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

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

#51

Post by etaty » Thu, Jun 28, 2018, 9:29 PM UTC

zmitri wrote: post #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?

This video is about : "Finance as Strategy: When and How Startups Should Build a Finance Function" - a16z https://www.youtube.com/watch?v=ns9_OGz4SeE

But this could apply to any Function in the business.

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

#52

Post by cbzehner » Thu, Jun 28, 2018, 9:29 PM UTC

volaski wrote: 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…

You should look at the articles from First Round Review[0]. I haven't read any in a while but they tend to be high quality long form write-ups from successful execs. Similar to this piece.

[0] http://firstround.com/review/

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

#53

Post by taytus » Thu, Jun 28, 2018, 9:31 PM UTC

volaski wrote: 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…

>they don't know why they failed, and that's why they failed.

You can very well know why you failed. Post-mortems (most of the times) try to answer that question

Knowing something doesn't make it inevitable.

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

#54

Post by camdenlock » Thu, Jun 28, 2018, 9:33 PM UTC

Fantastic article! I’m in a similar position as you, and will have to face the same decision you did, so this was refreshing and edifying to read. Thank you for taking the time to write it.

One thing that stuck out to me was your mention of focusing on “diversity and inclusion”. Why did that become a necessary thing for you to focus on? It seems political, and entirely unrelated to the actual work of building a good engineering team. Isn’t it enough to ensure that anyone and everyone has the same opportunity to get hired? At my company, my goal has been to ensure that all candidates get judged without focusing on attributes like gender or ethnicity; to make sure that the doors are open to everyone, no matter who they are. I then try to trust that the people who want to work in this field, and this company, are capable on their own to come to us.

Has that been your experience, or has there been good reason to put extra effort into finding/favoring candidates with certain characteristics?

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

#55

Post by asafira » Thu, Jun 28, 2018, 9:38 PM UTC

I have a few questions!

1) Did others in the org recognize you couldn't spend as much time on code, and they appreciated your time elsewhere? I can imagine there being some growing pains as you slowly gave your responsibilities to someone else, and in the meantime things not getting finished as quickly/productively. (Not to mention the fact that an average engineer wouldn't like spending 12-14 hours per day coding)

2) What is your favorite advice from the books you've read? What made the biggest impact on your actions?

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

#56

Post by cabaalis » Thu, Jun 28, 2018, 9:52 PM UTC

We went from 1 engineer (me) to 4 last year. So I'm in the 2-10 stage. I coded prototype and first X customers, which has become literally 20X in the past year. I still code most of the time, and the primary problem I am encountering is being willing to transition technically difficult aspects of the product. This has to happen, as I am finding myself becoming a huge bottleneck.

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

#57

Post by volaski » Thu, Jun 28, 2018, 9:53 PM UTC

timr wrote: post #49

volaski wrote: post #42

Earlier quoted context omitted.

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…

"But you don't deserve to tell others what you think is the right thing when only thing you've achieved in life is failure. You gotta earn it by taking the lessons you learned and applying it to come to a true success. These people are worth listening to." I am mostly neutral on what you wrote, but this is just wrong. If you think that only "successful" people have valuable stories, you're drawing a very bright-line…

The reason why your advice is not as useful as you think is because chances are, if you google around, most of that lesson would be already out there. Don't take this the wrong way I mean no offense. I'm sure you've learned a lot of lessons and I'm sure they're all valuable lessons, just saying most of what I read online nowadays are basically rehash of what these failed entrepreneurs heard from someone else, who probably heard it from some other successful person.

My point was "why listen to failures when you can listen to people who've both failed AND succeeded, especially when most of what the former would say is a rehash of what the latter said?" Think about it. I've thought about this myself as a once-failed-entrepreneur, and come to a realization that until you actually have succeeded in life and gained enough confidence to be able to think independently AND have the confidence to share your lesson you came to independently, most of what you think you understand are basically what you heard from other more successful people. You may think otherwise, but if you think deeper, that's what you're doing.

There's nothing wrong with this on its own, but the problem is that most of the articles I'm referring to actually mislead other people into believing in some seriously wrong interpretations of why they failed, and they all stem from the fact that these people have no idea why they failed but just try to come up with their own "theory" of why they failed with their limited knowledge. There are many reasons why people fail at something. Some people make all the bad decisions yet still succeed because they made one small decision that made a huge difference. Some people make all the right decisions yet fail because they made one small decision that messed it all up. Without this COMPLETE context, your advice is not complete because it's just small tidbits that may or may not work. If this comes from someone who has succeeded at least once, you at least know this is something that has happened. But if you follow "advice" from people who have only failed, then what are you really believing?

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

#58

Post by jgh » Thu, Jun 28, 2018, 9:57 PM UTC

cabaalis wrote: post #56

We went from 1 engineer (me) to 4 last year. So I'm in the 2-10 stage. I coded prototype and first X customers, which has become literally 20X in the past year. I still code most of the time, and the primary problem I am encountering is being willing to transition technically difficult aspects of the product. This has to happen, as I am finding myself becoming a huge bottleneck.

Congrats on the success! Yes definitely replace yourself sooner than later or you will regret it when you're dealing with company stuff and you need to fix a bug at the same time!

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

#59

Post by dasil003 » Thu, Jun 28, 2018, 10:02 PM UTC

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…

How do define success? I get there are a lot of clueless Dunning-Kruger cases writing Medium posts who are so far from competence that their ideas are worthless to anyone else, but those cases are straw men. What about the people who have some modest success but haven’t created a household name? There’s a lot more of those out there and yet they seem to get less credibility than some middle manager at Google who really had nothing to do with their success but just still gets to ride the coat tails of their success.

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

#60

Post by seibelj » Thu, Jun 28, 2018, 10:03 PM UTC

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

Wow! What an extraordinarily unhelpful and bad attitude you have