Matthew Bellows talks with AceUpThis month we had the opportunity to chat with Matthew Bellows, co-founder and current CEO of BodesWell and co-founder and former CEO of Yesware. We talked about how Matthew views and shapes the culture at the companies he runs including:

Read the full interview below (8min read):

Pat, AceUp: Let’s just jump right in with the good stuff. How important are workplace benefits in terms of creating your employer brand?

Matthew Bellows: The employer brand is incredibly important. It goes beyond benefits of course, but there’s a baseline of benefits that everybody provides: health insurance, disability, 401K match, dental, things like that, which is a small part it. Tangible benefits like those definitely factor into peoples’ decision about whether to take the job. But the most important thing, and the benefit that trumps all of them, is, “Who am I going to spend my time with?” That’s the thing that company leaders need to optimize for and continually improve.

If candidates go into their first interview and feel, “Wow, I don’t want to spend a single minute with any of these people,” then almost no matter the salary, the person’s not going to want to take the job. In comparison, we’ve had people tweet out something like “Had my interview at Yesware, didn’t get the job, but I love those people.” And that’s the kind of thing that really builds the employer brand. You build this reputation where Yesware becomes a magnet for great people to apply to because it’s such a great place to work.

"we’ve had people tweet out something like 'Had my interview at Yesware, didn’t get the job, but I love those people.'”

Pat: Is there a difference between perks like kegs, Ping-Pong tables, unlimited snacks and other benefits like coaching? Will there be a pushback where we see companies that don’t have the hoverboards to ride around the office but actually are sensitive about people’s work-life balance?

MB: Fun OfficeYes. Any day of the week people would rather have a more flexible work schedule than hoverboards or kegs. And frankly, the keg stuff cuts both ways because there are plenty of really high-quality professionals out there who don’t want to work in an office where everyone’s drinking every other night and stuff like that. For example, we don’t have a Ping-Pong table at Yesware, and we will never will at any company I work at because Ping Pong is a game with two people playing, making a lot of noise and affecting everybody else around them. I love Ping Pong on vacation or on the weekends. But it’s a terrible game at work.

Pat: How have your teams thought about using the resources that are allocated for everyone at the company so that everyone feels included and supported by the benefits and perks.

MB: Well, I mean, not everybody has to do everything, right? And not every outing or event or benefit has to be fun for everyone. We try to have lots of different things for lots of different groups of people, and people can self-organize. I find it’s best to have it driven by the folks who actually want to do it. As opposed to the top-down benefits administrators saying the company picnic will be on Thursday and we will all have a really good time. You want to make sure that the message that you’re sending to the entire group by supporting one subgroup’s activities is consistent with the message that the company has. So, for example, we would never sanction going to a strip club.

You’re looking at me like I’m crazy, but that is a very common thing to do in enterprise sales. It’s like you go to the conference, and then some small subset of people goes off to the strip club. And we would never allow anyone to expense that outing because although they’ll say it’s for work, it’s exploitation.

We try to do things that everyone can take part in, whether that’s walk-runs, races or scavenger hunts, or lectures, bringing in speakers or doing things like that. We want everyone to be able to think, “Even if I don’t want to do that thing or that thing, there’s something here for me.”

Pat: How do you balance offering amazing resources that are beneficial to team members and not overwhelming them to the point where what you’re providing isn’t additive to the culture anymore?

"Every day when you show up to work, you’ve got to 'make the team'”

MB: You want to strike the balance between, one, letting people feel like they’re taken care of and are able to do good work—the best work of their lives.

And, two, making sure that everybody on the team knows that you’ve got to earn it every day. Every day when you show up to work, you’ve got to “make the team,” in a sense.

meeting with coach

Pat: If benefits are only a small part of employer brand, where does coaching fit in? What led you to decide everyone at Yesware can have a coach?

MB: Coaching is one really interesting and potentially very powerful method to encourage people to actually experience work as a vehicle for personal growth.

Fundamentally I feel that work is more than just a paycheck, and actually work can be a vehicle for personal growth and development. It’s somewhat of a mindshift, but you can look at the time we spend at work more deeply. Sure, we are getting things done and accomplishing tasks and serving customers but if you want, you are also growing and developing as a human being. You’re developing your wisdom, you’re developing your compassion, you’re developing your ability to see through and analytically solve problems. The more your organization can help you grow in those directions, the better the team will function and the more successful the company will be.

I had a coach for the first seven years or so at my time at Yesware. His name is Jerry Colona and his firm is It was like an incredibly powerful, meaningful, helpful experience for me that got me through a lot of tough obstacles. At one point I thought, why am I the only one that gets this? Just because I’m the CEO?

Coaching is expensive, but when you compare that to what you’re paying for each employee to be at your company, it’s a very small percentage of the average salary at any software company in Boston. The theory is if that coaching relationship can help the company get better people in the door for your interview, keep them around longer and help them improve as they reach the goals, then it’s totally worth the money.

Pat: If everyone has access to coaching, how do you ensure it’s being used well and not taken for granted?

