Navigating Uncertainty: Lessons in Leadership with Chris Heaslip

Randy Wootton (00:04):

Well, hello, everybody. This is Randy Wootton, CEO of Maxio and your host of SaaS Expert Voices, where we bring the experts to you to talk about what’s going on in SaaS today and some of the trends unfolding for tomorrow.

(00:15):

Today, I’m delighted to have Chris Heaslip join me. He’s a four-time founder, CEO and exec chair of a company called Leadr, which is a great HR tech. I actually had a chance to chat with the CEO recently and then got introduced to Chris. But here’s the kicker, Chris is like the international man of mystery. He started off at KPMG as a CPA, and now he’s turned into a serial entrepreneur. He ran an accounting firm. He started several companies. He created a platform for faith-based and nonprofit organizations. He’s got a media company and he’s acting as the exec chair. Wow, Chris, what a background.

Chris Heaslip (00:54):

Thank you. It’s great to be with you, Randy.

Randy Wootton (00:56):

Yeah. So excited to have this conversation, but maybe just give the people the short version of like… Connect the dots from KPMG to now, all the things that you’re doing more broadly as an entrepreneur.

Chris Heaslip (01:06):

Yeah. I grew up in a single-parent household and my mother told me, “You’ve got to get a well-respectable, well-paying job.” And so, she figured I was reasonably good at math, and so, accounting was the path that she chose for me when I was young. So that was my goal at eight-years-old, to be a CPA.

Randy Wootton (01:25):

Wow. Some people want to play football, some people want to go play baseball. You wanted be an accountant.

Chris Heaslip (01:29):

Read all the accounting books, debits and credits. So I studied that, went to university in New Zealand, studied accounting, majored in taxation, of all things. Spent a little time at the New Zealand IRS and then made my way to KPMG. And I left there and ran my own practice for a little bit and quickly realized accounting is a great job. You get to meet a lot of really awesome people and get to learn a lot about business.

(01:59):

But I got to the point where accounting doesn’t scale. It really… If you want to add a 100 more clients, you have to hire 10 more staff and carry some more accounts receivable. And just as a business, it’s reasonably difficult to grow and scale the organization. And so I looked at my client list and saw that of the 10 most successful clients I had, they were all in some version of software or intellectual property. And at 30-years-old tried to figure out how to navigate the change from being a CPA to starting my own software company. So that was the short version.

Randy Wootton (02:35):

Wow. And you think about moving from this world of certainty, your first job at the IRS. You’re not going to get fired I’d imagine at the IRS.

Chris Heaslip (02:36):

Correct.

Randy Wootton (02:44):

You’re going to have a nice career, you’d have a nice pension, you have respect in the community. And then it seems like at each stage you took another step towards chaos and uncertainty.

Chris Heaslip (02:56):

Very accurate. And I remember after two years of the IRS I looked and I saw something like 70% of the people had been there 30 years or more, something like that, directionally correct. And I was like, look, if I don’t get out of here, I’m going to be here for 30 years or more too. So it was very comfortable, but I think that step from being comfortable into uncertainty and then doing that again multiple times over the next few years was really something that helped mold and shape my career.

Randy Wootton (03:26):

Well, clearly there was something inside you that motivated you in that direction to be able to take that risk. And then it sounds like you got good reinforcement through that and you had some wins, you had some setbacks, but you just have continued, and it’s just amazing to see what you’ve done. Again, four-time founder, CEO and exec chair.

(03:43):

And what I was really excited to talk to you about was that transition, not from accountant or CPA to SaaS founder, but more of the CEO to exec chair, because a lot of our audience are early stage founders, first-time founders and learning how to be a CEO and thinking about that, and wanted to spend a little bit of time on that specifically. And I think the way we were going to frame it was, I’ve been working on this book, we’ll see if it ever comes out, The Eight Secrets of Success for SaaS CEOs.

(04:13):

What I realized after rereading The Effective Executor by Peter Drucker, is I’m just basically re-purposing everything he’s already said. But these ideas, the eight components, and just quickly, one is driving overall results, because if your company isn’t thriving, you’re falling short. And often people like me and professional CEOs that come in, you’re playing with other people’s money and you got to be super clear about delivering those results.

(04:38):

To enable that, number two is establishing a winning strategy so that everybody knows where they’re going. And we’ll talk a little bit about that. Shaping the culture, which you’ve been involved with your entire career and now as exec chair of Leadr, the technology, and then also when you’re at Pushpay, the SaaS platform for digital giving and engagement. Clearly this idea of values and beliefs has been core to your success and just who you are. Building effective executive team, managing your board, allocating capital, investing in you. And the eighth one, which I think we’ll go into a little bit in more depth is unlocking the potential of your team.

