Selling virtually through data-driven conversations

How to gain a competitive edge when selling remotely

Selling virtually using data-driven insights with Dropbox DocSend



The Move to Hybrid Sales

Recently, Quartz reevaluated our tools. The sales team was very vocal in ensuring we kept DocSend. At the end of the day, it is our competitive edge.

Ryan Froats

Director of Partnerships, Quartz

Salespeople are confident, but deals go dark

In many respects, salespeople are poised to thrive in fast-paced virtual environments. Over half (56%) of sales professionals report that selling virtually is beneficial, especially because it offers new ways to connect and stay in touch with prospects and customers. Additionally with travel being uncommon, salespeople reported that selling virtually allowed them to expand their customer base beyond their local region.

Just as salespeople are optimistic about the rise of hybrid work, they are also confident when it comes to closing deals. Our research found that over 75% of salespeople believe a deal will close once they send out a contract for signatures.


But this confidence doesn’t always mean that deals will close as expected. Despite the confidence surrounding the evolution of virtual selling, salespeople still tend to face a high proportion of deals falling through. For many salespeople, deals go dark 25% of the time. Still others report that more than half their potential deals go dark.  

This isn’t a new challenge salespeople face, although there may be new factors at play in a remote world. Deals may be going dark more often because of the unique obstacles that selling virtually presents. Even though they’re confident about hybrid selling, sales professionals identified two main concerns about hybrid selling.

The concerns salespeople have about virtual selling suggest that they don’t have all the insights they need when making deals. Better insights lead to stronger relationships.

With DocSend, these two concerns can be laid to rest. DocSend’s analytics allow you to easily prioritize which deals are worth chasing based on real time page-by-page analytics of a pitch or proposal. You know who’s genuinely interested and strategically follow up based on where within your documents they spent the most time. This proactive approach leads to better conversations that build stronger relationships with prospects.

In a virtual environment, salespeople need to eliminate as many blind spots as possible.

Ask yourself – do you know what questions a prospect may ask before they reach out? Can you see when new decision-makers enter your deal?

It’s great knowing whether a prospect opened a document and how long they spent on our pricing page. Having this level of visibility and predictability in the sales process is unmatched.

Mark Parkinson

Vice President of Sales Enablement, CMOE

Using document analytics to build relationships

Our research found that deals sent for signature often look similar, regardless of whether the prospect signs or goes dark. Contracts that get signed and those that don’t average similar numbers of total views by about the same number of unique individuals.

The key here is knowing who those unique viewers are. Many times your contact may claim to be the decision maker but when it comes down to it, their boss (or someone even more senior) is looped in. Knowing if new stakeholders are introduced into your deal – when pitching or when out for signature – is critical to your probability for success.  

The moment I realized DocSend was mission-critical was when we sent out a 7-figure sales proposal. DocSend coached us to put 3 pricing options on 3 pages and utilize analytics like time spent per page to our advantage. Because of this insight, DocSend helped us negotiate much more effectively.

Matt Hammond

VP of Sales & Marketing, Campus

Getting deals over the line with eSignature

The move to virtual selling means the pace of deal-making has changed. Our research found that when deals close, they close quickly: eSignature data from DocSend’s platform shows that sales contracts get signed about a day (28 hours) after they’re sent out for signature. We found that prospects only spend about a minute looking over the contract, whether or not they ultimately signed.


While the difference in time spent on a contract’s signature page isn’t too noteworthy, what this tells us is that the decision to do your deal (or not) has been made long before you send out for signature. 

This is where the trust and relationship building that DocSend facilitates through document analytics becomes key. With all this insight at your fingertips leading up to a signature, you should be significantly more confident that it will close. 

With the ability to pitch, negotiate, and close a deal all in DocSend, prospects are at ease through the signature process. After all, a signature is your last hurdle and avoiding any added friction is critical.

I had previously looked into DocuSign, but it was too clunky. With DocSend’s eSignature, clients can easily review proposals and execute agreements in one product experience, without switching between bulky software.

Jon Cattivera

CEO and Creative Director, Sleepless Media

Our research methodology

DocSend’s sales research combines qualitative and quantitative approaches. We surveyed over 300 sales professionals in order to understand how their sales cycles had gone hybrid. We also examined our own product data, studying how nearly 2,000 sales contracts were sent, viewed, and signed or not. This data is B2B focused but was aggregated across different types of deals and sales cycle lengths.