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John Kaplan
Welcome to the Revenue Builders Podcast, a weekly show featuring B2B sales leaders and executives. Hosted by five time CRO John McMahon and Force Management Co Founder John Kaplan, the show goes behind the scenes with the people who have been there, done that, and seen the results. If you enjoy our content, please subscribe, rate and review the show to help us reach more people. Revenue Builders is brought to you by Force Management. We help companies improve sales performance, executing the growth strategy at the point of sale. Find us@Force Management.com Enjoy today's episode welcome.
John McMahon
To the Revenue Builders Podcast where we dive deep into the world of sales leadership and operations and the ever evolving role of AI in driving business success. Today our special guest is Matt Nolan who's the Chief Revenue Officer at Redwood Software. Matt is leading global revenue Strategies and he's scaling the enterprise automation solutions for Redwood. Before stepping into his current role, Matt served as the SVP of Global Sales at Redwood, helping to accelerate the company's market leadership. Matt's track record is nothing short of impressive. At turbonomics he launched their federal business, built a strategic accounts program and led record breaking deals that helped propel the company to its acquisition by IBM for 2 billion. Prior to that he held leadership positions at Pentaho, Fuse, Click Blade Logic, which was acquired by BMC and MicroStrategy. With a career spanning enterprise software automation, AI and data analytics, Matt brings a wealth of insights on how to build elite sales teams, navigate complex enterprise deals and embrace AI driven transformation.
John Kaplan
So Matt, talk a little bit about being a first time CRO. What are some of the top lessons you think you learned? Or do you have a different viewpoint of what that CRO job really is all about?
Matt Nolan
Yeah, I think it was sort of a role that I had always strived to get to in my career. I got to it an interesting way too because I moved from, if you look at my background, the majority of my career in VC backed companies. First time CRO in a PE backed company. So there were sort of two things to learn. One the role and two the difference between VC and pe. They they sort of run the organization somewhat differently. I think for me as I kind of reflected back over I'm about to hit the three year mark now about what I thought it was going to be and what it became. You know at first I probably focused more on sort of, you know, getting the three Rs into my leaders heads, getting the right cadences down, like a lot of this sort of operational stuff which is all critically important but. But candidly was kind of the Easy part, right. The, the harder part that I maybe wasn't as prepared for that I kind of had to learn, you know, maybe a little bit of trial by fire or a couple things. One, realizing that every word you say, people internalize very deeply. Right. And I think back to when I worked for you, John. There's still things to this day that I remember that you said 15 years ago. Right. That sort of still stick with me. You get into this role and that's a lot of responsibility that you maybe don't realize at first until you start to hear people repeating and realizing like everything you say and do is being watched and internalized. And then that sort of dovetails into culture. Right. So a lot of times as the CRO, you're really the. Not just the tone setter for the sales organization, but oftentimes for the entire company. Right. They, they tend to rally around like what is the tone that the CRO is setting from a culture perspective. Right. We have like the first slide in my, one of my leaders decks is culture is what you tolerate.
John McMahon
Right.
Matt Nolan
And that's, that's a lot of us taking a lot of our leadership principles and determining like, what do we actually tolerate from our ICs, from each other, from the rest of the org, how do we communicate with the rest of the org. And ultimately here it's been how do we build not just a winning culture, but a team based culture.
John McMahon
Right.
Matt Nolan
So I've been very fortunate and unfortunate. I've been on some highly talented teams that weren't very team based and didn't do very well. And I've been on some highly talented teams that have really been in it together like we have at Redwood. And that's driven, I think being able to keep that culture has driven kind of an outsized outcome for us recently. And then I think that the interesting complication for me personally when I came into the role was it was during COVID right? So building a company and a culture during COVID over zoom, right. I'm a very traditional grow up as a full stack rep in person, all that kind of stuff and trying to figure out with my leadership team, how do we get a culture built globally when we're not together in person very often. Right. And when I say culture, I'm not talking about because we don't have, you know, happy hours and you know, you know, ping pong tables and that kind of nonsense. But really, how do you get people to commit to each other and commit to that team and commit to holding each other accountable? How do you do that virtually? And how do you build relationships? And it's complicated, I think in this era for a lot of us, because a lot of the sellers now there's a bifurcation where many of them grew up on zoom.
John McMahon
Right.
Matt Nolan
So some of the more senior sellers grew up in the building and some of my younger sellers had never met a customer before in person. Right. We have a corny phrase now, shape of the building. I want to know the shape of the building that you're selling to. If you don't know that you're not selling to them yet. Right. Like you got to go get on site and be in person. So all these things I think have been really interesting about like how to build a culture and how important that is as a CRO. And then probably the, the last thing that I was completely unprepared for was managing a board. Right. So your role in sort of managing up and managing a board is something that, you know, I would encourage anybody who wants to step into a role like this to make sure that you've got a couple mentors around you who can help you understand what, what you can and can't do with the board, what your role is with the board. And, and I was very lucky here. My first board was from our last investment investors. They were incredible. They were great people. But. But something that not a lot of people talk about when they, when they talk about getting into this seat is board management with your CEO.
John McMahon
So.
John Kaplan
Well, that's a lot of stuff. So can we unbox? No, it's really good. Can we unpack some of that? So what was the biggest thing? What did you think the job was? And then you said what it became. So you talked a little bit about people, listen, culture team versus me. But what was the, was there one or two big shockers like. Oh, like.
Matt Nolan
Yeah, I think as we've grown. So when I got here, we were about 80 million in revenue. We're a little over 200 now. The past couple years, I think you start to realize that you're in deals a lot less. You're not just the more senior sales leader that's brought into deals. Really. You've got to be a systems person. Right. And that systems thinking starts to really take up a lot of your days. Like my days are jam packed from early in the morning to late at night. And a lot of it is going through, you know, everything from how are we going to model out how many BDRs you need or how many SDRs you need or reps or coverage. We have a fairly complicated company here and the fact that we have a plg, a PLG assisted and an SLG motion all sitting within the site in the same company.
John Kaplan
Right.
Matt Nolan
That creates a lot of complications about how to run the business. So I think for me, realizing that you've really got to hire really good leaders underneath you who can manage the customer relationships and the relationships with prospects and you get to do a lot less of that in this seat and you have to do a lot more kind of table setting. I, I've sort of been shocked that, you know, I said this. At gko, a lot of what I do is look at in the QBRs, the what's working and what's not working. And my job is to go turn all the what's not working into what's working.
John Kaplan
Right.
Matt Nolan
The simplest thing in the world, it sounds like. But that's really, I'm one of the only people who could do that for, for the salesforce. So for example, our legal was a mess when I got here and all red if you will, all the feedback, now it's all green. Right. We have an incredible legal function here. But that was something I had to go take on. Literally went out and found the general counsel myself, brought them in house with her, rebuilt that legal function. So things like that aren't necessarily what I expected being in the, in sort of the first chair was going to be about, but it, it's sort of clear that like your job is to sort of take some of these big rocks that nobody else can move and, and tackle them for the whole organization.
John Kaplan
And what about the board? What did you find out about, you know, interfacing with the board?
