Zero to a couple of billion dollars but NOT back again!


BoS 2014 a discussion on how to seize the opportunity of the second cloud front…
I’m a huge fan of the BoS conference. But when Mark asked me to talk at BOS this year, I had to think carefully. I love software. And his audience is full of great entrepreneurs, founders and CEOs building the next generation of software leaders. This is normally an audience I’m learning from, and supporting as an investor. So we settled on a mix of sharing and mutual learning from a story….

Back in 2003 I’d developed an investment thesis entitled “Everything as a Service”. Based on this I was lucky enough to back a great team to start a company called Demandware. Demandware was the first company to build a best-of-breed SaaS eCommerce platform — offering retailers the ability to focus on their core competence of merchandising, not infrastructure and software. Today the company has a market cap of a couple of billion dollars, and is a rapidly growing, public company.

I love Demandware, and remain a shareholder and board member, but I’d never make that same investment again today.

Why not? What can you learn from it? And what would be a great investment today?

We will discuss this at the Business of Software conference on September 16. Joining me will be Scott Dussault, formerly the CFO of Demandware who helped take the company from it’s early days through IPO, to share some of the key SaaS learnings. But this was in the first Cloud front. The second Cloud front is already upon us and it’s going to be 10x bigger and more impactful. [See 2014 Future of Cloud survey results here]

So how can you design a product to take advantage of this? I’ll share a specially updated overview of the my Harvard i Lab class on “Building Products into Valuable and Sustainable Businesses” including examples such as how the fastest growing software company in America today raced to over a hundred million dollars and is setting new benchmarks we can all learn from. [For those of you interested in the videos, cases etc on this, you can see more at and I have embedded the video below]

But most of all, I look forward to a session of mutual learning, so bring your own questions for a interactive fun inquisition!


One of the questions Mark asked me about is the challenge of transitioning to SaaS. Given it’s a bigger topic than we have time to address in an already full agenda, I volunteered to bring a case study forward and answer questions on it leading up to the event and at the event. Here is the link to the post – entitled “succesfully transitioning to saas”

If you’re a pre-revenue and pre-funding startup, less than two years old, and not a previous attendee there are special discounts courtesy of Twilio and Balsamiq. See here for details.

Hope to see you there!