Russ Heddleston is the co-founder and former CEO of DocSend, leading its acquisition by Dropbox in 2021 for $165M. Before DocSend, he co-founded Pursuit, sold to Meta in 2011, where he ran Product Management for Pages. Russ holds an MBA from Harvard Business School and a master's in Computer Science from Stanford. He has held product and management roles at Microsoft, Trulia, Greystripe, DocSend, and Dropbox. Now, he is the co-founder and CEO of Distill. His extensive M&A experience spans multiple successful exits and strategic acquisitions.
Every owner loves their business. This makes selling their company even harder than it already is. But aside from the emotional turmoil that founders go through every exit, there are also a lot of intricacies included in the process. In this interview, Russ Heddleston, Co-founder & former CEO of DocSend, discusses the challenges of sell-side M&A and how to navigate them.