Matt Nolan
You know, so here I came into a board that I didn't know and a CEO that I didn't know. Right. Which is, and I really came for the opportunity and put a little bit of trust in the fact that during the interview process, I really like some of the, some of the folks I interface with from the board and I like the CEO obviously, but, but honestly, you're gonna spend that first six to nine months proving yourself right. You've gotta come in with an opinion about, you know, here's, you know, here's what I believe and here's my view of the world. And mine was actually very different from the board. My board had traditionally run more PLG motions, a lot of inbound. They'd never had success with outbound before. They hadn't done high end enterprise before. So it was a really, I had a really Unique first experience where I think we had to learn together. How do I take some of their superpowers and sort of take them out of them and then how do I earn enough trust to start to do some of the things that I knew we needed to do to scale the company to where we are today and beyond, which is to start to build up a strategic accounts program and really do outbound and get intimate with the install base and not just be volume and velocity. And we do both here in different parts of the business.
John McMahon
Matt, I really like this point that you're on. And when you went into private equity, I'm assuming there was an established, there was some kind of culture, there was some type of existing motions and first time CRO, could you just dig go one level deeper on how to balance learning? I have a saying that says be the same before you're different, meaning you got to go in and you got to understand what they're doing, what they're doing well, what they're not doing well before. And at the same time you have to put what you know into place. How do you balance that in order to gain the trust, the, you know, the favor of the organization when you know there's got to be changes? How do you balance, especially in culture, understanding the culture and then, you know, supplementing or adapting it or changing the culture?
Matt Nolan
Yeah, I think the way that I've done it personally, really my whole career, and this was, I think a bit of a learning because when you first get into leadership, you sometimes mimic the leaders around you or that you've worked. And I think as you get a little older, which I unfortunately am. There didn't used to be gray in this beard. You realize that the only way to do it is really to be yourself.
John McMahon
Right.
Matt Nolan
So for me personally, it was about being extremely open. I probably take some risks with how open I am with my organization, but that's the way that I build a level of trust that then allows me to take or at least figure out who I can take along with me on the ride.
John McMahon
Right.
Matt Nolan
There's going to be some people who are always going to resist everything that you're trying to do, regardless of sort of your experience. And that happened here. Right. There's people who aren't. Who aren't here anymore because they sort of opted out or we decided that they weren't going to be the right fit culturally moving forward. There's a lot of other people who had been here 20 years, you know, who grew up in sort of founder led mom and Pop kind of business that we had now acquired and, and now have seen, you know, some pretty elite growth and, and have started to learn some of the playbooks that, you know, I think some of the best enterprise software companies run and I think the best way to get people on that track is you also bring some people in. Right. What I didn't do is I didn't fire everybody when I got here and build a new leadership team. We sort of. My leadership team's a bit of a hybrid of, of old and then from my network, you know, legacy and from my network, I shouldn't say old. And I think a lot of it was just like authenticity. Like how, how do you get people to believe that you have their best interests at heart and that you're really doing things for the team and not just the individual. And when you do, when you can sort of get people to believe that that's true and some of this is how you make decisions, I think you can get a lot of people on board quickly. Like, I'm, I'm very proud of a very corny thing, but it's been three years and there's never been an account conflict that's gotten to my level in my time here. Europe doesn't fight with the U.S. wow. Teams don't fight with each other. That's, that's not what we do here. Right. There's, I think, a lot of people who believe that this can be a $500 million billion dollars air company. And when we got here, the joke was it was the best kept secret in software. Nobody had heard of us. Right. And that, that's been my opening slide at every gko, like until this year. It won't be anymore because now we're a leader in the magic quadrant. Multibillion dollar acquisition and I think have done some pretty incredible things, but I think that none of that would have happened without that authenticity and getting people to really connect to the mission and, and making sure you, you got rid of any cultural rot that might have been there or people that were working against you and, and get everybody rowing in the same direction.
John Kaplan
Yeah, that's quite natural that, you know, when you walk into an organization as a CRO, you're going to find, like you said, some people that no matter what you do, they're not changing. You got another group that's just dying for your new leadership and a big group in the middle that's saying, okay, what's going to happen here? And it sounds like you really moved.
Matt Nolan
We had to that point. We do this engagement survey and when you look from the elt, largely got hired at the same time. So none of the founders are in the business anymore. If you look when we got here, it was, you know, 65, 70% favorable and a big chunk in the middle of the year. A little bit of negative and a big chunk of undecided in the middle. In our most recent engagement survey, it's 91% favorable. Right. So kind of best in class. We sort of, we sort of won the hearts and minds of the middle and gotten them on mission, which I think has been a, a huge key to, to the success of the company.
John Kaplan
I always say that the, the people that want to want your new leadership, they're too busy to sit around talking. But the naysayers, the people that don't want to change, they try to poison the people in the middle. Right. They know who doesn't want to hear from them. The performers. But they know that there's another group that just sitting there on the fence and that's the group. You have to move pretty fast. You have to get some wins early. But talk a little bit about, you talked about team versus me kind of culture and you said you have to commit to it. Talk a little bit about what you mean by you have to commit to this team versus me mentality or culture.
Matt Nolan
Yeah, I mean there's a book sitting here to my left that I had my whole leadership team read. By the way, your book's up there, John.
John Kaplan
All right, thank you. Appreciate it.
Matt Nolan
Background.
John Kaplan
Hopefully you actually read it. I did put it on the bookshelf.
Matt Nolan
Yeah. You're right below mindset. So you're right next to each other. You're in Carl Dweck. But I had my team read the Advantage by Lencioni for the, for those who've read it.
John Kaplan
Yeah.
Matt Nolan
A pretty interesting, I think sort of exercise and organizational health and we spent half a day together sort of, you know, everybody read the book, everybody took a chapter, had to talk about, you know, what does that mean to this room.
John McMahon
Right.
Matt Nolan
Who's your team? How does this change what your behavior is? So I think just going through exercises like that where people are, are open and kind of drilling deep about like what's really their role in the organization. You know, we have certain teams within the org because we're so multi layered in terms of our go to market where unfortunately some of our sales leaders are sort of constantly having people promoted off their team.
John McMahon
Right.
Matt Nolan
So I had to get those people to realize that I'm judging you based on how many people we can promote off your team? If you miss the number by 5%, but I'm promoting half your team, I can take that hit because we're moving them into a larger role where their impact could be greater from a revenue standpoint and we'll, you know, we'll go make up for that little bit of a mess. But getting leaders to sort of understand that level of commitment to the organization is, Is not natural for most of us. Right. Because, you know, most people that end up in these roles are highly competitive. Right. And, and they all want to be on top. So I think getting people to commit to that team is probably one of the hardest things that we do. And a lot of it goes to the hiring process. Right. So the DNA of the people you hire will ultimately determine whether or not you're able to pull off that type of culture or not. And it's. I won't use the word that I use in some of the internal meetings, but you can't hire jerks. Right. I mean, that is sort of a pretty hard and fast rule here for us. The job's hard and doing it with people that they can't commit to. A team based culture just isn't. Doesn't work in the way that we're structured as an organization here at Redwood.
