Unlocking Human Potential with Jim Morrisroe, CEO of 15Five

Dan Balcauski speaks with Jim Morrisroe, CEO of 15Five, on the SaaS Scaling Secrets podcast. Jim shares his journey from enterprise sales leader to CEO, emphasizing transformation moments, including his tenure at Zimbra and overcoming personal challenges. They discuss the importance of data-driven, targeted employee engagement, managing multi-generational workforces, and navigating the complexities of remote work environments. Jim highlights the critical role of effective leadership and mentorship in driving productivity and company success, offering valuable strategies for B2B SaaS companies aiming to scale.

00:30 Meet Jim Morrisroe: A Journey in Tech Leadership
01:35 The Zimbra Experience: From Minor Leagues to Major Leagues
03:11 Building High-Performance Teams
06:30 The Vulnerable Side of Leadership
12:27 Joining 15Five: A New Beginning
15:06 Employee Engagement and Performance
21:33 Remote Work and Productivity
28:45 Generational Differences in the Workforce

Guest Links
15Five.com
https://www.linkedin.com/in/jmorrisroe/

Transcript

Dan Balcauski: 0:20

Welcome to SaaS Scaling Secrets, the podcast that brings you the inside stories from leaders of the best scale up, B2B SaaS companies. I'm your host, Dan Balcauski, founder of Product Tranquility. Today I'm excited to speak with Jim Morrisroe, CEO of 15Five. Jim is a veteran technology executive with over 25 years of experience building and Scaling software companies. He has an impressive record leading four companies to successful exits. At 15Five, Jim's helping organizations develop their team through 15Five performance management and employee engagement platform. Let's dive in. Welcome Jim to SaaS Scaling Secrets.

Jim Morrisroe: 0:46

Thanks, Dan. I'm happy to be here.

Dan Balcauski: 0:48

I'm excited for our conversation today. I think you're gonna have a lot of good insights around leading, managing, increasing performance of teams across organizations for our audience. Before we get into that though, I wanna know a little bit more about you. We all have these moments in our lives where, our perspective, our mindset, our view of what the world looks like changes almost in an instant. I like to think of it as a superhero transformation moment. One day, you're Peter Parker, normal high school student. You get bit by a radioactive spider. Next day you wake up your Spiderman. What has that been for you and your journey?

Jim Morrisroe: 1:22

Yeah. Well, so, so thanks for teeing that up. I'm gonna, I'm gonna do a slightly more traditional version of that answer and then I'm gonna do a little bit more vulnerable version. I'll, and I'll try to break'em up. So, so the first one that, that. Transformed me was I was cruising along as an enterprise sales leader in Silicon Valley working for a larger software and hardware company. It's a company called Cable Tron. I was at Lucent, I was at Cisco, and I got a recruiter call for a VP of sales at a company called Zimbra. As an a company, we ultimately sold to Yahoo and then I spun it out and sold it to VMware after that the company was funded by Excel and Benchmark and RedPoint and had a CEO named Satish Dharmaraj and a president named Scott Dietzen, who have gone on to do amazing things. And the transformation that I went through, is it. Literally felt like I went from the minor leagues like not even triple a ball, like from single a ball to all of a sudden I'm in the majors, the the intellectual capacity of these people. The the drive, the passion, I. I'm not a hundred percent sure what they saw in me because I was a rookie pitcher coming out of single A, but it, it absolutely transformed my life not only relationship wise, but what it took to be to have the grit and determination to build a company.

Dan Balcauski: 2:42

You mentioned, it felt like all of a sudden you were in the major leagues. What was it that you saw that all of a sudden you're like, oh these people are operating at a different level, or they're thinking about things a different way from where you were sitting before, as in your previous roles.

Jim Morrisroe: 2:56

I mean there, there was no one thing, there were, millions of small things, but the the concentration of talent that they had assembled within this company, we ha we have, we all know this concept of a 10 x engineer. We had 10, 10 x engineers. We know the concept of long work weeks, but to do things organized and in a way where everyone's rowing in the same direction. I had never seen that type of polish in a company and that just raw collection of horsepower. And so that has stuck with me. And we, we I have a belief that. All humans are amazing. But a company to, to succeed in this environment it takes really a group of amazing humans that are going the same direction. And we had both of those things.

