The SaaS Revolution Show is a weekly podcast that brings insights and tactics from leading SaaS entrepreneurs and operators across the world. Hosted by Alex Theuma, the show is brought to you by SaaStock. You can subscribe on iTunes, Stitcher, Overcast.

Few people grow up deciding sales will be their career. Matthew Bellows, CEO of Yesware, is no exception. The latest guest on the Saas Revolution Show, he is something of an accidental salesman. It never was the plan, but as soon as Matthew began working, he figured that was where he could be of best use to a business.

Through the years he got into more managerial roles and eventually became a VP of Sales. After a few years on the job, however, he got fired from it. It was the last straw. For years he had experienced challenges doing his job. It was time he addressed them. Nothing had felt as painful as presenting the quarterly forecast to the board. It had been impossible to gather all the information from the reps to have any certainty in his numbers.

Software could help, Matthew was convinced. In 2011 Yesware was born.

Initially, it started as a freemium tool helping out sales people and for the first year had almost solely product-led growth. It then transformed into a tool that enabled VPs to tap into the workflows of reps to get a better sense for forecasting. For that, the sales team behind Yesware needed to increase. Matthew found himself in a tough situation of aiding that growth, all the while still acting as the company’s CEO, a predicament which became the topic of New York Times article.

Challenges and predicaments such as that have been a constant in Matthew’s and Yesware’s journey. He has never shied away from them, and on the contrary, believes it’s the main thing he gets paid for. Through confronting and figuring them out full on, he has managed to acquire over 60,000 paying customers, has banked $35 million in funding and Yesware currently sees $20 million in ARR.

In this candid interview, Matthew shares many valuable insights. From why appearance to employees is a CEO’s most important role, which requires personal care such as one-hour meditation every day in Matthew’s case, to much more specific topics such as:

  • Why Yesware killed freemium and what was the impact on customers
  • What are the go-to-market strategies that work for them now
  • Why companies should look for internal rather than external metrics for word of mouth
  • Why there never is an endpoint to the SaaS journey and what to do about it as a CEO
  • Why no one really knows what they are doing and that’s okay.

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P.S.

We are bringing SaaStock on Tour. First up is London on March 21st. Spend the day in the company of 300 SaaS founders, their executive teams and local VCs and see Des Traynor Co-founder and CSO of Intercom, Ryan Singer, Head of Strategy at Basecamp, Peter Holten Mulhmann CEO of Trustpilot, Philippe Botteri Partner at Accel and Laurence Bret Stern, CRO at Pipedrive to name a few.