One Key to Leadership is to Stay Curious with Mitch Greenwald at Cloudbakers

Thinking you know it all is the enemy to growth. When you can stay curious, you get to see perspectives. Today’s guest is Mitch Greenwald, CEO at Cloudbakers. Inc Magazine ranked them #1174 on the 2019 Inc 5000 list. Cloudbakers is the Google Cloud Premier Partner that will ensure a fast and quality implementation. Mitch gives us a look into why we must stay curious when we want to grow our companies. He and I explore what that means for leaders that can stay curious despite the pressure to know it all.

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Target Audience: Mitch Greenwald is the CEO and Founder of Cloudbakers. It is a Cloud Service Brokerage (CSB) that helps people work better, together. They specialize in helping mid-market companies transform their business and extract the most value from their technology spend by moving to the cloud. Experts in the best products out there, and employ a best-in-class change management program.

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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.

Mitch Greenwald 
When you’re an early-stage company, everybody has to do everything all the time. And as you mature, you have to get more specialized job function. And you have to build the team and trust them to do their job. So that’s really, really, really key and, and even within a company, as you grow it, you still have to have that trust and those operational excellence. But even as you’re doing this, you also have to have those pods that are more agile for people to do everything to get a new line, as the business started and always think fresh. But I think the number one challenges have gotten bigger is it’s, it’s kind of interesting, because I’m a pretty straight shooter. I’m pretty, I’m very transparent. My life is an open book. One of our core values is be authentic, be yourself. I realized that when I’m communicating to the whole company or talking to people, every word counts. So the communication aspect, having super clear communication and not leading people down the wrong path, and making sure that there’s minimal room for misinterpretation, because there’s always room for misinterpretation. And there’s minimal interpretation is probably one of the harder things I am.

Intro [1:11]
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 [1:28]
Growing your company is not something where there’s just one thing that you got to focus on. As a CEO or leader of a company, you know that there’s many aspects of growth. There’s the team, there’s the strategy, there’s the customers, there’s your partners, all of these things are necessary to come in alignment together. Today, we’re going to talk about one of the pieces of the puzzle to create a fast-growth company. We are talking to Mitch Greenwald, he is the founder CEO of Cloudbakers, they were a sixth time in company. They made the list under 1000, the first one of the first years, and then actually this past year on 2020. They were 1140. Now what could someone like that this run a company with that level of consistent growth? share with you?

Gene Hammett [2:13]
Well, one of the things we talked about today is how important values are, we talked about the value-driven organization? And what that means? How do you live these values? How do you recruit, recognize reward based on those values? And that’s the core of today’s message. If you think you’ve heard this before, maybe you have, but let me ask you this has it resonated to a point where you’ve actually said we need to do a better job of living by the values so that we can actually grow the kind of company that we love working at and that we can attract the talent to come to? That’s the real question. My name is Gene Hammett, I work with fast growth leaders. One of the things that I created recently, I want you to get the best training available for you as a leader. If you go to, you can get the three mistakes often leaders make to keep them from scaling their business. It’s really about how do you create a team of eight players just go to Now here’s the interview with Mitch.

Gene Hammett [3:14]
Mitch, how are you?

Mitch Greenwald [3:16]
I am doing great today. How are you doing?

Gene Hammett [3:20]
I’m excited to have you on the podcast and I’m doing great as well. I want to talk to you about growth and leadership. Before we dive into talking about those topics. Tell us a little bit about Cloudbakers

Mitch Greenwald [3:33]
Cloudbakers is a premier Google Cloud partner as well as as a premier Zoho partner. And we help enterprises migrate to the cloud. We do G Suite migrations. We do Google Cloud Platform migrations as well as Zoho over to Zoho platform for CRM. And all the other products that are associated with it generally work with companies that are 200 million to 2 billion in revenue, and the data analytics solutions, application development, infrastructure, migrations and improvements and have a bevy of happy clients. I’ve been in business for 10 years now.

Gene Hammett [4:11]
Well, we were talking about this before you hit the recorder on, one of the things that you have done is you’ve made the Inc list six times in a row. Most recently, the 2020 list came out just yesterday, I think you were at 1140. Beyond the growth. What are you really proud of as a leader of this team?

