Adam Greenberg 0:00

I look at business very differently than most of the CEOs that I talk to who are almost exclusively focused on financial KPIs. I mean, I look at other KPIs myself, but I'm under extraordinary pressure to achieve financial ones. Revenue, EBITDA, churn, turnover, cost of goods sold, lifetime value, cost of customer acquisition, all of these KPIs, concentration of revenue. I have to hit these KPIs all the time. Every single decision you make has a downstream impact.

Angela Robertson 0:31

Welcome back to the Stormy Stories Show. I'm your host, Angela Robertson, CEO of Ace Tech, a nonprofit membership society for tech CEOs and founders. We exist so that no tech CEO or founder should have to go it alone and that they can thrive in their business. And that's why this podcast exists, so that no one has to feel like they're living their own stormy stories alone. Today's guest is Adam Greenberg. He's the CEO of Makeshift and the founder of LeadersTogive.org, a seasoned SaaS executive with more than 20 years of experience building teams, driving growth, and leading people first innovation. He now leads Makeshift, helping businesses modernize workforce management while creating stronger employee experiences. Adam, welcome to the show.

Adam Greenberg 1:24

Thank you, Angela. Great to be here.

Angela Robertson 1:26

So you spent more than two decades in SaaS leadership. What lessons from the early years do you think still guide the way in which you lead today?

Adam Greenberg 1:35

Well, that's a great question. And I think one thing has stayed consistent throughout is that people generally want to do well. They want to be appreciated, they want uh to be recognized, they want to be, they want to make a positive contribution. They do their best, even though it's our responsibility as leaders to push them to do more and to do better. I think uh I've found throughout my career that giving people the benefit of the doubt uh that they they do want to succeed and and do great work and be proud and be a positive contributor is is what has been consistent throughout my career.

Angela Robertson 2:13

Yeah, I think that notion, that underlying piece is sometimes hard to surface, right? And so in continuing with that theme as your CEO of Makeshift Now, how do you keep that human side of work front and center while you're balancing rapid innovation? And I think that's especially true in the current times with AI on the rise and that notion of how do we stay in our human sense?

Adam Greenberg 2:41

Yeah, I a word that comes to mind that I think about a lot is belonging. So people inherently want to belong. And I think, I think if you can foster a sense of belonging in your in your corporate culture, that'll go a long way to helping innovate and helping create that sense of accomplishment for everybody. When people feel like they belong, they contribute at a higher level and there's more meaning behind the work they do. They belong to a group, they want to perform for that group. And if they don't feel they belong, it has an effect on productivity. It has an effect on happiness, which is something I was talking about earlier. Uh, and uh I think it's our responsibility as leaders to create that sense of belonging and foster that sense of belonging and in the work that we do and in the workplace.

Angela Robertson 3:33

So if I were to talk to someone at makeshift, uh what what is it that you've created that makes them feel like they belong to something maybe bigger than the individual contributor?

Adam Greenberg 3:46

I think if you talk to someone at makeshift, they'll tell you politely that it wasn't it wasn't me that created the sense of belonging. It's them. That they bring purpose to the work that they do. They understand what we're trying to accomplish, they understand their role in helping to accomplish it and and and they create that sense of belonging in the work that they do and the way that they interact with each other. Maybe, I hope, what they could say that I brought to the table is clear communication so that everybody knows what's expected, why we're trying to do the things we're doing, what their role is, so that they can then create that sense of belonging amongst themselves because there's various departments. And in each department, you have a very different type of person. If you think about software developers and software engineers, have a very different personality than sales representatives, who have a very different personality than customer success and customer service and support people, who have a very different personality than operational people or financing and accounting people. So the the trick is to create a macro sense of belonging and to foster that micro sense of belonging. And I don't believe that that micro sense can be done top down. I believe it has to come bottom up.

Angela Robertson 5:06

So, were there some ways that that developed over time? I'm just I'm so curious about this cultural aspect because I think it's something that, especially when we have work teams that are working out of different offices or are in different environments, right? You know, there is that personality piece, but how do you foster that that greater sense of connection across all those different places, like really forming that macro?

