Our Journey to Series C

Five years ago today, I was the VP of Sales at a venture-backed startup. I hadn’t yet been fired for applying for my CEO’s job. I hadn’t called Cashman to pitch “Software for Salespeople.” I certainly hadn’t made up the word “Yesware” five years ago.

Five years ago I felt pain, and I smelled opportunity. The pain I felt was from salespeople struggling to make their number, close that last deal, make club, and reach their goals. I’d stood before boards of directors defending my team’s quarterly pipeline—riddled with uncertainty and imprecision. The board knew it, and they knew that I knew it, but none of us at the time knew why.

The opportunity that I smelled was to start a virtuous circle.

If, by bringing the power of software to salespeople at every level of an organization, we could genuinely help our customers be more successful, our customers would earn more money. If they earned more money, they’d be able to buy more of our products. Since there are a lot of salespeople in the world, it smelled like the chance to build a real company.

Happily and luckily, when I shared my vision with my former business partner Cashman Andrus, he said, “I can build that” and we embarked on the best adventure of our careers. Just over four years ago, we brought in our first investors, threw away our prototype, recruited a few of the best engineers on the planet, and released our first version of Yesware for Gmail.

Looking back at our first funding round, I’m struck by how unrealistic our revenue projections were. How did I not get laughed out of every room I walked into?

But really the way it worked for us is the way it works for most startup people…

You talk with enough people, and make enough sense or don’t seem too crazy, that some of them smell the same opportunity that you do. After meeting with and pitching 45 angels, super angels, micro and macro VCs, and other associated people, we connected with Rich Miner from Google Ventures, Brad Feld from Foundry Group, and Matt Golden from Golden Venture Partners.

In our A Round we welcomed Pat Kineally from IDG Ventures to the team. In our B Round, we welcomed Neeraj Agrawal from Battery Ventures. And since that delusional business plan, we’ve built the foundations of a great company.

We have served almost 700,000 salespeople across the globe. We offer Yesware for Google Apps, Outlook and iOS. We are deeply integrated into the sales process at some of the fastest growing software companies in the world. We’ve built an incredible team and culture.

But there is so much more to do. I’m so proud of what we’ve done so far, and it’s gratifying to see so many of our initial ideas in the hands of our customers, and we’re only just getting started.

In order to accelerate our growth, I’m honored to announce that we’ve raised an additional $13.3 million.

Foundry Group led the round, with Battery Ventures, Google Ventures, Golden Venture Partners and IDG Ventures participating.

I am incredibly fortunate to have the opportunity to create my dream job. I’m grateful to our customers, our prospects, and the companies that turned us down but told us why. I’m forever grateful to our investors. I’m even grateful to the investors who turned us down but told us, honestly, why.

But mostly, I’m grateful to the smart, strange, wonderful people who work at Yesware. They give everything of themselves to bring our software to you. They push through personal struggles. They stretch themselves. For some of them, it’s all too much, or outside events intervene, but they leave Yesware a better place than when they arrived. The people who work here are, in the words of our first Yesware value, “Brave, Ambitious and Resilient.”

Thank you all for getting us this far. I’m so excited to see what our next stage of growth will bring. If you want to let me know your thoughts, please email me at matthew [at] yesware.com. Thanks. More to come.