Mitch Greenwald [4:30]
Well, you know, it’s been, it’s been pretty interesting. I was reflecting with some friends the other day and we just hit our 10 year anniversary. And if you want to get a look behind the curtains at Cloud Baker’s we posted a video about our 10 year anniversary, kind of a retrospective and one of the things that I was going with the company and COVID changes everything about your culture, basically, how you connect and you know, before we had a 10 year anniversary celebration virtually and before I showed the video, I said okay, I know that there’s a lot of Gamblers out there. What’s the Over under on that if I’m going to cry, if they all go, oh, we’re not taking that that. And, and I just been really, I’m really proud of the team that we built the partnerships, the happy clients. And basically, when I was sitting with these friends the other day they go, Yeah, I remember when you told us you’re going to you’re leaving your job, the job that most of the world we want is a CIO of a fairly significant company in Chicago, and leaving your job to go off and do something that they never even heard of before. And they all thought I was freaking crazy. And 10 years later, we have 700, over 700 clients and just about every state in the Union, few countries, top partner with Google top with Zoho, and still having fun doing it to enjoy my job almost every single minute of every single day.

Gene Hammett [5:46]
Well, I think that a lot of leaders that are listening in here can can relate to the story, but they also probably know, there’s some room for improvement on how much they enjoy their job. I’ve got to ask you, you know, you’ve you founder and CEO of the company. So you’ve continued to stay with this building your team? Your team has about 85 employees that right?

Mitch Greenwald [6:08]
Yep, yep. growing fast.

Gene Hammett [6:12]
But I wanted to ask you, what is the biggest struggle that you had to, you know, wrestle with yourself, going from a founder mentality to being a true CEO for your team.

Mitch Greenwald [6:23]
So there’s, there’s a number of struggles. First of all, you know, the big one is, you know, when you’re, when you’re an early-stage company, everybody has to do everything all the time. And as you mature, you have to get more specialized job functions. And you have to build the team and trust them to do their job. So that’s really, really, really key. And, and even within a company, as you grow it, you still have to have that trust and those operational excellence. But even as you’re doing this, you also have to have those pods that are more agile, or people have to do everything to get a new line. Basically, the business line started and always think fresh. But I think the number one challenges have gotten bigger is it’s, it’s kind of interesting, because I’m a pretty straight shooter, I’m pretty, I’m very transparent.

Mitch Greenwald [7:09]
My life is an open book, one of our core values is be authentic, be yourself, I realized that when I’m communicating to the whole company, or talking to people, every word counts. So the communication aspect, and having super clear communication and not leading people down the wrong path and making sure that there’s minimal room for misinterpretation, because there’s always room for misinterpretation that there’s minimal room for interpretation is probably one of the harder things I have to do. Because I have to, I want to be myself, which is one of our core values, be authentic, be yourself. But I also want to communicate the things but I don’t want it to be miscommunicated to which is a very important.

Gene Hammett [7:44]
Well, I’m glad you walked us through that and share a little bit of the background from your own journey. I asked you for a big question. Before we hit the recorder here. And it was this, you know, one of the most important aspects of this company’s growth, six years on the ink list. What would you say? I know, you said there wasn’t just one thing, what you said there were a few things, what were those few things?

Mitch Greenwald [8:07]
So one of the things that we’re you know, a cloud consultancy, right? We, we do a lot of clouds. And so the cloud over the last 10 years have gotten very, very big. So the business need when I first started out as what is that? Why would I do that? And now that the message is how do I get there. And it’s and so the business need has been great. We also have great partners and Google Cloud, as well as Oh, whoa, really important, and built a great team. So we have a team that has been a nice combination of youth and maturity basically. And that meshes well together really, really important. Have great clients, you know, the most important, the best business driver is having clients that really appreciate what you’ve done for them, and making them look like rockstars along the way, too. And actually, when COVID it, I can’t tell you how many of our clients that I’m so glad, you know, we work with you. And we implemented that solution, because I’ve looked like a superhero during this crisis because we’re able to, you know, work remotely without without missing a beat basically. And then the last thing is being a value-driven company that we’re really based on our core values, moving forward with our values, and we live and breathe and make business decisions, hiring decisions. We reward based on them, we reinforce them every day. And we make sure that we live by them.

Commercial [9:30]
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Gene Hammett [9:56]
I’ve talked a lot about the values of organizations We don’t go into the business strategy. So we’re not going to go into that. But but the values are something I think a lot of people could learn from because what you’ve seen from your your work as a leader here, Mitch is that values are not something that you do once and kind of put them on the shelf or, or put them on the wall. In a virtual world, it doesn’t matter if they’re on the wall. Right? Unless they’re showing behind you in the video. But what you did say is we live by them every day, we reinforce but we recognize, so let’s walk through and unpack some of those things. Let’s start with the recruiting. What What do you do to hire the right people based on the values of the organization.

