9 ms·

One job, many roles: The different skills needed to be a successful CTO

346 points by andreascreten 7y ago

thecupisblue 7y ago
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.
mooreds 7y ago
I have been the CTO at a startup, the effective CTO at a couple of companies with small teams (< 10 technical team members) and observed CTOs at larger companies. It's a hard job to do well in one phase of a company's life cycle, let alone all the phases. If you want to take the challenge of growing in the role, good on ya! But there's no shame in trying it and the realizing that though you liked the role in phase 1, you don't in phase 5 (or vice versa). They're as different as being a developer and a ux designer and no one would condemn someone for picking one of those roles (rather than trying to do both). I thought this post captured a lot of the intricacies of being a CTO: https://medium.com/swlh/the-codeless-cto-471ee6069288 https://medium.com/swlh/the-codeless-cto-471ee6069288
- stingraycharles 7y ago
  What are your thoughts of hiring a VP of Engineering to complement a CTO as the company grows? It’s my impression that there are multiple “types” of CTOs, and this always sounded like a reasonable path in case you have a more “technical” CTO.
  - marcinzm 7y ago
    I've talked to a seasoned VP of Eng who hated the concept (specifically of the VP of Eng reporting to the CTO). Essentially, a technical CTO would meddle in what the VP of Eng's team is doing leading to a power conflict between the two. I feel it'd work but only if the CTO is actually acting like a CTO instead of a glorified tech lead. That means focusing on strategy and the outward communications of the company rather than technical details.
    - barrkel 7y ago
      VP Eng should report to CEO, not CTO.
      - marcinzm 7y ago
        Which makes a technical inward facing CTO somewhat pointless to me and less impactful than a chief architect reporting to the VP of Eng.
juris-ws 7y ago
Shameless plug: Reminds me of https://www.about.wiserstate.com/post/startup-cto-many-hats-outside-comfort-zone https://www.about.wiserstate.com/post/startup-cto-many-hats-....
cik 7y ago
The thing about being a CTO (or any role for that matter) is that it changes over time, and needs to. They purpose, value, and goals of a CTO are completely different with 3 people, 30 people, and 300 people. This is much like software - what is ideal at a scale of "just do it" is completely different at a scale of "okay, breathe". It's the norm to rain fire and brimstone on someone's past decisions when they become your inherited present. At the same time, there's a reality that those past decisions were probably made for reasons, known to be not ideal, and have to change in the future. Personally, I'd much rather never have those technical trade-offs; but I'm also a realist. The same is true of process - certain things that are bread and butter to small companies are anathema to an organization of 300. We seem to lose sight of that.
- deleted 7y ago
  [deleted]
mrits 7y ago
Articles like these make me wonder where these people find the qualified CTO replacements. To have confidence in a replacement you have to find someone with a pattern of success in similar roles and similar industries. You then have to take a gamble that they will perform at the same level with often a lot less motivation.
jgrahamc 7y ago
I don't think there's anything very special about the CTO role here. A lot of this applies to any executive role. As the company scales the role will change enormously and you might have to change the person doing it. The one thing I would say though is don't hand out a title like CTO early. It's overly grand, reduces your flexibility to change and just isn't necessary. It's very tempting for a small team to give out grand titles but it's a mistake. Sure someone has to be CEO, but no one has to be CTO.
nostrademons 7y ago
The role the article describes is usually called a VP of Engineering. The distinction between them is that VP Eng is an operational role - you're responsible for managing a team of developers; instituting the appropriate process to keep productivity high and bug count low; dealing with technical debt; identifying portions of the codebase that won't scale and replacing them with solutions that will; and all of the nitty-gritty organizational tasks needed to ensure that the engineering organization doesn't grind to a halt. The CTO role is a visionary one. You're responsible for looking outside the organization at new technological developments and deciding how they may impact the organization's strategy; identifying new technical areas that warrant some exploratory investment; prototyping new systems, sometimes with the help of a small team of engineers who enjoy that stuff; and advocating for innovation within the organization. Think of the role of Larry & Sergey (technically Presidents of Product/Technology, respectively) vs. Urs Hoelzle (VP Eng) at early Google. Larry & Sergey were responsible for making sure that things like GMail, Google Maps, 