We’ve traded intimacy for convenience, but do we understand the consequences?

This week at DocSend we announced our $8M Series A raise led by August Capital. We’re incredibly thrilled to have this opportunity to help businesses communicate more effectively and bring all the intimacy of face-to-face conversation to the digital way we communicate today.

I’d love to offer some perspective on the scope of the problem we’re tackling, why it affects all of us, and why I’m excited for the future.

Communication Technology: A Long Trend Away from Intimacy

One of the first questions you’re asked when going on the fundraising tour at the early stages of your business is “Why now?” What has changed at a macro level that makes now the right time to build this business? Are these conditions temporary or part of a broader trend?

If you look at the history of communication technology, it turns out that at nearly every step we’ve traded intimacy in favor of convenience:

Long, long ago before any of this email business, if we wanted to speak to one another we did so face-to-face. There simply wasn’t an alternative to in-person conversation. Eventually, with the advent of written language and the printing press, we could send messages far and wide. Words could travel as neat little marks on paper, and we got quite sophisticated about transporting them, using groundbreaking technology that ran on hay: horses.

This was our first major step in connecting with people over long distances, and at scale. Ideas could travel, trade could be conducted, and relationships could be built remotely all because words on paper were enabling conversation where face-to-face meetings weren’t possible. But that came with tradeoffs. To add emphasis to our message we had to use things like underlining and making the words BIGGER. (John Hancock was a notable fan.) We couldn’t change our messages on the fly, and our words took days or weeks to travel back and forth, but it all seemed worth it. And in so many ways it was, as the alternative often was no communication at all.

But of course horses need people to ride them and weather conditions can be challenging, not to mention large bodies of water or hills. The telephone brought with it the promise of an instant connection with someone else, replete with the actual tone of your voice. Sure, you couldn’t see the person on the other end of the line — and if you were talking with an unknown party it could have been anyone for all you know — but you could actually communicate in real time.

The rise of the telephone was a unique step in the evolution of communication technology as it’s the singular innovation where both intimacy and convenience improved. Just imagine a face-to-face conversation but you can’t see each other. No facial cues. Otherwise it’s just like the real thing. And for these reasons the telephone remains such a high-quality communication medium today.

One of the major downsides to the telephone, however, and a reason why in some ways paper mail was more convenient, is that it required both parties to be available at the same instant. Particularly when considering communication over long distances, this posed quite a challenge. So, we came up with the digital equivalent of the Pony Express, the heavens parted, and down came electronic mail, also known as email. It’s almost funny now to think of the name “electronic mail” — it sounds so futuristic.

And truth be told it mightily is. It’s fabulous technology. So wonderful, in fact, that we use it all the time, even when sitting feet away from one another. Or miles or leagues or continents. With email we got all the convenience that paper mail provided of being able to send a message whenever we like, coupled with instant deliverability.

Relative to the phone, however, email was a major step backwards in terms of intimacy. We lost all sense of tone, all the flexibility that allows us to adjust our messaging on-the-fly based on how well it’s being received, and really that human element — an email that I send, at least on the surface, looks no different from one that my coworker sitting next to me sends with the exception of our message signatures. To leave our personal mark we’re left to the tools of Homer, of Joyce — pure words themselves. I have sent a few well-crafted emails in my time, but typically I just accept the fact that with email my personality isn’t shining through. It’s just not the same as talking face-to-face.

And so we arrive at our most convenient innovation in communication technology: instant messaging. By “instant messaging” I’m referring to any non-email-based medium that allows the transmission of short messages back and forth, e.g. SMS, Slack, Olark. Yes, email could be used in the same casual, rapid-fire manner, but we’d pull our hair out. A fundamental assumption with “instant messaging” is that each message itself is very short, just as each person’s speaking part in a conversation would be. As a result, if we do have something nontrivial to say, we often resort to trying to use as few words as possible or just sending a flurry of messages.

Our messages appear on the receiving end as nothing more than pixels behind a piece of glass. That’s it. It’s not you, it’s not your smiling face, it’s not your calm, confident voice. You’ve been reduced to a collection of pixels.

I can’t think of any better evidence of how much we value convenience over intimacy.

Do we realize the trade-offs we’ve made? It’s worth asking ourselves: are we consciously accepting that we’re forfeiting intimacy in favor of convenience each time we send someone an instant message or an email? Or are we merely falling back on “standard ways of communicating”?

Relationships are the bedrock of dealmaking in business, and the heart of any relationship is communication. Do we realize how poorly we’re communicating today?

Bringing Intimacy Back

In so many words, you could summarize modern communication media as asynchronous, remote, high-volume, cheap, and easy. It also happens to be rather dull, opaque, and discontinuous (I’ll explain in a moment). Face-to-face communication, on the other hand, is personal, transparent, and dynamic. Sadly it also happens to be time-consuming, hard to coordinate, and expensive.

At DocSend we’re striving to bring the benefits of face-to-face communication to the modern digital way we communicate today. To start, we’re focusing on a major factor in why email is modern communication public enemy #1: documents. Whereas emails in the course of doing business are often short, there are entire stories told within the documents we’re attaching to them. They’re your proposals, pitch decks, and case studies. They’re rich, illustrated experiences, and yet we as senders are not there to deliver our lines nor are we there to understand just how they fall on our recipients’ ears. We’re entirely blind.

There is a better way. We’re focusing on three primary dimensions where the status quo is deficient: meaning, transparency, and continuity. Allow me to explain.