Mitch Greenwald [10:44]
So as everyone on my team knows, and I interview just about everyone, that starts to cloud Baker’s, even if it’s for 15 minutes, or 20 minutes, because I think it’s important to have that human touch, as I always say that it’s important to that the interview is a two way street that you feel comfortable with, with working with us as much as us working with you, because that’s the only way we get a productive, fruitful, you know, happy working environment that both sides can be, you know, really be themselves. Because if you ever the third voice going off in your head, and you’re not able to say that, it’s not not a good thing, so we want you to interview us back as well as us interviewing you. And, and that really is all about the one of our core values is be authentic, be yourself. Another thing during recruiting, we caught up one of our core values is coach and be coached.

Mitch Greenwald [11:32]
So we want to know, you know, situations where you’ve actually coached somebody, and actually a situation where you, you know, where you’ve been coached also, and how you’ve reacted to that, right. So somebody could be coached, but not take action on it. And the coaching has to always be done with something that’s actionable. And something that’s positive, till there’s a certain way that he has a new coaching to make it work effectively, the life of one, you know, asking people about when they’ve succeeded, and also when they haven’t succeeded, and what they’ve done when they haven’t succeeded. So learning from your failures is, you know, one of our saying that we put off instead, it’s really easy to when we believe in partnerships quite a bit with you know, like, with Google, and Zoho, and even with our clients and our team too. And we quite often say, it’s easy to be a good partner, when things aren’t going well, if the test of a true partner is when things aren’t going well. So what you learn from that, how you learn from that, how you focus on the solution to going forward, really, really important. And that really goes right into our core values of integrity and accountability. It’s okay to fail, but learn how to learn, you know, fix it, basically, lifelong learner, what do you learn from that, and being solution-focused and how to move forward. So very, very important. So, we, we recruit for that, we also reward people on it, and people reward each other.

Mitch Greenwald [12:56]
So everybody from, you know, the least tenure, you know, because, you know, position the company to myself coach each other. And I love it, when people finally feel comfortable enough with me to coach me, because feedback is a gift. And that’s the only way I learned to if I get real feedback, that’s actionable, right? You know, they got to be actionable, and everybody else in the company. So it’s a complete matrix organization, as far as the coaching goes, and everyone should be open to that. And it’s not always an easy thing to do, by the way, especially sometimes in the heat of the, you know, in the scene, the heat of the battle, right, when you’re trying to get a deliverable off for a client, or in the middle of something, and you say, hey, maybe we should do it this way, or talk that way you got to, you got to always be open to those things. And you got to pick the right moments to coach to By the way, so it’s kind of important. So, our employees reward each other.

Mitch Greenwald [13:48]
We recruit for it, we actually have awards every quarter, based on each of the core values, and then we have an annual reward. And some of them you know, and I say enjoy the work most of the time will preach you know, it’s kind of fun at the end our virtual summer picnic this year. But at our we have a holiday party holiday picnic every summer, and holiday party every every December. And we always give words out that and if the December one is kind of the Year awards, and it’s so much fun to hand out the we actually have physical awards that we hand out to people that represent each of the core values. And it’s just so much fun to see the whole team hooting and hollering and celebrating everybody that gets up on stage and wins one of those awards and really supports each other just just a really nice thing. We also make business decisions based on those two. So I as you know, as I said many times that if anyone ever if if we’re having a, you know, discussion about something we should do in the business, and someone says, you know, that’s that really violates one of our core values. That’s almost an instant winner. That’s to say, Okay, I think you I think you’re onto something there. That’s not a path. We should go No doubt. So really, we, you know, we just talked about that the whole time.

Commercial [15:04]
Hold on for a second, Mitch said that it’s okay to fail. And what that means is to create a culture where people feel safe to actually try new things to say things and about big ideas, maybe ask, quote-unquote, silly questions, because sometimes in those silly questions, the courage that it takes for people to stand up, you find some of the best ideas to move forward, maybe the creativity and innovation happens when people aren’t afraid to fail. And so the real question here is, are you leading a culture where failure is appreciated, or that people are afraid to fail? Well, what I’ve seen in fast-growth companies is those that have a culture where failing, is appreciated, actually, are doing better. Don’t take my word for it. Look at some of the interviews I’ve done here, when we talk about failure on the podcast, it’s really important inside your culture, back to the interview.

Gene Hammett [15:58]
So I want to go back to a couple of things that you said inside there, recognizing the values, you might imagination of this, because I’ve worked with a lot of clients on you know, how do we really live by these values? What would we see as some of the rituals that you do day in and day out? As it relates to recognizing from peer to peer or from peer to leader?

Mitch Greenwald [16:19]
Well, one of the things is in conversation, people say, Oh, that’s a great example of being solution-focused, or thank you for the coaching, right? Or, you know, I want to or sometimes you prepare someone say, you know, you know, are you open to little coaching here, right, so those are people, people, people know those things, when you’re drilling into a problem with something and somebody says, you know, yeah, that’s not right, I need to fix that you go, you know, thank you for being accountable for what you’re doing for the, you know, for the customers best interest in the partner’s interest and for the teammates, best interest.

