Thoma Bravo's Behind the Deal

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, visit https://www.thomabravo.com/behindthedeal

Learn more about Thoma Bravo: https://www.thomabravo.com/

Learn more about Anaplan: https://www.anaplan.com/

Learn more about Coupa: https://www.coupa.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.

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 expectations, and why conviction was critical despite initial market skepticism. 

Looking ahead, Krishna outlines what’s next for enterprise AI: agents layered on systems of record, smaller purpose-built models, and why companies that scale AI deliberately will pull ahead.

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 IBM: https://www.ibm.com/case-studies/ibm-client-zero?lnk=hpls1us

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.

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 underrated skill in leadership today.

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.

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/