Courage, Curiosity, and Cold Calls | Joseph Lesser

Joseph Lesser: Speaking the truth in love, as it were, is a gift right to the other person, even if it doesn’t always feel that way and receiving that from somebody else. The same thing, like I tell a lot of new members when they come onto my team that I say, listen, you’re never gonna hurt my feelings or offend me by giving me critical feedback. 

What’ll really frustrate me is if you just tell me what I want to hear, and then show up one day and say, Hey, I have all these issues, and let me run through this laundry list of things. And it’s like, where did this come from?  

Anderson Williams: Welcome to Everyday Heroes, a podcast from Shore Capital Partners that highlights the people who are building our companies from the inside, every day, often out of the spotlight. 

With this series, we want to pull those heroes out of the shadows. We want to hear their stories, we want to share their stories. We want to understand what drives them, why they do what they do, how they might inspire and support others to become Everyday Heroes too.  

In this episode I talk with Joseph Lesser Regional Sales Director with Courser. Joseph was a part of PTG, the founding platform that partnered with Shore to create Courser. He talks about that experience, his misconceptions and realities, and the longstanding and critical mentorship he’s had with Reed Wilson, the founding CEO, including a great story of how and why Reed eventually hired Joseph. 

Joseph shares his transition from individual sales leader to a leader of people, and how he has grown to meet that challenge, including relying deeply on his faith to define the kind of leader he wants to be and his team members deserve.  

Before we dive into more of that, is there something just to get us started that we should know about you? Anything new in your life, Joseph, that you wanna update us on?  

Joseph Lesser: Yeah, absolutely. So we actually just had our second child about three weeks ago, so still in the very sleep deprived state. But feel very fortunate and very blessed to have him. So we have two boys under the age of four, so the rest of life is gonna be a wild adventure, I’m sure. 

Anderson Williams: What has, being a dad of two boys taught you about a growing business and leading sales with a growing business?  

Joseph Lesser: You know, it’s actually funny. We’ve been to some classes on things where they’ve talked about different topics and a lot of the things that I’ve learned for parenting can actually be applied to the business world, which sounds terrible to say and don’t mean that the way it sounds, but one of the things they talked about was. 

You know, if you always do things for your kids, you’re sending the message. You don’t have what it takes. You can’t do this yourself. And I actually took that away and took that back to my mindset with my team of I really need to empower these folks. If I’m doing the thing for them, I’m inadvertently saying, Hey, I don’t think you have what it takes, which is not true, right? And same with your kids.  

Anderson Williams: So tell us a little bit about what Courser is and what Courser does. So we have a little bit of context for your work life.  

Joseph Lesser: Absolutely. So we are a managed IT service provider or an MSP, and essentially what that means is we provide IT support and cybersecurity to small to mid-size businesses. 

And oftentimes that takes the form of their busy running their business, whatever that is. Whether it’s a law firm or a CPA firm, or a manufacturing facility or a nonprofit or a healthcare facility or any number of other things, they’re busy running their business and so they work with us so that we can handle the it. 

That way they don’t have to worry about it because especially in the current landscape, which how cyber threats have evolved and everything else, it’s a lot for somebody to try and manage themselves. And even if they have the expertise for it, usually their time is far more valuable spent elsewhere.  

And then there’s also a piece of our business that is working with folks that have an internal IT team, but they either are looking for cost savings as opposed to having to build out this giant team to get all these different specializations and boxes checked. Or maybe it’s a single individual and it’s just more than they can handle by themselves, or they’re extremely experienced and wanna do more strategic projects and initiatives and they don’t wanna help Suzy connect to the printer, so.  

Anderson Williams: So how did you get into that work? You said you’ve been there five years. Give us a little bit of background about how you got involved.  

Joseph Lesser: Yeah, it’s actually a bit of a funny story. I don’t know if I have time to go into the whole story on this, but essentially I worked in several industries before this, and the one right before it was selling copiers, but a lot of copier companies have also gotten into the IT space. So I was very familiar with that. 

Although our CEO jokes that when I started, I didn’t even know how to spell IT. So really I was part of the same executive level sales training that the CEO of our company and some of his team was a part of. And so I got to know him there and we had talked for several years about me coming to work for him and the stars had never just aligned quite right, but you know, third time was the charm. And got to come on board initially in a business development, pure hunting sales.  

Anderson Williams: Joseph chuckled a bit as he started to answer that question, which suggested there was more to the story. While he didn’t offer the details, his boss and PTG, founder and Courser, CEO, Reed Wilson did. 

