Short Story Long

Scott Fleszar’s Story: From Layoff to First-Time CEO

Beki Fraser Season 2 Episode 7

In this episode, we explore powerful themes of resilience, reinvention, and the importance of staying connected. Scott Fleszar shares how a sudden career disruption became a catalyst for reflection and transformation. Rather than being defined by circumstance, he embraced change with intention. His story demonstrates how a strong network can open unexpected doors.

Get inspired by Scott’s journey from corporate predictability to entrepreneurial possibility, revealing what it takes to lead through uncertainty. His story highlights the enduring value of relationships, the power of transferable skills, and the courage required to shape your own path. It’s a compelling reminder that leadership isn’t tied to a title, it’s how we respond to change.

Click here to connect with Scott on LinkedIn.

Share your story or inflection point with Beki

Connect with Beki on LinkedIn: Linkedin.com/in/BekiFraser
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Short Story Long is produced by Crowned Culture Media LLC

Speaker 1:

When I got to the small organization, that's when I realized that the well-rounded background was really helping me with being involved with every aspect of this business and being involved with, you know, growing the business. And that's really kind of where I realized, oh, I probably do have the skill set for the CEO role, so I stumbled into it. I would say it was not intentional and I benefited from having some great leaders.

Speaker 2:

Hi, I'm Becky. Welcome to Short Story Long. In this podcast, we discuss ways you can integrate who you are into how you lead. It's a sad truth of employment that your position can disappear Even when you know it's coming. It's a tough message. When it's unexpected, it can be devastating.

Speaker 2:

My guest today turned a surprise notification into an opportunity for change and growth. He has an inspiring story of starting over in a new environment. The good news is that he didn't start from nothing over in a new environment. The good news is that he didn't start from nothing. He started by recognizing all the transferable skills and talents and reaching out to talk about them. Today, my guest is Scott Flazar. He is a seasoned executive and CEO who has built high growth companies, led successful exits through strategic deals and fostered cultures that empower people and drive results. He has a passion for leadership, strategy and innovation. Scott knows what it takes to scale businesses and align teams for success. He has worked not only to build companies but also to cultivate high-performing teams and game-changing products. Hi, scott, welcome to the podcast. I'm excited to hear about one of the inflection points in your life that influenced your career and leadership style, and I'm just excited to talk to you.

Speaker 1:

Thanks, peggy. Thanks for having me. I'm looking forward to this. Thanks for the great introduction. That's probably better than I could have done myself and, yeah, looking forward to sharing and having a great conversation.

Speaker 2:

Good, good, I'm excited too, and I had warned you that we would be talking about an inflection point in your life here. And as you think about the story that you want to share with me here today, talk to me a little bit about what was happening for you before that moment had arrived.

Speaker 1:

Sure. So where I found myself right before this inflection point and it was certainly a big inflection point in my career I was working at a big global multinational corporation. I had been there over two decades, I had worked in a variety of different functions and then a big reorganization happened and all of a sudden I found myself without a job unexpectedly. And that's really kind of the backstory on this inflection point and kind of what happened from that point on.

Speaker 2:

Yeah, yeah, and it sounds like that was a bit of a surprise for you that you would be impacted by that reorg, because you and I worked together at that company and there were a lot of reorgs that would happen there and you had survived all of those. What was sort of the experience after that change happened for you?

Speaker 1:

I mean the first thing. I'll say I was pretty naive because I was surprised and, thinking back, you know I shouldn't have been, because these things happen at large organizations and you know, for me, as I think back to my career at this, you know large organization. You know I had an opportunity to work in a variety of different roles and lead different functions. I started in what was our this is a software technology company. I started in what we called user services, so that's support, customer service and trading and that's an operations role, and it was very much about how to run efficiently and do more with less, because those are cost centers in big organizations and you're going to have to run them with tight budgets. And it also taught me about how to take care of the customer and how important that is. Then I led marketing for five years and I had an executive. She believed in me. She promoted me into leading that function. I had absolutely no business leading that group, but she believed in me and she really helped guide my career and she knew I could grow into that role and at the time I was getting my MBA at the University of Michigan. So this was a real way for me to pivot my career and get into more strategic roles. And then I led product management for a number of years, which is working with our development team on what new products to build, what products to sunset and really what is going on in our marketplace with technology trends, profession trends, competitors.