(05:15):

And so help me understand, you were talking about your origin story and growing up on a farm and a single mother, being told, get a job. But how did you begin this journey of self-discovery?

Chris Heaslip (05:30):

Yeah. And to start with the end and work backwards, I think one of the maybe crazy beliefs I have is just the ability to end up in a situation where you have no clue what you’re doing and figure it out along the way. And I think that people have the ability to learn and grow more than what they think. They’re just limited by their own self-worth, self-belief, self… Whatever stories they end up telling themselves.

(05:55):

And for whatever reason, the environment, my mother always gave me a lot of leeway to try things and fail. And that whole mindset has been something that’s been integrated with me since I was very young. And so when you think about even this transition from being a CPA to going into a tech startup, when you start that journey, you literally have no clue on what you’re doing, because the background that you’re coming from is not from anything to do with technology.

(06:23):

And so I just remember sitting there 30-years-old thinking to myself, I’m literally going to be starting from zero again because I’ve put all this time into accounting that’s not really going to help me in building and growing a technology company. Little did I know that when the company went public, all those skills actually were very helpful.

Randy Wootton (06:39):

Yeah.

Chris Heaslip (06:41):

But the ability to analyze a situation and break it down into almost the constituent parts, then to say, which one of these can I learn at this point in time? And so it’s like this empirical knowledge and problem solving that I think that even as leaders and executives, that sometimes the most obvious thing is really the one that we just don’t even see run in front of our face.

(07:04):

And so I like to talk a lot about competencies, for example, and to say, well, the situation that you’re in, what are the core competencies that you need to be able to be successful in that particular situation? And I was talking to a young guy yesterday, he sits right out here, he’s just starting his career as an SDR. And I said, “well, what competencies do you need to be an SDR?” You need persistence. You need to be persuasive, and you need to be able to maybe think quickly on your feet.

(07:30):

Well, if you just imagine you’ve done a great job of this, you’ve developed those competencies over a 12-month period of time, and your boss comes to you and says, well, now you’re going to be promoted to being the team leader of the SDR team. Well, these three things that you’ve learned and developed, now as a team leader, what skills do you need? You need to be able to hire people, motivate people, and train people. That’s it. That’s the only three things you need to be successful as a team leader of a team.

(07:56):

But here’s the thing, that’s not the same three things that you needed as the entry level role. And this framework applies as an executive too. If you think about Ford and Tesla, Ford as a car company has some competencies which are mass manufacturing, building a lot of cars, very cheaply, mass marketing, and then having a dealership network across the states. Those are the core things as I look at Ford, the breakdown.

(08:22):

And then you look at someone like Tesla, exact same industry also selling cars, but their competencies are software, self-driving cars and some kind of online ability to market and sell cars not through a dealer. So here’s these two companies in the exact same industry that have radically different competencies that actually the question is, can Ford learn software, self-driving cars and selling them online faster than Tesla can figure out how to do the things that Ford is good at?

(08:59):

And so when you think about that, there’s so much of our work as leaders is this kind of ability to actually see the things that are obvious but not always dragged into the common discussions that we have. And then to analyze those and say, hey, we have a great company here. Are we an enterprise company or a transactional company? Well, what skill set and competencies do we have? Because these are radically different things that we need to have depending on which way we go, the culture of the team, the people on the team, the strategy we have.

(09:33):

Every single one of these things you’ve pointed out in your eight list, which I love by the way, is going to be determined by which competencies do we have and then how do we structure a strategy and a team and a go to market around those particular things? And it strikes me that no one ever talks like that, to be able to analyze those items and break them down into these little pieces and then say, okay, how do we take it from here?

Randy Wootton (09:57):

Wow, Chris. Lots to dig in on there. I do think though you may be undervaluing your accounting background, because the mathematical way, with which you approach a problem set, which is to stagger it down and say, what are the different components and what are you going to optimize for? Which in many ways is often… Accounting is recording, but it’s also when you add in that next layer of intelligence to it, it’s well, what do you do with that information?

(10:24):

Picking up on your strategy comment, it reminds me of one of my favorite books falling under that secret of success, about establishing a winning strategy is Playing to Win. And in Playing to Win, it’s just a wonderful book. I had a gentleman teach me this when I was at Salesforce, and I’ve used it at four different companies now, but it’s what’s your aspiration? Where are you going to play? How are you going to win? What capabilities do you need? And what management systems do you need to build to reinforce? So exactly to your point.