Here’s Reed’s version of how Joseph joined him at PTG.  

Reed Wilson: One of my favorite stories about Joseph is we were in a Sandler class. We still use the Sandler methodology very heavily here at Courser and well before the Shore hold, the PTG business was using it. And I actually met Joseph in a Sandler training class. He was there every single week, and I remember looking at him thinking, God, this guy is young, like he is young.  

And as a business kind of grew, you know, pre Joseph. I was involved less and less, and Sandler and, and the sales teams went and, you know, candidly, I kind of forgot about him and I just remember this story. 

I was on the vacation with my family. I was, my daughter was super young. We were playing in the sand, and my phone rang. I didn’t recognize the number and so I didn’t answer it, and they left a voicemail. And so I listened to the voicemail and the voicemail went just like this. I’ll never forget it.  

“Hey, Reed, Joseph Lesser. It’s really important that we talk. Call me back. “ 

I was scratching my head like, who is this guy that is calling me? I vaguely remember his name, but I can’t put a face with a name. So I got a shell. I, this is not a lie, like I remember this. I got a shell and I wrote the number down in the sand and I called the guy back and I was like, Hey Joseph, it’s Reed. What’s so important?  

And his response was, it is really, I. Important that you hire me. And I thought, wow. Like, you know, that’s a pretty gutsy move and I ended up hiring him and the rest is, is history. But I think, you know, that to me just epitomizes kind of his willingness to try new things. And you know, he won me over there and it was a very successful cold call. 

But I just think that’s a really good story of kind of how he thinks and how he operates.  

Anderson Williams: I love this story so much. It says something about both Joseph and Reed in the cold call, the courage and tenacity of Joseph and the openness, availability, and respect of Reed for this young man he didn’t even remember at the time. 

Clearly it worked out, and as this episode is celebrating Joseph five years later as an Everyday Hero at Courser, so I wanted to hear from Reed from his perspective after all these years, what has made Joseph so special to Courser and has proven him right in taking a chance on hiring him.  

Reed Wilson: There’s a lot. I think that makes Joseph a hero. 

I would say, if I had to pick one thing that makes Joseph a hero, it is just that he is incredibly curious. He asks so many questions, and I think the best people ask lots and lots and lots of questions. I think the best leaders give space for people to ask lots of questions. But if I think about Joseph over his, I don’t know, probably five years here, he has never, ever, ever lost kind of the thirst for learning. 

And I think a great example of that is, you know, prior to us joining the Shore ecosystem, Joseph and I had a one-to-one scheduled every Friday. ’cause I was the CEO of that business and he reported to me. And even post acquisition, you know, we’re 40 months into our hold here. Joseph no longer obviously reports directly to me, but he has been very, I’d say, adamant about keeping that time every Friday for us to spend a half an hour together. And without question, he brings me a list of probably six or eight questions. You know, things that he just wants to learn more about. And to me that, you know, there’s a lot that makes him a hero, but that would be kind of the underlying thing for me. 

Anderson Williams: Curiosity, what a powerful characteristic. And what I love about this story is that despite the growth of Courser, the evolving roles and responsibilities of both Joseph and Reed, it has been Joseph’s curiosity that has compelled him to hold that 30 minutes per week with Reed sacred and for Reed to return the investment. While he didn’t speak directly to his own curiosity, Joseph shows us in this next segment how this attribute has compelled his career forward.  

Give us a little bit about how things have changed since you started in that first role for you and for the company. Really.  

Joseph Lesser: Yeah, so it’s really interesting because a lot has changed, but also not a lot has changed, and that’s been very pleasantly surprising. 

So the biggest change has been just the growth opportunity. So when I started, like I said, I was doing new business development. I reported directly to our CEO and founder, and there was no room to go up. Like I came in as high up as you could go, and you know now as a regional sales director, it’s really interesting because sort of the progression there was started out as solution specialist, which is that new business development hunter role. 

Then when we partnered with the team at Shore and Courser came into being, I moved into a director role, which like I said, had previously been what our CEO was doing. But as he took over responsibilities of being the CEO of the whole company, it was no longer realistic for him to also be the sales manager. 

And I will say that was a little bit like coming in right after, you know, Nick Saban or one of the great coaches of all time because we had an incredible organization and he had built an incredible team. And so it was, sometimes, I think it’s easier to come in in a place where it’s a mess and you’re having to turn it around as opposed to coming anywhere. 