Speaker 1:

And then I got involved with acquisitions that this large organization was doing and that's where I got to understand a little bit about how to evaluate a company and understand enterprise value and we always knew we had a winner when we found a company that had an outsized product and engineering team and a small go-to-market team.

Speaker 1:

It means they have a great product that nobody knows about and we had some real success with those acquisitions and that's where I started cut my teeth as a general manager. I started running some of these businesses that this large organization had acquired and that really led me up to. I had had great success in this large organization, held various different roles and felt secure in my position there, but then very, very sweeping leadership change, like big leadership, team change, and you know that was where I found myself in the summer of 2019, you know, without a job for the first time in 24 years and that started me down a path of, okay, I need to get my next job, I've got miles to feed at home, and that's where I started networking. That's where I really kind of learned the value and the importance of having a really strong network.

Speaker 2:

Yeah, what got you started in terms of rebuilding that network? When you're inside a large organization like that for 24 years, you start getting very insulated and really inside the organization and now all of a sudden you have to sweep wide. How did you get started doing that?

Speaker 1:

That's a great question, becky. First of all, you know just I needed to network. So the motivation was there because I knew to find the type of role I was hoping to find. You know you were going to need to talk to people, build relationships and figure out where these opportunities were, because I had been in a number of either customer-facing roles or vendor-facing roles, where we're building partnerships with vendors. I had a fairly decent network, even though I was with the same organization for 20 years. But then what I did was ask those individuals to make introductions for me.

Speaker 1:

I think this is networking one-on-one, but it was all about reaching out and having conversations, not about can you help me find a job, but can we talk about what's going on with your professional career at this point and do you have any pointers for me and are there any introductions you can make?

Speaker 1:

And that's also where I got more exposure to executive recruiters and what they might be able to help with. At the same time, I was re-energizing my current network. I was using my current network to kind of branch out and have others help me with other introductions and pointing me to other opportunities. And the one thing I learned in that moment in time was even if you know there are people in your network that you might not feel you know very well or are very well connected to, that will go out of their way to help you. And and that's um, you know something that I've now always thought okay, I need to pay that forward. Anytime you know people are reaching out to me. Even if you know maybe I haven't spoken to them in three or four years or maybe we don't know each other very well, I still want to be, you know, have some assistance.

Speaker 2:

So yeah, absolutely, and I wonder if that was a lesson that others had learned so they were paying it forward to you in those moments, right, because I think there are so many times where we're shy about making that contact, and I've even had people reach out to me after 10 years of not talking to someone and I'm like, oh my gosh, I can't believe that they thought to reach out to me, right? Like you know, it's almost like an honor, in a way, that someone thought that you might be able to help them. So I can appreciate what you're saying there. And so, as that network started to work for you in some regard, I mean, how is it that you ended up landing in the role that you found?

Speaker 1:

Yeah, as I was kind of working my network, I would say there was, you know, a first wave of people I knew really well and then you know, a second wave with kind of the next layer out, and it was really the third wave when I decided to reach out to the co-founder of a business, a small technology company, a co-founder that had met a year earlier this large organization I was at. They conducted a user's conference every year and there were certain vendors that came to exhibit and I met this co-founder at that conference. We had kind of one conversation, a couple emails after that, but didn't know this person that well. But in the spirit of, you know, any networking is good networking. I reached out and this individual again, I went. You know, I was part of a global, big, global multinational corporation. This is a small technology company, I don't know exactly how small, but I know they're small. I reached out and this person immediately emails back and says, oh, I didn't know that you, I know they're small.

