Russ Heddleston is the co-founder and former CEO of DocSend, which was acquired by Dropbox for $165 Million in early 2021. Russ currently works at Dropbox continuing the vision he had for DocSend.

During this interview we hear how Russ went from studying at Stanford, to working at a startup called Greystripe, then as an intern at Dropbox, and then launching his own startup Pursuit.

Pursuit was later acquihired by Facebook, where Russ continued to work for two years. He shares some interesting insights into why Pursuit didn’t take off and the lessons learned, which he then took into his next startup, DocSend.

We spend a good amount of time talking about what marketing Russ and his team did to grow DocSend, how they revised their positioning and copy on their website to add fuel to their growth and how eventually the deal with Dropbox happened.

If you like B2B SAAS startup stories, this interview is for you.

Enjoy the podcast.