Dan Balcauski: 3:42

Well, I actually, I wasn't planning on going this direction, but you did bring up something interesting. I was listening to a podcast the other day and they were talking about how Patrick Collison at Stripe was able to recruit Greg Brockman who is, distinguished engineer one of the founders of OpenAI. Incredible talent and. Honestly the sort of lesson learned there was a little bit disappointing because they were asking, well, like, well, look, how did, how is Patrick and his co-founder able to, attract, a talent like Greg Brockman.'cause I hear a lot, people will be like, oh man, we, 10 x engineers, right? We want the rockstar engineer, right? How many PO job application posts are written with it? We want the rockstar talent. And so the answer was, well, it was basically game recognized game like Patrick was able to attract Greg because Greg recognized the, unique talent that Patrick was, that Patrick, and vice versa. Was there something that you saw that allowed these folks to be able to bring in those,'cause it a 10 engineer right? They've got opportunity out the wazoo, so, was there something that you saw in the way these guys operated that really allowed them to pull in that type of talent? In mass,

Jim Morrisroe: 4:47

Well, I think that's amazing insights there is that and it brings us ultimately back to, at some point, to what 15Five is trying to help companies do. But it's that, highly talented people, highly motivated people want to work with other highly talented and highly motivated people. The net. Netflix book no Rules, rules is another great example of that where, Netflix decided to pay 10 x for 10 X engineers and to do that everywhere and to put actually their money where their mouth is, and they realized if they weren't getting the, that 10 x value. That that person either had to be coached up or coached out because they were going to drag the rest of the superstars in the wrong direction. And I think that ultimately is what what I found at Zimbra was that the collection of this talent ended up having a snowball effect for attracting new pe, new people of that same flavor. And the reason it was so formational to me is I must have had something of that because the, these guys know how to interview these people know how to interview. But it, my, I, my imposter syndrome immediately kicked in and I had to it forced me to challenge myself to a whole different level of of grit and passion and and tapping into things I probably didn't even know I had.

Dan Balcauski: 6:04

There's something uncomfortable and comforting at the same time about feeling like you're in the wrong room, like you somehow snuck in the back door among all these talented people. But it could also probably be unnerving. And there's, I guess, I guess the flip side is the Groucho Marx. I would never be part of any club that would, I have me

Jim Morrisroe: 6:20

Right. Exactly. That's, that's the feeling I had every day for the first, six months probably.

Dan Balcauski: 6:26

Well, at the beginning you said you had two takes on my question. What was your second take?

Jim Morrisroe: 6:30

The last one is, as I mentioned, is very vulnerable and it it's on the other end of that journey. So a after zimbra I had a chance to become a CEO and I had, and I will, I'll give your audience a little bit of a glimpse when you're the enterprise sales leader. The venture capitalists do not normally give their best companies to the sales leader to be the CEO. So, they usually try to hang on to the founder for as long as they can. And if if they have superstars in their portfolio, they bring a Frank Slootman in or somebody like that, that has an engineering and product background. And I didn't know any of this. And so when a enterprise sales leader is off to get his CEO wings, whether that's smart or not the most likely candidate is a distressed company. And that was clearly where I landed. And I built a be of, bit of a track record taking distressed software companies, SaaS companies. Polishing them up and ultimately selling them. And, some of my companies after after Zimbra were exactly like that. In addition to that, my wife and I had four kids in the East Bay of the Bay Area and they were all growing and playing sports. And my company, my distress software companies were somewhere in Palo Alto or San Francisco or San Mateo. And the. The internal tension of a distressed software company, a family of six. A horrible journey between a a work meeting and a JV basketball game. Literally could take four hours on some days and having to leave early or miss a game. That whole just life showing up. I ended up dealing with that in a really unhealthy way. Mostly having to do with copious amounts of vodka. And so my stress release was was alcohol and that almost killed me. And so, what what ultimately happened just about five years ago now, just before Covid started is I needed to make a decision. Either I find. A way to deal with life on life's terms, or I die and my family helped me get to that point. But it's I'm happy to say after five years I haven't touched a drop. I'm happier. I'm more mentally healthier, I'm more physically healthy. I do the best work of my lifetimes 10. And so, as I've approached 15Five in four years with, no nothing but healthy stress release. Techniques and a whole new energy. I, it literally feels like I have a superpower at this company because I don't have that burden of how I used to deal with life.