(10:54):

And when you think about strategic positioning, which corner of the room are you in? How do you define the competitive landscape and understand what your core differentiated DNA is? And so your point around Tesla and Ford is spot on. Another great book by Bain, authors on Profit From the Core, where you go back to what is your essence as a company. And that’s going to lead you in a certain trajectory. And it’s really hard to be an apple if you were originally an orange. You could maybe create a fruit basket at some point, but understanding what your core DNA is as a company. How are you going to compete? Which segment with which category, with which capabilities is absolutely the essence of strategy. You nailed it.

(11:36):

You started the conversation with, though I thought it was super interesting with that same kind of framework apply to the individual. And the idea of the competencies you develop at different stages in your career. What struck me about that, and I want to dig in a little bit about that, is I always think of careers moving horizontal and vertical. There’s a set of experiences you need to build when you’re in a specific job, which is your horizontal experiences and to your point, it’s competencies and it’s capabilities. And so you got to learn. If you’re an SDR, you’ve got to learn how to do call scripts, you got to learn how to do objection handling, all of these different things, that you’ve got to master those skills, and build those competencies. So it’s the what and the how.

(12:17):

And then you step forward to that next level and you have a new set of competencies and skills. And so to your point, as you look back at your career, there is this through line between all the things that you did and you learned. But what you said in the pre-brief, which I thought was fascinating, was at your core what you learned was through reading books, like Rich Dad Poor Dad and How to Win Friends and Influence People. Can you talk a little bit, and bring us all the way back to when you were a little kid and you were operating at the edge of your own ignorance? So your number one capability or competency was a appreciation for we don’t know what we don’t know, and how are you going to build that broader understanding of the universe?

Chris Heaslip (12:58):

Yeah, absolutely. So when I was young, my mother also, she started by paying me money to read books and say, hey, she thought maybe that would help me in my career. And then over time I just kind of took on the habit and stuck with it. But when I found myself in a situation where I was trying to figure out something I didn’t know, I would just start reading everything there was to know about that particular topic, to try and deconstruct the problem into the constituent parts.

(13:24):

But really one of the books that changed my life was when I was a teenager, my uncle got given a copy of this book, Rich Dad Poor Dad for Christmas. He says, “I already have one of these. Here’s one, you have this.” And so I started reading this book, and one of the most unappreciated kind of comments or ideas in the book was, this one that says, never take a job for the money. Take a job for what you can learn. Because money is just simply a trailing indicator of how much you’ve learned.

(13:53):

And so this idea of focusing on learning. Because becoming a person of value and a person who can solve problems and a person who can deal with stressful situations or whatever, turning around a company, whatever it is that your audience finds themselves in, the answer is how do you solve that problem? Well, the answer is you have to have some learnings and skills that you have to be able to bring to that.

(14:15):

And so when you start your career, when I started my career, the goal was just to focus on learning and to really figure out, okay, how can I expand my skill set as much as possible? And you kind of referenced this idea of horizontal skills and vertical skills. The CEO of IDEO coined this term the T-shaped individual, which is you have to be… People think that Benjamin Franklin said, “a jack of all trades and a master of none.” But apparently how the phrase actually went was, a jack of all trades and a master of one.

Randy Wootton (14:47):

Oh, really? I never knew that. Oh, that’s brilliant. Okay.

Chris Heaslip (14:51):

So the idea is how do you go deep in one particular thing but have these adjacent skills that are also helpful? And especially if you’re a CEO or a board member, you can’t just say, well, I’m the sales board member. You need these skills that transcend different particular areas to be able to really take on a bigger problem.

(15:10):

Because most problems are not just one functional problem, especially as you get to senior executive positions or board member positions, the problems are generally multifaceted requiring manufacturing and sales marketing, products, software. It’s really at the intersection of these different skill sets is really how you can solve the problem. And that’s where you see people like Elon Musk who have these just crazy multidisciplinary abilities to solve a problem, not just through depth in one area, but through this learning and adjacency in this horizontal part.

(15:45):

And so just seeking… Back then, even while I was reading books, how do you develop people skills? That seems to be really important in business. So I Googled, what’s the book you should read and How to Win Friends and Influence People comes up. And I remember I was trying to figure out how to get out of the IRS and get a job in the CPA world.

(16:05):

Well, I was reading this book, and one of the stories he tells, Dale Carnegie, is that he was looking for a receptionist and he was like, “oh, well.” So put out this ad. He got 3000 responses and he was digging through them. He got demoralized, because they all seemed much of a muchness, until he came across a cover letter that said, dear Mr. Dale Carnegie, I’ve read your books. I love your stuff. I’m sure you’ve got 1000s of applications. Could I come down to your office and help sort these for you? And if at the end of a day or two we like working together, you can hire me and if you don’t, then nothing venture, nothing gained, right? And he was like, “what have I got to lose?”

