[Podcast] Scaling Sales with Matt Bellows of Yesware


Matt Bellows isn’t afraid to admit that he messed up.

Bellows is the Founder and CEO of Yesware, a SaaS company that provides more than 700,000 salespeople with email analytics, Salesforce and Google sync, and smart templates. The company has raised a total of $35 million and has customers like Acquia, Adroll, Groupon, Salesforce, Twilio, Yelp and Zendesk.

But it wasn’t an easy path to success. In fact, Bellows said that at one point, he had to publicly acknowledge the company’s early sales team was a complete failure.

“You would think that a former VP of Sales building software for salespeople would have an easy time building a sales organization,” he said. “Actually, it was so unsuccessful that the New York Times did a two-part case study on how badly it went. I was trying to do two jobs at once — trying to be a CEO of a fast-growing company, and also build a 10-person sales team quickly. Frankly I didn’t do a good job of doing both.”

In the latest episode of Ramp, Bellows shares how he went from sales failure, to sales success.

Listen now:

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Part of Bellow’s success is due to his ability to quickly adjust and pivot the company as it grew and the market changed. He explained that Yesware is incredibly data-focused, in terms of user acquisition and sales pipeline.

“There is so much data, and it can be so powerful when you get it right,” he noted.

In this exclusive 22 minute interview, Bellows explains:

  • How to sell to salespeople
  • Why sales should stop wasting time selling to unqualified customers
  • How to deal with tough competition
  • …and much more.

Learn why failure can sometimes be the best possible outcome in the newest episode of Ramp, the InsightSquared podcast.