Yesware Raises $4M Series A to Put Sales Tools Where Salespeople Live

Yesware, a Cambridge startup founded in 2010, today announced a new $4 million Series A round, led by IDG Ventures, and including previous investors Google Ventures and Foundry Group. Foundry Group’s Brad Feld also joins the Yesware board as part of the deal. The round puts Yesware’s total funding at $5 million, and will help the company go beyond its Gmail roots to explore additional platforms and provide its email-integrated sales cycle support tool to as many salespeople as possible.

Currently, Yesware operates as a Gmail plugin exclusively, providing salespeople using Google’s email solution the ability to create and share email templates, measure their effectiveness, and track clicks and other activity in outbound communication. Unlike a lot of other sales force support solutions out there, like Salesforce and SAP, Yesware is designed exclusively to be used on the front lines to help sales staff close deals.

“It’s a total turnaround from almost all enterprise technology which is deployed to salespeople now, which is largely around oversight, monitoring, reporting and transparency,” Yesware CEO and founder Matthew Bellows told me. “Instead, our approach is all about how do we help them do their job effectively, how do we help them be more successful, how do we give them tools to communicate with their customers and prospects better.”

Those benefits, along with a freemium sales model, helps Yesware gain traction from the ground-up, Bellows said, because salespeople appreciate the tool and share it around with their coworkers. That leads to wider adoption within enterprises, and eventually some customers, like Yammer, for instance, adopt it company wide as a result of its popularity among their employees.

On the other hand, Bellows also believes companies get access to more useful reporting data than with traditional tools like those listed above, because it’s tied directly to what sales staff are actually doing when they engage with customers. That makes it easier to jump in and suggest alternate courses of action at any stage in the process, not just in a post-mortem analysis after a deal is done.

For Yesware, this round represents the opportunity to expand on its initial vision, targeting new software integration and therefore achieving a wider potential audience (though the startup is off to a good start: it reports that 40,000 users are currently using its platform).

“The tool is available in Chrome or Firefox in Gmail only, but you know, 95 percent of salespeople use Outlook,” Bellows said. “We can’t really reach our potential with Gmail alone, although Gmail has been an awesome product to launch on. In addition to going to other email platform, we have to think about where salespeople work and how we can integrate with those platforms to make them effective.” For Bellows, that means working with mobile and tablet devices, and integrating deeper into telephony technologies and CRM systems.

Yesware has plenty of competition, including tools like Rapportive and Xobni that plug into Gmail and Outlook respectively, and also other startups like Crushpath who are also aiming to arm salespeople with software and features to get things done. But its approach is more focused than some of its competitors on sales staff in particular, Bellows believes, and also makes itself more suited to how salespeople actually work by living in tools they already use.

The key to success for Yesware will be integrating and achieving a natural fit with the myriad other email and communication solutions salespeople use in addition to Gmail, and that’s no insignificant engineering challenge to tackle. This round will definitely help, but we’ll see whether it can grow fast enough to outpace its closest competitors.

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