Ever, Ever Get to $100m in ARR? Finally, it’s repeatable, and repeating. But-- will we ever get to $100m in ARR before I need a walker? Before the team quits and goes off to Uber / Slack / Stripe / Wherever for 500 RSUs? How long does this damn SaaS thing take, anyway? 7-10 Years? Oy. But -- it gets easier at $10m ARR. Then, you have fat, more help. Get there as fast as you can without totally burning out and hire a few great VPs along the way, it does get easier. 5. How hard is it to become the CEO of a Fortune 500 company? Here are my learnings as a VP in a Fortune 500 company: It’s very hard of course but the path itself is slightly easier than you might think -- and there is a strategy to get there. Let’s start with the math: • Each company is different, but when I was a F500 VP, there were basically 40-50 VPs and a handful of SVPs (who were each previously VPs). Your title inflation may vary so map to the titles in your company. • Of the 40-50 VPs at any given time ... maybe 10 would even want in theory to be CEO. The rest have no interest, lack the cross-functional skills or aren’t VPs in important enough or P&L- focused areas. • Of the 10 who would be interested maybe only 4-5 have the true position, positioning, and skills to pull it off. The rest might have the IQ but not the visibility. They don’t have the relationship with the current CEO or more importantly didn’t quite hit the number for their division/product/BU. Etc. Maybe at any given time, if you assume promotion comes from within -- really there are only maybe 4-5 potential internal candidates in the VP base who could grow into SVPs that could then ascend to CEO. • Those 4-5 VPs are the candidates for the openings that come up in the top 3-4 SVP positions. Find a way to get to SVP in a SAASTR.COM 5