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This is one thing I've seen crushing startups - not changing CTO's after traction, but keeping the founder that wrote the MVP as a CTO. It isn't always a bad th

This is one thing I've seen crushing startups - not changing CTO's after traction, but keeping the founder that wrote the MVP as a CTO. It isn't always a bad thing, there are a lot of hackers that fill the role, but when it's not even considered because "he's a founder so he needs to remain CTO" vs "he's got the CTO skills" it is an alarming sign. I've worked in a startup (about 30 ppl) where the CTO was one of the founders and he was doing nothing but holding the company back with his decisions and his 0-architecture-spaghetti code. My first day, when I saw all the trash going on I thought "ok I can't really quit my first day so they'll have to fire me". Decided to take ownership and start treating him like any other team member, reviewing and declining his merge requests (those weren't use before I came, they just commited all over the place), refactoring, planning ahead because otherwise we would have never delivered on time - his own technical debt extended feature delivery time by weeks. He was aware and admitted his "lack of skills", but wasn't aware of how much he actually lacked. We managed to take it out the gutter and polish it up a lot in the next two years, but after all the mess and his obvious lack of knowledge, he still remained the CTO, long after I left. So please, if you are a CTO of a startup and are aware you lack skills, don't try to drive technical decisions and actively look for a replacement. Your decisions can create friction for whole company and burn it to ground right before it takes off. And if you work under a CTO like that, just take the damn responsibility and challenge dumb stuff or quit, or you might fall into the sloppy spaghetti.