Dan Balcauski: 9:06

I really appreciate the vulnerability and authenticity in that. And I know that, being a leader of, in any role, a CEO especially could be a lonely, very stressful job. And, was there anything. I guess that you've been able a pro, usually I ask this sort of at the end, but given that you've sort of outlined the story, like, are, were there sort of ways that you're you've developed practices group, like groups, like how did like how have you sort of managed outside of that?

Jim Morrisroe: 9:33

Yeah. Yeah. I mean, listen, anybody that we all in the US or in the world have addiction is a unfortunate, story in, in a lot of our lives, either firsthand or through our family members. And, it's not a happy ending for the most part. 90% of people that become substance addicted end up on a path that leads to death. Recover is is really, really hard and ultimately, my. Initial path was through 12 step programs and and those type of things. But it led me to a couple of techniques that that are in play every day. The first one is to be of service. So there's nothing I. Worse for our mental health than to be stuck in our own head. And there's nothing that helps us get out of our own head more than being of service to other humans. And that can be just the old tradition of holding the door open at the grocery store. That can be doing something extra for your wife or your family. But I actually put it in play by, volunteer work primarily in the homeless areas. So I do a set of homeless outreach and food kitchen type stuff in some of my spare time. That helps, but it's, it has to be a daily practice and that's just not practical for me in this age. So that's number one. And then number two, if if any of you get a chance to spend any time with Marcus Aurelius's me, meditations, or stoicism in general there is some amazing wisdom, whether you are trying to improve your mental health or just, be a better executive. And so, Ryan Holiday's, daily Stoic is a ex or Twitter follow that I highly recommend and any of those practices around being present not reacting emotionally because that's only going to compound things and make them worse. Those two things. So of service. And then being, staying curious and, about, about the works of kind of the stoics is, has been a big part of my journey.

Dan Balcauski: 11:30

I appreciate you sharing both of those and for yes I've, at one point no longer, but I used to subscribe to the Daily STO as well. And for those who aren't aware of Marcus Realis or meditations, Marcus Realis Roman Emperor so, this is not a woowoo guy wrote a, basically his journal. Of how he was dealing with the daily stresses of ev all the pressures put on him and, was able to apply this philosophy. And if you think there's anyone who would have, absolute control over their environment, it could make the world bend to their wishes. You would think it'd be a Roman emperor at the height of Rome's power. But we find out even in from those personal writings that even that is not the case. So, we are all on this shared journey together and. The more, nobody gave us a handbook when we were born to drive this incredibly complex machine. So appreciate you sharing those tips. I'm gonna make a hard pivot back to the business world after that one. So I don't, I have, I don't have any good segues to move back into the business world after that, but I appreciate you sharing those stories. So, you were running a couple of distressed companies and now you're at 15Five. So just quickly kind of catch us up to present day, like how'd you end up at 15Five.