Anderson Williams: It’s easier to be the hero there. Right?  

Joseph Lesser: Exactly. Exactly. But so I moved into that director role, which was totally new, not something that had been on the radar before. And then a year later moved into a regional sales director role, which again, was a position that didn’t even exist. And something that wasn’t even on my radar. 

It’s not like I sat there five years prior and said, in my five year plan, I want to be a regional sales director. So, long story short, a lot has changed internally as it relates to growth and responsibilities and everything else, but not a lot has changed as it relates to service to our customers.  

Anderson Williams: Well, when you go back to that time when you first knew that PTG was gonna partner with Shore and private equity, did you have concerns at the time? 

Just do you remember any concerns about private equity coming into the fold?  

Joseph Lesser: I remember exactly where I was, exactly how I felt. Yes, I thousand percent had concerns because with previous companies, I had been through acquisitions on both sides, both where you’re being the one acquired and where you’re doing the acquisition. 

And in all of those cases I had seen where it was new group comes in and old people are. Go oftentimes for no reason whatsoever, just, you know, cutting costs, cutting heads, et cetera. So, yes, was very nervous expected everything’s about to change. I have this great company, this great organization, we have great customers, and all of it is gonna change. 

And so that’s why I was saying it was a very pleasant surprise that really the bulk of the changes were highly positive in nature.  

Anderson Williams: Really, as you were describing, your pretty rapid growth since that time and new opportunities out in front of you that you hadn’t necessarily even thought of. You know, growing companies create opportunities for growing people. 

Joseph Lesser: Right.  

Anderson Williams: How have you grown? I mean, it’s one thing to be a high performer in a growing company. It’s another thing to be able to move to director as quickly as you did, and then to your regional role as quickly as you did. How have you made sure the company didn’t just outgrow you, where they hired somebody in for a director or they hired somebody in for the regional role, but rather built on what you were doing. 

Joseph Lesser: So I think there’s a handful of things that go into that one, and there’s certainly times where it makes sense to say no to an opportunity, but I think one of the things was not saying no to any opportunities to develop myself personally and grow, even if it meant more work in the short term. And interestingly enough. 

When the idea of a regional sales director, for example, was being molded around, my initial reaction was, ah, I don’t know if I’m ready for that. I don’t know if I wanna do that, et cetera. But when the time came, I said, this is a great opportunity. I can’t say no to this opportunity and I’m very thankful that I didn’t.  

But I think a lot of times in a really fast growing company, it requires a lot of hard work and a lot of personal investment. And so I think realizing that it’s not a one for one trade. It’s not like I’m gonna do this one thing and I’m immediately gonna see this result, but it’s constantly putting in a number of different inputs. 

And so for me, that looks like number one, I’ve been very fortunate from day one at PTG and now Courser to have a phenomenal mentor in Reed Wilson. And then when we had our CRO, Jim Patterman come in, he was also extremely instrumental in my transition into leadership because I had moved into a director role about two months before he came on board, and it was incredible having him come into the mix and be able to have somebody there who is helping guide and shape that. 

As well as I also have an outside mentor, who is experienced in sales management, and I had had several mentors prior who were mentors at the sales rep level. So I would say mentors is a big piece of it.  

The other is, you know, I read several books. So one is called Making the Climb and we’re a part of a like I said, executive level sales training called Sandler Training, and this was written by one of a Sandler trainer, and it was specifically how do you make the jump from being an individual contributing sales rep to a leader? I think it was him in this book. There was another book I read that was really instrumental that I’ll mention as well. 

One of them said the only thing that sales manager and sales rep have in common is the word sales. And I remember when I read that thinking that’s probably an exaggeration. That can’t really be true. But then after making the transition, that is very accurate.  

The other book that was really instrumental was a book called The First Time Sales Manager by Mike Weinberg. And so I think both of those combined with the mentorship were extremely helpful. And then I was fortunate to get nominated to go to the Shore Leadership Academy. Learned a ton from that. I’m sure my team is tired of hearing me talk about that and provide insights from it, and I’m sure there’s other avenues as well, but I think the biggest thing was just looking for those opportunities, not being afraid to ask questions and dive in whenever the opportunity presented itself. 

Anderson Williams: I love that insight of the sales manager versus the sales rep, but it’s little moments like that where the world crystallizes a little bit when you realize that distinction, and I think it’s really profound. And so I want to talk a little bit about that shift for you, because I read this on your LinkedIn profile and I want to ask you about this perspective. 

