Have a Clear Vision of Where You Want to Be

You became a CEO when you were just 32 years old, Rob. You took over the reins at Coupa then, you had ambitious plans to expand the company. But the global financial crisis hit and raising money was really, really hard. What kinds of setbacks did you face? And what would you say you learned from those setbacks?

Well, you know, really, it was all setbacks. I joined a company that was 19 or so people. And a few months later, only six of them were the same. We were running out of money…

And you kept on going?

True. And some of those were no’s, they were just non-responses, which is effectively no, because everyone wants to be very professional, but yeah, a lot of rejections. And ultimately, the investment came from someone who was really investing in me, knowing that the business itself was something, and the opportunity was something I was excited about. And so they gave me a chance to kind of pursue it.

But I’m curious, what kept you going. I mean, after getting dozens of no’s, maybe more than 100 no’s, it’s hard to keep on hearing that, getting the same level of rejection over and over again.

You know something, I spent my career in enterprise software, I worked in ERP, and CRM, and HCM, and this category that I wanted to develop that we call business by management, it was very clear in my mind’s eye what was possible in terms of developing that category. I could see the customer pain points, the customer problems, and I could see they weren’t being addressed. So, in my mind the only difference between someone who would invest or someone who wouldn’t, is just their lack of clarity in what I already saw. So, it was my job to just remove the blockers of visibility for them. And once I was able to do that, you know, raise one round after the other all the way through IPO, yeah.

What was the turning point? How were you able to remove that blocker for that one person and eventually got to a yes?

It’s momentum, right? It’s taking one customer at a time, one interaction at a time, one line of code at a time, having a very clear vision of where you want to be, let’s say, in a decade or beyond and in the space you want to develop, but putting one foot in front of the other and so it’s just that kind of perseverance that I try to put forth on a daily basis until ultimately, things aligned and we were able to break through.