO role. It doesn’t always work. And when I had a chance to see you in the role as CEO with your team, I wouldn’t say I had any doubts. Cause I have an extraordinary amount of respect for you. But I did have the question.
Silvija [00:11:25]:
Sure.
Darren [00:11:26]:
Who is Silvija gonna be in this new role because of that phenomenon. Right. It does take a certain transition and I was blown away. It seemed like you’re a real natural at this, at least with my limited experience with you and. And from what I hear from others. So I do want to spend some time talking about these two years. What has really surprised you and what has it been like? What have been the big lessons so far? And I imagine there’ll be many more, but so far.
Silvija [00:11:53]:
So Deputy was run by our co founder, who was our CEO for 15 years. A wonderful, wonderful co founder, an engineer, and I replaced him two years ago. We all know that founder is the mother of the company. And we don’t see often we see some success when professional CEOs come in. But listen, the deck is stacked against that new leader. It takes a lot to step into the shoes of the founder and to lead or attempt to lead with as much empathy for the customer, inspiration for the team, and technical competence that running a software company requires. And so what was super important to me as I was stepping into deputy CEO role was to ask myself, what kind of leader do I want to be? And what kind of leader does this company need? What kind of work does this company need? And is that the work? Are those the superpowers that I have? And one perspective that I had. I believed as I stepped into this role, Darren, that I was the founder too. I was the founder of Deputy 2.0.
Darren [00:13:11]:
Yeah.
Silvija [00:13:12]:
And Deputy 2.0 is a company that is global, that will have many products across the world, and a company that’s organizationally more stable and more ambitious. And so I don’t see my job as, oh, I’m going to be a professional CEO. I see it as I’ve been given this sacred opportunity to found the next chapter of this wonderful, wonderful business.
Darren [00:13:40]:
Yeah, what a great perspective. And when you say that, what do you mean? Because Paul Graham just penned an essay, founder Mode. It’s certainly in the zeitgeist right now that a founder brings a certain amount of energy that only a founder can bring. That’s at least one of the contentions. And what I hear you saying is you don’t have to be the founder. You have to have a founder mindset. Maybe. But what is it about that kind of founder energy that you believe you’re bringing into Deputy?
Silvija [00:14:10]:
So this is a really, really great question, Darren. And we all have been reading about founder Mode, of course, and I actually do disagree with the premise that it’s just the founder that can be in founder mode.
Darren [00:14:22]:
So do I so do I.
Silvija [00:14:23]:
And so calling myself founder of Deputy 2.0. Here’s what it means to me.
Darren [00:14:28]:
Yeah.
Silvija [00:14:29]:
First and most importantly, do I feel the empathy for our end customer? I am so incredibly fortunate that I grew up in a community and have been in the shoes of the community that Deputy supports today. I grew up in Croatia in a small community where every single one of my family members were shift workers working in factories, being truck drivers, being farm workers. And so I feel that that empathy, understanding the pains of our customers has to be present. You need to feel that. The second thing that I think I bring to Deputy is, you know, I talked about certain times require certain modes of operating. My team jokes that I can, when needed, not just micromanage, but nano, manage when there’s big risk and massive amount of detail is critical. Of course a leader needs to be able to dig in. And so I absolutely, absolutely bring that as well. And last but not least, you gotta be able to inspire. It’s not just the founder that can do that. And so, yeah, that’s how I approach my job every single day. I am building the next stage of Deputy.
Darren [00:15:55]:
Yeah, you can see it energetically, maybe even just if you’re listening to this just in your voice. There’s a certain energy that comes from that kind of mindset. So that’s sort of one thing. Founder of Deputy 2.0 I love that framing what other things have either surprised you or have been moments of learning for you in these couple years?