Jim Morrisroe: 12:34

Yeah, the, so I think I'll make the segue easily easy because they're directly related. So about a year into my journey I was and it was the first year of Covid, I was mostly doing homeless outreach work for my vocation. I. In fact, that's all I was doing. And they were paying me$12 an hour to go into the homeless encampments in the Bay Area to deliver food and basic services and friendship. And I had a kid at USCI had a kid at Colorado State and I had a freshman at Cal Poly and I had a big Bay Area lifestyle and I was making$12 an hour. I had gone, quite quite far in my. In my journey and the very, and I got tons of recruiter calls, but I talked to my wife and I said, I think I'm ready to put my new self back into my vocation. And the very first recruiter call I got at that point was from the 15Five recruiter David Hassell, who is this amazing human. Another kind of zimbra moment for me, which is wow. And David and 15Five were looking for at the time, a COO and David had this amazing business that the with a mission, which is we help humans be their best selves at work so they can do the best work of their lives. And the we've evolved. A lot of our product strategy, we've had to, and we've evolved our ICP and we've evolved how we have built products and, but this, the mission remains the same, is how do we help companies motivate, attract, and motivate people to do the best selves work of their lives, to be their best selves and do the best work of their lives. And I was like, wow, that sounds. One, not like a distressed software company because it wasn't, we had tons of money. We had, we were growing, we were so that was one thing I wanted to avoid, and two man, how. How tightly coupled is this to, to the new me, the stoic me, the the more enlightened, the less grinder and more intentional me. And so, I put those two things together and I told David at the time, if I ever, I. Wake up on a Monday morning and don't want to be here. I'm gonna tell you, and I can happily say I'm just about to hit my four year anniversary. I've been the CEO for a year. I have never once woken up on any morning, forget Monday, and not tried to just jump out of bed and attack this thing with passion because it is so integrated to the life that I've built.

Dan Balcauski: 14:55

Well that's fantastic. Glad that you've started this second chapter. Given your position at 15Five, I'm sure you've got some interesting perspectives on this whole employee engagement space. I guess, what do you see that leaders really get wrong about employee engagement?

Jim Morrisroe: 15:12

Yeah, so the the, the beautiful thing about humans is that we all bring our own unique capabilities to the workforce. The most complicated thing about humans is that we all bring our unique, own unique capabilities to the workforce. And on top of that, there's a, we are in a time that has never been more difficult for leaders. We have four fairly unique generations that are in the workforce. The boomers are just. Winding out the uniqueness of Gen Xers like myself and millennials and Gen Zers are like, are all have were raised with radically different childhood experiences and come to the workforce with different different expectations and different talents. And so that combined with. We've gone to this remote work scenario, which is which is, slightly going back into the bag, but is now forever a part of certainly knowledge work. And on top of that, we have these amazing opportunities around to continue to learn and be better with diversity and breaking glass ceilings and doing all these the, these amazing, positive things with DEI, not these, not the negative connotations that are coming out recently. So these things create this amazing opportunities for leadership to look at engagement historically, and performance and retention. All these topics historically companies have looked at engagement as a company wide. And a company wide opportunity. And the data just doesn't say that that's what's happening. Yes, there are some companies that need corporate programs that that that can that, that can unite. But we all bring. Like we started with these unique experiences to the workforce. Engagement and performance and retention is a target. It's not a blanket. And so, so what is critical in this environment is to understand your data. What is the intersection of my people data so that I can't, so that I don't necessarily just try to use a one size fits all sledgehammer, that I actually can go cohort by cohort. Manager by manager, person by person, and feel and identify what they need to do the best work of their lives. If you don't do that well. That's a needle in a haystack search. You like that? Could that, that's not the purpose of a company. The purpose of the company is to build better widgets and to make customers happy. Not to, search for what inspires each person. So you have, that's a mean the people programs are a means to the end. So how do you most effectively dive into your organization, understand your data, and inspire people on a cohort by cohort basis. Ultimately that's what 15Five's mission is right now, is to help HR leaders do that.

Dan Balcauski: 17:58

Well, I guess lead me kind of through maybe the before and after.'cause I'm not super familiar with what this looks like from a, employee engagement sort program. Right?'cause you mentioned this blanket versus target approach. Somebody sort of doing this blanket approach, I guess, what were they doing before versus, okay, now that they've sort of understand this more targeted approach, what does that look like?

