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. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Dayforce: dayforce.com  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 construed as an offer to solicit the purchase of any interest in any Thoma Bravo fund. Certain statements about Thoma Bravo made by portfolio company executives are intended to illustrate Thoma Bravo's business relationship with such persons rather than Thoma Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast participation, although they generally received compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Thoma Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest. In addition, this podcast includes forward-looking statements. These statements are based on current expectations and assumptions and involve significant risks and uncertainties that could cause actual results to differ materially.