Silvija [00:16:16]:
Sure. You know, I think at the end of the day, every single one of us CEOs, we’re in the people business. I think somebody said great companies are not built by great strategies, they’re built by great teams. And one thing that I lived by my entire career is that you have to work as one team. Darren, you may know this about me already, but I grew up on a farm, so I have a lot of animal metaphors. So I’ll give you one. Now, there’s this thing that I live by which is buffalo style leadership. So what is it? During the storms, buffaloes are the only animals that together in a herd, run towards the storm. All of the other animals during the storm run away from the storm and then get separated and go through a lot of hardship through that. Buffaloes are the only ones that run together towards the storm and get through it faster. And so that buffalo style aligned behind the same arrow kind of leadership and teamwork is super, super important to me. So I spend a lot of time thinking about, are we aligned? Is there One thread running through Deputy. Is everybody clear? Clarity is a big thing for me. Again, having English being a second language to me, it’s really important that I’m clear. And so is everybody clear on the goals and key priorities? And are we all aligned and moving in the same direction? That’s super important. And the last thing that I really, really realized is key for being in this role is adaptability. I think we all, you know, we all are students, right? We all love to learn about and read about leadership. And I think oftentimes things that I’ve read, even founder mode to some extent simplifies things. You know, some people talk about direct and command leadership, some people talk about you gotta be a servant leader. Right. Or you gotta be founder mode. And I just, I don’t believe in any of that. What I believe in is that if you wanna be a transformative leader, you have to be able to transform yourself. What this means you have to be adaptable as a leader, of course, with your values as the main anchor. And so what I’ve learned is this power of adaptability and learning different modes of operating depending on what situation requires. Sometimes it requires that inspiration from a leader, sometimes it requires ruthless execution, sometimes it requires nanomanagement. And so I think that for me, sitting in the seat is the power of adaptability of you as a leader and to teach your team to be adaptable too.
Darren [00:19:16]:
Yeah. What are the big areas of growth that you’ve experienced as a leader, whether it’s in these last two years or along the career? So I get the point around adaptability and not being locked into any one mode. But I’m also curious to hear from you because I know that self awareness is really important to you a moment or two where you’ve discovered something about who you are and you’ve transformed or grown in a meaningful way.
Silvija [00:19:45]:
I had a really, really transformative, I would say exponential growth as a leader. When I was at Groupon for many, many years. I was the executor. I was known across the company. Just give it to Silvija, she will get stuff done. And I got this wonderful executive coach, Jodi Michael, who taught me so much about leadership, but really taught me about myself. And she did this360, which was the first time a mirror was presented to me. Darren and I hope we all get to experience that in our lives. Not just that a mirror is presented, but that we look at it, that we sit with it, we ponder on it. And the mirror effectively said something like, I’m going to overshare. But I hope it’s helpful. Silvija is a business robot. I don’t know that Silvija cares. My team was saying this, that Silvija necessarily cares about me. She cares a lot about results. And it couldn’t have been further from what I was feeling internally. I felt I really cared deeply, and yet I wasn’t. The way that I was showing it perhaps was not received, and Jody helped me. It happened over time, by the way. This change, this transformation of leadership doesn’t happen overnight. It happened over time. Because at first I was very resistant to Adaren. I said, well, I do care and I show in my own way. And they should just know. Right. That’s the natural. You defend you, you know, you try to reason. Yeah, but over time. And also, I believe in authenticity. I really believe in that. I believe that you, you know, none of us are going to be successful if we try to be Elon Musk or Sheryl Sandberg or whoever. You got to be yourself. You got to be yourself. You got to show up as none of us are perfect. I believe I’m a work in progress. We all are constantly. And so it took some time for me to authentically become a more transformed leader that showed great care along with this deep desire for performance and for speed. And it’s a balance. And as you’ve taught me as well, it’s an integration. It’s not a balance. It’s an integration of high care and high performance.
Darren [00:22:08]:
Yeah, I know that’s been central to your leadership now for some time, particularly as CEO, a deputy, and I’d love to hear a little bit more about this polarity of performance and care. High standards, high care, and maybe even about polarities in general, because I know this has been a critical capacity for you as a leader, which is the notion of how to manage and integrate paradox.
Silvija [00:22:34]:
That’s right.
Darren [00:22:34]:
So can you talk a little bit about the role that that kind of wisdom or capacity has played in your own leadership?