Jim Morrisroe: 18:17

Yeah, so HR will run a company survey and they'll realize that they have. These psychological aspects of their organization. So an engagement survey is very much a, an organizational psych survey. And they'll realize that at a blended level, at an average level, they have a goal clarity problem and a leadership integrity problem. And so they're like, okay, we need to go buy some OKR software and we need to go to EOS. And we and oh, by the way, the CEO. It needs to be softer and gentler in the all hands, and so they attack these things in, in at a corporate level and those things. Might be needed. But what the real data is showing you is that your high performers from your last engagement survey, they don't have a goal clarity problem. They know exactly what they're supposed to do. It's the rest of the organization in a blended averaged way that has a goal clarity problem. And what they're really saying in that instance is. That they can't keep up with the A players. And so what do your A players have from an engagement standpoint, and how do we attack that cohort? Or what is happening in sales versus engineering? What is happening in a particular manager like. Every time, I pull up our people analytics dashboard. I can see that there's a that, that there are these hotspots within our organization. When I talk to our CHRO customers, we pull up their people analytics and we say, where do you think your hotspots are? They're amazed when they dive in and see that there's certain managers that are on fire and in many times they have some of the top employees in the organization. At that point, you start to target. Those cohorts with unique opportunities, nine outta 10 times that opportunity is to develop the leadership skills and develop the tooling of that cohort's manager. And so nine outta 10 times, this leads back to manager development, but even the manager development. Is unique. This manager a, needs to figure out how to be clearer with their communications manager B needs to know how to have hard conversations for, in performance issues in a more streamlined way. When HR is outnumbered on average 99 to one we need to be really efficient partners to, to help them do this. And that's ultimately where 15Five comes in.

Dan Balcauski: 20:45

Well, you're, as you were talking, it kind of was making me think of a, of an old cliche, which, always has a bit of truth. Otherwise it would be cliche, which is the people leave managers not companies. That was just kind of what was going in the back of my head as you were talking, right. Like this, Hey, we got this corporate level. Problem. But you're like, no, like I, my manager is annoying me for these specific reasons. And I can't be here anymore. So I'm gonna leave. And, there's, otherwise you're kind of blind trying to address it from this top down level. You did mention at your at the beginning both the generational issue, but but also this remote work issue. And that's obviously taken a lot of press lately. You got Amazon with their giant RTO push and you have big debates on, is it just a, backdoor layoff and but you've got other companies who are like, yeah, we've. We're very data driven and, we're not mandating back to office.'cause the productivity stats that don't actually support the people aren't productive. I guess. What have you learned about what actually drives productivity in remote environments? What, like, what companies are doing well with this? What companies are struggling? Like, what have you seen?

Jim Morrisroe: 21:42

Yeah, so I saw an amazing data point a few months ago, which was that the top 20% of your organization is five times more productive in a remote work environment. So you're. Your top performers aren't just a little bit more productive, they're five times more productive. And that's what's carrying the ultimate company benefits of remote work because the rest of the organization, the other 80% are only 60% as effective. So not quite half as effective as they were but 60% effective. And that makes so much sense because the top of the organization. Are the people that mentor and carry along and answer questions and help the rest of the organization be better. They're unburdened by that. So they're just away in the corner cranking and they're self-motivated and they don't need a lot of guidance and they understand the company priorities and they understand their manager, even if the manager just talks in grunts. And so those people are cranking along. And the rest of the organization your younger, less experienced, less potentially talented team members are fluffing along and struggling. What remote work ultimately does is it creates a background level of stress in a company. So I talked about engagement, performance, retention, all of these attributes that you can see in a people analytics dashboard. Anytime the company's under stress, those those gaps will will exacerbate, they'll multiply. So if and remote work is one of those stresses, it puts barriers between, people's ability to stay accountable and to people's ability to communicate well, et cetera. But there are other stresses. If the business isn't doing well, if if the economy goes into certain scenarios if there's a leadership issue if there's a compliance issue. So stressors, whether they're whether, they're remote work or generational shifts or whatever are real. And they can be micro and macro, but they just exacerbate these challenges of ultimately engagement, performance, and retention and manager pressure. And so remote work has, its be it's that, we love it. We're a hundred percent remote. We don't have a single office. We have 150 employees. We love it. but but we're cognizant of the stress that it puts on us and we take that into account as we build our people programs. I.