romanovcode 7y ago
Is the company successful right now? (After 2+ years have passed)
- thecupisblue 7y ago
  Eh, depends on your definition of success. When the debt got solved - and finally we could open the market in other countries and maintain old ones without causing chaos by each change - the company was nearly burned cash-wise. They got acquired, I left soon, they hired more developers and the situation is better now altho they pivoted.
pvinis 7y ago
I've had a similar experience, and I agree 100%. In my case the founder/CTO was very capable but after a point he just didn't want that position because of some reasons, and he left. The company then decided to just assign the next-in-line people as a group of 3 to act as the CTO replacement. That didn't work very well, and actually 2 of them ended up leaving too. After that we finally hired a guy specifically to be the CTO, and it's been great after that. (I left the company after a while, but it's still going great with that latest CTO)
golergka 7y ago
Oh, I've seen a very similar thing. The only difference was, it wasn't the architecture, it was people skills - classic lone hacker that doesn't trust anybody else and doesn't delegate.
fredley 7y ago
One issue is that once you've made someone a CTO, it's hard to hire above them without them leaving. To be honest, as someone who's been a CTO a few times, you probably don't want anyone with the title CTO until quite late in the game, if at all. This allows much more flexibility with where people can be hired and the responsibilities they can be given.
- k__ 7y ago
  This. I knew a few companies, where founders were fighting over C-level roles. If a company under 10 people has a CTO it is a bad sign. If a company over 20 people doesn't have a CTO it is also a bad sign. I also know a bunch of companies, where the CEO doesn't tolerate other C-levels, for ego reasons.
  - oarabbus_ 7y ago
    >If a company over 20 people doesn't have a CTO it is also a bad sign. I worked for a series A startup client with ~50-60 employees (30 or so were engineers) and they had a VP Eng but no CTO. SaaS/mobile app company.
    - k__ 7y ago
      What's the difference?
      - oarabbus_ 7y ago
        I'm a bit confused; I'm asking you the question. You made a claim it's a bad sign that a >20person company has no CTO. I've seen this occur in practice, and I'm asking you why that's a bad sign.
        banannaise 7y ago
        I'll take a stab: it means that either (a) the CEO has ego problems and refuses to allow other C-suite titles, or (b) the CEO has failed to hire the appropriate talent for a true CTO role (often because they're trying to do too much themselves).
StreamBright 7y ago
I have similar experience with more than 1 startups. The worst ones who you cannot even challenge even presenting all the facts, they defend their unscalable spaghetti till the end.
Khanhanhan 7y ago
I could be that founding CTO you're talking about, but, being aware of my shortcomings, I decided to put my trust in hired engineers and then in a relatively expensive CTO. It was the worst decision I've ever made as a founder and I spent a couple of years cleaning up the mess they've made. As a founder, if you decide to delegate any Cxx role, you'd better be lucky.
kostarelo 7y ago
I'm in a kinda similar situation unfortunately and I'm sure other people too. I understand that the question might be general but are you regretting the decision to stay and fight? I mean two years was a long time.
- thecupisblue 7y ago
  Ultimately, not - it was a fun time and a learning experience. Business wise, the decision wasn't the best, I could've gone worked for more reputable companies or bigger money.I t was kind of a quick decision to join them, but it gave me a lot of experience in how to create a technical team structure from stratch/a load of shit and most importantly I learned a ton about technical debt and overcoming it. I came from a place where mostly everything was mostly organised in "standard" ways so I decided to start implementing that - starting from pull requests, workflow, CI/CD, then refactoring bits of code, teaching separation and architecture. Having to set it all up from scratch and explain why and how to do/use it to someone who doesn't know it made be research it even more so I can be sure in my knowledge when I explain it to the rest of the team. I took on responsibility and helped where I could - PM, UX, product development - that gave me access to stuff that devs usually don't get to and the responsibility paid off with more authority and trust in me. I'd say it really depends on your situation - do you like the product? Do you like the team? Do you have stuff to learn? And most importantly, are they willing to let you take the lead instead of backstabbing you?
  - kostarelo 7y ago
    Did you have previous experience in a similar stage company? I had a lot and I'm almost feeling like "I've been through this stuff before" and that demotivates me. But I will accept the argument that learning (by teaching) never stops. I do like the team. The product? well, it's challenging but I'm not using it. I don't have stuff (at least technical) to learn unless they decide that we need to start moving quickly and not be stuck in legacy code. They started doing microservices with 0% testing and I'm still trying to teach them about contract-driven APIs
sharadov 7y ago
I was interviewing at a place for a DBA position, where the co-founder (CTO) of this company which had raised 100 million plus and about 150 people, was still updating prod on the fly. I told him straight up in the interview, that the first day am hired I would revoke his permission, he said I could not do that. The guy was too cocky, I did not get the job, they burnt through all the cash in a year, and out of business right after! You see the writing on the wall sometimes in the few hours you spend at the place.
- have_faith 7y ago
  > I told him straight up in the interview, that the first day am hired I would revoke his permission > I did not get the job Well that was a predictable outcome.
  - spookthesunset 7y ago
    > Well that was a predictable outcome. Which was probably a blessing in disguise.
    - sharadov 7y ago
      Absolutely!
  - xchaotic 7y ago
    As a CTO I’d probably hire the guy. OTOH I probably would not let prod be touched in the first place.
    - sharadov 7y ago
      Will you hire me :-)
mildweed 7y ago
Sometimes a founding CTO needs to hire both an Architect and a VP of Engineering. The trick of course is defining what the remaining duties are that fall up to the CTO. Specifically, making them desirable to that founder. Chief prototyper, evangelist, and vision-setter might be a good mix.

romanovcode 7y ago

Is the company successful right now? (After 2+ years have passed)

thecupisblue 7y ago
Eh, depends on your definition of success. When the debt got solved - and finally we could open the market in other countries and maintain old ones without causing chaos by each change - the company was nearly burned cash-wise. They got acquired, I left soon, they hired more developers and the situation is better now altho they pivoted.

pvinis 7y ago

I've had a similar experience, and I agree 100%. In my case the founder/CTO was very capable but after a point he just didn't want that position because of some reasons, and he left. The company then decided to just assign the next-in-line people as a group of 3 to act as the CTO replacement. That didn't work very well, and actually 2 of them ended up leaving too. After that we finally hired a guy specifically to be the CTO, and it's been great after that. (I left the company after a while, but it's still going great with that latest CTO)

golergka 7y ago

Oh, I've seen a very similar thing. The only difference was, it wasn't the architecture, it was people skills - classic lone hacker that doesn't trust anybody else and doesn't delegate.

fredley 7y ago

One issue is that once you've made someone a CTO, it's hard to hire above them without them leaving. To be honest, as someone who's been a CTO a few times, you probably don't want anyone with the title CTO until quite late in the game, if at all. This allows much more flexibility with where people can be hired and the responsibilities they can be given.