John Kaplan
We'll talk about. You also talked about culture. I want to know a little bit more about what you meant by is what you tolerate. Culture is what you tolerate when you describe that. Give me an example too.
Matt Nolan
Yeah. So it can be simple things like performance. Right. So there have been a couple leaders that, you know, a couple QBRs into it. And you're, you're talking about the same person for the third qbr.
John Kaplan
Yeah.
Matt Nolan
You're sort of asking them like, kind of, what are we doing here? What are we tolerating as an organization? Right. You already know the answer, but you're not willing to do what needs to be done. And, and you know, I think one of the lessons you learn the longer you do this is sometimes you let people go and it's the best thing that it's. It's the best thing that can ever happen for them. Right?
John Kaplan
Yes. Yes. To go deeper on that, Tell the audience what you mean by that.
Matt Nolan
No, I probably learned this from you way back in the day. So oftentimes, and I've been guilty of this myself, whatever it is, you're stuck in a, a bad emotional place. You're in whatever issue you're having. And ultimately, sometimes moving on from an organization is the Break that. You need to either go find the role that's a better fit for your personality or your, or your skill set. But also what you have to realize, like some leaders get focused on the individual and you've got to realize there's an sc, there's a technical account manager, there's a sales leader, there's all these people around them and if that person is failing, they're bringing all those people down with them.
John McMahon
Right?
Matt Nolan
And you have to look out to the greater good of the organizational health. And look, that doesn't mean you get rid of everybody who's a bad quarter. Right? You've got to get to the root of like what the problem is. But at some point what you can't tolerate is quarter after quarter after quarter that there's an excuse around everything. Right? An excuse based culture isn't something that we tolerate here. We, we're very much a solution based culture. Like, don't get lost in describing the problem to me. Get lost in describing the solution to me. Right?
John Kaplan
That's if you tolerate it too long as a leader, then the people start to look at you and say, doesn't he see what we see and what's wrong with our leader? So you almost, you have an obligation, like you said to all the other people, you know, to say, hey, this, this person is a problem or that is a problem and we need to fix it and fix it now.
Matt Nolan
There's nothing worse than when you get a text from a rep or a couple ICs on a team and it's about something that has been tolerated by their leader. And you're like, man, everybody can see this.
John Kaplan
They all see it. I always say that. They're always talking about you, like you said earlier on, that they listen to every word you say. They're also talking about you all the time, whether you, whether you believe it or not. They are.
Matt Nolan
Yeah, that part freaks me out.
John McMahon
Isn't this topic really the same symptom or the same underlying problem? It's recruitment pipeline. I find that that family tree conversation that you talked about earlier, Matt. I'd like to talk about that a little bit more. Like how do you really instill a culture of your best? People are going to get promoted and they should be getting promoted because that's what our culture is going to be. And really the only reason, what I find the only reason why that they hesitate, it's pipeline. It's like recruiting pipeline. And the only reason why people hang on to bad people or questionable people is pipeline. That's the only reason. So how do you get a culture to really understand that and not go to HR and say, hey, we have problems. We don't have enough resumes, blah, blah, blah, blah, blah. The best CROs ever seen really understand this point. Could you dig into that a little bit? Yeah.
Matt Nolan
I mean, it happened very early on in my tenure here. I had a leader who's still with us. He's sort of grown through this, but he had an underperforming team. We ended up getting rid of the whole team, rebuilding the entire theater in Emea. And he was complaining to me about the quality of the pipeline from the. From the talent acquisition team in hr. And I was like, man, you don't get the job. Like, that's your job. Like, Pipeline is recruiting. Pipeline is like your number one job, right? And that's kind of when I realized very early on, like, the three Rs recruit, retain revenue, like that recruiting piece. Like, I was going to have to hammer. Hammer home that point to the point where I started showing people, like, no, let's have daily standups on Pipeline of people Pipeline, right? Especially in the early days when we were having to build out and scale the org. But even now, like, it's. It's a relentless constant, right? Like, our ICs need to be doing PG all the time, and our leaders need to be doing PG around people, right? So they constantly need to be doing recruiting. I had somebody the other day kind of slip up, and they're like, oh, this is my last headcount to fill. And I go, well, wait a minute. Also talk about somebody on your team who we're not convinced about. Like, you need to go 3, 4, 5 more people that you're constantly keeping warm. I mean, we just. We hired a guy just last week, just started at GKO. Third time he's worked with me W2. Nearly $3 million last year. So, yes, those. Those W2s do still exist and decided to join Redwood. I've been recruiting him for a year and a half, right? So for a year and a half, I've been trying to get him out of that org. So at my level, I think what's interesting, and I've tried to teach this to the leaders, like, my favorite thing to do now is recruit. Like, there's nothing better. Like, I would rather, you know, hire that rep that I just talked about and get him into our org than win a new logo. Because to me, like, the multiplicative effect of having, like, great people is, like, once you see it, you can't unsee it. Having great leaders, having great ICs, getting like elite at recruiting, it just makes everything so much easier. And when you don't do it, you end up, you know, that's how you get fired. In 18 months when you're in my.
John McMahon
Job, I was going to say, do you think you can be a CRO without having that mentality?
Matt Nolan
No. I mean, you can.
John McMahon
I don't. Yeah.
Matt Nolan
When I look at people who have 18 months stints, I generally go, they probably didn't focus on recruiting. They probably focused on revenue first and kind of got lost and then got too deep and they didn't build the structure.
John McMahon
And it's probably the number one. When I think about like owning the number, that's just kind of table stakes. Right. It's the number one thing that I find that great CROs do is they teach their frontline managers how to recruit. Because I think that's the biggest area of opportunity for, for frontline managers. They just, they just do not have an experience of recruiting. If they grew up inside the company or they have like first time leaders or what have you. And screaming at the scoreboard is just, I see it happening all the time. And then all of a sudden hr, you know, HR is, everybody's talking about internal talent acquisition or what have you and you just know that company's going to fail.
Matt Nolan
Yeah, I mean we, that's not an excuse that anybody gets to use it. At Redwood, I think everybody is now very, very clear that like we own the people pipeline. I mean it's, it's sort of that simple. And you, you just, you can see it across teams. The teams that are great at recruiting are the teams that within a quarter or two have, you know, outlandish results. We are strategic accounts team. Last year, I think eight of the nine people in that team or from our network and I think the worst performer was 180% of his number.
John McMahon
Wow.
Matt Nolan
I mean, and that was because we were relentless about. And it's, it's multi year too. I mean it, like I said like that, that guy that we just hired, that was an 18 month recruitment process for me.
John McMahon
Yeah, it's a sourcing, it's a sourcing thing. Normally when I find that what people need help with, I mean there's a lot of stages of recruiting but let's talk a little bit about sourcing.
John Kaplan
What advice before you do that, Johnny? So, because we were talking about tough people decisions earlier but just gone to your point when, when you do recruit a superstar and you see Them and you think, you thought it's a really tough decision whether or not I'm going to let this person go. And because you've been constantly recruiting and then the superstar shows up, the decision is so clear.
John McMahon
Yeah.
