BTSM Interview: Matthew Bellows – CEO, Yesware

Our goal at Building the Sales Machine is to enable sales leaders in the tech community to learn from each other. We’re all in this boat together trying to help revolutionary companies disrupt the norm, to make people’s lives easier, better, & more fulfilling. We’ve been bringing some of these leaders and strategies to life through our articles, meet-ups, speaking events and interviews.

Matthew Bellows is CEO of Yesware, a software helping sales people to prospect + email smarter. It’s a tool in some of the hottest companies sales stacks. Matthew and his team spend their days doing the impossible: selling to sales people. And his software listens to millions of messages / month sent through the service to help understand trends in the marketplace. If you haven’t read their advice post, Say this, not that, do it now.

Matthew’s thoughts below:

What does your first hour in the office look like?

There’s a lot that can happen in the first hour of my day—sometimes I have to jump into a meeting, sometimes I use it to check email. But one thing I always make time for in that first hour is mindful meditation, even if it’s just for 5 or 10 minutes. It’s a priority for me both personally and professionally—and while finding time can be difficult, it makes all the difference. I look forward to that time to clear my mind. More importantly, I find it gives me a peace that permeates the rest of my day, and I’m able to approach challenges with patience and perspective.

What is one thing sales reps, in general, should be doing more of?

As the sales profession is changing, reps need to focus on how to differentiate themselves in the space. There’s a lot of discushero-yeswaresion right now about the erosion of the sales role, but in my opinion it’s an evolution. Just like every other industry, technology is revolutionizing sales. And one of the most important new resources available? Data. Like never before, sales reps have the ability to understand their outreach—they’re able to see things like what’s resonating with prospects or what the best time of day to reach out is. Automation is another major component of this new sales technology, allowing reps to collect data automatically as well as initiate entire campaigns all at once. That means sales reps today can spend more time actually selling. Sales reps must arm themselves with the right repertoire of digital tools; that’s how they’ll succeed.

Best tip for sales teams that are scaling?

Be transparent. When a company is small and on a growth mission, people are working together closely to achieve that common goal. But as the company grows, things internally are shifting constantly. There are many positive things that come with this: for example, a bigger team means your company can begin to tackle bigger challenges. However, it can also create unease when the entire team isn’t involved in every project or decision. The best way to keep everyone on the same page and quell any unfounded concerns is to make sure you communication channels are scaling with your organization. Having clear and open communication keeps employees feeling informed and involved, and in turn helps everyone stay motivated towards achieving that goal and keeps the energy positive, rather than fearful.

“…set the precedent that everyone has a voice. That’s where the best ideas come from, and that’s when innovation really happens”

If you were going to start a new team today what are the first 3 things you would do to get on the right track?

  1. I would set the precedent that everyone has a voice. That’s where the best ideas come from, and that’s when innovation really happens—when no one is afraid to say the crazy idea.

  2. That said, I would establish clear roles. While transparency is essential, that same level of clarity can be helpful in understanding ownership of tasks and responsibility. Especially with new teams when confusion can derail a take-off.

  3. If I were starting a new team today, I’d definitely want to make sure that we had the latest technology to make the take off smooth. Technology isn’t a fad—it’s a core business function. Without the right tech, a team will fail in today’s competitive environment. That’s a fact.

What is the thing you are happiest with on your current team?

At Yesware, I am proud of the culture of openness and honesty we have built. These two values are priority in every aspect of Yesware—from the day-to-day to the big-picture. This has served us well strategically, but also in terms of breeding a culture of mutual respect. Giving open and honest feedback is a priority for managers and their teams. I like to host “Ask Me Anything” meetings each month to communicate with the team and give everyone an opportunity to ask questions. Outside of these scheduled meetings, I make sure everyone on Yesware team knows they can come and talk to me at any time about anything on their minds. Keeping that level of transparency enhances the team synergy and motivates trust, something that cannot be undermined in a startup setting.




thumb_mbellows_headshot_newMatthew Bellows is founder and CEO of Boston-based Yesware, an all-in-one sales technology toolkit. Yesware  serves more than 500,000 salespeople at companies like Acquia, Adroll, Groupon, Salesforce, Twilio, Yelp and  Zendesk. Prior to Yesware, Matthew was the Vice President of Sales at Vivox, General Manager at Floodgate  (acquired by Zynga), Founder/CEO of WGR Media (acquired by CNET Networks), and as VP Sales and  Marketing of Interstep (acquired by Flycast/CMGI). More thoughts can be found at Yesware’s sales blog or  follow him, @mbellows, on Twitter.




See more interviews like Matthew’s here:

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Matthew Curl – Head of Sales, Fivestars



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