(16:48):

And so I was thinking about this and I was thinking, well, KPMG probably gets 1000s, maybe 10s of 1000s of applications a year. And if you just apply everyone else, then your application is just going to go in the round file on the floor. How do you… And I was like, well, I don’t even actually have enough knowledge to be able to understand what it is that someone looking for a graduate hire would look for. So I wrote an email to the managing partner of the local firm and I said, “I’m a young kid, I’m starting my career and would you give me some of your time to just let me understand a little bit about the CPA world and big four accounting. I’ll buy you breakfast or lunch. Anywhere, anytime of the day or night I will be there, you just tell me.”

(17:36):

And I thought, ah, no one’s going to respond to that. Well sure enough, 20 minutes later the response came back, “sure, I would love to help meet with you.” And I just assumed everyone would do this, but apparently that’s not a common thing, just to drop a note to the managing partner and ask for some time to help a young up-and-coming kid. And so we have a meeting and at the end of the meeting I was offered a role at the firm and I was like, wow, if I had just simply gone through that process, sent in an application letter, I would never have been considered, my grades are not good enough. But just simply managing to get in, have a conversation and to be reasonably presentable allows you to skip the queue and go to the front of the line.

(18:19):

And so it just showed me that power of, wow, one idea from a book. And even if you read 10 books and you get one idea, that one idea changed my life, I went big for accounting and that kind of helped me get some serious momentum. And just sometimes I wonder what would’ve happened if I hadn’t read the book?

Randy Wootton (18:37):

Isn’t that amazing? So just this whole idea of just this commitment to learning, operating at the edge of your own ignorance, is starting reading these books and taking lessons on having no fear doing that. And I think a lot of people would hesitate to do it, but you’re like, what the heck? And when you’re young, you’re like, I’ll give it a shot.

(18:56):

I think the idea of how do you think about doing something different, how do you be different is true, and you’re creating companies, right? Because you’re trying to create differentiated value. What are you doing, zig when other people zag. Leading with value, this idea of how do you deliver value the story of Dale Carnegie versus entitled to a job. Enormous amount of value there. And I love the point about take a job for what you learn.

(19:20):

I think one of the things I tell people, in my own life, once a year I go through a job satisfaction criteria. I do it on my birthday, it happens to be January 2nd, so it’s almost like New Year’s resolution. And I go through and I stack rank, four stack rank, what are the things that I want out of this stage of my career? And they move. Sometimes having a great manager is high, sometimes being aligned with a great leader is high. But the number one thing consistently over the last 10 to 12 years, is it intellectually interesting? Am I learning new things? I get bored really easily.

(19:52):

So for example, I shifted from go-to market tech where I’ve been for 20 years and said, okay, I’ve done the CEO thing a couple of times. I don’t have a helicopter, I don’t have a yacht. I still got to… I haven’t nailed it. I’m no Elon Musk. But I was like, man, what about going into a different industry and seeing if this thing would apply?

(20:09):

So to your point, it was I’m doing this very deliberately to learn about a new industry. It’s been super interesting. I’ve learned a lot and I’ve made a bunch of mistakes. But I think as I come out on the other side of that, having that breadth as a CEO who’s now been across multiple industries, they’re all SaaS, makes me even better as pattern matching. Now I have a sensitivity to the office of the CFO and how the CFO thinks versus just when we were selling to the CMO.

(20:33):

So I think that’s great advice. I want to go to the book club in a second, your CEO Book Club in a second, I wanted to tell one more story though. I do think that these tours of duty, that when you go to a job to accomplish something over a period of time. Again, that horizontal vertical skills. And it’s not going to happen in a year, it’s going to take a couple of years.

(20:56):

And I remember being at a internet company when I first started, I was product manager. And about two years into the role we did a huge layoff. It was right during the internet meltdown at 2001, 2002, 50% cut, people going off, no jobs available in Seattle at this time. And we went from 12 product managers to two. I was one, fortunately one of the ones left over. And I remember looking around and saying, “well, the people who weren’t cut were the salespeople.” And there was this aha where I went, “oh.” I need to move from cost center to revenue generator if I want to be guaranteed a job.

(21:34):

And as long as I could do that, generate revenue and produce that growth, people are going to want you on the team. And so that was one of those… I think you have these… You had, you had these different inflection points, these different realizations about what do you want your career to be? So then what’s the next experience you need it to be?

Chris Heaslip (21:54):

That’s exactly right. And I think this idea of personal development really stuck. Sometimes it gets a bad rep because it seems like Tony Robbins and it’s all kind of woo woo kind of stuff. But really it’s just about developing hard skills that are going to help you get more traction in your career.