Silvija [00:22:40]:
Of course. So it’s really unfortunate that so much of our world society is looked at through the lens of black or white. If you win, that means that I somehow am losing. And over time, I have learned that true joy and true satisfaction actually comes from finding a win win. So perhaps I’m going to first talk about how I see that in business outcomes, and then I’m going to talk about culture. So when I look at deputy and what we are building, we’re building software for businesses to help them manage their hourly workforce better. And so historically, of course, we look at this through the Lens of, well, if you give more to workers, that means that somehow businesses are going to hurt, right? Or if businesses are doing good or they must be squeezing the workers. And I truly believe that through the power of our platform and through the power of data, we can show businesses and we can show workers that actually there is a win win. There’s a sweet spot where win win can happen. So how do we enable that? Well, if you are a business and you want to thrive, you want your customers to be happy, how can you do that if your employees are not happy? Because if you are a restaurant, you’re a hospitality company, you are an elderly care company, you are a factory, your workers deliver your product, it is their hands that deliver the product into your customers hands. So if your workers are more engaged, more productive, they’re thriving, your business is going to thrive. And Deputy shows that. With our data, we show that Deputy, businesses that use our software for engagement, for communication, for labor compliance, for labor productivity, has higher retention, effectively completely eliminates no shows and has better productivity. And so we are building a business where we believe we can build win win outcomes. And so then how does that translate inside? Deputy, you know, and I say this to my deputies all the time, our vision is to create thriving workplaces in every community. Well, how can we create thriving workplaces if we are not one internally? And so what thriving workplace for me means is exactly what you said, Darren. It’s a workplace where we believe that being direct is being kind. We don’t believe in being nice, we believe in being direct because we believe by being direct we’re being kind. You know, another animal metaphor. I say to deputies, I don’t believe that we should bring elephants into the room. I believe that we should bring elephants into the room and put them on the table. So our meetings that we have are almost always cross functional meetings where the first thing we talk about are where are the risks, where are the obstacles? Let’s start with the elephants. Put them on the table first. And so that is incredibly, incredibly important to create high accountability, high standards, but also care where we care for each other. And, and so I hope this gives you a little bit of, a little bit of a flavor.
Darren [00:26:14]:
Yeah. What’s the, what’s been the hardest part of that? Because I think every CEO I speak to wants to build a high performing culture. Many of them are trying to integrate this natural, healthy tension of performance and care. It’s not easy. Where are you on the continuum of that journey and what’s been the hardest part of it?
Silvija [00:26:33]:
We are definitely on that journey. Still, it’s not an easy. If it would be easy, we all would be integrating high performance in high career. We as humans have a natural tendency, again, to simplify things. And so what I often tell deputies, artificial harmony is just as bad as a toxic culture. And artificial harmony is not going to help us build a magnificent and a lasting business. So if I look at deputy, where we skew a little bit, we skewed on that, like artificial. Just a slightly, slightly sort of tidbit towards. Do I really want to say this thing in the meeting? Do I? Ooh, do I? You know, will this feel like I’m throwing somebody under the bus? And it starts with me? I need to show how we can do that. And my leadership team, how can we model in our meetings where we’re not attacking each other, we’re attacking the problem. And by the way, if we solve the problem, we will help our customers manage their workforce better. We will help with retention of workforce. We will help where workers that tend to be underserved and invisible feel recognized and again, feel dignity at work. So connecting. I think the real superpower is connecting that culture of high performance and high care to the. Why? Why are we doing this? Why is this meeting so hard? And sometimes I pause. Darren, you taught me this. The power of going at 0.5 speed. As a person, I tend to be not at one speed, 1.5 speed. Talk fast, go fast, get stuff done fast. And you taught me, take a minute, sometimes pause. What’s the 0.5 speed? Because this conversation deserves 0.5 speed. And in those toughest moments that we have in the company, sometimes when we’re disagreeing, I acknowledge the disagreement. Here’s why we’re disagreeing. This is important. This matters. It matters to our customers. We gotta get it right. Let’s battle. Let’s battle it out.
Darren [00:28:53]:
Yeah.
Silvija [00:28:53]:
But it’s a. I think that is one of the greatest challenges that I have as CEO. How do I move us? Where we integrate and where we flow, where we have a flow of high performance and high care and deep, deep trust.
Darren [00:29:10]:
It’s interesting. You know, we’re talking about a podcast metaphor, and we’re recording a podcast. I couldn’t help but imagine what speed listeners are hearing us at right now. But I think it’s so important. Even in your description of that, I noticed a shift in pace, and it is something that I think is a really important capacity for CEOs is to understand that not only do we. Are we adapting to different styles of Leadership, but kind of our pace of leadership, we’re moving really fast in certain circumstances and then we’re taking the time to slow down. Even the way we communicate needs to slow down. So thanks for bringing that to life.
Silvija [00:29:48]:
You bet.