Adam Greenberg 5:30

A few different ways. You know, I started uh sharing some just jokes on a on a Friday. I'm now doing that on LinkedIn just for fun. Oh nice. I find the responses and engagement is incredible. I mean, I get way more engagement on a dumb joke than I do on a business article. I also talk about myself a lot, which I'm very comfortable doing, and a lot of people aren't, and that's okay. But I'll share stories about what happened this week with my daughter in high school, or something my wife and I were talking about, or plans we have for the future, or observations I have from from reading the news openly and authentically. And I hope and I believe that that gives people that permission that they can do the same. And when you do that, you start to get to know each other on a different level. It's not a transactional relationship. It's it's more of an authentic one where you you care about people's insights and you care about what they're up to as human beings. And and eventually and organically, that that tends to mold and create that that sense of belonging that I'm talking about. We also use technology. You know, we have Slack channels where we we have different channels for random things. We have a gratitude channel, which is one of our core values. We obviously have product and sales channels and finance channels. And then, of course, we try to get together physically and bring everyone together at least once a year, and groups get together a little bit more often when we can.

Angela Robertson 6:53

Yeah. Yeah. You give them permission to take off the mask, right? You have permission to really show out as their full selves. I love that idea of just being able to trickle in stories about who you are, especially as the CEO, right? Because I think formerly, you know, you get this sense of you need to be this, you know, particular like cardboard cutout version, but that's not going to allow people to connect to who you are as a person or what makes you tick, right?

Adam Greenberg 7:24

I I agree. And and I've worked on it myself. And I've been told in my earlier in my career, not when as I was a CEO, but even as a VP of sales, which was my background. I've had people that I trust say to me, you know, you come across as a little bit serious, and people can sometimes be intimidated by that. When I heard that, I was shocked because I don't think of myself that way. But I guess, first of all, I am I am kind of serious about what we're trying to do. And so that presence comes across in a way that might intimidate others. And so I've worked on that, tried to lighten up a little bit. I've had to work on starting calls with asking people, hi, how are you? How's not just get right into the into the matter, which is really hard when you've got a million things to do. I've been working on it and I can do better, but but it's intentional.

Angela Robertson 8:12

That hit home for me so much. I've received that same feedback. And it's always surprising, right? But it's true when you're meeting someone for the first time, you don't know them from Joe, right? Until you get a little bit more context, like who are their kids or who do they hang out with? What do they like to do outside of work? And then it paints a clearer picture. I just want to shift gears a little bit more and talk about, you know, tug on that thread of, you know, you mentioned your background in sales. So you've led sales, you've led operations, you've done executive management. How has that cross-functional experience shaped your decision making as a CEO?

Adam Greenberg 8:50

Uh enormously. Because when I was in sales, all I cared about was trying to conclude it and complete a transaction. I didn't bring a lens of how to actually execute or implement on the outcomes that the customer wanted. I understood them. So customer is coming to us to buy software because they have a problem they're trying to solve. And hopefully that software will produce an outcome that matters to the business. I always understood that as a salesperson and I always sold solutions to people's problems. But I did not have the lens of what happens once it's signed, what's the process, how long does it take, how many people are involved, what could go wrong, what are the steps to oversee it, to mitigate risk, mitigate exposure, legal, financial exposure, operational exposure. When I got into operations, that all came raining down upon me, and I started to realize just how important business process is, just how important governance and controls are, not just for you as a business, but for your customer as well. Think privacy, security, you know, redundancy, data integrity, hygiene in the data hygiene, all of these things matter. As a CEO now, I can take that full picture and not just make decisions based on trying to hit revenue goals, but understand the responsibility I have to govern the business in a responsible way and the impact those decisions have right across the entire lifecycle of a transaction.

Angela Robertson 10:19

What was the toughest part about making that shift?