Speaker 1:

I reach out and this person immediately emails back and says, oh, I didn't know that you're looking for your next opportunity and have you ever thought about working for a smaller business? And I said, absolutely. That's something that absolutely intrigues me. So we exchanged a few more emails, we had a couple of phone calls and then he invited me out to visit him his, his, his co founder. So the two co-founders and the CTO. So again, this is back in 2019. So I, I fly out to California and meet these individuals in person and you know, if, if I were to deflaunt, define the inflection point for this particular podcast, it's this conversation that I have in person with these two co-founders and the CTO Sit down and my entire career again is I've been in this large organization and I knew from joint customers of the large organization I was with and then this small technology company. I knew from joint customers that this product was very good.

Speaker 1:

So I had a good feeling about that already. But when I sat down with the two co-founders I had this huge epiphany. As they described their business to me, I said, wow, these guys are entrepreneurs, they're good at building products and starting companies, but they're not necessarily good at growing and scaling a business. And that's exactly what I've been doing my whole career, especially on the go-to-market side sales, marketing, customer success, anything customer facing. So left that meeting just really excited. I just came to this realization that we have very complementary skills. I am not the entrepreneurial type, I'm not the one that's going to start a business and bootstrap it for a few years to get it to a certain size. But I can come in later when there's already a product there, there's a good product market fit and now there's a real opportunity for the business to grow and scale.

Speaker 1:

So I left that meeting really excited about how I could help them and how we had complimentary skills. And they made me an offer to come aboard and it was for a title of Chief Operating and Strategy Officer. But the co-founder at the time that was CEO said in reality I don't enjoy leading this business on a day to day basis. So if this works out and we really start to grow. There'll be a CEO opportunity in it for you, because what I like doing because he's an entrepreneur again is I like working on the product, I like thinking of new ways technology can solve real world problems for our customers. That was essentially how I ended up landing this role. And again, as you think about profiles of leadership and you think about the backgrounds of people, you've got entrepreneurs. You've got people that come out of large organizations. Everyone's got their own unique background and experience and this was really kind of the Kind of the marrying of the best things.

Speaker 1:

Yes, yes.

Speaker 2:

Yeah, absolutely. And you know I mean you use terms there like go-to-market products, right Sales, and also really that idea of going from COO strategy to CEO. I know that at least one of the acquisitions that was done at that large organization you kind of ended up in that role in a sense of I mean it wasn't CEO title within that organization but general manager was essentially that you were running that business. How much did you feel that you wanted to keep on looking for the next opportunity versus wow, this epiphany has landed and I feel really good about doing this.

Speaker 1:

When I left that meeting I knew this would be a great opportunity. I didn't know exactly how the role would unfold and how the business would grow, but I knew I could help this business. That was the simplest way to think about it. I knew I could help this business, I knew I could help it grow and I knew they had a great product, which is kind of important too, because you want to fall into a situation where you want to find a situation where you can, you know, really make an impact. So I didn't have any doubt this is what I wanted.

Speaker 1:

And also you mentioned my experience, you know, running a business from, you know, in the larger organization. That was an acquisition. The experience there is very much translated to what I was going to be able to do at this, at this organization, and I knew that I could take my learnings from the larger organization, from running operations, from running marketing, from running product management, from running some smaller businesses and really apply that very nicely to a small business and help grow and scale it. So I was sure this was the right opportunity for me, Becky.

Speaker 2:

Okay, that's amazing. So, scott, as you were talking about your background at that large organization, you were moving from one function to another function and it sounded like there was growth and opportunity and some support. How much was that intentional by you in terms of that growth and maybe having that CEO kind of role in sight?

Speaker 1:

Yeah, that's a great question. It wasn't very intentional at all, actually, and I've had others ask me you know, how did you become CEO and was that your plan? It really never was the plan. I was very fortunate in that large organization to have a leadership team and you know people that are reported to that had confidence in me and looked for me to take on new challenges, new opportunities. So it was a bit more me being pulled into different functions, leading different teams, getting involved with acquisitions, than me raising my hand for it. So I feel very fortunate, I guess, in that regard.

