Strong Leaders Bring Courage and Confidence to All Things with Enrico Palmerino at Botkeeper

Every company will say they desire strong leaders. Few are willing to do the work or invest in their people to make that happen. Strong leaders do more than execute. They develop the people around them. Today’s guest is Enrico Palmerino, CEO at Botkeeper. Inc Magazine ranked his company #850 on the 2020 Inc 5000 list. Botkeeper is one of the fastest growth bookkeeping companies on the list. They leverage technology to keep your books straight. Enrico has built another company that made the Inc 5000 list that he started from his dorm room and exited it. Enrico shares wisdom on how to create strong leaders. We look beyond the typical messages on leadership. Strong leaders can engage people the right way.

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Enrico Palmerino: The Transcript

About: Enrico Palmerino is the Founder and CEO of Botkeeper. Botkeeper is an automated accounting platform that uses human-assisted machine learning and AI to deliver the fastest, most accurate, and lowest-cost bookkeeping available to accounting firms. Botkeeper allows accounting firms to scale their CAS practice, benefiting from software-like margins, while simultaneously improving the experience, reliability, and bookkeeping results for their small business clients.

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Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.

Enrico Palmerino
When you’re matching for culture fit, what seems very like natural and easy to do, it’s just because you have a lot of context around it. But as you start to grow and scale and hit that next level now you like, you’re starting to have to reach well outside of your network and you have to be more methodical and process-oriented around how you ensure that those people who don’t have all those years of experience where their contacts with actually are a good fit, so it’s definitely become a lot more refined. I’ve gotten pointers and tips from RBC is from other successful entrepreneurs along the way who have helped me.

Intro [0:33]
Welcome to Growth Think Tank. This is the one and only place where you will get insight from the founders and the CEOs, the fastest-growing privately held companies. I am the host. My name is Gene Hammett. I hope leaders and their teams navigate the defining moments of their growth. Are you ready to grow?

Gene Hammett [0:51]
Developing strong leaders is something you have to think about as the leader of your fast-growing company. We focus on the Inc 5000. And the founders and CEOs of fast-growth companies. And they talk about the importance of developing strong leaders. Today, we go deep into it with the CEO of botkeeper, they were number 850 on the Inc list, we’re going to talk to Enrico Palmerino. And he’s built multiple companies, many of them of the two of them have hit the Inc list. But I want you to think about what you’re doing to develop the leaders around you. And Enrico shares why questions are so important, what they really are able to do by asking the right questions and letting people figure it out for themselves. We also talk about some of the things that get in the way of common leadership and hiring the best leaders, developing strong leaders is the topic. And today you’re going to learn from Enrico, when you think about your own leadership, and you think about how you’re evolving, make sure you continue to put together a plan. be intentional about the skills that you’re putting together so that you can evolve as the leader that your team deserves. If you want to go to my website, You can actually start your journey with me and actually get on the phone and we’ll talk about what your next step is, in this growth acceleration call, you will understand exactly what you need to do next. It’s absolutely no cost to you. And I’m happy to serve you. Because you’re tuning in to this podcast, make sure you go to gene Hammett comm and sign up today. Now here’s Enrico.

Gene Hammett [2:22]
How are you?

Enrico Palmerino [2:23]
Doing well, thank you. How are you?

Gene Hammett [2:25]
Excited to have you on growth think tank to talk about leadership and culture in fast-growth companies’ environments. So tell us about botkeeper.

Enrico Palmerino [2:34]
Botkeeper is an automated bookkeeping platform for accounting firms. And it I think it combines the best of both technology AI and machine learning with a high quality high touch human support. So it’s kind of the old adage that machines aren’t perfect. Neither are humans, but the combination of the two is pretty damn close to being perfect.

Gene Hammett [2:53]
Well, I love the idea of this. We were talking a little bit offline here about how you know integrations have made these things possible. But sometimes they make them more difficult than they should be. You’ve built a team around solving this problem for accounting firms, and probably even companies. The team is about 200 and you made the Inc list last year, I’d never 850 Why do you think that was that was possible with your team?