John Kaplan
You and to everybody else. So just want to comment on that before we do.
John McMahon
So that's kind of that, the Johnny, that's kind of that rule of Right. You know, somebody's going to get demoted or moved out of the business. Not because they're bad people, just because it's not. Whatever's going on, somebody should be getting promoted and somebody's going to surprise you. And I think when you have that mindset, you know that no matter what, you have three openings on your team at all times. And, and I think like you say Johnny, when you see it, just show up and you just say like, who does this person remind me of on my team? And if the answer is nobody or if the answer is a superstar, it's really, really easy. But I find Matt, the, what I find the struggle is most of the people have the heart, the mind, the desire to do this, to participate in their own rescue. They don't know how to source. They do not know how to source. What. Talk to us about some of the things that you've come up with from a sourcing perspective over the years.
Matt Nolan
Yeah, I mean I, I don't know that we've unlocked any magic there other than we made some pretty good hires early. And as soon as we make a good hire, the first question we like, let's say it's a quarter in and they're not from our network. This happened in Emea. We sort of rebuilt Emea around a younger seller who wasn't from our network, but like we just loved him in the interview process. Three months in, I watch a gong call and this guy is running the best negotiation call I've ever seen. He's like a 30 year old rep and I, I immediately, you know, we share it with the whole company and I immediately ask him who's the next best? Who's the hardest guy you've ever sold against? Who's your, who's your, you know, your biggest competitor? And then we brought that guy in and both of those guys were over 200% of their number last year. Trying to think if they were over 300%, they've been that successful.
John McMahon
They run in packs, right?
Matt Nolan
Do, yeah. And then, and then that gives you, I mean it's as simple as like those two hires. You can rebuild an entire region around it. Because now we use them in the recruiting process and we just keep chipping away at, at top talent from, from other companies. You've got to be, look, part of my job is to be like, I have a pretty big network so I've got to be relentless about understanding what's happening at other companies that may have hired well but are now running into trouble. You then immediately sick, you know, your leaders onto those organizations to go try and recruit their top talent out of there. And look, we've been fortunate that we've, you know, one of the good things about PE candidly is we don't over hire. So because we don't over hire because we run a pretty profitable business here. What it means for the ICs is that they're actually, they've got good territories and they can make money.
John McMahon
Great.
Matt Nolan
So it's been an interesting adjustment to me. It's not like the hyperscale sort of thing that we saw when, when interest rates were nothing and money was free. We run a really profit. We've, you know, I won't say the exact number on the podcast, but it's well over 40% EBITDA with over 30% growth. Like for an IC, that is opportunity, man, that's dollar signs. So that's allowed us to continue to recruit at like the highest end of the market. And then look, part of it, John, goes all the way Back to. For 20 years I've been recruiting for being in this seat, right? So I was, as a, whether I was a first line or a second line, every year I would run through my Rolodex and call people, right. Just to touch base. And some of those leaders are working for me now here.
John McMahon
Right.
Matt Nolan
And a lot of these guys were guys that were actually at higher levels than me at the time when I first met them. But, but I knew that I was going to get to this chair one day and if I was going to do it, I was going to have to build long lasting relationships, right. And if I did, they were going to pay off. So I mean it's literally for me been almost a 20 year process of building out a network of people that I could call when I needed them. And it's, I mean, our general, I mean, think about beyond sales. I hired our general counsel, I brought in our chief product officer, right? That's not, that's not in my area of responsibility. But we thought we needed to make a change there. I brought our CPO in our head of rev ops, somebody from my network from 15 years ago. So Been pretty relentless about like keeping in touch with people and how I treat people. So that when the opportunity arose and there was a high performer out there, like we had a network of people we could go after. And I've sort of cascaded that. My leadership team has now seen that work and at play. So the next second line, third line leader that works for me, that wants to be a CRO, sees what the impact of recruiting that way can be.
John McMahon
On an organization and that moves to CEO.
Matt Nolan
Yeah, right.
John McMahon
I've seen people do that. I watched John do it. Being a five time CRO, I'm not saying he just took a band of characters and moved them because some people do that. They try to take cookie cutter, you know, my old team and place them there. That's not what I'm talking about. But one of the things I watched Johnny do in his five times as a unbelievably successful CRO is that fact right there. It was always thinking about this is a long term run with a pack of wolves and, and those pack of wolves just, just went and did incredible things. So I, I love that concept you're bringing. You know, act like you have the next job is the feedback you're giving to people. Even if you don't have it today, act like you're going to have it in the future. I love that.
John Kaplan
The other thing too is because it seems pretty evident but a lot of people don't do it. Like Matt was talking about where you have to constantly recruit. So I remember that this, this guy that I recruited, he's now a CEO of a company. But when I recruit, because I was constantly recruiting and I recruited him, I had no place for him and had no place for him. But I realized, oh my gosh, this guy's like a superstar, I got to take him and I got to get him on my team somehow, right? Go to the CEO and I say, hey, you got to interview this, this person says, well John, I already told you, like you have no more headcount left and we have no open positions. I said, okay, well, well why don't you interview him and then you let me know, hey. So the CEO interviews him and says, oh my gosh, we got to hire this person. I was like, yeah, no. So I made an opportunity and put him in an opportunity and said, all I want you to do is go on sales calls. I gave him a nice title, go to the training classes and something's going to open up. And sure enough, like four months later, something opened up. I popped him in the job and the guy took off from there. So sometimes when you run into a superstar, don't let them go. Find an opportunity to put them on the team somehow. Because to our point before yours, Johnny, where you basically have three openings on that team, that's the same thing for leadership too. There's a lot of leaders that are going to move around and surprise you.
John McMahon
Also, nobody should miss out on a. Heck, nobody should miss out on an A player from headcount.
John Kaplan
No.
Matt Nolan
Even when you can't. I'll tell you something I'm in the middle of doing right now. I don't have an obvious senior leader spot right now, but all my 1B's for a lot of the spots that I filled, if they're on the market, my goal is to go get them another job in another company. Right.
John McMahon
Great.
Matt Nolan
Point is every single lead that comes into my inbox, I am. Look, it's easy to just ignore every recruiter, right? You get 3, 4, 5 of these calls a week in. In a role like mine, especially after going through a recap like we just did. But there's people out there looking for stuff. If you can build loyalty, that's a guy you might need three point remembers that you got him the last job. So I think it's just being relentless about that is. It's just. It's sort of like, you know, medic, which, you know, I learned from you working back at. Or med pick, whatever you want to call it, working back at. Blade Logic, once it gets in your DNA, you can't unlearn it. And I think if you're a really great recruiter, once it gets in your DNA and you see the impact of it, you can't unlearn it. It becomes sort of what you index along.
John McMahon
You see people that are great networkers. I love that point that you just said is that they're connecting people with other people their entire life. Sometimes they come along with them and other times they. But. But life has a way of coming back. The universe kind of goes full circle. I love that. I haven't heard that in a while. That's a great one.
Matt Nolan
And look, I'm an introvert. I don't like doing it right. I'm like a lot of people. I'm the extroverted introvert or whatever you want to call it.
John McMahon
But.