Adam Greenberg 10:22

Well, there's a huge balance because I'm under extraordinary pressure all the time to hit financial KPIs. Right? I mean, I look at business very differently than most of the CEOs that I talk to who are almost exclusively focused on financial KPIs. I mean, I look at other KPIs myself, but I'm under extraordinary pressure to achieve financial ones, revenue, EBITDA, churn, uh, you know, turnover, cost of goods sold, lifetime value, cost of customer acquisition, all of these KPIs, concentration of revenue. I have to hit these KPIs all the time. Every single decision you make has a downstream impact. So that's been extremely difficult. When as a human being, as a person, I have a tendency to focus on how many kids did the business allow to go to university this year through great salaries? And was somebody not feeling well and had the benefits? How many first homes were bought? Who's getting married this year? Who's had a child this year? These are the KPIs that really I find really meaningful, but they can't happen without the financial KPIs either. So that's been the most difficult thing for me as a CEO is balancing all of that and learning how to make decisions quickly, because that's your responsibility, but also making them responsibly.

Angela Robertson 11:48

Yeah, kind of balancing that speed of decision making with the relative risk. You know, you think if you have to make so many decisions in a day, not all of them are going to be right. So which are the ones that are safe bets to potentially miss on right along the way?

Adam Greenberg 12:04

Yeah, for sure. Another challenge I've had, just to add to it, I'm sorry to interrupt, is learning not to make a decision, which is really, really hard for me because I'm a decision maker. I I like to decide and and accept what happens and move on and learn from it. But I've learned not to make decisions and to let a little time happen. And I I think my COO probably really appreciates that.

Angela Robertson 12:28

I think that's a really good call out. Yeah. Sometimes the most difficult decision we can make is to just hold back and let the team come through and come out with it right, too, or just let it lie, give it some space.

Adam Greenberg 12:41

Yeah.

Angela Robertson 12:42

I want to pull tug on that piece around the pressure that you've spoken about, and I appreciate you sharing that that's something that you feel too, even with as much experience as you have. Many founders and CEOs talk about the pressure that they get behind closed doors. What is one of maybe the toughest leadership storms that you've faced? And what did it teach you?

Adam Greenberg 13:02

Well, it's personnel always. It's having someone who's not performing that is bringing down it has an effect on everyone. It has an effect on me, certainly, but it also has an effect on their colleagues because everyone's relying on each other all the time. And when that person's not performing, you have to make a decision about what to do about it. And there's lots of different roads you can go down on, you can go down having a firm, assertive conversation about expectations. Sure, that doesn't always work out. Sometimes that can leave people feeling vulnerable and exposed and insecure. Then there's the legal recourse, so performance improvement plans where everything gets documented and you set timelines and expectations. Often what I've seen is that also has an implication in the way people produce and behave. Sometimes I think this is leading nowhere and I'm going to start looking instead of trying to improve. Or there's the ultimate, which is you have to let somebody go and it's time to move on and find someone else. But in my experience, replacing person X with person Y doesn't lead to the outcomes either. And it certainly takes more time. So I would say trying to uh help others that are putting the pressure understand that there's no quick fix to certain problems, and we have to go about solving them with integrity, give people the benefit of the doubt. I started this conversation with, and try to manage their performance in a meaningful way, helping them understand uh what these decisions are are leading to and what's the ultimate outcome that we're trying to achieve is the best way to go. But so I would say, I know that was a bit of a long story. No. Behind closed doors, the biggest storm and the biggest pressure point is what to do about people who aren't performing and how to manage that.

Angela Robertson 14:46

And what is one of the like key learnings? Like if you obviously don't name names, but if you had to like in your mind, I like think of an experience that you had with a difficult or challenging individual that you had to offboard from your team. What is one key? I really wish I'd done that and that you've now implemented into your process going forward.