Speaker 1:

I was certainly very willing and I loved building this kind of well-rounded background. But I also never really thought in my mind, well, someday I'm going to be able to parlay this into a CEO role. That was really not intentional in my part. And then when I got to the small organization, that's when I realized that the well-rounded background was really helping me with being involved with every aspect of this business and being involved with growing the business. And that's really kind of where I realized, oh, I probably do have the skill set for the CEO role. So I stumbled into it. I would say it was not intentional and I benefited from having some great leaders that believed in me and put me in positions to just lead different teams and lead different functions, and that was certainly great for my career.

Speaker 2:

Yeah, and one of the things that really stands out as you describe that is how many of those leaders were looking at you, identifying the talents that you had and how they might be able to contribute to rounding those out to be a fuller candidate for other roles within the organization, and I'm sure that was part of the reason that you were able to stay there as long as you did and have some enriching experiences that weren't the same day, over and over and over again for 24 years, and that's really important.

Speaker 1:

Absolutely. It seemed like almost coincidental, but anytime that the role I was in was getting stale, there was just something else there someone was asking me to step into. And I think that's that's great. And when I think when leaders in a business can identify that you've got, you know, high potential people that can do different things. You want to give them those opportunities so they don't get stale. And, and I certainly yeah or leave Right, and I certainly you know certainly benefited from that.

Speaker 2:

Yeah, that's fantastic. You know, one of the things that folks talk about a lot is how big corporate things don't match with a smaller organization. Right, Like, we're totally different, we're unique, we're special. Right, and be true about that is there are a lot of support systems within a large corporation that all of a sudden you're kind of bootstrapping it a little bit when you're in a smaller organization. Where were some of the moments that you thought, okay, I know what I did before, but now I have to really figure out how I modify it to fit where I am now?

Speaker 1:

Yeah, so lots of different areas, becky. So to give some scale here, the large organization I was a part of broadly speaking 25,000 employees, but the business unit I was in probably 1,500 employees. So that's the scale I was used to. And then I'm coming to an organization where there's 30 employees in the US and then there's an engineering team that's offshore. I think the first thing is, in a large organization you can certainly be a culture champion, but I don't know that you're going to have a huge impact on changing the culture. Well, in a small organization, especially in a leadership role, you can really have an impact on the culture and you can really shape the culture. And I loved that aspect of this role because the organization was so small that you really had complete ability to motivate and inspire people and really develop the identity of the business. And that was one aspect that was big.

Speaker 2:

Yeah, and I mean, you had powerful product that you knew was marketable and you just had to scale it and spin it up right, just right, make magic happen. There's just sparkles and everything that happened, and then it's magic. And then this building of the culture that you had some familiarity with, but in a vastly different environment. What would you say you learned about yourself as you shifted into this smaller environment, as you shifted into this smaller environment.

Speaker 1:

One of the things I really learned, Becky, was because I had a fairly broad-based background, I could be a true thought partner to almost everyone in the organization in the small business. So whatever the function was or whatever we were working on, I could partner with them. In a small organization, you're rolling up your sleeves and you're doing the work. And I liked the opportunity to help marketing, help sales, help product help finance, help the people function, because I had had enough exposure.

Speaker 1:

You know, prior to coming to the small organization I guess I probably didn't realize how well-rounded I was and how that was really going to benefit this business, because in a large organization you've got teams behind you, You've got lots of potential resources to help you. Small business, you don't. So not only as CEO, I'm wearing multiple hats, but everyone else is kind of wearing multiple hats. So the ability to be a thought partner and be involved in everything that was going on and have a positive impact, not only with getting the jobs done, the tactical, but also coaching and mentoring people and seeing them grow professionally, that was very rewarding and I guess I probably didn't realize coming into it that it was that good of a fit. I would say.

Speaker 2:

Okay, yeah, and I mean what a leap of faith that you took with that right. It's like I've never done this before, but I like these guys, so let's see what we can do together, because it feels like there could be magic. And when you think about that, how did that affect your choices going forward?

Speaker 1:

Yeah. So you know, getting into the organization, we kind of really needed to take advantage of the fact that this business had a great product and it was truly unique and differentiated. So at the time marketing was outsourced. I brought marketing in-house Sales team was very small Hired more people into the sales team leadership as well as sales representatives or account executives, and then an SDR function, a sales development representative function, and built out the customer success team.

