Thoma Bravo's Behind the Deal

Latest Episodes:

From $1M to $2B+ in Revenue: David Ossip on Leadership and Scaling Dayforce Apr 30, 2026

Show notes

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 leadership at scale: delegation. By surrounding himself with world-class operators and trusting them to lead in their domains, he’s built an organization that continues to evolve, innovate, and execute at a high level.

This conversation explores how great leaders balance hands-on involvement with real trust, why culture becomes a competitive advantage, and how Dayforce is positioning itself for continued growth in the AI era.

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 Dayforce: dayforce.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.

The Dayforce Deal: AI, Scale and the Future of Workforce Software Apr 23, 2026

Show notes

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 into real ROI for customers.

David Ossip also shares the origin story behind Dayforce, how he combined startup innovation with legacy infrastructure and why AI is central to accelerating both revenue and profitability.

This is a deep look at how product vision, leadership and long-term thinking come together to build a category-defining company.

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 Dayforce: dayforce.com

REVISITING: How Carl Thoma and Orlando Bravo Built the World’s Largest Software-Focused Investment Firm Apr 16, 2026

Show notes

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 — that helped build one of the most enduring firms in private equity.

Whether you're an investor, operator, or early in your career, this conversation is a reminder that great outcomes are built on fundamentals, trust and learning from mistakes.

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/

Beyond the Deal: Building the Explore Platform Apr 09, 2026

Show notes

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 pitches to navigating deals with imperfect data, this conversation offers a candid look at what it takes to build a platform—and a team—inside the world’s largest software-focused investment firm.

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/

Exostar: The Explore Platform's First Investment Apr 02, 2026

Show notes

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 transformation and exit—and reflect on what it took to transition Exostar from a shared-service joint venture into a high-growth, profitable enterprise software company.

In just three years, the business accelerated growth, expanded margins and positioned itself for a successful exit, making Exostar a defining deal for Thoma Bravo’s Explore 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/

Learn more about Exostar: https://www.exostar.com/

The Future of Restaurants in an AI World: Hudson Smith with Olo Founder Noah Glass Mar 26, 2026

Show notes

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 explore what makes restaurant technology uniquely complex, why structured data helps create a durable moat, and how AI is expected tol transform both the guest experience and restaurant operations in the years 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 Olo: https://www.olo.com/

Disclaimer:

This podcast may contain forward looking statements reflecting current views regarding market conditions, technological evolution, and anticipated developments, which are based on current expectations and assumptions, involve risks and uncertainties that could cause actual results to differ materially, and speak only as of the date of recording with no obligation to update.

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.

From Scotland to Sydney: Andy Watt on Leading Nearmap’s Global Growth Mar 19, 2026

Show notes

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 closes with A.J.’s lightning round — covering everything from Scottish traditions and Australian sports to rock bands and Vegemite.

It’s a lighter look at the relationships, personalities and moments that happen beyond the deal.

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 Nearmap: https://www.nearmap.com/

Nearmap: Building a Global Property Intelligence Platform Mar 12, 2026

Show notes

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 $40 million in revenue to more than $300 million and why the company sees a long runway ahead across insurance, construction, government and beyond.

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 Nearmap: https://www.nearmap.com/

Inside Thoma Bravo: Holden Spaht & Brian Jaffee on Building Performance Through Mentorship & Entrepreneurial Spirit Mar 05, 2026

Show notes

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 https://www.thomabravo.com/behindthedeal

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

Ellie Mae: The $3.7B Take-Private That Became an $11B Exit Feb 26, 2026

Show notes

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 Thoma Bravo’s Behind the Deal, visit https://www.thomabravo.com/behindthedeal
Learn more about Thoma Bravo: https://www.thomabravo.com/
Learn more about Ellie Mae (now ICE Mortgage Technology): https://mortgagetech.ice.com/

Our TOPPODCAST Picks

Follow Us

Stay Connected

Thoma Bravo’s Behind the Deal

Related Podcasts

Links

Stay Connected