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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

#131

Post by dfsegoat »

lancefisher wrote: post #124
nine_k wrote: post #122

Earlier quoted context omitted.

Pretty sad that it sounds as if security was an afterthought in your design.

There are a whole host of compliance and security issues that you don’t have to (and shouldn’t) worry about when you’re small. Employee background checks, documented disaster recovery plan, 3rd party pen testing, etc. Those are things you worry about once you have built something. It’s different than just application security which itself can always be improved over time even if it wasn’t an afterthought.

SarBox, GAMP, GAAP, cGMP, PCI-DSS... The devil hath many names.

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

#132

Post by jSully24 »

plinkplonk wrote: post #113

"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 this is a critical point for engineers to see, and it sends a great message for engineers joining a company: "You don't have to go to the mgmt. track to have great career growth."

In many organizations I have seen the deep technical skills one gains through their career are not valued in the same way "Mgmt. Skills" are. "Mgmt. skills" are or at least appear to be much easier for an organization to see and reward. This is a great story!

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

#133

Post by kulu2002 »

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…

Imagine your children are in high-school and you are still doing their homework.

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

#134

Post by lmeyerov »

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…

We use gusto across multiple jurisdictions where tax laws change every year and our bookkeeper our employees put them through funny circumstances. I've been impressed by how many problems they've made invisible (just notify us) or we sent over and they handled. Cannot say the same about other folks we use here (ex: zenefits caused multiple lapses in coverage).

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

#135

Post by loco5niner »

jefozabuss wrote: post #32
asdsa5325 wrote: post #18

Yikes, that open office picture looks like my nightmares.

Tbh it's not that bad... after getting noise cancelling headphones.

I have noise cancelling headphones(bose qc20s). They don't work well on voices. I actually ended up with tinnitus partly because of listening to noise cancelling headphones at work all day (also sinus issues at the time likely made me more susceptible). Now, I can't listen to music loud enough to drown out voices without it setting off my tinnitus).

Headphones aren't the answer.

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

#136

Post by ccmonnett »

vagab0nd wrote: post #117

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…

No! I was the only engineer at a startup for 18 months (!) and we're now up to 7. Some of the other 6 will never be expected to take on management roles.

One of the great things about being an IC at an early company is there is so much to do. You get to put your fingerprints on a lot of things across the company because there won't be enough people to spread out all those tasks. As the company grows, those foundations become opportunities for you to grow from sole contributor to technical lead on each one; so much so that the hardest part will be choosing what to give up control of, not to what to keep contributing.

If you find yourself in this situation, I strongly recommend being involved in the search for your VPE. It could be really frustrating to build the technical foundations for a company only to be so frustrated by a poor manager being hired above you without your input that you might even quit. Wouldn't be good for your equity, either :).

PS this implies that if you don't want to grow into mgmt, you'll need to grow into being a good lead developer. Early startups have no room for people unwilling to grow.

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

#137

Post by workinfunk »

yelloweyes wrote: post #74

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

I almost started writing a sincere answer to this question before I read your post history. Cynics like you would never understand anyway.

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

#138

Post by workinfunk »

volaski wrote: post #42
timr wrote: post #37

Earlier quoted context omitted.

"...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're right i'm being cynical, because i genuinely believe you have not much to learn from people who have failed but haven't succeeded yet. That said, there are PLENTY of successful people who used to be a failure. In fact 99% of the successful people have been a failure at some point in their life. THESE are the people you listen to. The things you read in the media about a genius who got it right on their first a…

The merely smart learn from their failures. The wise learn from others' failures.

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

#139

Post by mandelbrotwurst »

deathanatos wrote: post #98
mandelbrotwurst wrote: post #27

Earlier quoted context omitted.

In a place like SF where office space is as expensive as it is, I wouldn't be shocked if the savings in rent from this kind of floor plan outweigh any productivity losses and I'd bet that is a primary reason why there are so many open offices. Edit: That said, that one definitely doesn't look like the most efficient use of space.

> In a place like SF where office space is as expensive as it is You could always move . I for one would love more non-SF companies; it'd open up more options and opportunities to get off the sinking ship that is SF.

I would also love to see that, for a number of reasons.

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

#140

Post by awad »

edawerd wrote: post #121
awad wrote: post #85

Earlier quoted context omitted.

The old cliche to work your way out of a job really resonated with me when I made this transition. It is natural to want to take on a task for yourself and to think you're doing your team a favor by shielding them from details you have a mastery on. But, once you get into the mindset of enabling everyone by focusing on training and knowledge sharing, you find that people are far more capable than perhaps you give the…

+1.This is a great summary of my experience

Fun fact we took over the lease at 425 right after y'all. That picture on the blog with the couches does not do justice to how packed the office was when we did our site tours!
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