20% time, Chrome, etc. got funded and Keyhole, Android, Blogger, Writely, etc. got bought. Urs instituted the engineering culture, made sure the right engineers got into the right roles and were able to be productive, technical debt got paid down (slowly), new systems were written as necessary to scale, etc. The CTO role, properly defined, is the perfect place to kick a technical founder upstairs and yet still retain their expertise in innovation. The problem is that many CEOs conflate the two roles, assign VP responsibilities to a CTO with a personality type more suited for the CTO role, never hire a real VP, and then wonder why the organization devolves into chaos. If you're doing it right the bulk of the engineering organization should report up through the VP of Engineering and the CTO should have only a small number of special-projects reports.
- oarabbus_ 7y ago
  What is the difference between a President of Product, and a VP of Product? Obviously a President is "higher" than a Vice President, but most companies have a VP Eng/Product, but not a President of Eng/Prod
  - kesor 7y ago
    Usually, companies have just one President, with all the others being Vice Presidents of the various aspects required for the company.
simonebrunozzi 7y ago
This is a really interesting discussion, and I feel it could go even deeper. My story: after two tough "failures" and some temporary consulting for a few months, I have joined an investment firm in San Francisco as an external consultant/contractor for the last 2-3 months, with the goal of defining a long-term role after getting to know each other better. They are now offering me a CTO position within the firm. They want me (with a small team) to build a number of things that can be considered technology products, such as: a platform to manage a large advisory board; a system to perform a technical due diligence on large companies; a source engine to collect data and metrics with the purpose of augmenting deal-sourcing and decision-making. Other tasks include: defining and maintaining the taxonomy for the IT industry, and representing the firm as an "external" CTO (events, conferences, etc). Given it's a quite unique and uncommon role in an investment firm, I am now working on a plan to define these things in more details. <ask> If any of you had experiences in similar roles (perhaps at investment firms in the East coast?), or feel you can dispense good advice, I would love to grab a coffee and pick your brain on a few things. </ask> Also, wish me luck! One bad career turn is bad, two are really tough to handle. To make a long story short: #1 was as CTO in a startup for a bit over a year, the two founders made a ton of mistakes, not my fault; #2 I was founder/CEO of a company, things didn't go well and after ~1.5 years I had to leave the company, with some important disagreements among founders, but thankfully not much drama. Before that I had two very successful roles at AWS and VMware for a total of ~8 years.
- lioeters 7y ago
  Fascinating to hear all the different meanings of "CTO" depending on context. The whole history of ups and downs as founder/CEO/CTO and other roles you've had, sounds like it would make for educational story-telling time for other people who are learning to navigate these waters. Godspeed, would love to (somehow) hear how it turns out.
  - simonebrunozzi 7y ago
    Thanks! One day I'll write a book about everything :)
reggieband 7y ago
After skimming the article and reading comments here - I can't resist the urge to bad mouth some of my contemporaries. A couple of developers who I worked with, who I know personally to be useless, ended up joining tiny startups. These startups failed as I expected yet these developers translated the short time they were in inflated positions into careers. Obsession with titles is a real thing. Getting a "VP of Engineering", "Director of Engineering" or "CTO" onto your resume can affect how your career prospects change over time. It is frustrating that failing at being a capable CTO can set you up better than succeeding at being an exceptional Team Lead.
- dullgiulio 7y ago
  Epecially when the job description is exactly the same. Another top comment of this article describes what the tasks of a VP of Engineering are... except that those are really what a Team Lead does daily. Titles are really only of some use inside an organization. Between organizations, they are not comparable.
methodover 7y ago
Something that’s missing from this analysis, I feel like, is this: There needs to be a passionate owner. A technical leader who understands customers and their needs, understands what’s technically possible, and has the imagination to connect those two things. I don’t know what you call that person, but it sure helps if he’s got a c in front of his name. CTO, CPO, whatever. This something the article kinda glosses over, but maybe shouldn’t. (I’m not sure if this person is great for the CEO role, by the way, just because of how freaking busy the CEO tends to be. There’s too much for her to do to also fulfill this role.)