Speaker 1:

So one aspect of this was doing quite a bit of hiring. So you had to be very good at evaluating talent, using your network to find talent and scaling process. So it's about people, process and technology. The people part is the most important. But when you're adding so many new people, it's important to have organization, structure and design in mind and have the systems that you're going to need for people to be effective. And then the managers and directors in the business kind of coaching and mentoring them. The managers and directors in the business kind of coaching and mentoring them.

Speaker 1:

And all of that happened kind of in year one, which is kind of fast things. You know that things were going very well, the business was scaling, and that's when the co-founders appointed me CEO. So you know at that point I was doing many of the CEO type functions. Then I actually assumed that title and, you know, continued to grow and scale the business and then at this point the business is growing really well. We've doubled in size in terms of the number of staff and the co-founders because this was a bootstrap business at the time, you know decided to go to the private equity market. So that was kind of another inflection point.

Speaker 2:

Another shift? Yes, yes, absolutely yeah. And when you think about other people who are experiencing layoffs right In the last few months there's been a lot of that out in the news that companies are downsizing, reorganizing and changing, what is it from your experience that you think that other people should really hear?

Speaker 1:

Your network's really important. You should be always networking. Again, in my situation I was a little naive, didn't realize the pink slip was going to come my way. And then, when it did, I was fortunate that I had a job that allowed me to have a network. But I know from others that I've spoken with that have had a surprise layoff. They don't have much of a network. They are really doing lots of heavy lifting to network at that point.

Speaker 1:

And when you're networking and you're out of a job, it's a little bit harder. I think one takeaway and I've told my kids this, I've got some kids that are young professionals at this point keep building your network, keep your network active. It develops from the fact that you're forced to. You know, look out at what's available and potentially have, you know, a career pivot that's going to be really fruitful. And you know, I think I think it's important to try to keep that mindset.

Speaker 1:

And then I heard for many years that you know when you're finding it, when you're trying to find a job, that it's a full-time job. It absolutely is a full-time job. It's more than a full-time job. So just expect that you're going to need to have that kind of discipline. So the discipline of I'm going to put eight, nine, 10 hours a day in every day with this idea that I'm networking, I'm having conversations, I'm keeping an open mind and you never know when that opportunity is going to pop up.

Speaker 1:

And uh, you know, when I, when I went to meet these co-founders, I didn't know how great of a fit this was going to be. And uh, and I know, I said I had no doubt that it was the right opportunity. What I had no doubt about was I needed a job for sure, and that this seemed like it was going to be a great opportunity. And I also told myself, if it's not, maybe I'm there for a year and a half and then I look for something else and I've already got a network that is active enough that I could probably fire it back up.

Speaker 2:

Yeah, it might not be the right job, but it could be the right now job.

Speaker 1:

Yes.

Speaker 2:

And you really leaned into the idea of let's hope it's right. You know, and it sounds like you had a really powerful and great experience there. I also know that you have just recently successfully been through that job search process again. How was it different this time than it was back then in 2019?

Speaker 1:

Yeah. So that small business I went to that I helped grow and scale. There was a very nice exit with that. So that put me back into the job market looking for my next opportunity and this go around. I saw it coming and it wasn't. You know, layoffs are never positive.

Speaker 1:

This was certainly a situation where it was a planned exit and and also a a situation where I was a different point in you know kind of my life where, um, my wife and I are empty nesters now, uh, and I could just be choosier and um, and I also knew that much more about what it's like to work in a big organization, what it's like to work in a smaller, you know, high growth business. I knew more about the private equity landscape because we had gone through that transition at the business that exited. So I had a much more educated purview on what I wanted and what I didn't want. So I was able to really field quite a few different opportunities, said no to a number of them, just I wasn't that keen on them, whereas back in 2019, that was the first job offer I got was the one that I ended up taking In this go around.

