Yesware’s E-mail Plug-In Works “Down In The Trenches” With Salespeople to Close Deals and Kill Data Entry

Cambridge, MA-based Yesware kicked off late last year with the aim of building an entirely new e-mail system, one that would help salespeople close their deals and help enterprises actually understand their sales forces, says CEO and founder Matthew Bellows. It even raised $1 million on this premise. Then the company’s board spoke up. You see some of its investors knew the whole e-mail space pretty well, and told Yesware not to reinvent the wheel.

So Yesware scratched its plans for an e-mail reboot, and drew up new ones for a sales interface that would work with existing e-mail systems. Late last month the startup, which works out of Dogpatch Labs, opened up its beta version of an e-mail plug-in that offers customizable templates for salespeople. The objectives are still the same. At the individual user level, “we are down in the trenches with the salesperson trying to help them close that business,” says Bellows. And at the organizational level, “it extracts data that their enterprise needs from their activity, to learn from what they do and report on that.”

There are plenty of companies whose business is to generate and qualify sales leads (think Eloqua and HubSpot), and others aimed at managing sales account information (Salesforce), but few that provide tools for actually making the sale, Bellows says.

Yesware’s plug-in offers pre-set e-mail forms to help salespeople first connect with customers, and also to help them once they start getting objections from the customers they’re chasing. Say a salesperson keeps hearing from potential customers that the product costs too much, or that it can’t stack up to an existing offering from a big-name competitor. He or she can pull the appropriately template from Yesware addressing that concern.

“It’s a templates-on-steroids kind of thing,” Bellows says. “We help the salesperson with the right answers at their fingertips.”

The Yesware plug-in also has a button for automatically copying e-mails to a salesperson’s account on the customer relationship management system Salesforce. “It’s a very low cost way of having salesperson update Salesforce,” Bellows says.

Those updates are key to Yesware’s bigger mission of helping sales managers better track the work of their sales force—by actually looking at their communications with customers, rather than relying on the relatively cryptic notes salespeople often type into CRM systems, Bellows says.

“What a salesperson does from an action standpoint is going to be much more helpful than what they say that do,” says Bellows, who saw the frequent disconnect between the two firsthand while managing sales at companies like Vivox, Floodgate Entertainment, and WGR Media, the gaming media startup he sold to CNET in 2004. What’s more, “if we can save every single person and sales force manager a half hour to an hour a day throughout all our customers, that’s going to be a huge productivity gain,” he says.

Ultimately he hopes Yesware can track how potential leads respond to Yesware users via e-mail, and use that information to automatically populate the different fields in a customer account on Salesforce—much the same way Intuit’s scans financial transactions and automatically categorizes them. He says this will help sales teams better forecast sales and determine quotas.

For now, salespeople’s use of Yesware templates can help their managers see how well they’re doing their job. “As the salesperson is using the tool, they’re also leaving behind a trail of data,” says Bellows. That data could, for example, help a manager pinpoint where a certain salesperson is succeeding and utilize him or her in training others on selling a particular angle of the product. Bellows also hopes that ultimately a company can use Yesware to generate friendly competition among salespeople, to share the most successful e-mail templates among its staff via an interface like the iTunes store.

The plug-in, which so far works with Gmail only is now available for Google Chrome; Yesware is working on a Firefox version next. The company is also working on building out its interface for Outlook. Since launching its beta product about two weeks ago, Yesware has attracted a couple hundred users and is working with about four to five companies. For now the plug-in is free, but Yesware ultimately aims to charge on a monthly fee per user per company.

Yesware, which has seven employees, closed about $1 million in funding this spring, from venture firms very familiar with e-mail and Web app spaces, as well as Boston-area angels. Bellows declined to publicly name the investors at this time.

There are, of course, some big name sales software companies that could potentially benefit from scooping up Yesware and its technology should the system work out as intended, but Bellows isn’t looking to sell the company if and when it starts getting some buzz.

“We see this as a big company; I don’t want to flip this thing to some California company,” he says.

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