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.
Episodes
April 30, 2026 • 7 mins
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 cult...
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April 23, 2026 • 37 mins
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...
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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...
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April 9, 2026 • 22 mins
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 challenge...
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April 2, 2026 • 58 mins
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 a...
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March 26, 2026 • 36 mins
At Thoma Bravo’s 2025 AI Summit, Partner Hudson Smith sits down with Olo Founder and CEO Noah Glass to unpack one of the firm’s most compelling recent investments.
From its early days as a text-based ordering tool to becoming a category leader powering digital experiences for over 750 restaurant brands, Olo has spent two decades shaping how consumers interact with restaurants. In this conversation, Noah shares the origin story beh...
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March 19, 2026 • 12 mins
In this episode of Beyond the Deal, Thoma Bravo Senior Partner A.J. Rohde and Principal Peter Hernandez sit down with Nearmap CEO Andy Watt for a candid conversation about leadership, culture and building a global technology company from Australia.
Andy shares the story of how a move from Scotland to Sydney turned into a decades-long journey with a leading Australian technology company. The group reflects on Nearmap’s growth, the ...
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March 12, 2026 • 53 mins
In this episode of Thoma Bravo’s Behind the Deal, Senior Partner A.J. Rohde and Principal Peter Hernandez sit down with Nearmap CEO Andy Watt to unpack Thoma Bravo’s investment in Nearmap and the company’s evolution from an aerial imagery provider into a global property intelligence platform.
They discuss how the deal originated, what made Nearmap stand out, the complexities of taking an Australian public company private and how t...
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This week on Thoma Bravo's Beyond the Deal, the spotlight turns inward. Managing Partner Holden Spaht and Partner Brian Jaffee share their origin stories at Thoma Bravo — what the firm looked like in its early days, how responsibility comes fast, and why mentorship and entrepreneurialism sit at the center of the culture.
From cold outreach and the firm’s early focus on software to leading exits and mentoring the next generation, t...
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February 26, 2026 • 44 mins
In this episode of Thoma Bravo’s Behind the Deal, Managing Partner Holden Spaht and Partner Brian Jaffee revisit the take-private and sale of Ellie Mae — a leading U.S. mortgage loan origination system — and how a $3.7B investment became an $11B exit to Intercontinental Exchange (ICE) just over a year later. They break down the original investment thesis, the operational playbook, pricing and packaging strategy, and the M&A decisio...
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February 19, 2026 • 11 mins
In this episode of Beyond the Deal, Intel 471 CEO and Co-Founder Jason Passwaters joins Thoma Bravo Partner Adam Solomon for a candid conversation about the experiences that shaped him as a leader.
Passwaters reflects on his early years in the U.S. Marines — from infantry to counterintelligence — and the lessons he carried into building a global cybersecurity company. He shares how resourcefulness, team camaraderie, and mission-fi...
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February 12, 2026 • 34 mins
In this episode, Thoma Bravo Partner Adam Solomon and SVP Chandler Gay break down the firm’s investment in Intel 471, a bootstrapped, founder-led cyber threat intelligence company trusted by many of the world’s largest enterprises.
They revisit the rigorous diligence process — including moments when the deal nearly fell apart — and explain what ultimately set the business apart: proprietary, highly actionable intelligence, excepti...
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In this episode of Thoma Bravo’s Behind the Deal, Managing Partner Holden Spaht sits down with Charles Gottdiener, CEO of Anaplan, and Leagh Turner, CEO of Coupa, to discuss how enterprise software leaders are turning AI innovation into real business impact.
Drawing on their experience as both builders and users of AI, they share how AI is driving productivity, reshaping operating models, and expanding operating leverage—while hig...
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January 29, 2026 • 57 mins
Recorded live at Thoma Bravo’s 2025 AI Summit, this episode features a fireside chat between Thoma Bravo Founder and Managing Partner Orlando Bravo and IBM CEO Arvind Krishna. Krishna shares an operator’s view on why AI is unequivocally good for software—boosting developer productivity, expanding entry-level hiring, and unlocking billions in back-office automation that IBM has reinvested into software R&D and growth.
The conversat...
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January 22, 2026 • 9 mins
What separates good CEOs from great ones? According to Proofpoint CEO Sumit Dhawan, it’s the ability to build belief. In this episode of Beyond the Deal, Thoma Bravo Managing Partner Seth Boro sits down with Sumit to discuss the leadership principles behind scaling a high-performing, human-centric cybersecurity company. From growing up in Delhi and learning the value of hard work and ownership, to leading a global public company, S...
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January 15, 2026 • 41 mins
Season 4 of Behind the Deal kicks off with a deep dive into Proofpoint, a key investment within Thoma Bravo’s cybersecurity portfolio. Seth Boro and Andrew Almeida reflect on the conviction behind the firm’s largest software buyout at the time, while Proofpoint CEO Sumit Dhawan shares how the company has scaled, evolved its platform, and stayed ahead of rapidly growing cyber threats in an AI-driven world.
For more information on T...
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January 13, 2026 • 1 min
Thoma Bravo returns with Season 4 of Behind the Deal—the chart-topping, award-winning podcast that goes inside the strategy, leadership, and conviction behind the world’s largest software-focused investment firm.
This season brings listeners to the forefront of the software and AI landscape. Hear from Proofpoint’s CEO on how AI is reshaping cybersecurity and what it takes to lead at scale in an increasingly complex threat environm...
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January 8, 2026 • 49 mins
In this bonus episode, Thoma Bravo founder and managing partner, Orlando Bravo joins View From The Top from Stanford GSB for a candid conversation on his nonlinear journey—from leaving a small town in Puerto Rico to building one of the world’s leading software investment firms.
Orlando opens up about early career setbacks—including rejection, failed deals, and the mentors who shaped his investing and leadership philosophy. He shar...
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July 24, 2025 • 21 mins
Inspired by the book Getting Real, HubSync Founder and CEO John McGowan explains to Thoma Bravo Partner Ross Devor how operating under tight timelines and budgets with a lean team forced HubSync to focus on an engineer-first approach, providing a foundation for a company that was able to scale.
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July 17, 2025 • 34 mins
HubSync started as a bootstrapped idea from John McGowan, a former Big Four tax professional who saw the tech gap in mid-sized CPA firms. In this episode of ‘Behind the Deal,’ Thoma Bravo Partner Ross Devor talks with John about how he turned early consulting work into a profitable SaaS business, the strategy behind landing over 40% of the top 25 accounting firms, and how product market fit shaped every decision.
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