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

engineering.gusto.com

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

#111

Post by dang »

yarper wrote: post #38
seibelj wrote: 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

Come on, there's no need to attack somebody like that just because your experience is different. Instead, share your experience so we can all learn from both sides. There isn't nearly enough information in seibelj's comment to draw a conclusion either way.

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

#112

Post by beager »

Thanks for sharing this. I don't have any specific questions but being at the tail end of 2-10 myself, it's good to have reference points for when other people do certain things, like draw down to ~50% code or 0% code, how much time to spend on recruiting, etc.

I will say that I've been feeling a different type of code guilt. I feel guilty when I code, because I view supporting, coaching, and mentoring my team to be my 10x activity. If I'm coding, there could be 8 other people getting blocked or needing help, and I'm off trying to build 4 hours of context to solve problems.

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

#113

Post by plinkplonk »

"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 working out of an apartment doing all the technical work while the other founder focused on business stuff.

When the company grew to a point where he had to decide between staying technical and people management, he hired a VP of Engineering, stuck to coding, and still codes 6-8 hours a day.

The company is now at about 200 people, is profitable, raised a series A after figuring out the business model, and blowing past the goals set by the investors. His stake in the company is worth many tens of millions today.

Just an existence proof that 'sticking to coding', can be a viable strategy, if an unusual one.

He is not interested in blogging/social media etc, or else I'd have persuaded him to write up his experience.

I have to agree with dang. Most people running successful startups don't have (or take) the time to write about it.

Which is too bad (imo). We could use more writeups from the successful subset.

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

#114

Post by itronitron »

edawerd wrote: post #5
smt88 wrote: 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 can certainly share some of the meatier areas that engineers at Gusto work on. - Calculating payroll and filing quarterly and annual forms are very complicated tasks that (a) is different in every state and (b) changes frequently as federal, state, and local tax laws change. Doing payroll in 50 states is similar to doing payroll in 50 different countries - Benefits is similar to Payroll in the sense that it's also…

>> rid the world of the concept of a "payday"

you might face some ingrained cultural barriers with this as the higher-status the job the more infrequent/delayed the payday... day-laborers are paid at the end of the day, many blue-collar jobs are paid weekly or bi-weekly, and white-collar jobs are typically paid monthly

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

#115

Post by itronitron »

dayvough wrote: post #110
bla2 wrote: post #63

This surprised me at first: > having difficult conversations with individuals is never fun But apparently "difficult conversations" is a Valley euphemism for "firing people" and doesn't mean "discussing difficult engineering problems".

How is this specifically a Valley euphemism?

I think they are just hoping that it is highly localized.

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

#117

Post by vagab0nd »

What do people think about the career trajectory as an individual contributor in an early stage startup? I'm the kind of person who not only enjoys coding, but hates dealing with management, hiring, meetings, etc. I always fear that I will be pushed to take on a management role. At the same time though, I really enjoy working with a group to build something from scratch. In your opinion, do you think it's better that I don't join an early stage startup?

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

#118

Post by eropple »

enraged_camel wrote: post #78
eropple wrote: post #50

Earlier quoted context omitted.

Patrick works at Stripe. Before that, he consulted and ran a bingo card creator. I love the dude and his advice has been invaluable to me--but it has been invaluable because he is not a guy who has run startups, he's a guy who's had to make a buck.

Running a bingo card creator qualifies as a startup. Unless of course we are using the ultra narrow HN definition of a startup.

No, we're using the tech-industry definition of a startup.

I don't run a startup, either. I make money.

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

#119

Post by sethrin »

dayvough wrote: post #110
bla2 wrote: post #63

This surprised me at first: > having difficult conversations with individuals is never fun But apparently "difficult conversations" is a Valley euphemism for "firing people" and doesn't mean "discussing difficult engineering problems".

How is this specifically a Valley euphemism?

For most working persons globally, getting fired isn't something that involves a "difficult conversation". Working stiffs do not get that degree of attention to their feelings. Suggesting that this phenomenon is common to (or even characteristic of) the high-income and acutely socially-aware circles of Silicon Valley should not be construed to exclude its observation elsewhere, but SV is one of the few places where the behavior is common, and hopefully the only place that feels the need for a polite euphemism.

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

#120

Post by jstandard »

yelloweyes wrote: post #74

This guy flew from San Francisco to New York to read books in a hotel? Like... what?

I understand where he's coming from. Sometimes to create a big personal change you need to disrupt your routine in a big way. For me, a change in environment really helps me think or focus differently.

New York may have been special in some way that could help that change.

I think the anecdote underscores how tough it can be to make that shift from doing something you love and are good at into new responsibilities you're not as strong in yet.

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