(22:11):

And that, when we got into Pushpay and Pushpay grew very quickly from 10 staff in 2014 to about 400 staff five years later when I left. We had tried to hire from the outside and we went out to Google and Microsoft and all the usual suspects. And what we found was the success rate of those executives, in fact, we had hired about 15 folks from these really big name brand shops, and we batted about over 15.

Randy Wootton (22:40):

Oh my gosh.

Chris Heaslip (22:41):

And it was just like the culture, that we had rejected this big company bureaucracy. The way that they operated was just not hands-on enough and in the details. But through the process, we found we could develop talent internally that was culture aligned to what we wanted, that could do the same thing, in some cases better for obviously a fraction of the price. But you have some hits and misses.

(23:06):

But the idea of trying to focus on developing people and creating a structure in which you can give people opportunities to skip 2, 3, 4 years ahead in their career in 6 to 12 months, which they would just never get in big organizations. And so that then became a recruiting tool to attract those people who actually wanted to be challenged. They wanted to work hard.

(23:29):

And so I would sit with my team and I would say, “well, who were the highest potential people we have in the organization?” And they would say, “what are the executive priorities or biggest problems in the business that we have that don’t currently have an executive owner, because we just can only have so many?” I would take these high potential people when we would assign them one of these problems and would say, “look, you still got to do your day job, but if you want to take on this problem, one of two things will happen. Either A, you will succeed and get promoted or B, you’ll fail and you will learn.” But there’s no bad outcome because no one was owning these problems internally anyway.

(24:04):

And so it’s this culture of people development, was where this kind of idea came from. And it was finding people who wanted that kind of opportunity to really prove themselves. And so then we started saying, well, the problem with that is, if we back up people haven’t even got the requisite knowledge and infrastructure. What if we create this program where we would call it the CEO Book Club where we would give them books to read or they could choose any book that would help them in their job and that we would cover the cost of that?

(24:35):

This thing costs pennies on the dollar considering the value we got from it. And sending them to executive coaching and training would cost 10s of 1000s of dollars. That’s 30 bucks a book. I’m like, if you can’t get one good idea out of a $30 book, we’re doing something wrong. And so people loved that. This whole idea of, if you’re doing a great job getting the opportunity to prove yourself and the company would invest in you if you’re a director or an executive. Hey, if there’s a conference that’s going to help you grow in your career, we would cover the cost of it.

(25:06):

And being very intentional about saying, “we want people to learn and grow and develop.” Because that’s what our whole philosophy of people management was based on. And I didn’t know, I’d never done this before, I’d never worked in a big company before. I didn’t know that wasn’t how it was done. I thought that’s what every company did. Come to find out that’s not what every company does.

Randy Wootton (25:26):

Yeah, no. So I did have the chance to work at Microsoft for a while, for about seven years and left. And then I went to Rocket Fuel after doing a startup, which… Excuse me, not Rocket Fuel, I went to Salesforce. And fortunately at those two companies, I was on their bench program. And they do do an incredible job of cultivating talent. You’ve got to be someone who’s already demonstrated results. You’ve got to be good attitude, to be able to do all the interpersonal stuff. And then you got to demonstrate this ambition to want more. And more means it takes more time.

(25:55):

And so investing in these courses or taking on the special projects I think is one way you can breed that culture. At Maxio, we talk about one of our objectives is to grow our own, very similarly, it’s not just labor arbitrage opportunity. You get to teach people and attract talent that you want to grow, we call Maxio or not, so everybody has their way of referencing them, in the way you run business and you get to unlock their potential, which is the eighth secret of success, unlocking the potential of your team.

(26:30):

And I think the things you’re calling out, which we’ll go to in just a second about Leadr, is just being very deliberate and intentional about it, about having a program for developing great management, about having a program for defining the difference between what it means to be a leader versus a manager, and then having a program for hypos and how do you bring people through so they’re set up for success and you can take that next step.

(26:54):

The CEO Book Club, I just want to pause on that because you talked about it really quickly. So I’ve done book clubs. I was an English major, my first master’s was in the great books. I love books. I love sharing ideas. To your point, I find that a text and a conversation helps me learn every single time I do it. I’ve never incented people in terms of buying the book. The book club we have at Maxio right now is one where people have to buy the book. We do business books, we do nonfiction, we do fiction.

(27:23):

It’s kind of a collective. I don’t know, six or seven people show up. It’s a fun conversation. I think it also, Chris, allows for a real human connection, because you’re talking about a book. And I tend to build relationships through the work. People always become too intense, like, “hey, let me talk about the work and what’s working, what’s not, and let’s brainstorm and six ideas.” And people are like, “Randy, time-out.” But in the book club it creates a very different dynamic.

