Yesware now lets salespeople track whether their attachments are getting opened

Fresh off a South by Southwest talk about sales and startups, Yesware chief executive Matthew Bellows shared his company’s latest progress — a tool for making email attachments trackable.

This may sound silly to the average person, but Bellows, a veteran sales executive, sees it as a key step in Yesware’s product roadmap.

The company recently acquired Attachments.me, a San Francisco-based startup that was mainly working on improving file-sharing, sending large attachments, and tracking which files actually get opened by the recipients. In essence, Yesware is repurposing Attachments.me into its own product as the attachment-tracking feature it is launching today.

As Bellows explained, Yesware always has in mind its two primary purposes: to help salespeople close more deals, and to aggregate valuable data from which salespeople can analyze their work. This new feature has these goals in mind.

“Every bit of information or feedback that a salesperson can get about how someone is engaging with their email is helpful,” said Bellows.

“The most important business documents are sent via email as attachments,” he added.

For example, if a salesperson sent out a business proposal to a prospect, whether the prospect opens and views it in five minutes or not at all makes a world of difference regarding the effectiveness of the document and the likelihood of furthering the deal.

This again goes back to the well-focused path Bellows has in mind for Yesware, and how each piece is one step further along that path. Attachment opening is the fourth metric, or dimension as Bellows calls it, in addition to the already-existing metrics: email openings, link clicks, and reply tracking.

To date, Yesware has raised $19.7 million spread over three rounds, the last of which closed in November 2013. Its impressive collection of investors includes Google Ventures, Battery Ventures, and Foundry Group, amongst others.

Interestingly, Bellows pointed out that Yesware’s board of directors now includes Battery Ventures’ Neeraj Agrawal, who is also on the board of marketing automation software provider Marketo. It became clear that “what happened to marketing will happen to sales,” Bellows said, prompting interest from Agrawal and Battery Ventures.

As for his plans for the recent funding infusion, Bellows shared that the company will invest into two areas: growing Yesware’s customer base through sales and marketing, and breaking new ground into Microsoft’s Outlook and mobile.

Although only time will tell how valuable Yesware’s new tracking feature proves to be, the sales innovation market overall is estimated to grow to $30 billion by 2017. Yesware is still a small company by its own admission. But Bellows has already gained the faith of customers such as Groupon.

And I’ll probably open whatever attachments he sends me from now on — because he’ll know if I don’t.