You have on your profile, “My passion is helping other people. I discovered early in my career that when I help a business succeed, I’m helping an entire group of people live better lives.”  

Will you talk more about that mindset and where it comes from for you and how that has played into your ability to shift from that sales rep to that sales manager role. 

Joseph Lesser: Yeah, my faith is something that’s very integral to who I am. And interestingly enough, something that some people know about me, not everyone knows about me, was going through college, I was actually on a path where I was planning to become a youth minister and I was working on a business degree. ’cause I’d always enjoyed sales and that was the backup plan as it were. 

And through, you know, something we could certainly talk about over a cup of coffee sometime it felt like some doors closed and it made sense for me to move into the sales function. But the reason why I bring all of that up, the faith that I have is really around this idea that my job or goal in life or purpose, purpose is a good word for it, is to basically bring glory to God and also to love others, right? 

And so what that looks like to me, and when I think about loving my neighbor, it’s helping them reach their full potential, helping them be successful and live a better life. And so really that’s what drives that. Like that’s the big why behind it, but interestingly enough, you know, one of the things for why I wanted to get into management.  

I had seen the impact that it had on my entire life when I had a good manager and the impact when I had a bad manager. And so for me, I was like, you know, when I look out there and when I think about the stories I hear from people, I’m making up percentages here, but it seems like maybe 20% of managers are really good. 

But the impact that they have on those employees’ lives is really profound, and I wanted to be a part of that. I wanted to be that type of manager. And my hope is that I have done that. So I hope if you talk to my team that they would agree with that. And it’s similar to my wife and I were talking the other day. 

I was getting a little bit emotional thinking about as we had our second child, and just thinking about that this little baby is one day going to be a full grown adult who’s going to impact hundreds if not thousands of other lives. And it’s really incredible, the opportunity as a parent that now instead of just the people that I’m able to impact day to day, I’m gonna be able to indirectly impact hundreds, if not thousands of lives through our two sons. 

And I view it very similarly with our team. I want them to look back and say, I’m better from having been a part of this team?  

Anderson Williams: Well, I think it’s really profound. I think the clarity that your faith brings to you about your purpose on the planet and working through others and enabling others opportunity is exactly what faith is for, right? 

And it plays out at work. It plays out with your kids, it plays out wherever you take it because it’s not situational. It’s deeper than that. I think it’s really beautiful to hear you describe that, and I’ll say that to your point of your team. I will quote your Everyday Hero nomination now that said that you, in your annual engagement survey of your team got a hundred percent positive rating, which was the highest among all Courser managers. 

Joseph Lesser: Yeah, that was incredible to hear. You know, I’ve had several successes in my career, but that’s gotta be up there as in my personal opinion, one of the biggest.  

Anderson Williams: For sure. So now the hard question, how do you do it?  

Joseph Lesser: Well, you know, I think there are so many different things that go into that, so I’m sure that I’m going to miss some things. 

I think number one, I’ve been fortunate. I have a great team. I’ve been able to build a great team. There have been some other folks that were already on the team prior who have helped continue to make it a phenomenal team. I think, like I mentioned before, I’ve been fortunate to have a lot of great mentors and at the end of the day, if you think about it, with a survey like that, if the organization was terrible, it wouldn’t matter how I could be the greatest manager in the world and it wouldn’t matter, right? You’re still not gonna get those scores.  

So I think it says a lot about the team, a lot about the organization, but I think without knowing for sure, my gut says a big part of it is my team knows that I genuinely care about them as people and want what’s best for them. And I think they also know. I hope they know this. ’cause I try and say it a lot. I really, really, really value their feedback and input. And so I tell ’em all the time, I may not be able to solve every problem, but please bring it to me. Like, tell me what it is. ’cause if I don’t know about it, I can’t solve it.  

And I’ve told them this, I’ve made them this promise and I’ve, you know, thus far been able to back it up. I’ve, I’m never going to. Get upset with you for bringing a problem. I know a lot of organizations, people may have had bad experiences in the past and they’re worried of like, Hey, if I bring this up, they’re gonna be like, oh, this person’s just a complainer, or whatever it may be. But really my belief has always been that it takes a lot of courage and guts for somebody to come to their manager and share feedback. 

And so it’s not an easy thing to get. So I fight really, really, really hard to try and get them to share that as well as I also try and regularly do anonymous surveys through like Microsoft Forms. And then I think a big piece of that, and again, going back to being authentic and the team knowing that I care about them and that I trust them, is like I will share that with them. 