(27:48):

So maybe can you say a little bit more about what’s made your… How many people of your companies participate? What percent of the people participated in the book club? And were you doing it once a month, once a quarter? What were some of the things that you did to make it a real success?

Chris Heaslip (28:02):

So this is what we did back then, which was more self-directed, which was we wanted people to come to us with the idea of the book they wanted to read.

Randy Wootton (28:09):

Oh, so it wasn’t a conversation, it was individuals doing books on their own?

Chris Heaslip (28:09):

Correct.

Randy Wootton (28:09):

Okay.

Chris Heaslip (28:17):

But at Leadr now, we have two kind of programs. One is in the onboarding part. We would give people books and say, look, here’s a pathway of when we want the book completed. In an onboarding and induction classes we would have people read the book and discuss it in the actual onboarding part of their classes, as part of joining the Leadr team.

(28:40):

But then we also have a program at Leadr called Leaders Develop Leaders, which is for those high potential people, and they can be across the organization, where we have 8 to 10 week development program where there’s multiple books involved in that, with our reading it and discussing it with a cohort. And the thing with that is, Randy that costs very little to do. It’s just intentional. And it takes someone just organizing the people together to do it. They get stretch projects, they get opportunities to think about problems and problem solving.

(29:14):

And so books are a core part of that. And so that’s how I would do it today, which is a little different. We still have the CEO Book Club where people can basically say, I need this book. It’s 20 bucks, it will help me in my job, and we buy it for them. And that’s covered. But that idea of just developing a 10-week program, even for a small company, 50, a 100 people can have incredible outsized results versus the cost of putting it on.

(29:40):

Andy Grove was famous for this. He used to say The ROI on training is infinite, because the cost of the manager spending an hour or two with a staff member talking through, here’s the skills that you need or the competencies you need to get to the next level, and then training on those. And then if you get a 5% increase in productivity from that small investment, then that’s going to carry on for years to come from that one small input of actual cost.

(30:09):

So that, I just think how we as leaders need to think about it. And that’s not even kind of thinking about the long-term legacy of leaving with these people. I just got a letter today from a lady who was on our product team at Pushpay six, seven years ago, and she literally said, the impact of you sharing your story and how you managed to come from New Zealand and start Pushpay and the book club, it literally changed my life, and I’ve started a startup myself, working in a specific area, because of the ideas that you were sharing with me. And it makes it all worth while, right?

Randy Wootton (30:48):

It does.

Chris Heaslip (30:51):

We do it because we’re selfish business people. We’re like, we want to grow and develop a business. But people stick with us two, three years, and then obviously they’re going to move on to other things. And we hope that what they remember from the time with us was that we cared for them, that we treated them with respect, that we shared what we had, the knowledge, because someone took the time for you and for me to invest into us. And in some ways, that’s paying it forwards to the next generation. And even if you get zero business benefit from it, it’s still the right thing to do for those reasons.

Randy Wootton (31:24):

Absolutely. I think again, unlocking the potential of a team, we all… If you’ve been successful, it’s because of someone else. And so it’s the pay it back and pay it forward. And then to your point, the most satisfying part as we were talking about in our pre-brief, of the career is the people who reach out and say, hey, it was great.

(31:40):

In fact, just to that point, I have two people that are just joining the company now that I’ve worked with at multiple companies, and you just have this immense trust that’s already established, this camaraderie that you have built, and it’s a new set of problems to go after, but you’re not starting from zero with the relationship.

(31:59):

But let’s do this, Chris, because we’ve had a great conversation on this whole unlocking the potential of your team. But one of the reasons I wanted you on the podcast was because of your position as an exec chair, multiple times CEO, and now you’re an exec chair of Leadr. Can you help people understand what an exec chair role is and how is it different than a CEO? And then we’ll talk about what’s the value and how is it different between VC and board members? But just help give a definition, your definition of what an exec chair is.

Chris Heaslip (32:27):

So for me and Matt, we worked together for five or six years at Pushpay. And Matt is a great example of this philosophy, right? Started as the first SDR, first five hire at Pushpay, worked his way through SDR director and then finally VP of sales when he wrapped up there. And now CEO.

(32:47):

So over a 10-year swing of working together, that idea of development, he doesn’t have a college degree, he didn’t go to Harvard or any of that stuff. So just to point out, this is not something that is just an intellectual curiosity. This is something we live and breathe in and is truly something we embody. But how we worked together in that role is after my time at Pushpay, I thought, well, you know what I really wished I had? In my time there I had a board member, a six-person board, we’re a public company, and as a CEO, who’s in your corner fighting for you? Who is the person saying, I care about you and your development. I care about the company succeeding, don’t get me wrong. But who’s the person who shoots it straight to you and tells you, hey, you just did a terrible job in that board meeting, with candor.