Meaning

How would you say what you want to say if you were actually in the room with the other party in a business conversation? How might you inflect your voice to add emphasis or look them in the eye to build trust? How might you dress to reflect your professionalism and instill confidence in you, your company, and your offering? So much has been written about how to look your best in a business meeting and yet so often the advice is irrelevant as we sit from our thrones as armchair dealmakers, sending off one email after another, crossing our fingers that our message is compelling and inspires recipients to respond.

Sales in particular, where relationships are built from the ground up, places high demands of our abilities to communicate clearly and build trust. When the cost of initiating communication is nothing more than the click of a button, you can be sure that whomever is on the receiving end of your email is receiving plenty emails just like yours. Then how are you going to set yourself apart from the competition? Maybe you are the Virginia Woolf of sales emails, but what about the rest of us?

When pitches or proposals come into play, most often in the form of email attachments, we do however have a unique opportunity to layer our brand and personal touch into our messaging. You can think of these enhancements as the digital equivalent of shined shoes or a pressed shirt, although we’re not nearly getting enough mileage out of them.

The tools we rely on every day to send and view business documents — you can think of them as “envelopes” — simply weren’t designed specifically for doing business. PowerPoints are opened by recipients and read in PowerPoint, PDFs are opened by recipients and viewed in a PDF viewer. These programs end their promise at faithfully displaying the content — but what if the viewing experience were oriented specifically for the purpose of people communicating effectively in a business deal? A medium that allowed you to stand out and build trust?

Of course none of this matters if you literally can’t get your point across. Because it’s so easy to send an email, it’s natural that recipients — and the companies where they work — have over time taken protective measures to keep unwanted messages out of the inbox. Spam filters, virus scanners, firewalls, and file size limitations have become the first line of defense, keeping your message from reaching your recipients.

It doesn’t matter how good your proposal looks if no one ever sees it.

Transparency

In a face-to-face conversation, you can pan around the room at any moment to see who is engaged with your message. Suppose you see a particularly important person in the meeting is starting at their phone, disengaged. You can address them directly with a question to bring them back in. Or, you may see someone’s eyes light up when you dive into a certain aspect of your product. Well, now you know what they’re really interested in.

Now think about how this communication happens today. Suppose you have a meeting over the phone with someone and follow up with an email, attaching a document that goes into greater detail. How does the next conversation start? “Hey, so, uh, did you have a chance to read that thing I sent you?” What kind of a way to start a conversation is that? Particularly in sales where you’re trying to build a relationship from scratch, you’re basically asking the other person if they did their homework — the homework for a class they never signed up for.

The way we communicate today is effectively amnesic, and the problem is worst with email attachments. Following modern best practices with email we keep messages short and to the point. For anything we want to dive deeper on we include supplemental materials, most often in the form of an attachment. Yet, we are wholly blind to our recipients’ engagement with that message.

The reality is that when someone opens an attachment you’ve sent them they’re having a conversation with you. It’s just that you’re not there.

And so because we’re not a party to this hidden conversation, we don’t know if our recipients care or not, if they’ve shared what we’ve sent, and least of all what specifically is interesting to them. We also have no idea when they’ve read through it, so we’re left guessing, having to send arbitrary check-in reminders in an attempt to balance responsibly following up and being too persistent. We may as well be sending messages in a bottle.

Continuity

The sheer idea of a “continuous” conversation would sound absurd to someone in a pre-Pony Express era. What do you mean “continuous”? The conversation starts, and then it ends. End of story. Well, not the way we’re communicating today. “Conversations” — and I do use the quotes deliberately because how far they are from face-to-face conversations — happen in fits and starts. A little bit here and there, with each party engaging entirely at will, at whatever hour, with arbitrary delays in between. Ever have a rapid-fire instant message conversation with someone only to have them suddenly drop off the face of the earth, reemerging hours later? It’s incredibly frustrating. But that’s part of the instant messaging social contract. It’s entirely at-will.

At least in all those contexts we at least have the history before us — this message in response to that, and so on. There isn’t any other conversation that’s happening that we’ve missed or have no record of. When email attachments come into the picture, however, everything gets a whole lot messier. Because we have no knowledge of the conversation that happened when we weren’t there — the one between the recipients of our attachments and us — we can do little other than ask our recipients how it went. “Did you have a chance to read that? Do you have any questions? Should I loop anyone else in?”

Much has been written about using “buyer context” to align your dealmaking efforts with where prospects are in the process. Are they just in the research phase, kicking the tires? Or are things looking more serious, and it’s time to talk price? All of these signals lie in the digital body language of people reading the content we send them, yet we’re totally blind to it. If we could could instead pick up right where people left off, conversations could flow much more naturally, fostering a deeper sense of trust that makes for getting deals done.

So, what do we do? As a first step, it’s worth asking ourselves honestly whether we’re comfortable with the trade-offs we’re making when we opt to use one communication medium vs another. Perhaps that email should be a phone call or that phone call a face-to-face meeting. The power of human connection can’t be undervalued.

DocSend today is addressing these communication challenges by building a document sharing platform built specifically for those who make deals as a living — anyone who does business. We’re starting by replacing email attachments in dealmaking conversations with trackable, controllable links that actually push conversations forward. By lending more meaning, transparency, and continuity to our conversations we aspire to bring the intimacy of face-to-face communication to the modern digital way we communicate and forge deeper connections. And deeper connections mean more deals.

It’s time to say, “Goodbye attachments, hello revenue.”

We’re incredibly excited to have the support of our investors August Capital, SoftTech VC, Cowboy Ventures, and Lerer Hippeau Ventures. Looking forward to a great journey ahead.

Want to give DocSend a try? See how we can help you have better conversations with your prospects. Create your free account at docsend.com.

PS: we’re hiring! Connect with us at jobs@docsend.com.