Scaling Up Yesware

Yesterday Yesware announced that Battery Ventures led a $13.5m round that we participated in. A few days ago Xconomy wrote a great article about the very first Yesware board meeting on April Fools Day, 2011. When I reflect on the journey of Yesware over the past 2.5 years it’s a pretty awesome example of a company going from a seed investment with three founders (Matthew Bellows, Cashman Andrus, and Raj Bhargava) to a rapidly growing 40 person company.

On 4/1/11 Yesware had a vision, a crappy prototype (that we threw away immediately after the financing), and a huge obsession around a vexing problem that no one was addressing effectively. Today they have over 300,000 users, a broad product set that includes a recently released deep integration with and between Gmail and Salesforce, and a leadership team and culture that is clear about what it is trying to accomplish and is true to itself.

In March, I wrote a blog post about Shifting My Focus To Scaling Up. When I look at our Foundry Group portfolio of over 60 companies, I see many of them in two distinct scaling up phases. The first are companies like Yesware that are rapidly growing revenue and customers, are in the 30 to 100 employee range, are dealing with balancing resources to accomplish their goals, but have an incredible amount of open ground in front of them. The second are companies like Fitbit that are clear leaders in their market, are on the 100 to 500 person ramp, and pacing the innovation in their market segment. Many of them are companies that aren’t overhyped because they are Silent Killers, a particular type of company we love to fund and work with.

Yesware has now shifted from the startup phase to the scaling up phase. There’s an entirely new level of organizational development, different set of challenges, leveling up of leadership and management skill sets, and massive opening of new opportunities given the resources that the company now has.

I find this a particularly exciting time in the life of a company. And a very challenging one. Fortunately, Matthew continues to surround himself with amazing people, such as his first outside board member, Dave Girouard, who recently ran the entire Google Apps business and is now CEO/founder of Upstart and his newest board member Neeraj Agrawal from Battery Ventures.

Plus, Matthew has a bunch of peers in our portfolio to talk to. We are together with many of them today in another Foundry Group summit – this time for full executive teams across our portfolio right in the middle of Denver Startup Week. Like all of our internal events, our goal is an extremely high signal to noise ratio. We leave the pomp and circumstance to others.

The enormous and powerful conversation around “startups” will continue. But as I turn more of my attention to “scaleups” I believe the next phase is even more powerful.

  • I somehow forgot you had invested in FitBit. My wife and I got it as a wedding present..and have looooooveeed it! Just bought 2 to gift to our parents.

    I only wish it did a bit more than what I find to be it’s primary function – tracking steps. A simple digital display of the time, for example, would be really nice.

    • Glad you like it. Have you used it for sleep – that’s one of the key functions I use it for. We’ve got lots more great stuff coming.

      • Can I understand what you like about it as a sleep tracker, Brad?

        I’ve been using the sleep cycle alarm clock app on my iPhone that I like lots. What features do you like here?

        • 1. Historical data.
          2. Awake / asleep data (which it detects automatically).

  • Very cool product Brad and I really admire their commitment in attacking the problem first & then with the integration just nailed it to what the users really needed to save time in the Sales cycle (Gmail + Salesforce).

    You all have a great advisor there too, Ben, who works with one of our first partner leads at Cazoomi, with some cool advise here which I just had a peek at…good for any Sales folks:


    • Matthew Bellows

      Thanks for the kind words, Clint. In our earliest days of Yesware I was really surprised at how much Brad and Rich Miner encouraged/made us focus focus focus. Going into the VC relationship I expected them to be pushing us to expand with a land grab. Luckily for us, they both understand that, even with everything going for us, we can only go a step or two at a time. Focus.

      • Exactly Matthew and that is why Brad is so smart:) as if you really just focus on your long term strategy, focus on solving your target customers problems the rest seems to fall in place.

        I have learned a lot from sports over the years and land grab strategies in tech land are kind of like Pro Football dreams, in that only about .08% of those coming out of the best high schools trying out make it thru the gauntlet:)

        High school players: 1,108,441

        College players: 67,887

        Draftees: 255



  • Yesware is awesome. Our sales team loves it. Funny that you mention fitbit because a few of us at work have one! I wonder what is the correlation between yesware users and fitbit users? It seems fitbit can target yesware users 🙂