Adam Greenberg 15:09

Well, you'll you'll be surprised by the answer because it's two things. One is I wished I had just made the decision sooner. And then the other answer here is I haven't implemented that uh cadence yet. So I it's I I feel the tug on both sides. I know there's people in the business that need to go, but they're they're just not going to meet expectations. And it's probably best for them that they move on. Why can't we just get that done? I don't have an answer for you. There's always some hesitation that it's not fair to them. I've failed as a leader. It's not their fault, it's my fault. What are the risks to the business on a project that they're involved in if we do make that decision? Then there's the human aspect. This person's going through something. This person has this happening in their life, whether they're gonna have a child or or they've just bought a house or they're gonna get married, whatever it is. Uh, and and these these things affect the decisions that we make. So to reiterate, the big lesson is should just should have done it sooner. But I have not yet come to just making those snap decisions and moving on.

Angela Robertson 16:17

I hear you there. I think it's always a work in progress, right? Yeah. And I do always come back to this notion that there is a weight that lifts from both you and the individual, and more broadly in the company when it does happen, but it's hard in the moment and even in the steps leading up to see where that lift comes from. So yeah, I think a lot of our listeners are going to nod their heads along and go, yep, I'm still working on this too. So definitely not alone in that.

Adam Greenberg 16:49

Yeah. Thank you. I do sometimes feel alone and it can be lonely at the top, but I'm at least self-aware.

Angela Robertson 16:56

There you go. That's great. I also want to take a little bit of time because it sounds like you know, having your heart in it is a really big part of your why. You founded leaders to give. How is building a nonprofit changed the way you think about success in business?

Adam Greenberg 17:13

Well, a nonprofit is a business, so it has to operate like a business. And I never really thought of it that way when I wasn't running one, but there's still financial KPIs and there's still an outcome or a, and this sounds shallow, but it's not meant to. There's a customer or there's a product, even if that customer is a vulnerable child or a vulnerable family. But you also have a customer that's a donor. And that donor expects certain outcomes and certain governance and certain KPIs to be met as well. Uh, and so running a business for profit has helped me understand the importance of meeting uh certain KPIs, of having structure, of having good board governance, making sure you've got the the proper talent, uh, codes of conduct and setting expectations, all of those things running a business have helped me establish a nonprofit and make sure that the outcomes in the nonprofit, which are incredibly important because talk about authentic, non-transactional human stories. I mean, there's just it's tough out there for people. And I I feel also uh it's incumbent on me as a leader to try to solve some of the problems uh that I see in in our communities and in society as a whole. Uh, and I have a a responsibility to to try to solve some of those problems as well. I don't know if that's the answer you're looking for, but uh that's that's sort of my reaction to the question.

Angela Robertson 18:38

No, I'm right there with you. I mean, I think it's so great to hear and to echo that sort of sentiment out there because I think sometimes nonprofits, you know, really it's business and it's uh at a whole other complex layer because you have all these different stakeholders that you're answering to, and you need to kind of dress down those particular KPIs that would be so normalized in business, and it creates some ambiguity sometimes. And at the end of the day, all you're trying to do is have positive impact, right? And to create an organization that's self-sustaining too, right? And I think sometimes nonprofits struggle because they go, okay, well, I'm trying to just get this balanced budget every year and bow and end up, you know, sort of cutting short what their longevity can be by not maintaining that same kind of business sense of, okay, well, I've got to make sure I have room in the coffers to invest in the future, right? Of the business.

Adam Greenberg 19:36

Absolutely. I mean, I'll share if you'd like, I'll share a real life, real-time story and expose a little vulnerability around that. I don't know if you have time for it, but I'm happy to share it.

Angela Robertson 19:45

Oh, please. We'd love that.

