How Yesware Rethought Amazing.


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Yesware presents an interesting case study about the business pursuit of getting it right.

About starting.


About finding success.

It seems like it has been several years since I had my first conversation with Matthew Bellows. It’s actually been a little over a year. We talked about a brand-new product called Yesware that he was prototyping with his partner Cashman Andrus.

As I began to look at the screenshots that he had put together for me, I began to get really excited by what I saw. Matthew and his bootstrapped team planned to design a web e-mail client built specifically for sales people. Matthew had a deep background in sales (and talked with a lot of sales people) and understood how differently sales people view e-mail interactions. He saw the struggle that sales people went through on a daily basis to get answers to their e-mails.

So he decided to build a platform that would tell you when e-mails weren’t being answered and more about the company that was replying to your messages. That was just for starters. More features like company stock prices and executive research presented a powerful set of social tools for sales people as they were doing what they do most of the time — sending sales e-mails.

But that product never came to market.

Matthew and I had quite a few conversations over the time that he was building this technology. Frankly, I think he was probably becoming a little annoyed at my e-mails asking how far away he was from building a product that I could begin to use. And then one day he called me to talk business strategy. On the call I learned that the sales tool Matthew was building would never come to be.

Instead Matthew and his team were working on a different product — a plug-in for Gmail that would allow salespeople to save and send e-mail templates.

I have to admit that I was disappointed. It was hard for me not to be devastated by what I heard from Matthew. I had set my hopes on getting this amazing new sales platform; and a tool to store and save sales templates just seemed like too small of a vision. After all, if I wanted a series of templates I could just use TextExpander to send the same message over and over again.

Admirably for them, my disappointment didn’t distract them from their core vision. And over the last six months, the Yesware team has delivered a series of sales tools that are nothing short of amazing.

I was wrong. Here’s what I didn’t know.

All along, Matthew was making the right decision. Behind-the-scenes he was listening to some wise counsel from investors like Brad Feld and his business partner Cashman. Despite his wild enthusiasm for building a brand-new e-mail client just for sales people, Matthew realized that even if he were able to build the product he envisioned that it would probably present additional challenges to sales people.

  • It would require them to use an additional web portal to check e-mail and send messages — more time and another web destination.
  • It would need to be fast in order to compete with online e-mail platforms like Gmail and Yahoo — more competition and higher operating costs.
  • It would come between conventional CRM platforms like sales force and desktop tools like Outlook — more frustration for enterprise customers.

It just didn’t feel like the right user experience to Matthew .

So he decided to do the crazy (but right) thing. And stop.

Matthew took a step back and paused to reflect. He and his partners consciously took time to think and strategize about what they could build that would have the most impact. What could they do that would enhance the lives of millions of sales people who earn their living through their inbox?

And then they started over. Months later Yesware is completely different.

The new Yesware is freakishly impressive.

And is certain to be more helpful for sales people than the original application they were designing a year ago.

Now, it’s more than just a simple plugin to serve up email templates. The plug-in for Gmail allows users to forward their correspondence directly into their CRM of choice. As well, the plug-in will automatically track your e-mails and tell you who is reading your correspondence and from where. New team functionality allows groups to share e-mail templates and managers to see reports of e-mail messages that seem to work better than others. Most recently, Matthew and his team unveiled the option to create goals for team members, further enabling high performers to close more deals each year.

The story of Yesware is still being written. While the technology is novel and their mobile apps look impressive, the story behind their success starts with stopping.

It’s a lesson we all could stand to remember.

If you want to be successful in business, putting your head down and getting things done is a good idea. But it’s wildly important to stop and think about how best to use your talents and resources. Put together a plan. Don’t be afraid to rework your plan. Be brutally honest about your future.

Is what you are doing now going to deliver you the wildly success you dream about?

Chances are, if you take a step back you’ll be in a better position to run forward.


DISCLAIMER: For more information about Yesware, you should navigate to If you find their technology helpful, use it. I don’t make a penny either way. For the record, I was not paid, bribed or otherwise seduced into writing about these dudes. I just admire awesome people doing amazing things. They fit that mold.

Republished with author's permission from original post.

Dan Waldschmidt
Speaker, author, strategist, Dan Waldschmidt is a conversation changer. Dan and his team help people arrive at business-changing breakthrough ideas by moving past outdated conventional wisdom, social peer pressure, and the selfish behaviors that stop them from being high performers. The Wall Street Journal calls his blog, Edge of Explosion, one of the Top 7 blogs sales blogs anywhere on the internet and hundreds of his articles on unconventional sales tactics have been published.


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