Podcast · Business

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

New episodes: Weekly
Typical length: 35 min
Latest: 30 Apr 2026
Language: English

Latest episode

30 Apr 2026 · 8 min

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…

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Earlier episodes 29 most recent

23 Apr 2026 · 38 min
The Dayforce Deal: AI, Scale and the Future of Workforce Software
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…
16 Apr 2026 · 38 min
REVISITING: How Carl Thoma and Orlando Bravo Built the World’s Largest Software-Focused Investment Firm
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 —…
S4 · E13 · 9 Apr 2026 · 23 min
Beyond the Deal: Building the Explore Platform
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…
S4 · E12 · 2 Apr 2026 · 58 min
Exostar: The Explore Platform's First Investment
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…
S4 · E11 · 26 Mar 2026 · 36 min
The Future of Restaurants in an AI World: Hudson Smith with Olo Founder Noah Glass
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 behind the company, the strategic thinking behind taking Olo private in 2025, and how data, network effects and AI are redefining hospitality at scale. They also…
S4 · E10 · 19 Mar 2026 · 13 min
From Scotland to Sydney: Andy Watt on Leading Nearmap’s Global Growth
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 experience of scaling a global company from Australia and the behind-the-scenes moments that helped Thoma Bravo win the trust of the Nearmap team. The episode…
S4 · E9 · 12 Mar 2026 · 53 min
Nearmap: Building a Global Property Intelligence Platform
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 the business has expanded through AI, software and strategic acquisitions. Andy also shares his journey from Scotland to Australia, how Nearmap scaled from roughly…
S4 · E8 · 5 Mar 2026 · 20 min
Inside Thoma Bravo: Holden Spaht & Brian Jaffee on Building Performance Through Mentorship & Entrepreneurial Spirit
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, this episode offers an inside look at how performance is built — and sustained — over decades. For more information on Thoma Bravo's Behind the Deal, visit…
S4 · E7 · 26 Feb 2026 · 45 min
Ellie Mae: The $3.7B Take-Private That Became an $11B Exit
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 decisions that drove one of the firm’s landmark exits — including the rare “reverse re-trade” that moved the final agreement from $10B to $11B. For more information on…
S4 · E6 · 19 Feb 2026 · 12 min
From Infantry to Intelligence: Grit, Discipline, and the Making of a Founder
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-first thinking became foundational to Intel 471’s culture, as well as the personal commitment required to bootstrap a business while raising a family. The discussion…
S4 · E5 · 12 Feb 2026 · 35 min
Intel 471: From Bootstrapped Cyber Intel to Enterprise Leader
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, exceptional retention, and disciplined, profitable growth. Adam then sits down with CEO and Co-Founder Jason Passwaters, a former Marine and FBI cybercrime investigator,…
S4 · E4 · 5 Feb 2026 · 35 min
Scaling Enterprise Software with AI: Holden Spaht with Anaplan CEO Charles Gottdiener and Coupa CEO Leagh Turner
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 highlighting the importance of governance, disciplined pricing, and domain expertise as AI adoption accelerates. For more information on Thoma Bravo's Behind the Deal,…
S4 · E3 · 29 Jan 2026 · 57 min
Orlando Bravo and IBM CEO Arvind Krishna on AI, the Future of Software, and IBM’s $34B Red Hat Deal
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 conversation also explores IBM’s $34 billion acquisition of Red Hat, including the strategic investment in hybrid cloud and OpenShift, how the deal scaled beyond…
22 Jan 2026 · 10 min
Building Belief at Scale: Proofpoint CEO Sumit Dhawan on Leadership, Transparency, and Performance
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, Sumit reflects on how transparency, storytelling, discipline, and mentorship build trust and unlock the best work from teams—and why building belief may be the most…
S4 · E1 · 15 Jan 2026 · 41 min
Proofpoint: The $12B Deal Behind an AI-Driven Cybersecurity Leader
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 Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo: https://www.thomabravo.com/ Learn more about Proofpoint:…
S4 · 13 Jan 2026 · 2 min
Thoma Bravo’s Behind the Deal is back for Season 4
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 environment; gain a rare perspective on the future of AI in a candid conversation between Thoma Bravo Founder and Managing Partner Orlando Bravo and IBM CEO Arvind Krishna;…
8 Jan 2026 · 49 min
View From The Top: Orlando Bravo on His Journey to Building Thoma Bravo
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 shares why discipline, humility, strong partnerships, and “doing your own thing” became the foundation of Thoma Bravo’s approach, as well as his long-term commitment to…
24 Jul 2025 · 21 min
Beyond Constraints: From Starting Lean to Scaling Up
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.
17 Jul 2025 · 35 min
How HubSync Became the Tax Automation Platform for Top 25 CPA Firms
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.
10 Jul 2025 · 20 min
Beyond Building NextGen Healthcare’s Successful Remote-First Company and Culture with David Sides
In the Beyond the Deal mini-sode with Thoma Bravo’s A.J. Rohde and Peter Hernandez, hear NextGen Healthcare CEO David Sides explain his approach to leadership, inspired by his family’s medical roots, and how NextGen Healthcare grew into one of the most trustworthy companies in America. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedealLearn more about Thoma Bravo: https://www.thomabravo.com/Visit NextGen Healthcare's website: https://bit.ly/3TN6i7s
3 Jul 2025 · 56 min
How NextGen Healthcare Aims to Achieve Better Healthcare Outcomes for All