Dan Balcauski: 24:04

Yeah. Well, it's making me think. How we're such social creatures and there's all those studies of like, somebody have somebody acting like really odd in a crowd, and then everyone else is like paid actors who's supposed to respond a certain way. And then the response is always like, the one person doesn't know what's going on. Like, they look around to everyone else to see like, is this okay? Is this normal? How should I react? And just in a remote environment. We're not pinging off of our other mammals that way like we normally would, like, Hey, is everyone else seeing this or is this just, is Oh, everyone else. Okay. Okay. And then we calm down again and we just don't have that in our remote environment. So I can see how those

Jim Morrisroe: 24:41

I'll give you an example. Two years ago, 15Five had to go through a fairly major transformation. We had churn that had increased. We had product market fit challenges. We had an ICP problem. We had to kind of radically reinvent ourselves. And for the first nine months of this reinvention, I was continually getting frustrated that. The organization wasn't putting our strategic shift into play fast enough. We were continuing to do things in the spirit of the old 15Five and not the new 15Five. And because we were in transformation. I was naively watching every penny that we spent. I was like, cash burn, cash burn, cash burn. And so any opportunities for us to get together as a team in person, we locked down and somebody told me, they said, Hey, we've been. We've been trying this for so long, maybe it's time we bring back in-person meetings. Let's get together as a company and let's, unleash a budget that allows small groups to get together. Just those investments of bringing back in-person, three, four day kind of retreat style meetings at the company level, and then small team cohorts ad hoc getting together in a particular city to solve problems. It radically shifted, like almost overnight the company buy-in and company alignment to the shift that we were trying to make. And, I still have to be the chief repeating officer every day. I have to remind people of of the what and why of this shift. But the the energy that is underneath that is so much more powerful now that we started to see each other in person.

Dan Balcauski: 26:19

I, yeah, I love that shift from business as usual to transformation and as part, so, so business leaders who are listening, as you're thinking through, all the, x's and o's of the plan for that transformation, bringing people together in person to, for the x execution pieces over time can have a big impact. I

Jim Morrisroe: 26:36

I mean the execution piece for sure. But you can do the execution piece over Slack and Zoom and Google Docs. It's the buy-in, it's the commitment, it's the it's the energy that, that we saw significantly improved.

Dan Balcauski: 26:49

Well, I, I guess has the shift of remote work in your way in your mind changed, like how you view or what makes a high performing team? I.

Jim Morrisroe: 26:58

I don't think it's, I think back to this stat, which, which just says, how do you get your high performers more entwined with the rest of the organization, especially in r and d? That is that is just something that, that we're hyper cognizant of that we have that we have formal mentorship programs. If the data. Presents itself that we need it, that we have extra communication and standups that we don't let the high performers isolate because that because we need the whole company to be getting leverage from the whole company. And the best way to bring the rest of the org up is through the me mentorship and participation of the of your top 20.

Dan Balcauski: 27:38

Well, and just the whole time you've been talking, right? I have I, if I'd gone back to college, I probably would've majored in statistics or double majored in statistics because the, you're just talking, right? Like from the very beginning it's this flaw of averages, right? It's like we've got average data but. When you look at the distributions right across cohorts, you segment those different groups out. You see a very different story from what the average tells you. And on my side, I have a DDI remember working in open office environments. They were terrible. Especially in a, the type of roles I was in, you'd always have, you were in meetings most of the day when you weren't, you'd have people come by your desk and you're like, alright your two minute question has now reset my brain 20 minutes to get back into what I was trying to do. Right. And you don't have 20 minutes before you get the next interruption. And so, no, that everything you just said really

Jim Morrisroe: 28:25

And that's why you're so much more productive in a remote work environment. But that's why this poor person that asked you reset your brain for two minutes, that's why they're 40% less productive is because they don't have you to tap into as easily.