Mitch Greenwald [16:49]
So we do that all the time. We also have, you know, media channel setup, that we have a wins channel, basically, and those wins channel quite often goes through and says, I want to, I want to recognize, you know, Amy for really exhibiting the solution focus, core value with his client, because this is what they did today. And so we, we celebrate each other quite a bit. So it’s a good thing. And you know, it’s just very rewarding to see that. One of the favorite things I love, I love when I watch somebody else, do it with somebody else and know that I’m not involving Okay, they totally get it.

Gene Hammett [17:24]
You kind of stole the thunder. My next question, what was kind of percolating in my head was, tell me a story of something where you watch this happen maybe from afar, where someone truly was living by the values. And, and you saw that it was, it was really creating the kind of culture that you want there in the company, this is a story come to mind about?

Mitch Greenwald [17:44]
Let me think about that for a second. I can think of lots of them with me personally, I remember one person that’s been with us for a long time. And you know, she does a great job. And, and I said, Hey, I think I actually think you have something to say to me, and then she said, Mitch, if you’re going to handle it this way, it would have been, you know, that much easier for me to figure that out and adopt it. And, and to take action on that, you know, and I said, Thank you. And I said, Thank you for the coaching. And, and I thought I saw that as a breakthrough moment. These, she might have normally been intimidated by me or I don’t think I’m that intimidating. But I do have a certain just by nature, position of power, I guess. And then from then on, it was a whole different ballgame to watch that. And I’ve watched, many, many of our teammates do that, you know, off off, you know, throughout every part of the whole history of the company. I was gonna say one of the fun parts about the core values that we have, we have a words I always say that one of the core values is that is that is the biggest award. So we know that’s not the biggest one, I don’t think anyone’s more important than other ones. And I guess this is a coaching moment on myself too. And I’m going you’re right, that’s my favorite core value, right. And my favorite core value is to be authentic, be yourself. But everybody seems to have their own favorite core value, which is kind of fun to see that too.

Commercial [19:03]
Hold on for a second. Mitch said that the employee said, maybe it would be better if you handled it this way. When’s the last time that you were able to get feedback from an employee that you felt like they had the courage to say something that others weren’t saying? And it really did help you see from a new perspective when you are the kind of CEO that has people around them, that they’re not afraid to give that feedback to the boss to you. You have what’s called transparency or remarkable transparency. This is a very important aspect to a culture that is able to stand the test of time to be able to overcome challenges and work together as a team and transparency is such an important piece. Are you transparent with your employees? Probably to a degree are you allowing them to be transparent with you? Are they are you allowing them to be transparent with each other and encouraging it that is the critical factor of having a transparent culture, and it really does help you create the kind of place where people love to come to work. And they love to give their all. Back to Mitch.

Gene Hammett [20:08]
Absolutely. I want to ask you, you’ve mentioned coaching quite a few times. And I get asked this a lot from, from leaders, even my clients going, you know, how do I improve as a coach? Are you guys giving specific training around how to truly coach people, because a lot of people misinterpret what that is, inside of leadership?

Mitch Greenwald [20:27]
Yeah, so we do new managers, we have training programs for new managers, to help them with things like doing, doing coaching, managing people’s time, holding people accountable, career development, doing annual reviews, things like that. And I guess coaching is inherent in all of those basic, to do that. So we do develop, we do outside some outside training in those and then we also do a curl training, a lot of us do, probably not as good as we should do. But we also hire people that are kind of have that natural ability to do that also.

Gene Hammett [21:07]
Well, I appreciate you saying that. So you know, it’s a testament to your own culture of investing back into these people with the soft skills of leadership so much. I want to say thank you for being here on the podcast.

Mitch Greenwald [21:19]
Okay. All right. Thank you.

Gene Hammett [21:21]
What a fantastic interview with Mitch, he really has a lot of experience around teams, some of the things that we recorded offline, as he talked about how important you know, the team was over the financial success of the company. He’s really proud of growing those people investing in them, coaching them. And that’s really shows and his his kind heart, but also his ability to create results for the company, a lot of leaders wondering what their next step is as a leader that keeps them moving forward. If you have those questions in your head, make sure you go to my free training is, who will help you create a team of a players? Why do you want a players because the best people want to work with the best people if you want to hire talented people that raise the standard of who is on the teams, and you have to raise your capacity to lead those people to a player status. And how do you do that? Well watch this video at And finally, I want to remind you if you want to think about growth, you think about leadership, make sure to 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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