Thoma Bravo's Behind the Deal

Thoma Bravo’s Behind the Deal podcast takes you behind the scenes of one of the largest software investors in the world. You'll hear the strategies and stories behind building Thoma Bravo’s portfolio of innovative, industry-leading software and technology companies. Presented by Orlando Bravo, “Wall Street’s best dealmaker” (Forbes), each episode offers a first-person account from the deal leads and CEOs that forged some of the largest software acquisitions at Thoma Bravo to date, and how they partnered together to innovate and grow those companies. Go ‘behind the deal’ to learn how these deals came together, gaining insight on how Thoma Bravo helps great companies do even greater things. Head to www.thomabravo.com/behindthedeal for information on the podcast, show notes, and more.

Thoma Bravo's Behind the Deal is a business podcast hosted by Thoma Bravo, with 82 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Thoma Bravo hosts Thoma Bravo's Behind the Deal, a business show with 82 episodes published.

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  Episode #16

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

  Apr 30, 20268 minS4

  <p>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.</p> <p>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.</p> <p>David also unpacks one of the most critical—and often misunderstood—aspects of leader...

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  Thoma Bravo's Behind the Deal

  The Dayforce Deal: AI, Scale and the Future of Workforce Software

  Apr 23, 202638 minS0

  <p>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.</p> <p>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.</p> <p>...

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  Thoma Bravo's Behind the Deal

  REVISITING: How Carl Thoma and Orlando Bravo Built the World’s Largest Software-Focused Investment Firm

  Apr 16, 202638 minS0

  <p>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.</p> <p>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.</p> <p>This episode traces the early missteps, hard-earned lessons, and defining principles — around partnership, performance and integrity — that helped build one of t...

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  Episode #13

  Beyond the Deal: Building the Explore Platform

  Apr 9, 202623 minS4

  <p>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.</p> <p>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.</p> <p>From cold starts and conference ro...

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  Episode #12

  Exostar: The Explore Platform's First Investment

  Apr 2, 202658 minS4

  <p>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.</p> <p>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.</p> <p>Together, Carl, Adam and Richard unpack the full lifecycle of the investment—from sourcing and diligence to transformation and ex...

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