strategic management
A Leader Struggles to Sell Software Meant to Aid Sales
Yesware’s Matthew Bellows on His Ironic Challenge
By JOHN GROSSMANNAUG. 20, 2014
Matthew Bellows, chief executive of Yesware, on the roof of his Boston-based software company. His sales team foundered when trying to convert the product’s free users into paying customers.
YESWARE is a four-year-old company that designs and sells software intended to make it easier for sales teams to record and analyze essential data. Released in late 2012, Yesware’s basic version, which can be downloaded free, quickly attracted more than 100,000 users.
By early 2013, even with a newly hired 10-person sales team, Yesware’s sales were abysmal and the company had yet to turn a profit, casting a pall over pending efforts to raise venture capital. Because he was struggling to sell a product built to make sales easier, Matthew Bellows, a co-founder, felt like the shoemaker whose own children pad about barefoot.
THE BACKGROUND Mr. Bellows and a software engineer, Cashman Andrus, founded Yesware in 2010 to improve upon existing customer relations software and address problems that Mr. Bellows had experienced throughout his 15-year career managing sales teams.
“As a sales manager,” Mr. Bellows said, “I want to know all the deals my sales team is working on — make sure they’re actually following up on each one, help them if I can with encouragement, tips, introductions or other ideas for how to reach the decision makers in these companies. I want to be involved in the process.”
But this kind of oversight requires sales people to type updates into customer relations systems, rather like police detectives pecking away on case reports back at their desks. Sales agents hate doing it, and sales managers hate hectoring them. “Frankly, they don’t do a good job of it,” Mr. Bellows said. “They’re not paid to do data entry; they’re paid to close deals.”
The idea behind Yesware, which is based in Boston and employs 48, was to
Yesware’s Matthew Bellows on His Ironic Challenge
By JOHN GROSSMANNAUG. 20, 2014
Matthew Bellows, chief executive of Yesware, on the roof of his Boston-based software company. His sales team foundered when trying to convert the product’s free users into paying customers.
YESWARE is a four-year-old company that designs and sells software intended to make it easier for sales teams to record and analyze essential data. Released in late 2012, Yesware’s basic version, which can be downloaded free, quickly attracted more than 100,000 users.
By early 2013, even with a newly hired 10-person sales team, Yesware’s sales were abysmal and the company had yet to turn a profit, casting a pall over pending efforts to raise venture capital. Because he was struggling to sell a product built to make sales easier, Matthew Bellows, a co-founder, felt like the shoemaker whose own children pad about barefoot.
THE BACKGROUND Mr. Bellows and a software engineer, Cashman Andrus, founded Yesware in 2010 to improve upon existing customer relations software and address problems that Mr. Bellows had experienced throughout his 15-year career managing sales teams.
“As a sales manager,” Mr. Bellows said, “I want to know all the deals my sales team is working on — make sure they’re actually following up on each one, help them if I can with encouragement, tips, introductions or other ideas for how to reach the decision makers in these companies. I want to be involved in the process.”
But this kind of oversight requires sales people to type updates into customer relations systems, rather like police detectives pecking away on case reports back at their desks. Sales agents hate doing it, and sales managers hate hectoring them. “Frankly, they don’t do a good job of it,” Mr. Bellows said. “They’re not paid to do data entry; they’re paid to close deals.”
The idea behind Yesware, which is based in Boston and employs 48, was to