Darren [00:29:49]:
Yeah. You’re also on a couple boards, the board of Lemonade, a really cool company, Kiva, another extraordinary company. And I’d love to explore for a moment your experiences on those two boards, what they’ve taught you about being a board member and what that’s helped you, if it has, in understanding your role as CEO and how you manage and lead your board.
Silvija [00:30:14]:
Absolutely. Both Lemonade and Kiva are these wonderful, wonderful companies. Lemonade is trying to transform through machine learning and AI, the insurance industry. And Kiva, a wonderful, wonderful not for profit that is one of the largest micro lending organizations on the planet. And you know, the kind of energy that I bring to those boards, and then the opposite, the kind of energy that I bring to my board, a deputy, is that I consider myself part of the team. I don’t believe in, quote unquote, managing the board. The board is on my team. I’m accountable for bringing them along, for being transparent and direct, also for inspiring them. I believe in that. And so I truly consider my board as my team, a deputy. One thing that I have learned at Kiva that’s been so powerful, Darren, is this power of deep, deep mission driven leadership. Of course, Kiva invented the microlending space. When you look at the impact that Kiva has given, has created over $2 billion has been lent to entrepreneurs across Africa and Latin America and Asia. Those are generally sole proprietors, women refugees that start their businesses from on average $150 that somebody lent them from America. By the way, the repayment on those loans, 98%. No bank in the world or a lender has those repayment rates. It’s a powerful, powerful, mission driven organization that has created such amazing work. And at Kiva, I think what was ignited and really clarified for me through the leadership of our wonderful chairwoman, Julianna, one of the most brilliant technologists alive today, is that you can use tech for good. And I have adopted that as my own hashtag whenever I talk about deputy technology. We want to build an enormous company and we also want to build a company that creates enormous societal good. So Kiva really taught me that. And at Lemonade, I just think it’s such a special company. They have used machine learning and AI when it wasn’t cool. And they truly have been the picture of resilience. And grit. What a tremendous, tremendous business and what a Runway they have ahead of themselves to build a transformative, modern insurance company that will be used by generations.
Darren [00:33:05]:
Yeah. There is a bit of a debate on whether CEOs should sit on boards and you’re sitting on two of them. So I imagine I know where you sit on this question, but what would you say to CEOs that maybe are first time CEOs considering taking a board seat? Is it a good idea? And if so, why don’t do it.
Silvija [00:33:23]:
In your first year of becoming a CEO? Maybe that little, especially a CEO that needs to travel around the world. Maybe, maybe that. You know, I think it’s another source of tremendous learning for me. And I said earlier, I believe that we are constant work in progress. I hope that I contribute to those boards, but they contribute more to me because I learn, I learn about different industries, different business models, ways that they’re solving problems. And so I think it’s another wonderful source of learning for CEOs. So I’m a huge proponent.
Darren [00:33:59]:
Yeah. So we talked a little bit about the integration of opposites, head and heart, high care, high standards. You’re also more than just a CEO, you’re a mother. You lead a family, you have a big personal life. And those of course are completely intertwined right in today’s day and age. So I’d love for you to talk about a little bit, bring a little bit of your personal life to light here and the integration of all aspects of your life. How do you do it in a way that allows you to do it all and feel full and abundant in doing so?
Silvija [00:34:33]:
Yes. Thank you so much, Darren for bringing the personal into this. I love this. I have been married for soon to be 22 years to my high school sweetheart. We practically grew up together, met in Croatia as high schoolers and then had long distance relationship when I was in college in US and, and then he followed me in America and we built our life in Chicago, our adopted hometown. We’re Midwesterners at heart with four suitcases and $400. And he truly my team knows that a deputy, I would call him my anchor. He is someone that has been both my greatest champion as well as truth teller. I don’t think I’ve ever made a decision, big decision without hearing his advice and getting his wisdom. So he’s been, he’s such a tremendous, tremendous partner, truly, in every sense of the way, you know, in every sense of the word. I know many CEOs do this differently. Karuno is a stay at home parent as well. He’s a stay at home dad and he knows about my executives, he knows about the dynamics. We talk about it. I choose to bring him along on that journey intentionally. It’s not like I have a work life and then I have a home life. There is just life. And that’s super important to him. And I think that kind of integration where he knows what’s happening at work and how the challenges are and can provide that advice, I think that truly is a secret to our partnership. And we have two wonderful kids who are 11 and 9 and they also, they’re a part of the deputy journey themselves. And you know, they, they proudly talk about it. And a funny story, my son, this talks about. I spent a lot of time, Darren, talking about Gen Z and thinking about Gen Z and Gen Alpha and how do those new generations work and live? And my son and my daughter are in Gen Alpha. Okay. If you’re a CEO and you’re not thinking about that generation, you’re missing out. Talk to your kids. Talk to your youngest employees in your business. Their perspective on work and life is just oftentimes foreign, but so incredible. So I’ll give you one example. This is. I had nothing to do with this, but my kids write a Santa letter every year. Right. They sort of believe in it, but I mean, they’re 9 and 11. And this year I woke up one morning, you know, I knew they were working on their Santa letters. Underneath the Christmas tree was a printed out paper with a QR code. Yeah, the QR code was a Santa letter that my son wrote, created a QR code, then created a PowerPoint presentation.