Speaker 1:

I had four different job offers I turned down and the fifth one was something that I was very keen on and that came after probably 12 different conversations so meeting with investors, meeting with most of the leadership team in that business and doing my own homework. So I guess I was just not only more educated about the opportunities that were out there, but also I had more flexibility to be choosy and just more savvy, because now I had more background and experience with different types of jobs, different size organizations, so I could just make a more educated decision.

Speaker 2:

Yeah, and I mean you recognize how prepared you were to be able to lead a small organization where that first step out there had to be questions about, well, what's this going to look like for me? And now you know that that's a possibility and that you can find success with that. I'm curious is there anything else that I didn't ask you about that you would want to make sure that the listeners heard.

Speaker 1:

I think you nailed it there with. When I took the role at the small business, I had confidence that I could help the business. I didn't know how much I could or how it would evolve and would I have an opportunity to be CEO. Once you've had those accomplishments and you can kind of check those things off, you go into your next role, you know, with that much more confidence. And I guess what I would say a good takeaway, I think, is this next role I'm taking is another CEO role. It's a CEO of another small technology company that improvements from the first time to the second time. So I had a great run as CEO in this small technology company that just recently exited.

Speaker 1:

Now I'm going to a new one. I even have that much more confidence because I already know I'm going to a new one. I even have that much more confidence because I already know I'm going to have fewer blind spots, I'm going to be more proactive and again you're just going to make more improvements, especially between the first time and the second time you do something. So I feel good about kind of all aspects of what I can bring in terms of leading people, in terms of developing strategy, in terms of developing strategy in terms of thinking about a product roadmap that's going to help us grow as a business and then, just you know, working with, partnering with investors and other stakeholders, all those sorts of things. Now I'll be doing a second go around and I feel I'm ready to get started right now.

Speaker 2:

So yes, absolutely no. I can fully appreciate that and I'm just thrilled that you were able to join me on the podcast today and really share this story with the listeners. I think there's a lot for people to learn, and I just want to thank you for joining me today.

Speaker 1:

This was great. I appreciate the opportunity, becky, and I don't know how long we've been going, but it feels like it flew by, so it must have been well. It was an engaging conversation, for me for sure, so.

Speaker 2:

Yeah, me too. So thanks again. I appreciate so much of what Scott shared in his story and I'm thankful he joined me today. It's especially poignant right now. So many people have lost or are losing jobs. These days it's hard to find the right role in any situation, and that much harder when you feel the bitter sting of a layoff. Scott faced the pressure to provide for his family and put in the time to find that next role. Maybe you've been putting in the work and still not finding the right role. That next role Maybe you've been putting in the work and still not finding the right role. Before I talk about anything else, I'd encourage you to give yourself a bit of grace. If that's you, acknowledge the work you are already doing. Beyond that, I hope you also heard something in Scott's story that inspired you to try something new or re-engage in a meaningful way.

Speaker 2:

Scott admits that his career trajectory wasn't particularly intentional and he was grateful for others paying attention and guiding him. Recognizing how transferable your skills are doesn't show up in a dream. Scott spent time talking to people about his efforts and contributions and that realization surfaced for him. He did have powerful building blocks and you have your own version of that career story. Whether you want to position in your current function, industry, organization or not, knowing the value of your skills and contributions is key. Scott needed that career story for the powerful networking he did. Scott needed that career story for the powerful networking he did. Yes, the goal was to find the next position and that included asking for help. That said, he was truly focused on connecting and building relationships.

Speaker 2:

Networking isn't about asking someone if their company is hiring. Networking is about sharing that you are in a search mode and acknowledging they may not have an opening or even be a hiring manager. The biggest ask is who do you know that would be good for me to meet? In the end, it's how you put the pieces together. The career story changes depending on how it applies to the possible new role. Confidence sells. If you want anyone else to believe you can do something, it's critical to cultivate that belief deeply within yourself. Maybe you're interested in connecting with Scott to network and learn more about his story. Check out the show notes to find him on LinkedIn. If you do, be sure to ask him who may be good for you to meet. Thanks for listening. If you found this episode helpful, share it with someone who could benefit from it. Until next time, I'm Becky Fraser, reminding you to integrate who you are with how you lead. Okay, bye.

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