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How my role as CTO has changed as we've grown from 1 to 100 engineers

engineering.gusto.com

141–142 of 142 posts

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#141
post #4

I use Gusto and like it for it's simplicity. It makes a complicated part of running a company much smoother. That said, I'm very curious what exactly all those engineers are doing every day. What's the most meaty part? Payroll? Dealing with govt? Keeping the servers up? I think unexpected scaling pains are one of the most interesting and unsolved issues with being a CTO and would love to hear more about that at Gusto…

I used to be a PM at Gusto so I can add to Eddie's answer. As Eddie mentioned, it's non-trivial to keep the existing applications running as well as they do. That being said, a non-trivial amount of time/resources is spent making an already amazing product that much better. For example, my friends just launched a new product that lets you pick your payday (https://techcrunch.com/2018/06/21/gusto-flexible-pay/). To get this to work, there's a lot of data science involved to make sure you're not exposing Gusto to financial risk (it's effectively lending money). Since taxes are withheld with every paycheck, the payment flows associated with flexible pay become incredibly challenging. They're an amazing team. Go Eddie!

Re: How my role as CTO has changed as we've grown from 1 to 100 engineers

#142

"At this point, I believe technical co-founders have a binary choice: Stay on the technical track and hire a professional manager (usually given the VP of Engineering title), or give up coding and focus on the management aspects yourself. It really isn’t possible to do both." For me this is the key quote. I have a friend who went the other way from the author of this article. He started as one of two company founders…

I think that the pressure for initial programming founders to become head managers is a Peter Principle trap - your success at the tasks required as a senior engineer does not correlate very well with success as a manager. Even if it works for you (as it seems to have in this case!) it's important not to establish a culture in which you get promoted to managerial positions iff you are a good engineer.

I've seen a lot of fantastic coders get promoted to management and be bad-to-mediocre at it, and a lot of meh coders who can take over a room passed over for managerial jobs they'd probably be better at than their purely-technical ones.

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