k__ 7y ago
This. I knew a few companies, where founders were fighting over C-level roles. If a company under 10 people has a CTO it is a bad sign. If a company over 20 people doesn't have a CTO it is also a bad sign. I also know a bunch of companies, where the CEO doesn't tolerate other C-levels, for ego reasons.
- oarabbus_ 7y ago
  >If a company over 20 people doesn't have a CTO it is also a bad sign. I worked for a series A startup client with ~50-60 employees (30 or so were engineers) and they had a VP Eng but no CTO. SaaS/mobile app company.
  - k__ 7y ago
    What's the difference?
    - oarabbus_ 7y ago
      I'm a bit confused; I'm asking you the question. You made a claim it's a bad sign that a >20person company has no CTO. I've seen this occur in practice, and I'm asking you why that's a bad sign.
      - banannaise 7y ago
        I'll take a stab: it means that either (a) the CEO has ego problems and refuses to allow other C-suite titles, or (b) the CEO has failed to hire the appropriate talent for a true CTO role (often because they're trying to do too much themselves).

StreamBright 7y ago

I have similar experience with more than 1 startups. The worst ones who you cannot even challenge even presenting all the facts, they defend their unscalable spaghetti till the end.

Khanhanhan 7y ago

I could be that founding CTO you're talking about, but, being aware of my shortcomings, I decided to put my trust in hired engineers and then in a relatively expensive CTO. It was the worst decision I've ever made as a founder and I spent a couple of years cleaning up the mess they've made. As a founder, if you decide to delegate any Cxx role, you'd better be lucky.

kostarelo 7y ago

I'm in a kinda similar situation unfortunately and I'm sure other people too. I understand that the question might be general but are you regretting the decision to stay and fight? I mean two years was a long time.

thecupisblue 7y ago
Ultimately, not - it was a fun time and a learning experience. Business wise, the decision wasn't the best, I could've gone worked for more reputable companies or bigger money.I t was kind of a quick decision to join them, but it gave me a lot of experience in how to create a technical team structure from stratch/a load of shit and most importantly I learned a ton about technical debt and overcoming it. I came from a place where mostly everything was mostly organised in "standard" ways so I decided to start implementing that - starting from pull requests, workflow, CI/CD, then refactoring bits of code, teaching separation and architecture. Having to set it all up from scratch and explain why and how to do/use it to someone who doesn't know it made be research it even more so I can be sure in my knowledge when I explain it to the rest of the team. I took on responsibility and helped where I could - PM, UX, product development - that gave me access to stuff that devs usually don't get to and the responsibility paid off with more authority and trust in me. I'd say it really depends on your situation - do you like the product? Do you like the team? Do you have stuff to learn? And most importantly, are they willing to let you take the lead instead of backstabbing you?
- kostarelo 7y ago
  Did you have previous experience in a similar stage company? I had a lot and I'm almost feeling like "I've been through this stuff before" and that demotivates me. But I will accept the argument that learning (by teaching) never stops. I do like the team. The product? well, it's challenging but I'm not using it. I don't have stuff (at least technical) to learn unless they decide that we need to start moving quickly and not be stuck in legacy code. They started doing microservices with 0% testing and I'm still trying to teach them about contract-driven APIs

sharadov 7y ago

I was interviewing at a place for a DBA position, where the co-founder (CTO) of this company which had raised 100 million plus and about 150 people, was still updating prod on the fly. I told him straight up in the interview, that the first day am hired I would revoke his permission, he said I could not do that. The guy was too cocky, I did not get the job, they burnt through all the cash in a year, and out of business right after! You see the writing on the wall sometimes in the few hours you spend at the place.

have_faith 7y ago
> I told him straight up in the interview, that the first day am hired I would revoke his permission > I did not get the job Well that was a predictable outcome.
- spookthesunset 7y ago
  > Well that was a predictable outcome. Which was probably a blessing in disguise.
  - sharadov 7y ago
    Absolutely!
- xchaotic 7y ago
  As a CTO I’d probably hire the guy. OTOH I probably would not let prod be touched in the first place.
  - sharadov 7y ago
    Will you hire me :-)

mildweed 7y ago

Sometimes a founding CTO needs to hire both an Architect and a VP of Engineering. The trick of course is defining what the remaining duties are that fall up to the CTO. Specifically, making them desirable to that founder. Chief prototyper, evangelist, and vision-setter might be a good mix.