(33:41):

But you have to have, to me, two or three things are really important in that role. Number one is you can’t be completely divorced from the operation of the business. Because then how do you know how to give relevant, timely, accurate, candid feedback? I don’t think it’s possible for someone to do that, being removed from the organization. The second one is they have to care about you as equally, if not more than the results from the business. Because sometimes these things become intertwined, the business results and the capabilities and capacity of the leader. And you have to be able to have a conversation with a whole degree of trust and emotional safety to be able to provide this kind of feedback that’s really about helping the leader grow and develop.

(34:26):

And the third one is it has to be non-political, because the second that politics becomes involved, it’s like, do you really care about me and my development or are you just trying to position me because the board has politics involved? And so that role led us to create this role where we work together actively. Matt’s leading the day-to-day role of the company, but I give him a lot of flexibility and leeway to make those decisions. However, my role is to say, Matt, you need to think about this, or you need to focus on these areas of improvement because this is not where it needs to be right now. And he can take that without worrying about all those preconditions I just mentioned before.

Randy Wootton (35:08):

That’s awesome. Yeah, my seventh secret, not trying to make it all about the secrets, but is investing in you. And that includes building your tribe, having a mentor, a coach, a peer group, and what I call a personal advisory board. Personal advisory board of people who’ve known you for a long time who can call you out on your BS.

(35:24):

The mentor is someone who’s stage-specific, has been able to help you navigate like a turnaround. A coach is someone… I found when I did my first public company. I’ve only done one, but my first company was a public company. I needed help how to manage a board. So having someone through the interpersonal effectiveness. And then the peer group I’ve been in Vistage, I’ve been in Alliance to CEOs, but having a group of people that know how hard it is to be CEO.

(35:49):

But your suggestion of this exec chair is really interesting. When I started at Rocket Fuel, this public company, I had an exec chair, it was someone on the board, but it was more about in that role, much tighter alignment between me and this person, Monte Zweben, who’s been awesome, one of my mentors, great guy. And it was almost like having CEO training wheels on. They wanted to make sure I could do it for some period of time. And then there was a period of time where he said, okay, Randy, now you’re really CEO.

(36:15):

But you’re kind of outlining, describing a slightly different relationship, which I would think of boards when they bring on an independent board member. So someone who’s not a VC, someone who’s brought on as a go-to-market expert. I’ve done this for a couple of boards. How do you draw the distinction between what an exec chair and an independent board member might do?

Chris Heaslip (36:35):

Yeah. I think it’s kind of that idea of the T-shape before, like an independent board member. And Matt, we hired an incredible coach for Matt at Pushpay, Peter Wooster, he’s on our board at Leadr. That’s how much we respected him, first AE at Salesforce. And he was almost single-handedly responsible for Matt’s growth and trajectory. Going from being a 27-year-old leading a 100 SDRs and AEs. That’s a lot to take on.

(37:03):

And so having that person with that deep functional experience is absolutely critical. You need that. But being able to see the whole field of play at one time, the problem with a sales independent board member is everything is a sales problem. And as a CEO, the challenge is you’re the only… At any size and scale of an organization, the CEO is the only generalist in the company, because you need eight different disciplines to be successful in that role. And so the problem is, if you just have one functional skill, you can’t see the whole field of play.

(37:38):

And so the analogy I like to give, is it’s like Bill Belichick and Tom Brady, they’re both required for success. Tom Brady’s on the field throwing darts to the wide receivers, he’s seeing a particular perspective, but his perspective is locked in tunnel vision. This is all I could see on this particular play. Whereas Bill Belichick, the coach in the box is up here looking down at the whole field, and he’s got this extensive repertoire of football knowledge. Over the last 100 years he’s watched every game tape known to man, and he starts to say, “hey, wait a second. This play that’s being drawn up here is like this other play that Army versus Navy in 1965 ran. I’ve seen this before. This is how you counteract this thing.”

(38:22):

And so especially for young ambitious up-and-coming executives, what they lack is that groundedness in almost business history, and that experience. Because they’re just doing this for the first time, like Tom Brady on the field, locked in on this is what we’re trying to execute. And having someone come along behind you who’s not just focused on one discipline and say, hey, wait a second, this thing is this other thing that I saw over here and I’ve got 20 years or 30 years more experience than you to help bring to the table. Say, what about this? Or what about that? Or Have you thought about this thing? Or why don’t you go and research what happened in such and such a business case?

(39:03):

And that’s invaluable. Because you’re not saying you need to do this. You’re saying, here’s some things that you might not have thought about. And inevitably the person with the experience ends up being correct. Now that doesn’t tell the executive himself how to apply it in the situation. It’s just like, oh, there’s a lot of context here that I’m missing that I wasn’t aware of.