346 points by andreascreten 7y ago

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.

mooreds 7y ago

I have been the CTO at a startup, the effective CTO at a couple of companies with small teams (< 10 technical team members) and observed CTOs at larger companies. It's a hard job to do well in one phase of a company's life cycle, let alone all the phases. If you want to take the challenge of growing in the role, good on ya! But there's no shame in trying it and the realizing that though you liked the role in phase 1, you don't in phase 5 (or vice versa). They're as different as being a developer and a ux designer and no one would condemn someone for picking one of those roles (rather than trying to do both). I thought this post captured a lot of the intricacies of being a CTO: https://medium.com/swlh/the-codeless-cto-471ee6069288 https://medium.com/swlh/the-codeless-cto-471ee6069288

stingraycharles 7y ago
What are your thoughts of hiring a VP of Engineering to complement a CTO as the company grows? It’s my impression that there are multiple “types” of CTOs, and this always sounded like a reasonable path in case you have a more “technical” CTO.
- marcinzm 7y ago
  I've talked to a seasoned VP of Eng who hated the concept (specifically of the VP of Eng reporting to the CTO). Essentially, a technical CTO would meddle in what the VP of Eng's team is doing leading to a power conflict between the two. I feel it'd work but only if the CTO is actually acting like a CTO instead of a glorified tech lead. That means focusing on strategy and the outward communications of the company rather than technical details.
  - barrkel 7y ago
    VP Eng should report to CEO, not CTO.
    - marcinzm 7y ago
      Which makes a technical inward facing CTO somewhat pointless to me and less impactful than a chief architect reporting to the VP of Eng.

juris-ws 7y ago

Shameless plug: Reminds me of https://www.about.wiserstate.com/post/startup-cto-many-hats-outside-comfort-zone https://www.about.wiserstate.com/post/startup-cto-many-hats-....

cik 7y ago

The thing about being a CTO (or any role for that matter) is that it changes over time, and needs to. They purpose, value, and goals of a CTO are completely different with 3 people, 30 people, and 300 people. This is much like software - what is ideal at a scale of "just do it" is completely different at a scale of "okay, breathe". It's the norm to rain fire and brimstone on someone's past decisions when they become your inherited present. At the same time, there's a reality that those past decisions were probably made for reasons, known to be not ideal, and have to change in the future. Personally, I'd much rather never have those technical trade-offs; but I'm also a realist. The same is true of process - certain things that are bread and butter to small companies are anathema to an organization of 300. We seem to lose sight of that.

deleted 7y ago
[deleted]

mrits 7y ago

Articles like these make me wonder where these people find the qualified CTO replacements. To have confidence in a replacement you have to find someone with a pattern of success in similar roles and similar industries. You then have to take a gamble that they will perform at the same level with often a lot less motivation.

jgrahamc 7y ago

I don't think there's anything very special about the CTO role here. A lot of this applies to any executive role. As the company scales the role will change enormously and you might have to change the person doing it. The one thing I would say though is don't hand out a title like CTO early. It's overly grand, reduces your flexibility to change and just isn't necessary. It's very tempting for a small team to give out grand titles but it's a mistake. Sure someone has to be CEO, but no one has to be CTO.

nostrademons 7y ago

The role the article describes is usually called a VP of Engineering. The distinction between them is that VP Eng is an operational role - you're responsible for managing a team of developers; instituting the appropriate process to keep productivity high and bug count low; dealing with technical debt; identifying portions of the codebase that won't scale and replacing them with solutions that will; and all of the nitty-gritty organizational tasks needed to ensure that the engineering organization doesn't grind to a halt. The CTO role is a visionary one. You're responsible for looking outside the organization at new technological developments and deciding how they may impact the organization's strategy; identifying new technical areas that warrant some exploratory investment; prototyping new systems, sometimes with the help of a small team of engineers who enjoy that stuff; and advocating for innovation within the organization. Think of the role of Larry & Sergey (technically Presidents of Product/Technology, respectively) vs. Urs Hoelzle (VP Eng) at early Google. Larry & Sergey were responsible for making sure that things like GMail, Google Maps, 20% time, Chrome, etc. got funded and Keyhole, Android, Blogger, Writely, etc. got bought. Urs instituted the engineering culture, made sure the right engineers got into the right roles and were able to be productive, technical debt got paid down (slowly), new systems were written as necessary to scale, etc. The CTO role, properly defined, is the perfect place to kick a technical founder upstairs and yet still retain their expertise in innovation. The problem is that many CEOs conflate the two roles, assign VP responsibilities to a CTO with a personality type more suited for the CTO role, never hire a real VP, and then wonder why the organization devolves into chaos. If you're doing it right the bulk of the engineering organization should report up through the VP of Engineering and the CTO should have only a small number of special-projects reports.