Like we’ll go through it in a meeting and I’ll say like, here was this question and here’s a pie chart of the responses. And so, you know, in my mind I don’t wanna hide anything. So if they all gave me terrible reviews on something or great reviews on something, I want them to know. Obviously I don’t share the written response feedback for fear that it might lose some of the anonymity. But the anonymous feedback, yes, is all shared. I think that’s the big thing.  

I think the other thing is I don’t tend to sugarcoat things, but I’m also not the kind of person that would come out and just be aggressive or say something mean or in a rude way. But I will be very direct with somebody and I, as much as it makes me uncomfortable, and as much as I would rather overlook it or not bring it up, I’ve learned that, you know, if something’s happened twice or certainly three times, now you have a pattern. And it’s way better to address that now, as opposed to letting fear win the day and you put that off and then it comes back to bite you down the road for both you and that individual.  

So several things there. Like I said, I’m sure there’s a lot of stuff that I’ve forgotten. It’d be interesting if you asked my team that same question. I’d be curious to hear their answer and I may have to ask ’em now, so.  

Anderson Williams: Your nomination specifically mentioned, your listening and your feedback sessions and some of the things that you’ve described there. I’m just curious your thoughts, I can’t help but think about your conversation about both your faith and that sense of purpose. 

You know, a lot of new managers in particular, and certainly young managers, your a young manager, would find it really difficult to hear hard feedback on their own performance and find it difficult to give someone else hard feedback out of empathy or a sense of caring, but you’ve been able to do that, and I wonder to what degree you attribute that to that sense of purpose. 

That sense of purpose is bigger than the short term discomfort of receiving difficult feedback or giving difficult feedback. It just is on my mind as I listen to you.  

Joseph Lesser: I think to your point, yes, it does tie back to that deeper purpose and why, and you don’t have much of a relationship if you can’t say the hard true things. 

I remember something that you shared in the Leadership Academy that I think applies there as well is trust is something that’s built up over time and the time to build trust is not when you need to withdraw something from the bank of trust, as it were. So you need a lot of trust already to be able to have that conversation or to receive that feedback.  

Because what I think was really hard early on, though, I think now is in the culture of our team, is this idea of you sharing critical feedback with me is not going to hurt you. It’s not going to impact you negatively or the way that I view you. It’s actually, like I said, I view it as a huge asset because I know that feedback is out there and it exists. 

And if I don’t know it, then I’m blind to it and potentially I’m going to run into a brick wall ’cause of it. That could have been avoided.  

Anderson Williams: To wrap up, I asked Joseph what was the best advice he’s ever received and he referenced a quote from a book he’d read somewhere along the way that brought him back to the depth and roots of his faith. 

Joseph Lesser: Whatever you let validate, you can also invalidate you. And so I think, you know, going back to what I said at the beginning of faith being really critical and important to me is, you know, at the end of the day, the only thing that I can or should let validate me that I know for certain won’t ever invalidate me is my father God. 

Right. Like so trusting that what he says about me and who he says I am is more powerful than what anybody else thinks about me or says about me, because otherwise I’m just gonna be up and down with the waves, right? So when I’m doing really well and having a lot of success, I’m gonna be like, wow, Joseph’s, you know, really valuable and is this great person? 

And then when I’m having a bad day and I’m not being the parent that I should be, or I’ve you know, lost the big deal or had the major failure at work. Having that view prevents a lot of that up and down.  

Anderson Williams: Joseph Lesser is an Everyday Hero whose superpower is his faith. Through it, he has found deep purpose in leading and developing opportunities for others to learn, grow, and find their own career success. Joseph has leaned on his faith to find balance and even out the highs and lows that come with rapid personal growth, life changes, and a hard charging career. 

If you enjoyed this episode, check out our other Everyday Heroes at www.shorecp.university/podcast. There you will also find episodes from our Microcap Moments as well as Bigger. Stronger. Faster. series. Each highlighting the people and stories that make the lower middle market space unique. This podcast was produced by Shore Capital Partners and recorded in the Andrew Malone Podcast Studio with story and narration by Anderson Williams. Recording and editing by Austin Johnson. Editing by Reel Audiobooks. Sound design, mixing, and mastering by Mark Galup of Reel Audiobooks.  

Special thanks to Joseph Lesser and Reed Wilson.  

This podcast is the Property of Shore Capital Partners, LLC. None of the content herein is investment advice, an offer of investment advisory services, nor a recommendation or offer relating to any security. See the Terms of Use page on the Shore Capital website for other important information.