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. Seven years later, Yesware currently has over 60,000 paying customers and $20 million in ARR and to date has raised $38 million in VC funding.
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 customersWhat are the go-to-market strategies that work for them nowWhy companies should look for internal rather than external metrics for word of mouthWhy there never is an endpoint to the SaaS journey and what to do about it as a CEOWhy no one really knows what they are doing and that’s okay.If you like the episode, please leave a review.
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. https://www.saastock.com/ontour/city/london
Check out the other ways SaaStock is helping SaaS founders move their business forward:
🇮🇪 SaaStock Europe: 14-15 October 2025 | Dublin, Ireland
Book you tickets: https://saastock-europe.com/tickets/
🇺🇸 SaaStock USA 2025: April 2026 | Austin, Texas
Join the waitlist: https://saastock-usa.com/
🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/)
🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)