Episode description

This week the Bowery Capital team hosted Matthew Bellows, Founder and CEO at Yesware, to talk about turning sales failure into sales success. Yesware’s suite of sales tools improves prospecting and tracking abilities, leading to more closed deals with less time spent. In our podcast, Matthew and I discuss identifying failures, crafting solutions to turn them around, and then effectively implementing those solutions. He speaks about the definition of sales success, and how long a startup early in their cycle might need to observe before they can accurately judge their situation. One of the greatest challenges at Yesware was how to tackle sales in a freemium model. More precisely, they struggled with the question of how to convert free users into paying customers. This also raised the issue of how to appropriately evaluate customer acquisition alongside paid conversion. Should every new customer brought in be considered a sales success, or merely those who generate revenue? Matthew takes us through what ended up working for him at Yesware, and how he tested each strategy.