Matt Nolan
But if you do a bunch of good things, you figured that if I had to place my bets, I'd rather do it that way than not helping people.
John McMahon
I always used to think that for me no matter what wasn't going well for me when I was out recruiting. I always felt fantastic because it tested my mettle on whether I really believed in the opportunity because I could hear it in my own voice. If I didn't believe what I did mattered or I knew I wasn't good in front of recruits, but I knew that I could always change my world. One new person could change my world in a company and it's like one new deal. Can that change your world? You know, sometimes. But I always felt like the people part could change my destiny more than the, more than the accounts could, if that makes sense.
Matt Nolan
So we just came off gko. Really good example. As you can still hear my voice. I lost my voice 10 days ago, the first day of GKO. Right? Terrible time to lose your voice as a CRO 3 GKOS ago, 70% of the content I built and delivered myself like this was the Matt Nolan show. Which is not a good, not a good long term strategy. This gko, I lose my voice and it's the best GKO we ever had because we've built a leadership team where I'm candidly not as important as I used to be, which is the right. So how do you build up sort of that talent pool around you where hopefully I'm not completely unimportant but, but in things like that, you've got, you've got people that you can rely on and like there's just no way to do it by like we're like very anti hero ball here. Like it's, it's systems and it's good people and it's process and like that's how we're going to, that's how we're going to scale and achieve. Not by having, you know, somebody like myself or one of my leaders be incredible. It's a, it's a team of people who are all really talented.
John Kaplan
So yeah, it has to be a top priority for leaders. They, they have to do all the stuff that you normally do during the day and during the week, but they have to commit that the top priority is recruiting, especially if you have some sort of opening. So I can even remember when I had an opening in China for a leader and I thought, okay, this week I'm doing nothing but recruiting a leader in China. And man, it was hard. But when you then focus all your attention and network as much as you Ken, like you pointed out, Matt, all of a sudden, bang, here comes the person, they turn up and that person.
John McMahon
Had an impact for decades.
John Kaplan
You're talking About Steve, you know who it is.
John McMahon
Steve Zhu is one of my favorite people on the planet.
John Kaplan
Right.
John McMahon
Holy. You know, and this is a point I, I want to make too. Is that like what I also hear you guys saying is for me, the best people I've ever recruited were the not in play players. And people say, well, what does that mean? It's the people that were in jobs and successful and it took you a while to recruit them. The value proposition developed, the intimacy developed. That's the importance of the recruiting pipeline. Most people, when I look at, okay, show me your pipeline. It's all these resumes of people that are in transition. Nothing against people in transition. I've been in transition before, but I have found that the, the best examples of the most impact players over time are the ones that took a while to recruit. I've got examples of a person that I recruited actually for 10 years at force Management and he went on to replace me at Force Management, Brian Walsh, and just did incredible things. Some of my favorite ones are people that took me a year, two years, three years. And those are some of the best performing and relationships I've ever had. It's hard for people to understand that because it's like it's not instant gratification. John. I have an opening now. We got opening now because we don't have a pipeline and it's a hard.
Matt Nolan
Right.
John McMahon
It's a hard, hard thing to do.
Matt Nolan
You get it coming into this year, which is like higher ahead of even the board approved plan. Like let's go start like no open headcount to start the year. Let's. We had it. We doubled parts of the salesforce. We had almost all those people at gko. I mean there was very little open headcount. I've got plenty of text messages to your point, John, of people that I'm relentlessly after that don't yet work here. That better within the next 12 to 18 months. Like they're super high performers. They're in good places right now. But the second that there's a little bit of weakness in the spot that they're in, I don't want them going into market. I want to be the first person that even has the conversation.
John McMahon
And they know too, like I love those relationships, Matt. They trust you and they're like, I my head down here. When it's right, Matt and I are going to talk and you know, I'll make a move when it's right. And that those are the best transitions, the expectations, everybody understands them.
Matt Nolan
I think to Your like, it takes work, right? I think the one thing leaders need to realize and most, actually most of my leadership team candidly didn't have this in their DNA. They actually did not come from places where this was like driven into them. But the discipline that we teach the ICs around PG, like the leaders have to understand it is the same level of discipline as a leader around recruiting. It's not just a number because it's going to show up at some point because you haven't recruited, you're going to have some weakness and now all of a sudden it's going to take you nine months to recover.
John McMahon
Johnny, you did such a great job of this. You know, back in the day, I'd be in a forecast call and I'd hear McMahon say recruit. I would be in a product management call or whatever problem in the company, a problem in the. And I would hear McMahon's voice recruit. And it, it was a cultural thing that recruiting. It's like pipeline solves all ills. It's the exact same thing in, in, in recruiting. You just get new, you get new blood, new ideas, new momentum. I'm not saying to change over your entire salesforce, but I'm saying if you have a mentality that really everything is about recruiting top talented people to your organization, I've never seen that formula equal failure.
John Kaplan
It's a mindset. No matter where you go, you go to a party, you go to a barbecue, you get invited over somebody's house, hey, what do you do? I'm a salesperson. Really? What do you sell? You know, all that stuff and next thing you know, you're turning up somebody or to Matt's point, you're building a relationship with them over the course of course of three or four months until you have an opening and bang, you can put that person in, in the job. But it's not like a, it's not a faucet. It's not something you turn on and off, right. Something that has to be on all the time. It's that total mindset as a leader. Like I'm recruiting and constantly looking to upgrade my team. And if you don't have that mindset, yeah, you're going to miss, you're going to miss out on some superstars that were right in front of you going.
Matt Nolan
Back to sort of the first time CRO stuff. I think one of the things you start to realize is the, is the math of the larger problem becomes very obvious to you. Right. Like what are the levers I have to pull across the entire organization. And two really easy ones are I can't have open headcount and I've got to shorten the time to ramp.
John McMahon
Right.
Matt Nolan
I've got to be graded enablement so that I can beat the math of like what my expected ramp is for people so that I can beat the plan that's, that's hiring not, not late, not on time, but hiring early.
John McMahon
Yeah.
Matt Nolan
Doing graded enablement so that I can. So that I can shorten the ramp. And I think that's one of the things that maybe you don't see it as much as the first line. Maybe you start to see it as a second line. But man, when you get to the highest level of the org and you see the, you know, little open headcount spots all over the place, and you add that all together, you really understand the math of like, why becomes critical and then ultimately why enablement becomes sort of the next step in that to.
John Kaplan
Yeah, let's go through that. So what, what Matt's alluding to is, and, and I've actually seen this in some companies that I went and consulted with where they didn't do well in the quarter. And they did. The salesforce was sizable. So then let's say the productivity per Sales rep is 1.2 million per year. It's 100,000amonth. So you go around the room, you stand up and ask the first line leaders, even the second line leaders, how late were you in recruiting? Well, I wasn't late. I was only a month late. You go to the next person. I was only a month and a half late. It's not a problem. You know, I, I hired the person two months late. But that's, that's not that big of a deal. It's not going to affect me. And actually at the first line level, they have a chance to make that up with a bigger deal or, or ramp in the rep a little bit quicker. At your level as a CRO, it's the aggregation of all of that. So let's say you have 50 first line managers and they all miss by only one month, it's $5 million. How the hell are you going to make up $5 million? Where are you going to find it? You can't find it. You know, given that productivity stays at 1.2 million and even 30 of them missed by one month, 3 million bucks. Good luck. As a CRO, you just lost your job. Yeah, I mean, that's why it has to be so powerful at your level, because you are the aggregation of all of Their mistakes, which they don't really pay a high penalty for.