Darren [00:37:45]:
Amazing.
Silvija [00:37:47]:
So I, I think that, you know, we impact our kids, but our kids are impacting us too.
Darren [00:37:52]:
Yeah. Yeah.
Silvija [00:37:53]:
So talk to your kids about your work. Listen to their, you know, ideas. And again, QR code as a Santa’s list blew my mind. Haven’t seen, haven’t anticipated that before.
Darren [00:38:03]:
Amazing. I often say parenting is the ultimate kind of leadership school. Has there been anything about your parenting that you would say parallels your leadership journey as a.
Silvija [00:38:16]:
Absolutely.
Darren [00:38:16]:
Yeah.
Silvija [00:38:17]:
Darren. I would say, you know, Karuna and I didn’t have children for many years. We were together for 11 years before we had kids. So we were well into our, you know, adulthood. And one skill that we really try intentionally to build inside our kids is the skill of adaptability. That’s it. There is one word to describe how we parent. We try to teach our kids that change happens, stuff happens. What are you going to do about it? What do you control? How are you going to show up and how are you? We teach them. Don’t react. Take a minute, take a second act. It’s something that I try to embody as a leader, and sometimes I fail, sometimes I succeed. We all slip sometimes into our tendencies, right? Let’s not pretend that we’re perfect. No, we’re not. CEOs are human too. We slip. And I hope that we then are lucky to have partners and teammates who tell us, hey, maybe this was not the best way to show up in this meeting. And I look for people like that. Both, of course, Kruno is that person at home, but also my teammates. I want them to tell me, Silvija, this was a rough one.
Darren [00:39:31]:
I’ve seen that happen. You have a few of those.
Silvija [00:39:33]:
Exactly. You’ve seen my team in motion. It makes me a better leader for people to tell that truth and have the courage to tell you that truth. So I think, again, one word around parenting is how can you make your kids adaptable? And we practice that. We took kids out of school there, and a couple of years ago, they go to school in Marin. We took them out of school, moved them to Croatia. They went to a public school in Dubrovnik, Croatia, for six months. And there was a moment where both Kruna and I were thinking, are we going to screw them up? This is very different culture, different language, different way of teaching and learning. In first grade, my daughter had four hours of homework a night. Talk about intensity in first grade. But we came from that experience so enriched. And I think that was a big step in my kids learning adaptability, how to adapt to different cultures, languages. So, yeah, I think there’s a lot of connectivity between parenting and being a leader.
Darren [00:40:42]:
So as we bring this towards a conclusion, I’m struck that we’re having this conversation towards the end of the year and can’t help but ask whether you’ve had time to reflect on 2025 and 2025. I’m sure you’ve. You’re in planning, you’ve been focused on the business for sure. But what does 2025 look like for you? What is if you said. If you looked forward and said the end of the year, December 31, 2025, almost a year, a little bit more than a year from now, what is the area of growth that you’re most committed to as a leader?
Silvija [00:41:20]:
I’m doing a lot of thinking on that right now.
Darren [00:41:23]:
Yeah.
