Yesware Teaches Us How Valuing Employees Boosts Sales

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bridget gleason yesware

Everyone at Sales4Startups loves Yesware for tracking their emails and creating handy email templates integrated with Gmail and SalesForce. Last fall Yesware raised more than $13 million in series B to scale up their operations.

In my interview with Yesware’s new VP of Sales, Bridget Gleason, I learned how Yesware’s excellence in creating a powerful sales product and selling that B2B product have are built around a deep value for people. As I recall by my interview with Guy Kawasaki, who asserted “empathy” was one of the most important qualities of a great salesperson, Yesware reminds me the importance of valuing your own human capital for achieving sales success.

Interview by Heather R Morgan, copywriter & sales/marketing consultant for startups at SalesFolk and Co-Editor at Sales4StartUps.


Heather: How does management at Yesware empower its sales team?

Bridget: We firmly believe in the notion of “Bring the ‘whole person’ to work” because we value our employees development beyond the office. We want our employees to view Yesware as an environment where they can thrive and grow professionally and personally, not a place where they are eager to leave the office with a “TGIF mentality.” Our motto is embracing “success beyond success,” which comes from a deep sense of awareness. For more on the importance of awareness, read Conscious Business; it’s a great book for entrepreneurs and members of startups.

We also have ongoing weekly trainings and work together on time management with regards to how to focus and prioritize. Because scale requires consistency, each sales team member works to create their own good processes.

Heather: How has Yesware grown and changed in the last 3 years?

Bridget: Well, I actually joined Yesware 4 months ago, but I can tell you what I know. We started in a little apartment in Kendall Square in Cambridge, and now we’re in our own office about to take over an entire floor. It’s a really exciting time for us, and there’s a lot of energy. I think the biggest challenge and change has just been growing so much so fast.

Heather: What do you think the core of Yesware’s success has been?

Bridget: It’s definitely the way Matthew (Yesware’s CEO) and management views the Yesware employees. When I came here, Matt told me that he “wanted to build the best product for sales while also building the best company anyone had ever worked at.” It’s a very rich and collaborative environment to work in, and they have been deliberate in creating that.

We go out of the way to make sure we continue to have honest and difficult conversations even as we continue to grow. There’s even an open conversations course held in the office that employees are encouraged to attend.

Heather: How does Yesware “dogfood” it’s product?

Bridget: We actually have an alias for our sales team called “the fat dogs” because we are the biggest users of our own product. We’ve made many tools for the sales team, and so sales works closely with the product. That’s led us to create a number of cool new features that we’re working on including mail merges features.

Heather: What is Yesware focusing on moving forward?

Bridget: Although we do struggle with focus like everyone else, seeking balance between prioritizing core tasks and adding cool new features, we focus on four core areas that help us decide what to pursue or save for later.

They are:

1. Operational excellence–do whatever we do very well.

2. What do existing customers need?–It’s important that we stick with our existing customers and prioritize the feedback from our larger customers.

3. Revenue Number–how much revenue a new feature would bring in.

4. Innovativeness–We want things that are revolutionary.

Heather: What do you look for when hiring employees for sales at Yesware?

Bridget: This may change, but I hope it doesn’t too much. We look for sales people who are dynamic, self-directed and driven; the kinds of people who can handle everyone going at 100 MPH and ambiguous situations. The type of people who can put some sort of order in chaos. It’s also important that they are smart and savvy, as well as coachable–open to learning and change. I also always look for sales people with integrity, personal self-awareness, and a track record with success.


If you or your company would like to be featured in a Sales4Startups interview, please contact Heather (at) You can also get in touch with Heather if your business is looking for help with your copywriting and content marketing.