Enrico Palmerino [3:19]
I think it was, it was awesome. And quite frankly, I was disappointed. We were only 850 and not, you know, further up the list. But I think I think it just ultimately comes down to we’ve hired extremely passionate successful individuals in the leadership positions here a bookkeeper, and that we’ve made sure that they, I think like one of the first things I’m searching for is a culture fit to be fit culture. Next, it’s a skills match. And, you know, we try to find the people who fit our culture the tightest and have the best skill set, but I think it just boils down to like I’m not an expert at really anything these days about keeper but we’ve got a team who’s just like who are experts at the thing that they’re doing and just incredibly passionate and focused on it and you put enough passionate focus people together that are having fun at what they’re doing and success usually comes

Gene Hammett [4:08]
Well, we’ve had many leaders talk about this culture fit and you see that’s important. Give us how you actually do that when you’re when you’re hiring a leader like I know there’s a lot of ways to do this in frontline but you’re hiring an executive leader to bring into to manage a team What does that culture fit look like for you?

Enrico Palmerino [4:27]
So first I’m I’m screening on you know what, what are the drivers are the things that keep this person up at night? Like what do they care about? What does success look like for them? What are their goals ambitions? Like how long do they see themselves at a company? Why are they even working? A lot of the people have been successful enough that they don’t have to work anymore. So why do you keep doing it? What are you chasing? What are some demons that you have inside that you know you want to beat off or you know, like combat or win or claim victory over And then I think the other thing I’m looking for is like when you think about like a few values that you live by what are those values? And then you take a look at all those things. And we decide like how closely does that match up to what we what we’ve instilled as our values and company here. And ultimately, blocky rose values are, I think, just an embodiment of myself. Like, that’s the that’s one aspect of me that calls it like, larger than life. Because, you know, ultimately, the first few people I hired were people who were probably like-minded, like me, that I knew I’d be able to work with. And now I’m just trying to instill that.

Gene Hammett [5:36]
Into this whole concept of values in the hiring process. A lot of people don’t really understand you went through a lot of questions there that show me that you have put some thought and intention around hiring the right people, you probably also know, that’s probably one of the most expensive things you can do as a young company that’s trying to grow fast is hire the wrong people. Does has as this process, rough, you know, been refined over the years, or did you just kind of come out, and this this company, and, and have it more like it is today.

Enrico Palmerino [6:09]
So it’s definitely been refined over the years. I think, you know, the early stage was, you’re picking people that you likely know, to join the company. And so it’s like, it’s people like close in your network. It’s like friends that you’ve had for a while that you know, have like succeeded at this thing. That might not be your expertise, but that’s their expertise. And so in the beginning, or the earliest stages, what, when you’re matching for culture fit what seems very like natural and easy to do, it’s just because you have a lot of context around it. But as you start to grow and scale and hit that next level, now you’re like, you’re starting to reach well outside of your network. And you have to be more methodical and process-oriented around how you ensure that those people with who you don’t have all those years of experience where their contacts, actually are a good fit. So it’s definitely become a lot more refined. I’ve gotten pointers and tips from our VCs, from other successful entrepreneurs along the way who have helped me out with it.

Gene Hammett [7:05]
Now, when you said strong leadership, my mind immediately went to the executive leadership team. And I know there’s more to leadership than just that core set of people. But I would like to focus on you hiring that executive leadership team and kind of how you’re working with them on a day-to-day basis. When you think about that, did you hire them from within and train them up? Or did you go outside your, your current team and find experts in certain individual areas and hire them or mixture.

Enrico Palmerino [7:37]
I’d say a little bit of a mixture. So we’ve definitely had on the executive leadership team people have were among the early hires here who have like proven themselves and continue to grow and scale with the business and evolve. And that’s a tough thing to do, just like constantly having to like up the ante on your skill set if you don’t have that track record or previous past. But there are people who are more than capable have proven themselves time and time again here. And then we’ve reached we’ve gone outside, you know, outside the company to find and hire other experts that we needed, at different points in time in the business. So I’d say the combination of both.

