Reflecting On Haystack’s Investment In HelloSign (Acquired By Dropbox)

Over five years ago, as I began to deploy the first Haystack Fund, I was lucky to select HelloSign as my sixth investment ever. I discovered the product much like you might have – I used it to help handle the paperwork and signatures for the new fund. I had a friend who worked there (thanks Joel Andren!) and he was patient and over time found the right time to introduce me to Joseph Walla, one of the company’s cofounders. I took Joseph out for lunch, told him about me and Haystack, and asked to invest in the company.

Ultimately, Joseph invited me into the seed round. That turned out to be a good lunch. At that time, back in 2013, Docusign was known to be a well-performing company. In early 2014, Docusign became a unicorn and eventually went IPO in 2018 at a whopping $4.5B price tag. And it nearly tripled in the first year, now settling to be around the same market cap at Dropbox. During this time, the tech world didn’t really know how to think about these products. Was Dropbox just a storage provider, or a collaboration platform? Was Docusign just a place to get electronic signatures done, or could it have more tentacles into document-management systems across a variety of sectors?

Back to HelloSign, an early criticism that may have been used against the company is that electronic signatures is just a product feature of a larger platform. But over that five year period, signing documents online turned out to be a very important and profitable product feature, to the tune over $10B in market value. That provided an even bigger shot in the arm to the folks at HelloSign — after having tens of thousands of corporate customers, a growing suite of APIs for document management and signatures, and growing nicely without overspending, the surprising scale of Docusign’s success meant that, by proxy, HelloSign was more than just a product feature. It was a critically important product feature for modern workflows.

Dropbox agreed, today announcing it had come to terms to acquire HelloSign to help bolster its product suite for enterprise customers. It’s the largest acquisition by the company, ever. I’m really excited for Joseph, Neal, and their team. One thing that struck me about Joseph is how quiet and hardworking he is and no doubt his team is that way, too. In a way, it’s also a little bittersweet because, like Docusign, I think the company could’ve grown and grown because we now know the market is huge and growing. And Joseph is an authentic CEO – I recall we had to have one serious chat about product and Joseph personally called me to follow-up and I could hear in his voice how seriously he took that issue. He and his team really care about the perfection of the product. But that’s just me, and I’m waxing poetic – Dropbox is an incredible home for the HelloSign team, and I wanted to thank them all for all the work and for saving a small seat for me on their ride. Best of luck at DBX!