Making Big Bets

It was Bridgescale’s Mentor Monday this week and one of the speakers was David Ossip, formerly the founder and CEO of Workbrain, now founder and CEO of Dayforce.  David is creating Dayforce by making big bets, but as a successful four-time entrepreneur, his bets are calculated.

David believes that it is easier to enter established markets with new or better technology than to invent new markets with new technology. In building Dayforce, he is following a prescribed process of letting the technology define the market segment that he is pursuing and then let the market segment define the Partnership and product strategy. In the case of Dayforce, he is following the long established technology trend of Mainframe to Mini’s, DOS to Windows, Client Server to Internet and now HTML to Rich Internet Applications (RIA). From his Workbrain days, David knows there is a huge market for Workforce Performance solutions. He also knows that the technology he used to develop Workbrain created sophistication and complexity that limited its use to larger enterprises that could afford the expensive service costs to implement and maintain the application.  With Dayforce, David is using RIA capabilities and the now commonly accepted SaaS philosophy to create a robust, sophisticated, but easier to use and easier to implement Workforce Performance solution.  This simpler approach not only makes his solution more compelling for the traditional enterprise market but opens up the SMB market segment. This leads to the next challenge of defining the partnership and product strategy and this is where the big bet comes in.

There are three major players in the RIA market, Adobe’s Flash, Oracle-Sun’s Java and Microsoft’s Silverlight, with the first two being the dominant applications found on most desktop and notebooks today. While not being the dominant player in RIA, Microsoft is certainly the dominant force in mid-market, so David has made his bet on Silverlight and this has defined his product and partnership strategy. Dayforce is built on Microsoft, head to toe, starting with .Net and ending with full integration into Microsoft Dynamics. He has “doubled down” on one architecture and one partner and built his whole company around it.

And if you are not yet convinced about how committed Dayforce is to Microsoft, just compare their logos.

 There is no ambiguity here about Dayforce’s Go-to-Market strategy.

So what does it mean to make big bets?  David has had success in his previous ventures but this time he is clearly swinging for the fence and this has big risks. As an experienced entrepreneur, David can mitigate many of the execution risks. He has proven that he knows how to attract talent and manage to scale, but how do you mitigate external risk.  By limiting everything he does to one technology partner, he has simplified his development, product maintenance, and partner relationship processes and costs. There are no mixed messages to manage. There are no multiple partner relationships to dance around.

Clearly, Microsoft can also put a lot of wood behind the Dayforce arrow. As a strategic partner, Dayforce is giving Microsoft an application that runs on Silverlight therefore aligning his best interests with their need to show traction on their platform. Also, by being built on Microsoft from top to bottom, Dayforce is a poster child for Microsoft. This allows Dayforce to tap into Microsoft’s significant partner programs and funding.

All of the above is good but Microsoft also changes strategies. In the past, they have moved on from technologies that didn’t gain traction so this presents risk. It is uncomfortable as a small company to be sleeping in the same bed as an elephant. If it rolls over, you will get squashed.

You have to admire David and Dayforce. He knows the risk, he is doubling down  and is swinging for the fence.