Matt Nolan
Yeah, I mean we, I, I make sure I'm very transparent about what that math looks like all the way up and down.
John Kaplan
Good, good.
Matt Nolan
And I think part of that is, look, I've got some people who want to be CROs. So part, part of it is kind of paying it forward. Like hey, here's some of the stuff nobody really told me here, here's what it looks like and here's why it's important and here's your, your kind of role in the operation. Because I can tell you when I was a first line leader, I didn't see that at all. I was absolutely, I'm going to make up for that with this deal over here. Don't worry about it. Right. And sometimes you can, look, there's quarters where you can do more with less and, and, and, and that can happen, but it's not a long term sustainable strategy for anything other than to be replaced by somebody else.
John Kaplan
Yeah. That's why it's so important to make it fully and sounds like you're doing it fully understandable by the first, second, third line leaders of why you have to recruit ahead of time.
Matt Nolan
I'll go so far as to say this is now getting pushed beyond the, the org that I handle. Right. So into the engineering orgs, the product org. Some of these parts of the orgs that maybe don't traditionally have this type of DNA. We're starting to sort of try and teach those parts of the organization like how this is critical really everywhere. It's not just sales and quota carriers and our services people and our Tams and our seas, it's you know, our, our, our SaaS team. If we're six months late hiring the right leader for the SAS team, well then we're not going to deliver on product. And if we don't product the right way that is. These things all have revenue impacts. Right? All, all the roles are revenue impacting. Some are more obvious than others, but they all have an impact. And I think it's important for the CEO, the CRO, the CEO, whatever, whatever the power structure is in the company to start to get some of that philosophy outside of sales as well and to start to drive it into the DNA of the entire organization. And if you can, like that's a company I don't want to compete against. Right. Because that's a company that's like really firing on all cylinders.
John McMahon
And that's why you're killing it in private equity, bro.
John Kaplan
Yeah.
Matt Nolan
I mean It's.
John McMahon
You get that. You don't get that kind of growth without that kind of mindset. No, no chance.
Matt Nolan
No, it's. I mean, we accelerated this thing pretty rapidly over the past couple of years with really no major product developments. Right. It was mostly, you know, coverage, messaging, recruiting, and. And it's been awesome. And now our product teams are catching up, and we're about to, I think, deliver a bunch of really interesting sort of product to market over the next 12 to 18 months. But it's. It's been a fun ride so far.
John Kaplan
Talk a little bit about, you know, we keep touching on sourcing, but we never really. It sounds like right now, if I'm a listener, the way you source or the way all three of us source is just by constantly talking to different people. But is there a method or certain sources that you can reliably source from?
Matt Nolan
So I'm probably pretty relentless on LinkedIn. I'm three times a day on LinkedIn myself, looking to source people in different organizations that I learned. Anything I learn about an organization, if I think there's some organizational weakness, I go after it in kind of.
John Kaplan
It could be an organ, organizational strength. Right. Because it could be a company that recruits really well, trains really well, develops really well, and. And maybe they're not growing that fast all of a sudden. So it doesn't have to be an acquisition. Doesn't have to be the other thing. It can be that they. They execute pretty well with. With their people. Right.
Matt Nolan
If a leader I respect leaves, I immediately. And I know they're, you know, they've got sort of the same DNA. I'm immediately all over that salesforce, right. Figuring out who the best people, and oftentimes texting that CRO like, hey, who are the people I should be going after? I saw you just left. I think the other thing we do is sometimes we'll have almost like we do with pg, where you may have like a full day block of pg, but a lot of times we do small groups of PG where everybody's working on the same, you know, everybody bring five accounts and everyone work on it collectively to try and break in. Oftentimes, we'll do the same thing for a role with leaders. Right? So huddle up a bunch of leaders together for an hour, and let's like, kind of relentlessly. Because part of recruiting is if it's not in people's DNA and they don't slow down to do it, oftentimes you find out by just slowing people down and putting a meeting on the Counter to go through their network. It's like, oh yeah, I hadn't thought about so and so or so and so. So just having the discipline to make it structured, I think a lot of times allows you to, to uncover some hidden gems in people's networks that, that maybe they hadn't thought about. Right.
John McMahon
I like that. I, I like it a lot. And, and Johnny, to your point in Matt, your earlier point of making it part of your DNA, like three great ones for me for sourcing were the interview itself. Myself, if I love the person I knew they ran in a pack of dogs and I told them, look, I want to hire you, but in order to hire you, you got to bring me two people. You got to bring me two additional people because we want to grow this thing and we want the other dogs with us. That's one. If it was not a great interview, I would find out who the number one person was in that company though, you know, so it's a mindset. In interviews, reference checks. I have people look at me and say, you're crazy. You know, we. They're just going to give you a good reference. That bull crap. I wanted to do the reference checks. Why? Because I wanted. If it was a great person, I wanted to find out who else that person knew that was like that person because they're going to naturally want to help those people do well in, you know, in the next roles. And customers was a great one where customers I would go to customers and I wouldn't say, hey, who's the most? Who's our biggest competitor? You know, I wouldn't say, who do you like buying from the most? Like if we weren't winning because they're not going to give you their a player because they have a relationship, they need that product to work, blah, blah, blah. But like when we win, I love to go to them and say, who would you have bought from if they had our product? What seller would you have bought from if they had our product? And it's amazing how loyal people are to people that do great jobs in like a sales campaign and they wanted to, they wanted to give them the business. They just didn't have the right product. Those are three great areas that if you make it part of your mindset, you're doing that every day.
Matt Nolan
I'll give you a slight twist on that. That we did here. So always do back like we do back channel. We don't references, but we all do. We do back channel. One of my leaders was going to hire somebody without he's like, oh, you wouldn't know anybody from that company. I looked the guy up. I know the head of Revops. So I called the head of Revops, long time connection of mine, back channel the guy. She's like, you should definitely hire him. The UK is a mess. He performed, blah, blah, blah. So great, we get a good back channel. What's the next thing I do? Are you happy there? You just told me the UK is a mess. Right. Let's talk about your career. Where are you at? She's now running Rev Ops for us here. Right. So love that. Recruit the people that you're doing the back channel with as well. Right, Love that.
John McMahon
So I think that that's a mindset. That's a mindset.
Matt Nolan
Yeah.
John McMahon
Those aren't tactics.
John Kaplan
The other thing that I found in sourcing, especially when Matt, you probably ran into this. When your people, you now ask them to build pipeline, there's two things that occur. One, they have to know what good looks like. And number two, which is always surprising to me, they can't sell the opportunity. Yeah, you have to actually learn how to sell the opportunity for that specific person. So you have to, you know, really uncover what that person does well and what they're looking for, what motivates them, what demotivates them and actually then turn that into how do I sell my opportunity. But if they don't know what good looks like and they can't sell the opportunity, which happens a lot, it's really difficult to recruit.