In this episode, Thoma Bravo Senior Partner A.J. Rohde sits down with Peter Hernandez, a Senior Vice President on our Discover team, to detail the strategic take-private of NextGen Healthcare, a leading provider of innovative, cloud-based healthcare technology solutions. They are joined in the studio by NextGen Healthcare CEO David Sides and discuss their bold vision for the future of healthcare IT. Hear perspectives on NextGen Healthcare’s exciting new chapter, marked by a recent investment by Madison Dearborn Partners, to further accelerate the company’s growth. For more information on…
S3 · 26 Jun 2025 · 15 min
Beyond the Classroom: Shaping the Future of Learning with Steve Daly
In this Beyond the Deal minisode, hear Instructure CEO Steve Daly share how his past experiences informed his mission to create a results-oriented, customer-centric company and a culture where people genuinely enjoy coming to work. Thoma Bravo Managing Partner, Holden Spaht, and Partner, Brian Jaffee, speak with Steve Daly about his leadership philosophy and building a company culture that emphasizes collaboration. 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/ Visit Instructure's…
S3 · E11 · 18 Jun 2025 · 52 min
How Instructure Grew into a Leading EdTech for K-12, Higher Ed, and Professionals
Instructure’s Canvas, the learning management system used by over 4,000 school districts and 2,500 higher education institutions, became a lifeline during the pandemic. On this episode of Behind the Deal, Thoma Bravo Managing Partner Holden Spaht and Partner Brian Jaffee sit down with Instructure CEO Steve Daly to discuss how they worked together to refocus Instructure to grow into a leading EdTech 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/ Visit Instructure's…
S3 · 12 Jun 2025 · 14 min
Beyond Performance: Building a “10-10” Company Culture with Andre Durand
Ping Identity Founder & CEO, Andre Durand, explains that in a 10-10 culture, “the how matters as much as the what.” Over time, through his experience as a multi-time founder, he has come to resonate with one simple cultural north star that he refers to as “10-10” to strike a balance between performance and attitude. In this Beyond the Deal minisode, Andre Durand sits down with Thoma Bravo’s Orlando Bravo and Chip Virnig to discuss some of the pivotal moments that shaped his journey as an entrepreneur and what guides his leadership style today. For more information on Thoma Bravo's Behind the…
S3 · E10 · 5 Jun 2025 · 57 min
How Ping Identity Mastered Identity Security for Global Enterprises
Ping Identity helps some of the largest enterprises in the world secure the logins of their employees and customers, helping to keep systems secure, prevent fraud, and decrease friction as companies undergo their digital transformation. In this episode of Behind the Deal, Thoma Bravo Founder and Managing Partner, Orlando Bravo, and Partner, Chip Virnig, sit down with Ping Identity Founder & CEO, Andre Durand, to discuss the $2.8 billion take-private transaction and the strategic rationale behind combining Ping with ForgeRock to create a leading identity security platform for some of the…
S3 · 29 May 2025 · 21 min
How Applitools is Using AI to Improve Speed, Scalability, and Accuracy with Adam Carmi and Alex Berry
In this Beyond the Deal mini-sode, Applitools Co-Founder and CTO, Adam Carmi, and CEO, Alex Berry, speak with Thoma Bravo Partner, Carl Press, about the evolution of Applitools from its early days to a leader in AI-enabled test automation. Adam discusses the initial problem he and co-founder Moshe Milman sought to solve and Alex shares his perspective as CEO and how he embraces the founders’ vision. 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/ Visit Applitools's website:…
S3 · E9 · 22 May 2025 · 42 min
How Applitools Uses AI to Revolutionize Test Automation
Hear the story behind Thoma Bravo’s investment in Applitools with Partner Carl Press in conversation with Alex Berry, CEO of Applitools, and Adam Carmi, Co-Founder and CTO of Applitools. The company’s all-in-one, AI-powered testing platform revolutionizes the way businesses approach quality assurance and test automation. Carl, Alex and Adam discuss the evolution of the business, the market trends driving the adoption of AI in application testing, and why thousands of companies worldwide trust Applitools’ technology to elevate their testing processes and improve digital experiences for their…
S3 · 15 May 2025 · 23 min
Beyond the Friend Zone: Building Mailgun into a Leading Technology Company with Will Conway and Josh Odom
In this Beyond the Deal mini-sode, former Mailgun CEO and CTO, Will Conway and Josh Odom, join Thoma Bravo Partner Hudson Smith to share their experiences of leading a growing technology company starting as college friends turned business partners. They highlight the critical role of a strong, supportive team culture, how their friendship strategically plays to their individual talents and strengths, and how that impacted the business. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedeal Learn more about Thoma Bravo:…
S3 · E8 · 8 May 2025 · 53 min
How Mailgun Quickly Evolved into a Leading Email API Provider
Mailgun enables over 150,000 companies to send, track, test, and optimize more than 250 billion emails per year effortlessly for marketing and business communication to their customers. Thoma Bravo Partner Hudson Smith sits down on Behind the Deal with former Mailgun CEO Will Conway and CTO Josh Odom as they dive into Mailgun’s journey from a spin out from Rackspace to a leading email delivery service for businesses around the world. 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/…

About Thoma Bravo's Behind the Deal

Thoma Bravo's Behind the Deal is a English business podcast from Thoma Bravo. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: Thoma Bravo
Language: English
Category: Business
New episodes: Weekly
Typical length: 35 min
Latest episode: 30 Apr 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id1668194496
Rights: AnuZu7AecVNjgD4X6dco

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