HelloSign e-signature is Dropbox's 'gateway drug' to workflow automation

Profile picture for user pwainewright By Phil Wainewright November 11, 2021 Audio mode
I caught up with Whit Bouck, COO of HelloSign to find out about life as part of Dropbox and what's next after organizations switch from paper-based processes to e-signature.

Mobile phone with sign here post-it - Photo by Kelly Sikkema on Unsplash
(Photo by Kelly Sikkema on Unsplash)

It's probably not an original idea, but this notion popped into my head while I was chatting the other day to Whit Bouck, COO of HelloSign, which is part of Dropbox. It's the notion that adopting e-signatures is the corporate equivalent of a 'gateway drug' that gets an organization hooked on ever-deeper digital workflow automation. The point is that, once you digitize the signature, you remove paper from the process, which means you can now focus on the actual workflow rather than the process of passing pieces of paper around. Bouck agrees:

Once you start to get rid of paper, it lets you start to reimagine the process and perhaps revamp it in a way that makes much more sense to users.

She cites the example of Instacart, one of HelloSign's largest customers, which used its API to be able to capture digital signatures when signing up gig workers to be its local shoppers, rather than having to send out paper documents and collect them back. Trouble is, signing a PDF document on a mobile phone is still pretty inconvenient. The dropout rate stuck at 30%. But by redesigning the onboarding process for mobile using HelloWorks workflow automation, Instacart was able to cut the dropout rate down to 6-8%.

Rush to e-signatures

As offices closed with the onset of the pandemic last year, physical signatures suddenly became a huge obstacle to continuing operations. Organizations rushed to replace them with e-signatures instead. Prior objections and inertia that had prevented the switch in normal times were swept away as longstanding paper-based processes went digital overnight. This made Dropbox's acquisition of HelloSign a year prior look even more astute in retrospect, and the subsequent investment in internationalization was just in time to take advantage of the accelerating uptake. In July last year, HelloSign expanded its reach into 21 new languages in addition to its original English, well ahead of the schedule it would have planned as a standalone company. Bouck adds:

People couldn't be together in person. That includes, you don't want to go into a bank to sign a document in person, you don't want to hold a pen. At that time, we all thought it was surface transmission. So there were lots of reasons that having the product available in European and Asian countries became incredibly timely.

We saw a massive spike in usage in the early months of COVID, that has not completely tapered off. We've actually seen a sustained level of activity since then.

This has helped make HelloSign the fastest-growing part of Dropbox since the acquisition. It has benefited from Dropbox's scale and resources, while still able to pursue its own market opportunity. Bouck says:

We got the best of both worlds. We still have this ability to act fast, act as a team and make sure that we have a shared sense of purpose around what we're trying to do for e-signature and workflow. And we get the benefits of being part of this larger organization that has global scale and great employee benefits.

Expanding integration

No wonder Dropbox has continued to invest in HelloSign, including last week's launch of an all-new mobile app which has made it easier to do tasks such as setting up documents for signature and sending and tracking signature requests. HelloSign sales are not broken out separately, but it's clearly contributing to the larger company's continued growth. Last week, Dropbox beat Wall Street expectations in its Q3 results, posting year-over-year revenue growth of 12.9% and a rise in paying subscribers to 16.5 million. It again raised guidance for its full-year results, to $2.15 billion.

HelloSign has continued to expand its integrations to other collaboration tools, including most recently Microsoft SharePoint, alongside existing integrations to Google Apps, Salesforce, Slack, Evernote, Keap, HubSpot, Microsoft Dynamics, OneDrive and Word. Deep integration into sales processes includes integrations to CPQ apps from Salesforce and Oracle. It's important to be able to add its e-signature capability alongside existing tools in an organization, even if they're Dropbox competitors, as Bouck explains:

As much as we recognize that there is benefit and value for our customers to be able to use Dropbox and HelloSign together, they may choose to use Dropbox with a different signature provider, they may choose to use HelloSign with a different storage provider. There's no question that we want to maintain that flexibility for our customers, because it's what's best for them. It's what they want.

HelloSign is looking to do even more on the integration front, particularly in building workflow around the signature. Bouck elaborates on the thinking:

How do we both go upstream toward negotiation and redlining and go downstream? Obviously, storage being part of that, but there's a whole bunch of other third-party things that we can trigger at various points in the process. For example, if it's a hiring process, it might be a background check, criminal record check for somebody. It could actually be to trigger a payment through something like Stripe. It could be to trigger any number of third-party activities, ie notarization of documents, for example. So there's a lot of things there that we want to make sure we address the whole end-to-end workflow.

Virtual-first work

Dropbox itself has been taking a lead in embracing a virtual-first pattern of work, using both third-party tools and its own new products, such as Dropbox Capture, which lets users record short video clips for others to view separately. Finding ways to do more asynchronously rather than everyone convening at the same time for live meetings is a big part of the adjustment. Bouck explains:

We're moving toward asynchronous-first. Do we really need to have 12 Zoom meetings a day? Or can we do some of this in a different way now that our main way of working has changed? Can we start to look at ways to do work asynchronously, and yet still be meaningful?

Why get together in person? If I can use something like Capture, which lets me do a video, voiceover and pictorial capture of me, say, giving a talk track to a presentation or a document or an image or what have you — it's actually a way to convey the same information, but I let people adjust it as they wish, when they wish, asynchronously. Maybe if we do have to have a meeting, it's purely to ideate, after people have ingested information.

I do feel like we're being very thoughtful about how we change the way we work and how we build tools that help us do our work better and help our customers do work better.

In the same way that some of its customers have been surprised at the ease of integrating e-signatures into their routines, Bouck has found the use of digital whiteboards like Mural or Miro to be an eye-opener. She says:

I never really thought that was going to be that possible to do online. I was thinking that was one of those things where you necessarily have to be in person. But it actually turns out to be pretty effective. So I'm really intrigued by what's happening in the market and how that influences how we work and new tools that are coming to bear.

The common theme here is the need to get people to take the first step and try these new ways of working. While the switch to distributed work has been a big help for HelloSign, it's important to build as much support as possible to show people how to get started. Bouck elaborates:

What are the triggers that get people to do more in the product? What leads them to be more engaged and potentially recommend it to other people? [We're] trying to bring people to those capabilities faster by tutorials, or in product prompts, or email campaigns, or anything that illustrates how people can use it. One of the things that we found that people use most frequently, that causes them to use the product more and maybe recommend the product more, is the use of templates.

My take

HelloSign certainly seems to be fulfilling the potential that was evident when its acquisition by Dropbox was first announced. There's much more to tap into by extending the workflow around e-signatures and it's clear from what Bouck says that the product team is alert to the possibilities.

The first step is taking paper out of the equation by turning that physical signature into a digitally captured gesture. This is the gateway to so much more. With every user verified when they log in on their device, the signature then becomes a simple approval step in a digital workflow that can be reimagined to be far more efficient than the old paper-based process. You might even call it building towards a metaverse. I prefer to think in terms of Frictionless Enterprise, but whatever you call it, it is a fundamental transformation of the old ways of working.