Solving Yesware’s dilemma…

We understand Matthew Bellows to be a dedicated leader for the company he founded that is Yesware – a firm that devises and markets software to make life easier for a company’s sales and customer relations division.

This software particularly eliminates data entry by sales reps and helps in analyzing significant customer data.


Matthew Bellows, Yesware CEO

Problem is, things has not taken off. The software. The lingering 100,000 sales leads. And of course, the sales team – at least 6 or 7 out of the 10 sales executives of Yesware has faltered. Worse, this team not only missed its quota by miles but was also caught dilly-dallying at the conference room – drinking beer and playing loud music.

With this, Bellows came up with 3 possible solutions, so let’s see them first..

Clean up. That is to fire all underperforming sales people. Personally take charge of the sales department. And hire a CEO to take his place. Hire a VP for Sales. He’ll be doing all the firing, hiring and training. Bellows remains in his post. Promote the best sales executive. Let him handle the sales team.

And so, also other business leaders came up with their own inputs..

Like, Suzanne Paling of Sales Management Services and Zeke Adkins of Luggage Forward were both in favor of Bellows hiring a Vice President for Sales; while Andrew Brooks of SmartThings wants Bellows to get dirty by being a hands-on executive.

Nonetheless, the author sees it from a different perspective. If the sales team could just dilly-dally just like that this means they are either not motivated or scared meaning incompetent. I would not hire a VP for Sales just to strain my current people. Instead, I’ll do the firing. Everyone who participated in that conference room hullabaloo is out. If it includes your top performer then you might as well give him a serious talk but never consider him for any position of responsibility while on probation.

Once you’ve removed the undeserving reps then you could hire a VP for Sales to build your sales team. Basis should not simply be on experience but on motivational factors among others.

Sometimes, you might even want to analyze how your product or service affects your very own people, or the key people of your potential customers’ department as it might be affecting their sense of security thereby demotivating them.

What’s your take?