Commentary [8:15]
Now hold on, Enrico just said something really interesting. He’s got a mixture of people on the executive leadership team that has come from within. So he’s developed them over time, and he’s hired experts from the outside, you want to make sure that you have both of these because they really do create the ability to grow the right team. Sometimes you have to go outside, but you also want to have a plan for developing those around you developing their leadership skills so that they can be strong leaders and giving them a chance to, you know, make it to the executive leadership team. It also signals to the others in the culture, that there is a path forward, that they’re not just going to be someone from the outside is going to be hired above them. But if they’re stepping up in the right way, if they’re taking ownership and they’re being leaders inside their current role, they have a chance to move forward and be on the executive leadership team. Back to the interview with Enrico.

Gene Hammett [9:09]
Now when you say your job now I’m looking at you on video. You’re a pretty young-looking guy. Your company’s only five years old had you built an executive leadership team before?

Enrico Palmerino [9:19]
I had to this is my third venture. So the first company I started was and this is probably why my expectation for the ranking on Inc was a little bit higher. But the first company I started in my dorm room, we were 46 on the Inc 500 list and went from like dorm rooms about eight and a half million in a couple of years. So and there’s I look back and there’s like a photo of us and I think it was like the Wall Street Journal or Yeah, it was one of the newspapers. It’s like me and my business partner was like 18 years old, and everyone else is like in there I think the 40s or older and so we just we hired people who were skilled like we knew, the tech that we were building we knew like the vision that we have for how we were going to execute on this, and a lot of we had a lot of energy and like sleepless nights too, like, get it done. But we also knew we needed people that would make sure we don’t make a whole ton of mistakes along the way.

Gene Hammett [10:09]
What industry was that first business in?

Enrico Palmerino [10:11]
Lighting, So as we were automating how you do lighting, analysis, design, and manufacturing.

Gene Hammett [10:16]
And you said, this is the third venture. So there’s one in between what was that industry?

Enrico Palmerino [10:20]
Cloud accounting, so my biggest headache with the lighting one was our accounting couldn’t keep up or give, you know, issues of accuracy or detail. And so I got into Cloud accounting and then ran into scale challenges with cloud accounting because it’s heavily human dependent. And so botkeeper emerged as a consolidator of the app stack for accountants, and a way to automate a lot of the manual bookkeeping.

Gene Hammett [10:46]
Well, it’s good to have that history that you bring with you. So now in this new version of the company, bookkeeper, you are optimizing your executive leadership team, what does that look like? If you had to describe to me your rhythm of communication and style of communication to develop them to be stronger leaders? What would it look like?

Enrico Palmerino [11:08]
And I’d say like, I’m, I’m becoming a stronger leader, I’m learning from them, I’d say almost equal parts becoming a shop as well. So we have a cadence where it’s we meet as a team, once a week to kind of do some updates, and then, you know, hit on a few of the big, like, hot topics that have come up. And then I do one on ones with all my executives to, you know, spend time or focus in on, you know, it’s, I almost say like, one of the screening criteria for people here is like, how comfortable you are with dealing with problems because I feel like all we deal with problems, it’s like always overcoming hurdles.

Enrico Palmerino [11:43]
So, you know, most of that one is just talking about hurdles or challenges that might be going on in a department and how we’re going to overcome it and setting dates and, and timelines around when we will and what success looks like and how we avoid that same headache again. So it’s an I’m a sounding board, I almost feel like and instill our tribal knowledge. And just a question asker. So I think I asked a lot of questions. That helps pull out, you know, some things that that person probably already knew, I just made things that they might not have thought of, now at the forefront of the table. And, you know, I’m just sounding board bounce ideas off of and give another opinion to.

Gene Hammett [12:26]
You know, asking lots of questions. Sounds like your kind of coaching them more than the traditional kind of authoritarian leadership. Have you found that to be the best way to develop the leaders around you?

