Thoma Bravo's Behind the Deal

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.

In this episode of Behind the Deal, Thoma Bravo Founder and Managing Partner Orlando Bravo sits down with Partner Tara Gadgil and Dayforce Founder & CEO David Ossip to unpack one of the firm’s most significant investments—a $12.3 billion acquisition of Dayforce.

They explore what set Dayforce apart in the human capital management space, from its single data architecture to its ability to replace up to 12 disparate systems with one unified platform. The conversation dives into the diligence process, the importance of customer validation and how Dayforce’s product simplicity has translated into real ROI for customers.

David Ossip also shares the origin story behind Dayforce, how he combined startup innovation with legacy infrastructure and why AI is central to accelerating both revenue and profitability.

This is a deep look at how product vision, leadership and long-term thinking come together to build a category-defining company.

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.

In this special re-release of Behind the Deal—now brought to life in video—Orlando Bravo sits down with Thoma Bravo co-founder Carl Thoma for a conversation on the origins of modern private equity.

Widely regarded as one of the pioneers of the industry, Carl shares how he developed the “buy and build” strategy, why discipline around risk and valuation matters more than ever and how mentorship shaped the trajectory of Thoma Bravo’s software investing strategy.

This episode traces the early missteps, hard-earned lessons, and defining principles — around partnership, performance and integrity — that helped build one of the most enduring firms in private equity.

Whether you're an investor, operator, or early in your career, this conversation is a reminder that great outcomes are built on fundamentals, trust and learning from mistakes.

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/

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.

In this episode of Beyond the Deal, Thoma Bravo Partner Carl Press is joined by Adam Kinalski and Sam Yules to tell the inside story of building the Explore platform from the ground up.

What started as a blank slate in 2019 has grown into a high-velocity investment platform focused on emerging enterprise software leaders. The team shares how Explore was created to stay true to Thoma Bravo’s middle-market roots, the early challenges of building a pipeline from scratch, and the lessons learned from sourcing, mentorship and long-term relationship building.

From cold starts and conference room pitches to navigating deals with imperfect data, this conversation offers a candid look at what it takes to build a platform—and a team—inside the world’s largest software-focused investment firm.

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/

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.

In this episode of Behind the Deal, Thoma Bravo Partner Carl Press and Principal Adam Kinalski are joined by Exostar CEO Richard Addi to tell the story behind one of the firm’s most hard-fought investments.

Exostar, a mission-critical platform serving the aerospace and defense industry, wasn’t for sale. What followed was a multi-year effort to build trust with six joint venture shareholders, navigate complex stakeholder dynamics and ultimately get the deal across the finish line.

Together, Carl, Adam and Richard unpack the full lifecycle of the investment—from sourcing and diligence to transformation and exit—and reflect on what it took to transition Exostar from a shared-service joint venture into a high-growth, profitable enterprise software company.

In just three years, the business accelerated growth, expanded margins and positioned itself for a successful exit, making Exostar a defining deal for Thoma Bravo’s Explore platform.

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 Exostar: https://www.exostar.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.