#283 - Joel Stevenson, CEO of Yesware  - on competing in a dense market

A story about the puzzle to solve to find product market fit and create defensible differentiation

This podcast interview focuses on product innovation that has the power to enable Sales Teams to do meaningful email outreach at scale. My guest is Joel Stevenson, CEO of Yesware.

Joel loves building businesses and has 20+ years of experience doing just that. He built a supply chain business from $2MM to $30MM, a B2C eCommerce business from $50MM to $100MM, and a B2B business,  from scratch to several hundred million. He earned a BS from the University of Illinois at Urbana-Champaign and an MBA from Yale School of Management.

In March 2017, he joined Yesware as their SVP of Sales & Marketing. He then transitioned into the COO role – and today, he’s the CEO.

Their mission: To help sales professionals deliver positive buying experiences and build the valuable relationships their customers deserve.

This inspired me, and hence, I invited Joel to my podcast. We explore Joel’s journey with Yesware and the challenges he had to overcome growing it in an extremely dense market with many better-funded competitors. We discussed how he’d carved out his niche and what that meant for product strategy, marketing, and sales. Joel then elaborates on how a rise in prices during COVID-19 had an unexpected positive effect on the overall quality of the business. Lastly, we discuss the effects of the merger with Vendasta. 

Here’s one of his quotes

A lot of our early value as a company was driven because we have a very good Salesforce integration. But the peril with that strategy was that with Salesforce as a system of record, we’re effectively putting all of our data inside of Salesforce. 

And then if somebody decides that they’re unhappy with Yesware, for whatever reason […] it doesn’t end up becoming that difficult to switch. 

And so I wish we would have done earlier what we’re doing now – is completing the story where Yesware becomes more of the system of record. I think that would have massively increased our stickiness. The promise of product-led is easy acquisition. The peril of product-led is retention. And that was the thing that we had to keep working on.

During this interview, you will learn four things:

  1. How you can create meaningful differentiation in an extremely dense market 
  2. The true value of your saas is often about what you offer, but how and where you offer it. It’s all about context.
  3. How one simple (but controversial) change can help attract much better quality customers
  4. The power of reflecting on the potential of the success of your SaaS business – and taking an open mindset (without ego) on how to achieve it.


For more information about the guest from this week:


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