Silvija [00:41:23]:
You know, there is this little word, AI, that is changing everything about our world, about our life, about our businesses. And what I’m thinking about. I’ll answer this question first as an operator, as a business leader, and how I think about business, and then I’ll talk about culture. What I’m spending a lot of time on is how can we enable innovation? We all see too much. I think about, oh, use AI in marketing or use AI for getting leads, or use AI for customer support. I’m not thinking about it in that way. I’m actually thinking about how do we, by the end of next year, have the most amazing platform for any single deputy to innovate with AI? Because I believe, just like Internet, AI is everywhere. So I hope that by end of next year, AI is everywhere. It’s a part of our DNA because of the platform and the foundation on which then all of the 452deputies can innovate as it relates to culture and what I hope the next year brings. Every year, I tell deputies one sentence that defines the next year. The year of 2024 was the year of GSD, or as in deputy, we love to say, get shift done.
Darren [00:42:51]:
That’s good, right?
Silvija [00:42:52]:
We help shift workers get shift done. So 2025 is the year of Deputy 2.0. Okay. Where we transform our business truly to be global, to become a platform business, and to truly, truly integrate that high care and high performance into everything that we do.
Darren [00:43:13]:
Yeah. Wonderful. Anything that we haven’t covered that you’d want to add or even revisit and summarize that you want to put some emphasis on before we we wrap things up?
Silvija [00:43:25]:
I have. I’ve been thinking a lot about founders that are leading transformative businesses, and especially being a leader that came in and took a company and replaced a founder, I think a lot about that journey and what that must have been like for my own founder. And so my advice for those founders that are leading companies with so much passion and grit and care, if you want to build a transformative business, you have to be willing to transform yourself.
Darren [00:44:07]:
And by that, what do you mean?
Silvija [00:44:09]:
What I mean by that is you have to be willing to change. Be honest with yourself. Acknowledge where you’re exceptional, where your superpowers are and where they’re not. Acknowledge where your passion is. I know many founders that love that, zero to one. But once you start scaling, a whole set of chaos and complications happen. There’s a different set of muscles and skills that are required in order to get the company into that next phase. You have to learn and strengthen those muscles. You can be pretending that you’re still 0 to 1 if the company is scaling.
Darren [00:44:51]:
Yeah.
Silvija [00:44:52]:
And so that’s what it means truly, truly embracing different modes of operating and leading and because the way that the company grew and the way that the modes that were required from 0 to 1 in company’s life cycle is very different. What will require to get it from 1 to 100?
Darren [00:45:15]:
Yeah. I notice a tension and maybe we can just spend a minute or two more on this before we wrap that. There’s something really powerful about a founder knowing who they are, being unapologetic about who they are and leading and building a company from that place and at the same time having the self awareness and capacity to expand and take different ways of being on. So again, it’s not an either or.
Silvija [00:45:42]:
That’s right.
Darren [00:45:42]:
And I think oftentimes we’re stuck in a black and white thinking about either I’m unapologetically me, I get to do whatever I want, whatever I want, or I lose myself.
Silvija [00:45:52]:
Exactly.
Darren [00:45:52]:
And I’m trying to be something that I’m not. And maybe what I’m hearing you point to is there’s a possibility for integration here.
Silvija [00:46:00]:
That’s right.
Darren [00:46:01]:
You do not want to lose the essence of who your anchors, but there’s an openness to sort of expand and grow beyond that.
Silvija [00:46:09]:
That’s exactly right. I think that’s a wonderful way to conclude integration of your authenticity.
Darren [00:46:15]:
Yeah.
Silvija [00:46:16]:
With desire to evolve your moves so that your company can thrive.
Darren [00:46:21]:
Great. And might even sound like the 2025 mantra for. For Silvija.
Silvija [00:46:26]:
Absolutely.
Darren [00:46:26]:
Which you’re already doing for all of us. For all of us. Yeah. I’m taking a note on that one as well. Well, this has been an amazing conversation. I’ve loved being in it. So appreciate your time and your willingness to share your incredible journey and background with all of us. Thank you very much, Silvija.
Silvija [00:46:42]:
Thank you so much for having me, Darren.
Darren [00:46:44]:
You’re very welcome. There were so many valuable themes in this conversation. In particular, I found Silvija’s commitment to lead as the founder of Deputy 2.0 to be really inspiring. And I loved her advice that you can’t expect to transform a company if you’re not willing to transform yourself. I look forward to being with you on the next episode of One of one. Until then, I hope you live and lead with courage, wisdom, and above all, with love.
One of One is produced by Erica Gerard and Podkit Productions. Music by John LaSala.