Building a company takes focus. Exiting one demands a different kind of discipline. The shift from founder to wealth steward is about building the structure to handle whatever comes next. Markets turn. Opportunities appear and sometimes, the five Ds (death, disability, divorce, dispute, and distress) force decisions on someone else’s timeline. The founders who stay ahead are the ones who plan for change long before it arrives.

The path to a successful exit looks different in 2025. In the age of AI, building a strong engineering team or a slick feature set isn’t always enough. Valuations are shaped by what surrounds your product, distribution, data, trust, and deals are structured with new metrics and risks in mind. These five shifts offer a real-time snapshot of how tech M&A is evolving and what builders and buyers alike will need to know to stay ahead.

Copperleaf’s path to a $1B exit wasn’t easy (or typical). Under Judi Hess, with support from early backers like Pender Ventures, the team turned tough markets, early setbacks, and complex customer challenges into a foundation for long-term growth. Their story offers practical, lived experiences and insights for founders on building a business that’s truly exit-ready. Here’s how they did it and what you can apply to your own journey.

Greg Malpass didn’t set out to sell. He set out to solve customer problems and that mindset turned a solo consultancy into one of the largest Salesforce partners in the world, 1,100 employees, 1,800+ clients, and multiple product spinouts, culminating in a 2022 acquisition by Salesforce and a $100M+ exit for Traction Guest. Greg’s story is a case study of how exits aren’t events; they’re the result of continuous strategic choices. From customer-led growth to reclaiming product IP during acquisition, Greg built a company that was both resilient and highly acquirable.

Most founders think about their exit as a final chapter, a moment of payoff, or transition. But what if it’s not a moment at all? At TechExit.io, Jack Newton shared how Clio redefined the concept of an exit by treating liquidity as a continuous strategy and not just a one-time event. What followed wasn’t just a record-breaking $1.2 billion CAD financing round but rather a masterclass in secondaries, partner selection, and long-range planning. If you’re building a SaaS company with ambitions beyond the next round, this is the blueprint.

In this article, we explore the firsthand experiences of two founders; Jason Leeson of Squirrel Systems (Acquired by Valoris Group) and Kris Hartvigsen of Dooly (Acquired by Mediafly), who each took very different paths when it came to selling their companies. Jason led the exit of a decades-old legacy business, while Kris navigated the sale of a high-growth AI startup in an everchanging tech market.