Enrico Palmerino [12:37]
Yeah, I find, I think, for me, part of our philosophy and culture is that you know, the way to best lead people is by influencing them, not by telling them what to do. And that comes with collaboration, like I’d rather have you be the one that comes up with the idea, and it be an idea that I’m going to come to the table with, but I get you to see it as your idea. And I just it just that kind of style takes a little bit longer because you’re like trying to pull it out of them, you let it know that you that the other person across the room would come at the same answer, potentially, or they call it with something that’s better.

Enrico Palmerino [13:12]
And now you didn’t go and tell them what you think the answer is, and they take it for granted. So yeah, it’s just it’s like prying and trying to understand all the inner workings and the details unexplored. And either someone follows your path to the solution, or they take a different path. And maybe it’s a better one than you thought than yours was, you know, kind of coming to the table.

Commentary [13:32]
Hold on for a second. And Rico just talked about the need to influence others instead of telling them what to do. Now, this whole idea of influencing them can take many shapes and forms. But one of the most powerful ways to influence others is to ask questions and allow them to figure it out for themselves. We’ve talked about it in this episode, but I just want to put a spotlight on it for a second. If you aren’t, you know, developing your own skills to coach people to higher levels of confidence, courage, and even clarity and what to do and how to solve these problems. You’re actually making it harder for yourself. And the real key here is to slow down, ask the right questions, let them figure it out for themselves, and support them when they get stuck. But not to solve the problem for them. When you become that kind of coach. That is the type of leadership that people admire. They feel fulfilled around, they feel like they’re growing. And you will get better performance out of the people around you. And you’ll be judged as a stronger leader because you help them figure it out instead of just telling them what to do next. And back to the interview with Enrico.

Gene Hammett [14:35]
Now, we haven’t said this today. But a lot of my interviews end up at the same place. It sounds like when you’re asking these questions. You’re really trying to get them to take ownership of kind of what the issue is so that they can actually own the process to get there. Do you think about this, this sense of ownership, and your leadership very much?

Enrico Palmerino [14:54]
I think it’s important. I think people want to be empowered. They want to feel like they have to mean They want to feel like, you know, they’ve got a purpose and that they’ve had it, they’ve impacted and influenced the success of the business. And so, you know, if someone just, I’m just coming into saying, we’re going to do this, and this and this and this, and you’re just kind of like, you know, showing up and following a drill. That’s, that’s not super fun. And you don’t really feel dedication and commitment to it. And I also think that like, the reality is, I don’t have all the right answers. So I shouldn’t be coming to you with a laundry list of what should be done. I should be sitting down and asking you what you think should be done, and asking you like, why you think that? And are you sure that’s the right way, and just kind of like, probing deeper and deeper, and eventually finding like the, you know, finding the solution in you? And maybe I’m like, Oh, that’s awesome. I actually kind of thought, similar thing, look, here’s a model I put together about it, and what do you think, and my goal is to have an outcome be whatever, I think is the answer, that I leave walking out with something that’s probably a little bit different than what I came in with. And that usually means we found the right thing.

Gene Hammett [16:00]
You know, I love this approach. And I even have to work on it with my clients. And this executive coaching that I do is, is helping them not solve the problem, but actually just help the person that they’re leading, understand and solve the problem for themselves. And it’s very dangerous, you know, this happens all the time in sales, you take that the high performing salesperson and they become a leader or manager of sales. And all of a sudden, they just want to tell them what to do next. But that’s actually the most effective way to actually lead and develop people. When you’re doing this. And Rico, you know, did you learn this through the other companies, you’ve gone to? Or is this something you’ve really kind of attached yourself, in this version of your entrepreneurship journey?