Dan Balcauski: 28:39

Well, may maybe those roles were flipped. I'm not gonna put myself on either side of that of either side of that, but I appreciate that nonetheless. Well, you also mentioned these generational differences and, one thing that's been, sort of apparent to me is, kind of. We learn so much indirectly and socially, right? From observing like our superiors and how they act, right? Like you overhear people in conversations on, at the desk next to you right? And you're just like, oh, that's how they're sort of thinking about that, right? It wasn't an intentional, HR certified training moment, but like that, like we just sort of suck that up from our environment and. I do wonder about, the, say the sub 30 group where, maybe they're, still really early career and they're thrown into a remote environment. I. What, have you seen work where we're not leaving those folks behind? Where, maybe they're not, it's like, hey, I'm mid-career, mid forties, I'm gonna, I know how to do the work, right? I, there's obviously, I could always grow and get better at what I do, but like, I'm not sort of at like, how does the business world work at all sort of stage, right? So how do we not leave those people behind in a remote world?

Jim Morrisroe: 29:44

Yeah, no, I think it's super powerful and in addition to having a company somewhat full of folks in the Gen Z, millennial area, I have four kids that are in that bucket as well. And so here are two things that have stood out to me number. Number, and I don't think I'm the first person to say these, but when I put'em into practice, they work. The first thing is because that gen, these generations have been raised with a supercomputer in their hands and and social media in their hands that that there, that has given them two, two qualities. One, if something feels opaque or non-transparent. They're gonna freak out'cause they can Wikipedia, they can google search, they can find instant access to the world's information. And so at a company, if there's this concept of, Hey, that's senior leadership, there's a need to know basis if this is a, if you hold your cards close to the vest and listen, there's some things that you just can't be transparent about. But being overly and uncomfortably transparent is is is advice number one. And I'm good thing is through my journey, I'm and I'm also like, Hey, life's too short. Not to let people know what's happening. I am that way by nature, but a lot of leaders aren't, and overly and uncomfortably transparent, I. Number two, and it gets back to this chief repeating officer. They are, they're naturally filters. Like my kids will get a thousand Snapchats in a weekend. And and, the human brain can process that information, but only if it triages things very quickly and says, this is important, this is not important. And in order to to reach things for them that are important. You have to continuously repeat it. You have to re in multiple mediums. You have to say it in the all hands. You have to type it in Slack messages. You have to insert yourself into Slack channels. You have to put it in the corporate decks like this. It's an imp. It's an important thing that if you want it to land, you have to be vulnerable and transparent and you have to say it all the time.

Dan Balcauski: 31:49

I love this chief repeating officer. It's like, yes yes. I said that yesterday. Yeah, we gotta say it again. It doesn't matter.

Jim Morrisroe: 31:55

And to some people like that hear it are like, dude, stop. You say this way too much. And it's like, it's not for you, it's for everybody else. And and there's a reason for,

Dan Balcauski: 32:07

Like, no I know I don't wanna continue saying the same thing over and over again, but I have to it's part of the job. No, I very much appreciate that.

Jim Morrisroe: 32:13

Look just leave you with one last thing too

Dan Balcauski: 32:16

sure.

Jim Morrisroe: 32:16

The upper 10% of these younger generations look a lot like my career or someone. In the boomer's generation career, the upper 10% is motivated by career. They see the American dream of buying a house. They see upward mobility and being able to provide a better life for their family than their parents provided for them. And so, the Harvard kids, the Stanford kids, the, the Ivy League kids that, that end up in investment banking or in, in private equity or in the, the top of Google, those kids look the same, the other 90%. And it's not that they don't have different talent, but they look at this hurdle that it takes to buy a house or the cost of having a family or or these various things. And they're like, man, my career is. Part of my life, but it isn't my life. And in order to cater to that mindset you have to make sure that mission and purpose of your organization is crystal clear to them that, because if it's not, and they'll just say, Hey. I'm gonna go to Australia for six months and live in my van and see the world because that's that, that's their that's not a bad thing. I, I think I would've done that then if I had to look at a$800,000, starting price for a house at 24 years old. I would be like, yeah, my career is second to my personal life experiences. So, so making sure that mission and purpose is front and center to to all of your employees, especially your younger employees, is a really important kind of, lesson that, that took me a little bit to learn.