Matt Nolan
Yeah, I mean we, we just spent to that point, John, four hours with my leaders at the end of gko. So the last day I kept them for half a day and almost the entire session was, was teaching. Well, actually candidly a lot of your playbook, but a lot of it was around how to recruit, how to sell, how to hook people, how to connect specific questions to ask why you ask them. Like there is a whole playbook that needs to be taught around how to do that. It's not the, and no offense to my, you know, my colleague, we have a great HR team here, but it's not like the list of interview questions that you get about, hey, make sure we, we tie off on these things. There are, there are tactics and strategies to interviewing and recruiting that are absolutely critical to learn to land high profile talent. And if you're just sort of winging it and if you're not prepping for your interviews, if you don't have a strategy, if you don't know like what you're trying to accomplish, you, you generally don't end up with top talent. You absolutely, as John, you know, as Cap said earlier, like, you've got to sell the opportunity to top talent right to those, those. And, you know, a lot of times in an interview, like, all right, the first 15 minutes, I'm absolutely. I got to hook this person, right? I, I, and I need to teach my, My job is to teach my leadership team how to do that right? So that we're not just, you know, relentlessly berating people with stupid interview questions, that we, we have a purpose and we've got a strategy for what we're doing to uncover top talent.
John McMahon
I love that. I saw, I saw one of the best exercises I've ever seen it. Like a GKO or an SKO or what have you is a leader. Go through the room and ask somebody to stand up with no preparation, to be audible ready and said, in your case, Matt, let's just use Redwood. Why Redwood? Go. Like, in the recruiting process, like, I want you to recruit me, so explain to me why Redwood. And one person stood up, totally fumbled their way around. Okay. The next person stood up, they did a little bit better. And what the person said was, if you're not excited about this opportunity, why should I be? And it really set a tone in the entire room that said we are responsible, like, we're a walking audition for what it's going to be like to be in this company. And, you know, if you can't explain and what this person did was great, like, hey, let's get out of the role play for a second. But, like, why do you love it here? And they just started talking about why Redwood and what was great about Redwood and what it was able to do for their. Themselves, their families, for the people around them. And then slowly they built this value proposition. It's one of the greatest exercises I've ever seen. And their recruitment totally changed because the people going out, you're getting judged. Like, when you're trying to get an A player, they're looking in your eyes. And if you're not excited about what you do, why should I be?
Matt Nolan
There's nothing better than at the end of an interview when, when the candidate tells you, like, how, how excited they are because of how you've pitched the. Especially in my role, like, I'm the last interview and I still interview all the ICs we hire and we'll continue to as long as I can scale that. Yeah, it's the best feeling in the world. It's when it's our choice, not theirs. And they're leaned in and they're excited.
John McMahon
Totally.
Matt Nolan
But that's a skill. You got it. Or, you know, you got to teach it. You can't just, you gotta prepare for it. Like, it's, it's a skill.
John Kaplan
And the other part of the sourcing, which we talked about is, you know, what is good look like? So what does a good resume look like or a good LinkedIn profile look like? So we used to take, let's say 10 different resumes, cross out the names of people that were either in the company, got promoted in the company, came and left the company. And then what we would do is break the leaders into groups and say, okay, take these 10 resumes, rank them in order of who you would hire or even source for this case and come back to us and stand up there and explain the whys. Like, why. What do you see in these resumes and what do you see as lacking? I found that that's an amazing exercise. Amazing.
Matt Nolan
One of my favorite exercises to do. We haven't done about six months, but it's good reminder.
John McMahon
It's a great reminder. And then the punchline is, would you hire this person? And in some cases the group says no. And then we just, you got to make sure you protect, you don't want to, you know, you don't want to be bringing a bad situation from an HR perspective, whatever. But my favorite thing is then why did we, like, we actually hired that person? Or what was, what would they find like Johnny and Adam Aarons, Like a resume from Adam Aarons would have been like Cutco knives or whatever the hell he was doing. Would you hire this person or say, hell no, he's selling Cutco knives. Well, he's the CEO of a company today.
John Kaplan
Like, exactly.
John McMahon
That's a great exercise. Thank you for reminding me on that. That's a really good one.
John Kaplan
Well, there's a lot of things that, and, and it's brilliant because you have, you know, your first and second and sometimes third line leaders in that discussion. And sometimes they, they see things that you might not see and it teaches the whole group like, wow, that's, that's pretty good insight. You know, just what you picked up just from that Resume or that LinkedIn profile. Right.
John McMahon
I like this Johnny, because from a CRO, Matt, I think one of the great things that you can do is I call it getting in the pit. Like we can tell people you got to recruit. And you know, I think recruiting alongside of a, of a new leader or a leader that's struggling, recruiting is Some of the best experiences I've ever had. It's been the funnest of my career where somebody tells me we can't get anybody in Germany because all of our customers believe that Germany, you know, PTC in Germany is Scientology. That's a whole nother podcast. I'll go into it later. But I'm telling you. And I'm like, okay, so you're telling me. You're telling me we can't recruit anybody in Germany. And it was so good for me, because, first of all, it was real. There was cultural issues. There was. And I was finding that out. I'm in the pit. But some of the best people we brought to the company were people that I had to go stumble through with the. With the. The leader right alongside of me. And then what I used to love to do is get a couple of pairs of eyes, have two people. So if I was teaching somebody great, I was also learning too. I went into a new part of the world or what have you. I was learning about what was going on. And you have one person in there that you say, okay, what I want you to do is I want you to look for opportunity for, like, additional people, like three more names or something. And there's. So they had a role and responsibility. It wasn't just, you know, two people sitting in a room and one person. Person saying nothing. So I found that there's some ways to really mix this up. So everybody learns. Everybody learns.
Matt Nolan
Yeah. Yeah. I mean, I think it's fun to your point, when you take. We kind of went through this year in emea when we rebuilt that team, My leader had never seen great. He had been here a decade. It was a different kind of company. And when he started to see the impact of, like, he made one grade hire, and then, you know, the second guy came along with him and his world changed. Right. Actually, he got sales leader of the year last year. I forget the 240% of his quota. Something like that. Like, it's just an incredible year as a leader. Right. You don't see a lot of 200 plus as a leader very often. And. And you look at that team today and what it was three years ago, and it's like, if you don't understand recruiting now, like, I can't ever teach it because it's so obvious what. Having that talented team and doing that with him, I think was a super fun exercise, to your point. Like, doing it next to each other. And. And like, we got to the point of his daily standups on Recruiting, like, all right, we're gonna have a daily stand up on recruiting and let's figure out where we are, what's the people pipeline, who are we moving, how fast are we moving them? And getting understanding that from a leader standpoint, like, no, this is the job right now. And then this needs to become a part of your DNA and your cadence forever. Like, I think it's fun to watch people transform from never having seen great to. To now seeing great and then getting the benefits of it right. With, you know, getting on stage and getting a trophy a couple years later.
John McMahon
Holy.
