Yesware 2016 Goal? $30m Annual Run Rate with CEO Matthew Bellows

Matthew Bellows The Top Podcast Episode 172

In Episode #172, Nathan speaks with Matthew Bellows, the founder and CEO of Yesware which serves more than 750,000 salespeople. Listen as Nathan and Matthew talk about the field of software sales effectiveness and when to hire a salesperson.

Famous 5

  • Favorite Book?— The Alliance by Reed Hoffman
  • What CEO do you follow?— Reed Hastings
  • What is your favorite online tool?— Not a tool, but Hearthstone
  • Do you get 8 hours of sleep?— No
  • If you could let your 20 year old self know one thing, what would it be?—Business is a lot more fun and creative than you think it is.

Time Stamped Show Notes:

  • 01:00 – Nathan’s introduction to today’s show
  • 02:03 – Matthew joins the show.
  • 03:18 – Matthew just raised a total of 33 million in capital for his company.
  • 03:40 – They needed to go the venture capital route for Yesware in order to hire the engineers they wanted.
  • 03:57 – The company has 80 employees. Of which 30 are developers. About 25 people in the sales department.
  • 06:04 – Yesware has about 750K registered users. They are well above 10 million in annual topline revenue.
  • 07:02 – Yesware’s target customer is a company with 1K-2K employees and 200-300 salespeople.
  • 08:51 – The business’s average deal size is 500$ per month.
  • 10:08 – Hiring a salesperson depends widely on the product being sold.
  • 13:05 – Matthew generally wants customers to install Yesware because they try to provide value as fast and much as possible.
  • 15:27 – Matthew gives some advice on usage data .
  • 16:15 – Yesware is in the field of sales effectiveness or sales consideration. Their competitors are InsideSales or ClearSlide.
  • 17:24 – Matthew would like to end the year with a 30 million dollar run rate.
  • 18:37 – Famous Five

3 Key Points:

  1. To be able to hire engineers to work on the projects they wanted, Yesware had to raise millions in capital instead of being bootstrapped.
  2. Sales effectiveness is a field in which companies offer the service of using software to market more effectively.
  3. Business is sometimes stereotyped as dry and boring. Matthew found that it could be creative and fun in contrary to his belief at 20.

Resources Mentioned:

  • Edgar – Nathan uses Edgar instead of other scheduling tools for Twitter because Edgar cycles through content over and over (buffer/others you have to re-input content over and over – time consuming). In the last several months, Edgar has driven Nathan over 3728 clicks that he didn’t have to work or pay for. Here isNathan’s Edgar Content Calendar:
  • Yesware – Matthew’s business.
  • LinkedIn – Matthew’s LinkedIn
  • Reed Hastings – CEO Matthew follows
  • The Alliance – Matthew’s favorite business book
  • Hearthstone – Game Matthew plays
  • NY Times – Article featuring Matthew Bellows



Matthew Bellows is Founder and CEO of Yesware. Yesware serves more than 750,000 salespeople at companies like Acquia, Adroll, Groupon, Salesforce, Twilio, Yelp and Zendesk.

Prior to Yesware, Matthew was the Vice President of Sales at Vivox. Before that, he served as General Manager at Floodgate (acquired by Zynga), as Founder/CEO of WGR Media (acquired by CNET Networks), and as VP Sales and Marketing of Interstep (acquired by Flycast/CMGI).

Matthew earned his B.A from Naropa University and his M.B.A. magna cum laude from The Olin School for Business at Babson College.


Show Notes provided by Mallard Creatives