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

engineering.gusto.com

31–40 of 142 posts

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

#33
post #28

it's refreshing to see someone who actually successfully scaled a company write an article about "here's how we did it", instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post (answer: they don't know why they feailed, and that's why they failed. T…

That would be great, but there's a structural limit: people running successful startups don't have time to write about it, while people who have wound down their companies do. When a company is going strong and HN sees a post like this, it's usually because they're hiring :)

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

#34
How did you maintain compliance and security before you could have someone full time on it? How did you deal with audits? Did you hire an engineer full-time dedicated to this, outsource it, or do it yourself? (I ask because I do this now but at 8 people it's starting to take up too much of my time as CTO)

How does it work at your size now?

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

#35
post #28

it's refreshing to see someone who actually successfully scaled a company write an article about "here's how we did it", instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post (answer: they don't know why they feailed, and that's why they failed. T…

There is a certain amount of luck/risk involved in doing a startup. You can do everything “right” and still fail.

That is not a weakness, that is life

edit: this is a star trek reference

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

#37
post #28

it's refreshing to see someone who actually successfully scaled a company write an article about "here's how we did it", instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post (answer: they don't know why they feailed, and that's why they failed. T…

"...instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post"

That's really cynical. For a long time, people were complaining about the opposite on HN: you never heard about the failures, which leads to a massive selection bias.

I've always felt that you can learn far more from failure than success. Successful people often have little actionable insight into why they succeeded (e.g. "we worked hard and made something people wanted"), but most people can write volumes about what they've done wrong in life.

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

#38
post #13

I am a CTO, going from 2 engineers to a total engineering org of approximately 20. Much of my time is non-coding, but I don't believe you have to totally give it up. I try to leave a day per week free of meetings to code / review code. I keep some projects that, while useful for the company, can be worked on irregularly and slowly, and are not super essential to be accomplished quickly (which is why they aren't prior…

Giving up coding is what you do for your team, so they don't have to deal with the half finished B grade work you did inbetween doing the serious shit they can't do

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

#40
post #36

At what point do you start calling people direct reports? I find this turn of phrase really jarring

Reporting hierarchy is there for a good reason. If you report to multiple people, you're the one that's going to have a bad time when they're not aligned with each other, each trying to give you a different list of priorities.
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