John Kaplan
When they see great and it's great is throughout the whole organization, then everybody actually sees it, even the secretaries. So you bring somebody up that's going to interview with you, and as the person walks in the door, you can say, I had a secretary that would go like, no, just waver ahead, back and forth, like, there's no way this person's gonna make it. Or like this person's gonna make it. Because they go down and they interface with that person right away and they start asking them questions and it might be a three minute walk up to your office and they, they extract a lot of information. They know what good looks like because they're in that environment, you know, And I wouldn't say that 100% of the time they were right, but they were pretty close most of the time. Time.
Matt Nolan
It's a data point. If nothing else that, that can.
John McMahon
Yeah, you birds got my juices going, man. It's like no matter what state you're in, whether you're great situation and you want to continue to be great and win multiple championships, whether you have a horrible situation, you can change it around. Like, look at your eagles, Matt, that are playing, you know, for the super bowl this, this weekend. They go from, you know, from winning a championship to going down to like bringing in top talent. How quickly that turns around. Like, you can change your world immediately today by bringing in top talent to your company, no matter what you do. Yeah.
Matt Nolan
I'll sort of leave you with us on the topic. We had coach Todd Desorbo, who's the head coach of the University of Virginia women's swimming and diving team. Four time national champions. Right. And we brought coach in. I got to spend a bunch of time with him kind of one off to. To speak at our GKO that we just had. And what do you think the big secret to building a dynasty was? Right, we look at our redwood, we've won a championship, we're now trying to build a dynasty. It's recruiting, right? Like go get like it's culture, right? Go recruit and then build culture around those people and then you get a couple of those top recruits and it, that flywheel just starts to take effect. And, and the thing around culture that I think what, what coach and I agreed on is like you don't have to morph your culture to everybody. It can't be homogenized. You have to build a culture. That's what you are. And people are going to opt out or opt in from that culture and that's okay, right? It doesn't have to be the right culture for point. My culture is very different than what it was when I got acquired into IBM. That culture wasn't for me. Probably very different than Microsoft and very different than a lot of other companies, right. We have a very specific way that we want to carry ourselves and how we're going to go win our version of a national championship here at Redwood. And, and that's I think a critical component of kind of all this, right? Like recruiting is sort of the, the foundation and then the culture is the thing that sustains you and allows you to win. Multiple, multiple Natties ripped our face.
John Kaplan
I think you remember like I went into, I won't say who it was, but I had, I went in with a D1 football coach and he asked me to help the team and the leaders recruit. And I basically took a modified version of Ned Pick and taught them that where basic, you know, you bas trying to understand what's the decision criteria, identify the pains that this person has or their initiatives for going to a school or some going to some other school, who's the coach and who's the champion. Like who really has influence over this person. You know, maybe it's somebody that's down the street that used to play in the NFL. Maybe it's their mom, maybe it's their dad, maybe it's their brother or sister. But these guys were never, they were going in and recruiting and only seeing how great the program was, blah, blah. But they were never really looking for different motivations and criteria to recruit and that next year they had them. According to like I, you know, I can't remember the name of the company that looks, I think if it's called Scout.com they got the number one recruiting class. It is only by changing a little bit of things and giving them some insight into what's going on in this family. You know, what's going on with this kid, you know, how should I recruit them?
John McMahon
You know, it's funny. I When you think about everything in life to be successful at, you have to have command of the plan or the number. You have to have like, command of that. And you have to have command of the talent. You have to have the ability to attract and retain. We haven't talked a lot about that. That's another podcast. But, like, no matter what you're doing, a new administration comes in, a new whatever, those two things. To simplify this podcast. If you have command of your number and you get command of your people, you're going to go a long, long way. And Matt, sounds like you sounds like over the last three years, you've been doing that really, really well.
Matt Nolan
My friend made a lot of mistakes before I got to this place. So it's.
John Kaplan
That's learning from your mistakes is what makes you good, Matt. We all have them. I call them the scars of experience. So thanks a lot for doing this, Matt. That. This was awesome. I think it's really valuable to the audience.
John McMahon
Great.
Matt Nolan
Well, I appreciate being here. Good to see you guys again. And you know, if, if anybody learned anything, anything from this podcast. You can be bad at everything. If you're great at recruiting, you can, you can cover for a lot of sins and, and fill those in in other ways, but hard to do the inverse, right.
John Kaplan
Thanks, John Kaplan. Thanks, Matt Nolan. Thanks to everyone for listening to another episode of the Revenue Builders podcast.
Thanks for listening to today's episode. Be sure to check us out at forcemanagement.
John McMahon
Com.
Episode: Navigating the CRO Role while Building a Great Culture
Host(s): John Kaplan, John McMahon
Guest: Matt Nolan, Chief Revenue Officer, Redwood Software
Date: April 24, 2025
This episode dives deep into what it’s really like to step into the Chief Revenue Officer (CRO) seat for the first time, particularly in a private equity-backed company, and the challenges of building and scaling a winning sales culture. Matt Nolan shares his journey, lessons learned, and actionable best practices gleaned from transforming teams and growing Redwood Software’s revenue from $80M to over $200M. The conversation goes far beyond operational playbooks to address softer leadership skills, culture-building, board management, and—above all—the critical role of relentless recruiting.
Timestamp: 02:17–08:55
Timestamp: 07:03–08:55
Timestamp: 09:00–14:53
Timestamp: 15:31–17:40
Timestamp: 17:56–21:30
Timestamp: 21:30–34:28
Timestamp: 34:29–59:51
Timestamp: 50:54–54:58
Timestamp: 41:18–44:36
Timestamp: 61:21–62:49
On Leadership Responsibility:
“Everything you say and do is being watched and internalized.”
— Matt Nolan (02:54)
On Team vs. Me:
“I’m judging you based on how many people we can promote off your team. If you miss the number by 5%, but I’m promoting half your team, I can take that hit.”
— Matt Nolan (16:32)
On Recruiting Relentlessness:
“There’s nothing better... than hiring that rep I just talked about and getting him into our org than winning a new logo. Because... the multiplicative effect of having like great people... once you see it, you can’t unsee it.”
— Matt Nolan (22:57)
On Board Management:
"You're gonna spend that first six to nine months proving yourself right."
— Matt Nolan (09:02)
On Pipeline Math:
“As a CRO, you just lost your job... You are the aggregation of all of their mistakes, which they don’t really pay a high penalty for.”
— John McMahon (43:44)
On Cultural Accountability:
“Culture is what you tolerate.”
— Matt Nolan (04:06)
On Recruiting as Universal Leadership DNA:
“Pipeline is recruiting. Pipeline is like your number one job.”
— Matt Nolan (22:31)
If there’s one lesson from this episode: Recruiting is the single highest-leverage activity for revenue leaders—it surpasses closing deals, managing the board, or operational fixes. Relentless, disciplined recruiting at every level, reinforced by a healthy, team-centric culture, is the foundation for both rapid growth and eventual dynasty status.
“You can be bad at everything. If you’re great at recruiting, you can cover for a lot of sins and fill those in in other ways, but hard to do the inverse.”
— Matt Nolan (65:14)
End of Summary