Russ Heddleston

Russ Heddleston, founder of DocSend, shares his incredible journey from the brink of bankruptcy to a $165M acquisition by Dropbox. He dives into the painful lessons learned from chasing enterprise sales and the surprising success of a self-serve model. Russ also discusses strategic pricing changes that skyrocketed conversions, the emotional complexities of selling his company, and what he wishes he had done differently. Now, he's focused on his new venture, Distill, with a fresh perspective on innovation and growth.

Russ Heddleston, former CEO of DocSend and a seasoned pro in tech acquisitions, shares his journey from VC funding to selling his company to Dropbox. He discusses the art of building relationships with potential buyers and competitors. The conversation explores product-led growth and capital efficiency. Russ also dives into the challenges faced during the acquisition process, emphasizing the importance of trust and adaptability in the tech landscape. Plus, he unveils a new initiative aimed at revolutionizing professional online identities.

Russ Heddleston, CEO of DocSend, shares insights on managing feedback and the importance of open dialogue in the startup world. He discusses how tracking technology in pitch decks benefits founders and investors, emphasizing privacy concerns. Heddleston addresses the challenges of user engagement and transparency in data collection. He reveals strategic growth insights, highlighting decentralized decision-making and the significance of aligning marketing with user behavior. Lastly, he reflects on evolving VC dynamics in a remote era and the role of secondary financing for employee satisfaction.