Randy Wootton (39:23):

Yeah, I think when board members are at their best, to your point, I think this is what VC and PE board members can help with, as well as the pattern matching, they’re watching success across lots of different companies and they’re able to say… And we see this at SaaS, in particular in terms of having specific benchmarks for gross retention, gross margin, LTV to CAC, all these different components that they’re triangulating on to say, are you competitive with the field? And what is it? What’s the play?

(39:51):

So one of the plays I got clear on at this job was monetization and how important pricing was. And so we went through… The two and a half years I’ve been here, we’ve done four different rounds of pricing. And the general partner, Chelsea Stoner said this to me when I walked in the door. She said, “most companies they start with don’t know how to do strategic pricing.” They’ve got to build that capability in-house. I didn’t have it. I hadn’t done it before. And it was a long journey and we’re getting better at it.

(40:19):

But it was one of these things because her pattern matching. She was like, “this is where there’s a huge opportunity.” I was, “really?” Well, part of our pricing is based on the trailing 12 months of billing with our customers. So yes, of course it’s a huge deal. And so that was one of those shift to the new industry and be humble enough to say, I don’t know, what are the levers you can pull? And having someone on the board who could help provide some context and perspective.

(40:44):

The other thing you said, which I really liked was this idea when I’m on a board, I talk about nose in, fingers out. Nose in means ask lots of questions, just sort of help me understand your assumptions, what data you’re using. Or to your point, here’s some things to explore. But at the end of the day, I’m not the operator. And if they hired me as an independent board observer or a board member or observer, it’s, hey, you go do it and let’s talk about it in a month or a quarter when we do our next board meeting. But it’s your call.

(41:11):

So maybe help me understand how you think about drawing that line between when is it Matt’s call and when is it your call? Have you made that explicit? Because you’ve got a lot at stake, you’ve got a big stake in this company. And if he’s running down the rabbit hole and you’re like, dude, you’re going the wrong way. I’ve seen it 10 times before. You’ve told him, hey, I’ve seen this 10 times before. He’s still running down the… Not that he would, he’s wonderful. But just hypothetically, how do you think about dividing or making clear when it’s his call versus your call?

Chris Heaslip (41:42):

That’s a great question. I think in our case, we started Leadr together, we’re involved from early on. I probably a bunch more context, just having been more involved in this type of stuff at Pushpay. And early on I think it was more we’re in it together, actually butting heads sometimes backwards and forwards trying to figure out which is the correct answer. And at that point it was more like we weren’t… But I was like, CEOs. Hey, we’re really kind of in this because the decisions we make now are going to shape the next five and 10 years. And there’s decisions that just aren’t reversible.

(42:17):

So you have to be able to be in lockstep in alignment of those decisions. Because once you’ve made them, there’s no going back on them. And then there’s others that I early on pushed for that I got wrong. We had an adjacent kind of HR suite of products and services that we have since exited, that I said, “hey Matt, I think we should do this.” And he maybe tolerated my stupidity for a while, and appeared… He was correct about that. And the idea to refocus on the core and get out of that HR side of things was really important.

(42:53):

And so I think at that stage… It’s stage dependent. I think once we get further on from that, now it’s less about this decision is going to change the trajectory this way or this way and more… I just don’t think that you are going to be able to attract and retain great people if you’re micromanaging in the business. And so I just know as someone who was a CEO, if the board is telling me, hey, your pricing should be A, B and C, it’s going to be very frustrating and at some point great people are just going to be like, “Randy, what do you need me for if you’re just telling me how to do all the stuff? You can hire an order taker for half the price. I’m going to take my services somewhere else.”

(43:32):

And so I think a part of it’s ultimately just leading people how you yourself want to be led with that, as much self-awareness as possible because we don’t want to be micromanaged as senior executives. And so we’ve got to try our best not to do that with other folks too.

Randy Wootton (43:47):

Well, Amen, Chris, I’ll tell you what, this is a great conversation. I really enjoyed it. Thank you very much for all the insights you provided in terms of unlocking people’s potential, your story, the CEO Book Club. I’m going to take that for action, and then just your insights on being an executive chair. If someone wanted to find you is the best way LinkedIn? Or do you have other places you’d like them to track you down?

Chris Heaslip (44:09):

Well, LinkedIn, Twitter is probably my preferred go-to just at Chris Heaslip, H-E-A-S-L-I-P. And love to hear from anyone in your audience.

Randy Wootton (44:18):

Awesome. Well, we will put that in the show notes. We wish you lots of luck and many thanks for joining us today.

Chris Heaslip (44:25):

Sounds good, thanks Randy.