Enrico Palmerino [16:42]
I think I’ve evolved over time. So I think I used to be a very controlling person initially, and you don’t want to, like group work, Matt, like, I’m going to do my piece of art like really, really well. And here, you go to being much more like, let’s work together really, as a group. And instead of putting, like assembling a bunch of individually contributed pieces as a group project, like actually collaborating, and, and the outcome just always looks so much better. When there’s like real collaboration and real work together, it’s just more cohesive, and it tends to be, there’s more passion, I think fire in it. And what I’ve found is that you know, the reality is like, if I start coming to people with all the answers, that I’m literally just going to be dragged into everything like I don’t want to be I want to be focused on raising more capital, like begging to the market is like my vision of how this is going to play out and where I think it’s going, and that to do that I need to be freed up and to be freed up, I need my leadership team to be able to think on their own and make decisions on their own and feel comfortable doing it and not feel like they have to run everything by me or asked me for the answers.

Gene Hammett [17:44]
Enrico, I’ve recently launched a series around optimizing your time as a CEO, what would you say has been the most impactful, you know, kind of strategy that you’ve been able to implement that optimize your own time as a CEO?

Enrico Palmerino [17:59]
So I spend real time trying to figure out, like, what are the two or three things I’m going to do on a quarterly basis that is going to move the needle, and maybe like, what’s the two or three things they’ll do over the course of the year that will move the needle? And none of those things should involve me doing anything operational? So it’s like, you know, from a partnership standpoint, who can I work with to land a big partnership with the company that will get us there? And that means, how do I enable or support the existing teams that are already working on partnerships like that? And how do I provide the air cover? Or how do I give a talk somewhere that influences them partnering with us because they see us as a thought leader? So, you know, for me, it’s, it’s, I gotta free up my time. So I got to hire smart people who can think on their own, I got to enable them to think on their own, I gotta get out of their way. So they can do it. And then let me just be a sounding board, and help out when they need. And that will let me work on these big projects.

Commentary [18:53]
If you’re listening on iTunes today, make sure you go to YouTube and find us there, you can go to, we have some special content only on YouTube, that will help you be the visionary leader that your team deserves. Just go to That’s an absolutely mature way to look at it. And I help a lot of people find that when you think about how the business has evolved, once you’ve started putting this into place, what we see I mean, you actually doing these kinds of projects and not being dragged into the operations.

Enrico Palmerino [19:27]
So I think the funniest thing is like I see it’s, I think a constant, you know, roller coaster of like my time I slowly will get pulled into stuff. And then I hire someone to like, take me out of it. And then I listen I see personally like a lot of freed up time, a lot less stress, a lot more success, and, and we’re moving faster at that thing than it was moving when I was involved in it. And, you know, the irony too, is like our VCs, like, see me as a better CEO. So the more I hire really smart people to do all the work for me, the more I’m seen as like A great CEO, because I’m not trying to get bogged down in the weeds or I’m not trying to control every aspect. And the reality is it just boils down to, I’m one person, I can’t be an expert at anything. Unless I’m, that’s the only thing I’m doing and being a CEO means you really can’t like, the only thing you’re you should be doing is raising capital, you know, being a thought leader, and being a sounding board, to other experts you bring in and so I gotta find and hire the experts that just care about that one thing that they’re doing, and they obsess about it and, and will crush it.

Gene Hammett [20:34]
Enrico, thank you so much for being a part of the growth think tank to talk about how you’ve structured your own leadership and evolved as a leader to grow a company that has been able to make the same list, I’m sure we’ll see you again, probably in this company for a little while longer there.

Enrico Palmerino [20:49]
We got, we got a few more years to go.

Gene Hammett [20:51]
Even another company down the road. So thank you for being here. Let me just wrap this up for the audience here. If you have learned something today about your own leadership about your evolving aspect, whether it be finding people to invite on the journey, and the culture fit of this or maybe it’s just how you’ve learned to really develop leaders by asking questions, I want you to ask yourself this big question. Who do you need to be the leader that your company deserves when you think about your leadership and growing to the next level? My job as an executive coach is to help you do that and help you really push yourself and challenge yourself to evolve. Just like our guest today has talked about so make sure you can keep tuning in to these episodes. If you want to find more details about how to evolve as a leader that is Find three resources there where you can be a visionary leader, you think about growth, you think about culture, think of Growth Think Tank, as always lead with courage. We’ll see you next time.


Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.


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