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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

#91
post #21
post #19

Sup Eddie. Besides books, did you go and ask people about how to be a great CTO? Who did you pick to ask, and how did you find those people?

Hey Wil! Yeah, I found a few mentors who I would feel comfortable asking questions and getting advice. I met some though investor introductions, and others through friends of friends.

Did you find their advice helpful? Could you tell ahead of time who was going to be more helpful than others?

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

#92

Earlier quoted context omitted.

The justification I hear for ignoring the data against open offices is: "Every other unicorn has an office like this and they get work done so why can't we"?

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.

That seems unlikely.

I think they're in Boston, but, even in New York, which, for office space is even more expensive than SF, the excuse that square footage is too expensive seems shaky, especially since it's been trotted out routinely over the past 3 decades.

This blog post shows a credible calculation, even assuming remarkably low salaries (and a fairly credible $5/sqft):

https://business.linkedin.com/talent-solutions/blog/hr/2016/...

The real key, though, is at the end:

> the calculation above doesn't count the cost of setting up the offices

For an early startup, that cost, both in dollars and, perhaps most importantly time (move-in delay), could easily be prohibitive.

Of course, once the company is past the early stage, it may just be habit or cargo cult.

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

#93
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 are much more people who failed than people who suceeded, so it make sense that there are more blog posts about failures than about success.

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

#94
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…

Your reason also apply to success. The o lu way they know what they think they learned through success was actually something meaningful is to apply lesson in their future endeavours and see if it works out. Until then all your interpretation are nothing more than Your opinion.

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

#95
This comment is hard to word without sounding like I'm grinding an axe with the author or the blog post or something. I'm not. It's a good post.

Anyway, I was disappointed but unsurprised to find that Ctrl-F "leadership" yielded 0 results. Anyone can read management books, and I am sure they're super valuable for learning techniques to maximize the value the company gets out of its employees.

However based on my experience over the last many years, it's not enough to be a skilled manager. "Necessary but insufficient."

Leadership is a different skillset. I am sure Mr. Kim has learned a lot about leadership, he just didn't split out the two in the blog post. Undoing the semantic smushing of management + leadership so they can be focused on independently is important, IMO.

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

#96

to offer a counterpoint to the lovefest going on here, TFA is almost completely uninteresting. the role changed exactly as one would expect and predict. the only interesting part is reading about the humble beginnings, the dedication and belief. what would actually be useful to read about is failings, where OP failed in transition to manager and how he overcame those failings. I mean there's a paragraph in there but…

The common failure point, which the author mentions, is that people management is not like coding. And trying to do both at once is a losing proposition. I always stress to new managers that managing is different than coding in its execution but similar in its perception. What that means is that when you code a system and it works well, it operates smoothly and when things happen (like you lose a disk drive, or a server crashes, etc) it continues to operate and perhaps degrade gracefully. This is also true of well run organizations. Most people recognize when the organization is running smoothly, and appreciate it when the organization responds quickly and without disruption ton changes in the environment. To me, I see that as the essence of good people management.

Sometimes when you have a piece of code that in spite of rewriting it a couple of times the system still bottlenecks or whatever, you restructure. Same with groups, except instead of code being moved around you move people around. Being able to see people as a team with unique capabilities and putting them in roles that are successful has been compared to programming.

The next step in the growth of a CTO (or perhaps the one after the next step for the author) is when the company gets big enough to start making choices about which problems they are going to focus on. Are they the payroll company that you can run from your phone, or the one that integrates with Salesforce? Or the one that blends remote workers from the largest number of areas into a single payroll. That is when you have to start thinking as both a business person and a technical person so that you can help steer the priorities to solve the customer problem as it arrives and before it is solved in dozens of ways by your other competitors.

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

#97
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…

I certainly agree that this is refreshing and a very interesting read. At the same, because of survivorship fallacy, I think the best way to get insight into what makes stuff tick is to get a balanced mix of both success and failure stories.

Survivorship fallacy is one thing, but I would say overall there is far more value to success stories where a majority of stories are failure ones. Generally speaking it would seem the path to success, varied as it is, is far narrower than the path to failure.

From a failure story you can look at what they did, but if they did X that doesn't mean X leads to failure, as others could do X and succeed. It's possible they succeeded in spite of doing X, but it's usually apparent when that's the case. Maybe X only worked because of a perfect storm of conditions/timing.

I would also say a vast majority of people who fail go on to fail a second time, making their whole reflections write up from the first failure kind of weakened by the fact the lessons they learned from their previous failure were not enough to avoid it the next time. Paying too much attention to what not to do just leads you down a totally different road to failure. Common pitfalls are worth knowing, but it would seem there are 10 ways to fail for every 1 way to succeed. Often big successes do the exact opposite of all the "don't do this" advice.

But that's just my perspective working in games, where creativity and rule breaking is a lot more substantial to the success, I think. However, I feel it all applies to a broader scope of business and software.

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

#98

Earlier quoted context omitted.

The justification I hear for ignoring the data against open offices is: "Every other unicorn has an office like this and they get work done so why can't we"?

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.

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

#99
post #60

Earlier quoted context omitted.

Wow! What an extraordinarily unhelpful and bad attitude you have

No, you have the bad attitude. You're getting some good advice and you are responding in a way that shows that you are not open to input. Which is exactly why you should stop coding.

I disagree, every CTO I’ve worked for has their own side projects, no need to lose your mind over it

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

#100
post #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 :)

That's a bizarre claim. Writing about the company is one of the big PR tasks of a CxO or SVP.

As you noted yourself, blogging is a form of marketing.

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