oarabbus_ 7y ago
What is the difference between a President of Product, and a VP of Product? Obviously a President is "higher" than a Vice President, but most companies have a VP Eng/Product, but not a President of Eng/Prod
- kesor 7y ago
  Usually, companies have just one President, with all the others being Vice Presidents of the various aspects required for the company.

simonebrunozzi 7y ago

This is a really interesting discussion, and I feel it could go even deeper. My story: after two tough "failures" and some temporary consulting for a few months, I have joined an investment firm in San Francisco as an external consultant/contractor for the last 2-3 months, with the goal of defining a long-term role after getting to know each other better. They are now offering me a CTO position within the firm. They want me (with a small team) to build a number of things that can be considered technology products, such as: a platform to manage a large advisory board; a system to perform a technical due diligence on large companies; a source engine to collect data and metrics with the purpose of augmenting deal-sourcing and decision-making. Other tasks include: defining and maintaining the taxonomy for the IT industry, and representing the firm as an "external" CTO (events, conferences, etc). Given it's a quite unique and uncommon role in an investment firm, I am now working on a plan to define these things in more details. <ask> If any of you had experiences in similar roles (perhaps at investment firms in the East coast?), or feel you can dispense good advice, I would love to grab a coffee and pick your brain on a few things. </ask> Also, wish me luck! One bad career turn is bad, two are really tough to handle. To make a long story short: #1 was as CTO in a startup for a bit over a year, the two founders made a ton of mistakes, not my fault; #2 I was founder/CEO of a company, things didn't go well and after ~1.5 years I had to leave the company, with some important disagreements among founders, but thankfully not much drama. Before that I had two very successful roles at AWS and VMware for a total of ~8 years.

lioeters 7y ago
Fascinating to hear all the different meanings of "CTO" depending on context. The whole history of ups and downs as founder/CEO/CTO and other roles you've had, sounds like it would make for educational story-telling time for other people who are learning to navigate these waters. Godspeed, would love to (somehow) hear how it turns out.
- simonebrunozzi 7y ago
  Thanks! One day I'll write a book about everything :)

reggieband 7y ago

After skimming the article and reading comments here - I can't resist the urge to bad mouth some of my contemporaries. A couple of developers who I worked with, who I know personally to be useless, ended up joining tiny startups. These startups failed as I expected yet these developers translated the short time they were in inflated positions into careers. Obsession with titles is a real thing. Getting a "VP of Engineering", "Director of Engineering" or "CTO" onto your resume can affect how your career prospects change over time. It is frustrating that failing at being a capable CTO can set you up better than succeeding at being an exceptional Team Lead.

dullgiulio 7y ago
Epecially when the job description is exactly the same. Another top comment of this article describes what the tasks of a VP of Engineering are... except that those are really what a Team Lead does daily. Titles are really only of some use inside an organization. Between organizations, they are not comparable.

methodover 7y ago

Something that’s missing from this analysis, I feel like, is this: There needs to be a passionate owner. A technical leader who understands customers and their needs, understands what’s technically possible, and has the imagination to connect those two things. I don’t know what you call that person, but it sure helps if he’s got a c in front of his name. CTO, CPO, whatever. This something the article kinda glosses over, but maybe shouldn’t. (I’m not sure if this person is great for the CEO role, by the way, just because of how freaking busy the CEO tends to be. There’s too much for her to do to also fulfill this role.)