Adam Greenberg 19:47

So uh our organization, Leaders to Give, embarked on a very ambitious uh journey to build a brand new facility to house children whose families are experiencing a medical crisis. This is in Baja California, Sur Mexico. So we received a request from the Mexican community to do this very thing after somebody, Mexican national, her daughter had leukemia, childhood leukemia, which is one of the leading causes of death in this area. And what she discovered was that often when single mothers, mostly living in poverty, have an illness or one of their children have an illness, there's nowhere for their children to go that's safe to provide for them while they're getting their treatment. And so we were approached to build this facility to house these children. Great. Everybody bought in. We started, we did a ton of research to validate that this is a problem. Research, UNICEF research, United Nations research, local government statistics, talking to local mayors, talking to oncologists, talking to hospitals and and families. There's a need. We went through this massive five-year process of fundraising, constructing, land was donated, staffing the facility. We got it up and running. We had a child come in and and and exit very quickly. We thought this is all going very well. And since then, it's really not being used. The facility is not in use. Why? Why isn't it in use? And what we've learned is that there's a real, real, uh, valid fear that parents have, even if things are terrible, of letting their children go to a what they seem like to be an institution. There's a fear they'll be trafficked, there's a fear they'll disappear, there's a fear they'll be abused, there's a fear that they'll be stigmatized and never get them back. And these are very complex social problems that uh while we were very well equipped to build and facilitate this project, we're not really well equipped to manage and solve for this problem now. How do you explain this to donors? How do you explain this to the board and to your supporters? And and how do you ask for more time and more money? To continue to explore how to now use this asset. We're going through that right now. It's incredibly, incredibly difficult, especially when you hear the stories of people who need this facility, but they're afraid to go and use it. So I wanted to share that story because it's real, it's happening now. We're struggling to operationalize and deal with these complexities. We have a great board who's super engaged. But it's it's it's it's a struggle for sure.

Angela Robertson 22:26

No kidding. And it's that notion of like, okay, you know, you build the solution and then you expect that they will come, but there's many layers, right? It's not always self-evident. And I think that's true for nonprofit or for-profit businesses, right? So that's a lesson that can be applied across, you know, you you get to a milestone in a you know, new launch of a product or in a, you know, in a new facility in this case, and you expect, okay, now the, you know, the market will come, but it doesn't, it's not always there. You haven't always uncovered the next steps. So yeah, having that support network around you, whether it's the board or your team or whoever, to be able to lean on and figure out what the next steps are is so important.

Adam Greenberg 23:13

Yeah.

Angela Robertson 23:13

Thank you for sharing that, Adam. I really appreciate it. Um, one more question for founders or CEOs who are scaling a company right now, for profit, not for profit. What habits or mindset shifts do you think separate those who grow well from those who burn out?

Adam Greenberg 23:32

Yeah, that's a tough one. Um two things. Make sure you have a real strong view of your financial runway before you start something. Because money gets spent so fast and expenses are so predictable, yet revenue is so unpredictable. And also everything takes longer than you think. So financial um acumen, uh financial analysis and having real strong financial controls is absolutely critical. I mean, cash is king. That's number one. Number two is it's absolutely critical to surround yourself with people that you trust who are as invested in the outcome as you are. Because if you can't rely on them to go the extra mile, you're doing it yourself all the time. You will absolutely burn out. I've experienced it myself. Luckily for me, although I'm not widely surrounded by all of the same uh people with the same determination, I have a few real core members of the team who are absolutely as committed as I am. And that makes all the difference when you go to sleep at night and you know that someone else has got the ball.

Angela Robertson 24:41

Yeah, it's the people, right? You started with people, we end with people. It's all businesses, people, people, people, right?

Adam Greenberg 24:48

Yeah, it's not location, location, location. People, people, people.

Angela Robertson 24:52

That's absolutely right. Well, Adam, I'm so grateful to you for taking the time to spend with us today and for sharing a bit about your journey. I think we're all the better for it. And uh I hope our our paths cross again soon and that more great people uh come into your world as well.

Adam Greenberg 25:10

Me too. Thank you, Angela. Great to meet you and uh good luck with your with your show.

Angela Robertson 25:14

Thank you.

Adam Greenberg 25:15

Thank you. Bye-bye.

Angela Robertson 25:17

At Ace Tech, we believe one of the most valuable resources a leader can access is another leader's experience. That's why I created the Stormy Stories show to bring you honest conversations about the moments that test us, shape us, and ultimately make us better CEOs and founders. Thanks for listening, and I'll see you next time.