Thoma Bravo's Behind the Deal

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: https://www.proofpoint.com/us 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.

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; and learn how the CEOs of Anaplan and Coupa are navigating AI-driven transformation. Season 4 also features in-depth examinations of major acquisitions, including Intel 471 and Ellie Mae, unpacking the strategic thinking, decision-making, and execution behind each deal. Featuring some of Thoma Bravo’s most senior voices and most timely insights yet, Thoma Bravo’s Behind the Deal offers a look at how leading software companies are built.   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/

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 entrepreneurship and impact in Puerto Rico. This conversation offers rare insights on leadership, resilience, mentorship, and what it really takes to build enduring software companies. 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 View From the Top: https://www.gsb.stanford.edu/business-podcasts/view-top-podcast

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.

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.