April 30, 2026

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

In the final episode of Season 4, Orlando Bravo sits down with Dayforce Founder and CEO David Ossip for a deep dive into what it takes to scale a company without losing its edge.

From transforming Ceridian into Dayforce to building a business that has surpassed $2 billion in revenue, David shares the leadership philosophy behind that growth—including a standout year with 43% sales expansion. At the core: a relentless focus on culture, clarity of purpose, and running the company like a high-performance team.

David also unpacks one of the most critical—and often misunderstood—aspects of leadership at scale: delegation. By surrounding himself with world-class operators and trusting them to lead in their domains, he’s built an organization that continues to evolve, innovate, and execute at a high level.

This conversation explores how great leaders balance hands-on involvement with real trust, why culture becomes a competitive advantage, and how Dayforce is positioning itself for continued growth in the AI era.

Disclaimer

This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma bravo funds generally hold interest in the companies discussed. This podcast should not be considered as an offer to solicit the purchase of any interest in any Thoma Bravo fund.

AIR DATE:

April 30, 2026

LENGTH:

7:54 minutes

DAVID OSSIP (00:00):

I’ve always taken the approach that you run the company like a sports team. And depending on what inning 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 (00:29):

Welcome to Thoma Bravo’s Beyond the Deal. I’m 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.

(01:04):

David, I want to go back to Ceridian. 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 (01:21):

Yeah, look, it was an old company. When I did my research, I missed a few things.

ORLANDO BRAVO (01:27):

How did you lead through that?

DAVID OSSIP (01:29):

I’ve always taken the approach of we see you. 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. 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. From a customer perspective, I give out my email 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. 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’ve been 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 (02:35):

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

DAVID OSSIP (02:53):

It’s the same philosophy. What has changed is the team. And if you look at our executive team, it’s just a truly unbelievable team of superstars. I’ve always taken the approach that you run the company like a sports team. And depending on what inning 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. And it’s created, again, a very strong culture because there’s that immediate respect that people have for one another.

(03:39):

We run the company with, again, clarity of purpose all the time, and it makes communications very, very easy. 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. 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.

(04:13):

If you speak to Joe, you’ll see some of that. When Joe came in, we’re about to release something we call The 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, “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, the boxes are square. They have hard corners.” I’m like, “Okay.” He’s like, “No, no, they have to have curve.” He has a certain eye for experience that I don’t have. So I learned from him each time.

(04:50):

The same thing happened recently with the people analytics agent. I looked at it, I thought, “Wow, that UX looks great.” And Joe’s like, “No, the bolding’s off.” And I was like, “The bolding? 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.

(05:12):

Same is on delivery. When we brought in Steve into the organization, he’s now our president. 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 (05:46):

It’s all about leadership. We say that when the leadership is good, everything is good, and the leadership here is just outstanding. You mentioned something that I really want the listeners 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 build 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 said, “This team is very, very important.” That showed a lot of leadership, a lot of depth, and of course it shows in the results.

(06:34):

David, what’s next? Do you think you can take this company to 10 billion?

DAVID OSSIP (06:40):

I think you’ll see a lot of growth for the actual business. If I look at just… Again, I need to look at actual data points. We know that last year, our sales grew by 43%. When I look at the age of AI, there are obviously organizations that’ll do very well, and there are some that I think will give up market share. 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 market share still is about 4%. So yes, I do think we can continue to grow the company.

ORLANDO BRAVO (07:27):

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 (07:33):

That’s great. Thank you very much, and thanks again for being here.

ORLANDO BRAVO (07:36):

Thank you.

(07:41):

Listen to Thoma Bravo’s Beyond the Deal Season 4 on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts.