From $1M to $2B+ in Revenue: David Ossip on Leadership and Scaling Dayforce

David Ossip: I've always taken the approach that you run the company like a sports team, and depending on what innings you're in, you might actually have to change the team to bring in the right person for that particular role. And every person that I've ever brought into the organization is someone that I feel that I can learn from and that the team can learn from, and that together we can do much better.

Orlando Bravo: Welcome to Thoma Bravo's beyond the Deal. I'm, um, Orlando Bravo, founder and managing partner at Thoma Bravo. Last week we shared all the details behind our exciting deal with Dayforce. This week I'll be sitting down with David Ossip, founder and CEO of Dayforce, to talk more about his experiences starting and growing the company and what he views as challenges and opportunities in today's business world. David, you want to go back to Seridi, and you transformed the company through that deal once again, putting together just an incredible innovator with a very established company. And when you came in, you discovered a whole range of big problems.

David Ossip: Yeah, look, uh, it was an old company and when I did my research, um, I missed a few things.

Orlando Bravo: How did you lead through that?

David Ossip: So I've always taken the approach of, we see you. And, uh, as you know, I do a lot of summits, I'm on stage a lot. I do a lot of global all hands. And I always start this way, which is I see you, I hear you. If you call, I will respond. And it applies both internally. If any of my employees reach out to me, whether they text me or whether they call me or teams me, I will get back to them as soon as I see the message. Uh, from a customer perspective, I give out my emails to everyone. I tell people if they find me on LinkedIn, they can reach out to me and I will respond to every message. I may not solve the problem, but I will get someone to solve it. And I think that has created a very special culture both internally, because people know that they are being heard and if it's a customer, they know that they're being taken care of and they're dealing with an organization that truly cares and will be there with them in the trenches to help them out.

Orlando Bravo: From what you're saying, it seems like you run the company with the same hands on, empathy, uh, philosophy for customers and employees as when you were a million dollars in revenue. Now you're 2.2 billion in revenue.

David Ossip: It's the same philosophy. What has changed is a team. And if you look at our executive team, it's just a Truly unbelievable team of superstars. And I've always taken the approach that you run the company like a sports team. And depending on what innings you're in, you might actually have to change the team to bring in the right person for that particular role. And every person that I've ever brought into the organization is someone that I feel that I can learn from and the team can learn from and that together we can do much better. And it's created, again, a, uh, very strong culture because there's that immediate respect that people have for one another. We run the company with, again, clarity of purpose all the time, and it makes communications very, very easily. And I do believe in proper delegation, which is if I bring someone to run the sales organization, I expect that person to be much better than me in terms of sales. And I trust their decisions as to what they're actually doing. Uh, the same as on the product side, where I'm obviously very strong product wise. But I will bring in the best person who can run the product organizations in ways that I could never think of. Uh, if you speak to Joe, you'll see some of that. You know, when Joe came in, we're about to release something we call the huh Hub, which is kind of the landing page of our application. And I actually thought it was spectacular, perfect. And Joe looked at it and he said, um, you know, we're going to hold off a bit. We can lift up the experience. And I was like, what are you talking about? He said, well, you know, the, the boxes are square, they have, they have hard corners. I'm like, okay. It's like, no, no, they have to have curved. And, you know, he has a certain eye for experience that I don't have. So I learn from him each time. Uh, the same thing happened recently with the People analytics agent. I looked at it, I thought, wow, you know, that UX looks great. And Joe's like, no, you know, you know, the bold ends off. And I was like, the balding. Right. Uh, I didn't know about that. But you pick up on these little details which collectively come together to make a big difference in the overall experience. Uh, same as on delivery. When we brought in Steve into the organization, he's now our president. Uh, Steve radically transformed how we did delivery. And if you look at how successful we are in terms of implementing the projects, with a very, very high probability of success, that the projects go live on time, on budget, with a very high NPS score across the actual delivery, it was completely transformed by Steve, who looked at our delivery organization at the time and said, you don't run a delivery organization like that. These are the three things you have to do.

Orlando Bravo: It's all about leadership. We say that when the leadership is good, everything is good. And the leadership here is just outstanding. You, you mentioned, uh, something that I really want the listeners to, to grasp that is also very special is how you are very hands on. You know more about the space, in my opinion, than anybody else. You built the company and at the same time you delegate to an exceptional team. And that for me really came across in the meeting that we had in Miami when you brought your team and you did very little talking. You let the team deal with their disciplines. We were beyond impressed. And then you walk outside with me and Holden and you said, this team is very, very important. And that showed a lot of leadership, a lot of depth, and of course it shows in the results. David, um, what's next? Do you think you can take this company 10 billion?

David Ossip: I think you'll see a lot of growth for the actual business. Um, if I look at just again, I need to look at actual, uh, data points. We know that last year our, uh, sales grew by 43%. So when I look at the age of AI, there are obviously organizations that will do very well and there are some that I think will give up market share. And I think that our clarity of purpose and our focus on how we're building the company in a differentiated way, both from a culture perspective and from a product perspective and from a customer experience perspective, has allowed us to grow very successfully over the last, I guess, 10 plus years. And our, uh, market share still is about 4%. So yes, I do think we can continue to grow the company.

Orlando Bravo: Well, David, thank you so much and thanks for your partnership, your leadership and we look forward to being together for many years.

David Ossip: That's great. Thank you very much and thanks again for being here.

Orlando Bravo: Thank you. Listen to Thoma Bravo's beyond The Deal Season 4 on Spotify app, Apple Podcasts, YouTube or wherever you get your podcasts.