Matt Bellows of Yesware: Helping Salespeople Manage Their Emails

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EM: Tell me a little about your background.

MB: I’ve worked with startups for my whole “career” which stretches back to 1994.  I’ve worked in a series of companies including other people’s startups, which were sold and rolled into very big companies during the Internet boom.  My own start up just sold to CNET and Yesware is my current startup.

EM: What was the motivation and story around Yesware?

MB: The problem that we’re trying to address is one that I’ve felt throughout my entire career.  There are two sides of it.  One, is that sales people who are a very valuable and highly productive segment of the professional population, use generic tools to do their job – they use generic emails, generic cell phones, generic spreadsheets – even CRM systems which are the most customized in a sense, to the sales task are really general tools and they really suffer from a garbage in, garbage out problem.  From a product standpoint, we thought, how can we make a tool that sales people already use, better for them?  We started with email and asked: how do we customize email to make it work better for sales people?

The second problem is, how do sales managers figure out what’s actually going on?  Email is a tremendous database of past activity and current activity with each of your account’s prospects – how do you get that information into a form that you can really use as a sales manager?  Yesware as a service and as a whole addresses both of those needs, making sales people more effective to close more deals faster, and helps the managers understand more of what’s actually going on.

EM: Aside from email, are there any other key components or tools of Yesware that help salespeople?

MB: Right now we focus specifically on email.  There are 3 ways that most people do their job – in email, on the phone, or in person meetings.  We’ve decided to start with email for one, and build up from there.

EM: What experiences in your life helped prepare you to be an entrepreneur?

MB: The key experience I think I have was after an MBA and after joining a company and selling it to a bigger company and rolling into this giant company called CMGI, a giant holding company.  As the internet boom started to deflate, we went through round after round of layoffs and I saw all these executives which were high powered, high paid folks, really working hard to save the company.  I realized that while I wasn’t the smartest guy in the room, I also wasn’t the dumbest guy in the room.

Basically, starting a business is not a fundamentally crazy, weird, hard thing to do – it’s actually really easy to start a business.  Starting a business is something a lot of people do.  A huge number of businesses in the US are small 1 to 10 person businesses and they were started by somebody who said, “I want to run my own thing”, and they’ve done it.  It’s not all that special of a thing to do.  It’s like making bread.  Making bread has this mystique about it but if you actually read and follow the recipe, you can do it.  It’s really different than being a huge, successful businessperson, but starting it is actually not that difficult at all.

I remember the time when Jack, the co-founder of Yesware, and I started a business together before, and when we first started we thought, “let’s just try it and see what happens” It was in the middle of the recession. We were both potentially getting laid off and there wasn’t much opportunity cost, so we thought, ‘let’s just try this thing’.

We set target goals such as: In 6 months we need to have paying customers.  Then we went about trying to build it in a way that we thought would make sense, and we did and so we could continue.  In a way it was a demystification of the process and structure of business and in another way it was this wonderful sense of perseverance, like work means something.  You’re creating something out of nothing, which is really rewarding and fun, regardless of how much money you make.  It’s really cool to hear the joy in your customer’s voices when they tell you how much they like your product.   Those are two foundational experiences.

EM: What piece of advice would you offer to entrepreneurs in start up companies?

MB: So many people start their business planning process as – they have an idea, they bed it out internally, decide they want to work on it, they start working on it – and a lot of people that I talk to are at that early stage of, ‘what to do to prove/demonstrate/experiment on in order to raise money?’

I think that’s completely the wrong way to start a business.  The right way to start a business is to ask yourself, ‘what do I need to do to make this into a business?’

Along the way you can figure out if and when you should raise money.  The main focus should be, get the business up and running.  That design constraint of ‘I need to get a business up and running’ is an incredible lens to focus your efforts.  By removing the distraction of ‘if I do x y and z then I’ll raise capital’, focus instead on, ‘I see a need in the marketplace, I want to serve that need, here’s how I can serve that need, here’s the people I can sell it to, what am I going to do to knock those down.’

Consequently, if you execute that approach, you’re in a much stronger place to raise money if you decide to go that route.

EM: What tips would you give for driving growth?

MB:It really depends on where you are and what growth means to you.  If it’s a seed round investment then the first priority is not revenue growth, the first priority is the product.  The reason why you raise the money is so you don’t have to focus on revenue and instead focus on product.


EM: How do you promote and maintain collaboration?

MB: Leaderboards, sales competition, presidents clubs, and all that stuff are basically gamification techniques that management has developed in order to spur productivity.

We don’t do any of that stuff.  The reason why I’m not sure we’ll ever do them is that we’re not trying to beat each other up here.  Everyone’s got their own things they’re working on.  If they do well, they’ll make a lot of money and if they don’t do well they won’t make a lot of money.  We have an overall team goal that’s very obvious.  It’s on a real time dashboard so the entire company sees.  That’s our goal to reach that number by the end of the month.  But it doesn’t have anything to do with what others sell – it’s a reminder of do we get there.

Yes – each individual salesperson gets commission based on how many deals they close in that overall goal.  One of the ways they promote collaboration is that there is no individual goal.  There’s a quota but it’s kind of a made up number.  We don’t split commissions and we don’t have individual leader boards or ranking.  It’s all about one individual team goal.

EM: What are the differences between selling for a corporation and selling for a start up company?

MB: It depends on the company.  There are definitely some huge companies that seem fun to sell for that maintain a start up culture.  I think the biggest thing is that you have a very definite impact when you’re selling for a start up.  Every single deal that you bring in as a start up sales person has a very significant impact on the company.  You can bring in a deal and put it on the desk of the CEO that doubles the value of your company.  That ability to contribute at that level is really quite cool and unique to the start up world. Of course, if you don’t get that deal and the company needs it, it’s feast or famine.

EM: How can small and large businesses use Yesware?

MB: I think sales people in any sized company can benefit from Yesware because it adds a bunch of features to Gmail that helps close more deals.  I would say download it and give it a try and see if it works for you.  It’s free to download – so see if it gives you more business and if not, be sure to write me an email because we want to fix it and make sure it does.   We have entire organizations giving Yesware to all their employees because it’s helping the organization get better at sales as well – it works on both levels.

EM: What should your users be expecting next?

MB: We’re putting a lot of work right now into making Yesware more real-time so you’re getting up to the moment data about what’s happening in the world.  We’re also working on several new features.  We’ve got a great team of engineers that are working on building more enterprise software.