MB: We’ve made various tweaks over the years to the program. Two changes I would have made earlier if I could go back: The first is to say you only get access to the coach after a certain period of onboarding and ramping time, which is like the trial period after you get hired to confirm that you’re actually going to make the team, which is three months or so.

speaking to groupThe second is, once you’ve done that, you need to apply. You need to express why you think coaching is important to you as the team member. And you need to communicate that in writing. You probably should have a meeting with your manager and say, “I really want to apply to this program.” And then you get to work with a coach, because then you’re clear that it’s more meaningful.

Having gone through that, you’re already invested, you took the first step and it’s going to be more meaningful to the people who get to that stage. Then I think it kind of makes sense, this is a company benefit for people who want to go through a few steps.

Pat: And so I’d love to ask, what did you find most valuable about coaching? How did you engage with your coach? What were the benefits you got from it personally?

MB: Well, I’ll answer that question for me personally, but I think the broader way to think about that is to ask yourself, think of any famous person, any musician, any athlete, any senator or a congressperson, any CEO at a big company. Did that person just materialize into that role in those skills? No.

"How many coaches does Tiger Woods have? It’s not like Tiger Woods was born as the world’s greatest golfer. No. He worked at it, and he got a lot of help to get there."

How many coaches does Tiger Woods have? It’s not like Tiger Woods was born as the world’s greatest golfer. No. He worked at it, and he got a lot of help to get there. So, those people who say, no, it's a meritocracy, and if you've got it, you got it. They're just wrong.

That's all there is to it. It takes work to get better at your job. That’s the role coaching can play.

The company I ran before Yesware was a bootstrapped company that Cashman and I started. It was a tiny little business. It was profitable and growing quickly, and it was a great company, but it was very small. And you know, Yesware got to be almost 10 times that, with me as the CEO. That journey was hard, there was a lot of change. There was a big step function that I needed help navigating.

I had to develop a new set of skills in order to be able to 10x my skills. I’m talking emotional skills, personal skills, professional skills, communication skills, how to structure a board deck skills, very tactical skills. Without my coach and my coaching relationship, I am 100 percent sure that Yesware would not be where it is today, and I would not be who I am today as a CEO.

Pat: You said it took you five years to find the right coach. Could you talk a little bit about the process for finding the right coach, looking back, is there something that could have expedited that process. 

MB: There’s a wide range of coaching approaches. There’s what I call productivity coaches, who are mainly aimed at how to answer more emails faster, how to organize your day, how to run meetings efficiently—very tactical productivity-oriented coaching. Which can be very helpful for people who are underwater, or not organized or have tons and tons of work to do.

On the other end of the spectrum there’s coaching as personal development. Those folks are almost therapists or psychologists. In the middle is coaching as professional development, which sort of touches on both things. I needed someone in the middle, and so it just took a long time to find it.

"you have to be very honest with yourself about, like, is this actually working?"

There’s no way to know what the fit is going to be. You have to go and talk to the coaches. You have to meet them and see if they resonate with. You might have to do like two or three sessions together, and then you have to be very honest with yourself about, like, is this actually working? Do I feel comfortable with this person? Are they helping me?

It’s okay to say this is not working and to find somebody else and switch it up. It’s way more productive than, “Well, I signed up for this person, therefore I got to dah, dah, dah, dah,” because that's a total waste of time. 

Pat: How important is it for you to view qualitative and quantitative ROI? How do you view successful coaching?

MB: It’s hard to do a real ROI on coaching because there’s no control group, you don’t know what an individual would have been like if they hadn’t gotten coached. You can’t A/B test it like an advertisement.

The easiest way to measure coaching ROI is on retention. If retention is important to you as an employer, then it’s easy to see if people who have coaching through the business that they’re employed by are staying around longer than ones who don't have that coaching relationship.

Which means that all the costs of finding a replacement for that person, and retraining them and making sure they’re a fit, etc., are spread out over a longer period of time.

That said, I don’t think ROI is the most important thing at all about coaching. I think the most important thing is much harder to measure, which is what is the impact on your culture, and your business and your employer brand? And that’s arguably much more valuable than six months longer average retention.

Pat: Lastly, as a leader and founder of companies, what’s the thing that you want most for your people?

MB: I want that when they are retired from their professional career, when they’re sitting on their porch in their rocking chair, looking out over the lake, or the field, or the mountains, or wherever they are, and they’re thinking back on their life, and they ask themselves, “What was the best job I ever had?” I want my company to come to mind. I want them to think back on the time they worked on my team, and they think, “That was the best job I ever had.” That’s what I want.


2018 headshotMatthew Bellows is the co-founder and CEO of BodesWell ( - a personal finance software company that helps you live your best life. Matthew is also the Board Chair at Yesware. He co-founded Yesware and served as CEO for the first eight years of the company. Yesware is the leader in sales productivity, serving over 60,000 salespeople at companies like Box,, Twilio and Yelp.  Prior to Yesware, Matthew served as CEO or executive at several software companies in the videogame and media industries. Matthew became a certified meditation instructor in 2004.