Matthew Bellows headshot
Winner Tag

Location: Boston, MA
Founded: 2010
Industry: Technology


Matthew Bellows
Founder and CEO


Yesware’s sales platform is designed to help members of a sales force, and their managers, exceed goals. “If we are successful, everyone will benefit; the salesperson will make more money, their manager will make more money, their executive will make more money, and the company will be more successful,” says Yesware founder and CEO Matthew Bellows. As customers use the software, Yesware gets access to their sales-activity data. With that data in hand, Bellows says, “we can improve sales forecasting, enable data-driven coaching, and help make sure that prospects are getting the time and attention they deserve.” More than 800,000 salespeople have used Yesware; some 100,000 of those use it daily.

Quick Tip “Employees expect and appreciate directness and honesty, and we can all be more effective as a team by being more open.”

As Yesware grows, it is keeping a close eye on product and feature adoption and retention, with a view to learning how many salespeople are active, daily users. Bellows calls himself a “big proponent of transparency” in fast-growth companies. “That philosophy was put to the test in the middle of my latest 360-degree review. An employee found out about the review, and asked if I would share the results with the company in one of my Ask Me Anything sessions,” he says. “After some tap-dancing, I swallowed hard and shared everything and tried to own it all. The team was really appreciative of the openness, willingness to live our values, and the modeling this showed for the rest of the organization.”