Musings of a Gambler
In Part 1, I argued that hiring a CTO starts with clarity about the problem you are solving. This piece assumes you have already crossed that threshold and are now evaluating candidates. A common mistake at this stage is treating attributes as personality traits rather than systems. Strong CTOs are not great because of who […]
Companies usually start to look for a VP/CTO at Series A/B, and it is one of the highest-leverage decisions you’ll make. It’s also one of the easiest to get wrong. That’s not because strong candidates are rare. It’s because most companies don’t define what problem they’re trying to solve with this hire. And then everyone […]
I’m Shail. I’m an engineer at heart, even though I’ve spent the last few years mostly doing management things. Right now, I’m a lead at Netic AI. Before that, I was a Senior Staff Engineer and Director of Engineering at Rippling, where I helped launch Global Payroll across ~10 countries and built a team of about 60 […]