Dan Balcauski: 33:52

I love that. Well, and I resonate with that because I went and backpacked the world for a year and a half,

Jim Morrisroe: 33:56

uh

Dan Balcauski: 33:56

as well. So I'm somewhere stuck in the middle. I'm not part of it. I'm in that weird middle of two generations. So that don't fit neatly in any category. I did my, did that later in life. Look Jim, I could talk to you all day. There's a whole bunch of topics. I didn't even have a chance to broach with you that I was hoping to maybe we'll have to get you out for part two at some point. But I do wanna respect your time and the audience this time. This has been fantastic. I want to finish out with a couple of rapid closeout questions. Is that a cool,

Jim Morrisroe: 34:19

Sounds great.

Dan Balcauski: 34:20

Alright. First one is a fun one. If we have the chance to get rid the world of the mosquito, should we,

Jim Morrisroe: 34:27

Of course,

Dan Balcauski: 34:30

no, no Second order effects that you see

Jim Morrisroe: 34:32

I mean, context. Live on the west side of the Rocky Mountains for a reason. I hate bugs. And they exist a little bit on the west side of the Rocky Mountains, but nowhere near like the east side of the Rocky Mountains. And so, I've built my life partly around avoiding bugs.

Dan Balcauski: 34:53

What is your greatest hope that comes out of this trend of AI that we're seeing?

Jim Morrisroe: 34:59

Yeah. My my hope is that I is that we don't prematurely freak out like this. This ha human innovation has, I. Radically changed our lives. And every stage of innovation has threatened somebody. And the innovation has overcome. This one on the surface can be really scary. It can also radically change future generations quality of life and life expectancy. And I, I hope like any of these transformations, we don't freak out too much and we, we let it make our lives better.

Dan Balcauski: 35:39

Keep calm and carry on. When you think about all the spectacular people you've had a chance to work with, interact with, learn from, is there anyone that just pops to mind and has disproportionate effect on the way that you think about building companies now?

Jim Morrisroe: 35:49

Yeah I mean I've mentioned them, but um, Satish Dharmaraj a, managing partner at RedPoint, who was the CEO of Zimbra. Changed my life in a major way as a business person. And then David Hassell, who was the original CEO of 15Five helped me just become a much better human in the workplace. I was already on the way through my through my journey. But those two and definitely bookends of my career have been instrumental.

Dan Balcauski: 36:13

If I gave you a billboard and you could put anything on it advice for other B2B Sass CEOs trying to scale their companies, what would it say?

Jim Morrisroe: 36:20

It would say it would say, be disciplined to your ICP. So, there is, we didn't get a ton to talk about it, but there is no better, path there, there is only one path to success, and that's a deep product market fit that gets word of mouth. And and it's impossible to do that in a huge market. And so you have to get disciplined and win win an ICP and then expand your ICP from there. And we far too often get. An allure of a big deal in an enterprise company are we far too often get get excited about self-service and, no, no sales costs and in reality, none of those things matter until you win an ICP.

Dan Balcauski: 37:09

Be disciplined to your ICP. Absolutely love it. Jim, this has been fantastic. For our listeners, wanna connect with you, learn more about 15Five, how can they do that?

Jim Morrisroe: 37:17

Yeah, so I you can always reach me on LinkedIn and I will point you on the right direction. I'm pretty responsive with my outreach and even if you wanna message me and then 15Five.com to get started on everything. Everything there. I highly encourage HR leaders COOs presidents that want to look at targets and not blankets for their people engagement and performance programs to check it out. It's a pretty powerful platform.

Dan Balcauski: 37:42

Targets not blankets for increasing your human performance in your organizations. Love it. I will put those links in the show notes for listeners. Everyone that wraps up this episode of SaaS here, it's thank you to Jim for sharing his journey Insights, valuable tips for our listeners. You found this conversation as enlightening as I did. Remember, subscribe so you don't miss out on future episodes.