
One job, many roles: The different skills needed to be a successful CTO - andreascreten
https://madewithlove.be/one-job-many-roles-the-different-skills-needed-to-be-a-successful-cto/
======
nostrademons
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_
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

~~~
nostrademons
"President of Product" is somewhat idiosyncratic to Google - I don't know any
other company with that particular title.

The etymology, I think, is specific to some quirks in corporate law, which
still has some anachronisms from the 1600s. When you form a new organization,
there are 3 positions that are assumed to exist: President (overall leader),
Treasurer (responsible for keeping the books & finances), and Secretary
(responsible for writing down meeting minutes). These are enshrined in
corporate law, so when you form a new corporation, the bylaws need to specify
holders for these offices (it's common for the founder to hold all 3, or to
split them up among founders). The idea of a corporation in the 1600s didn't
really envision today's massive multinational tech companies, so the actual
org structure departs fairly significantly from these "official" offices.

There's a rough correspondence that's developed though: President = CEO, and
Treasurer = CFO, and Secretary = whoever's keeping the minutes. Sometimes
you'll see this in official titles, as "President and CEO of X". Sometimes -
particularly when you have a visionary CEO who needs a strong operational COO
- the President title will be assigned to the _COO_. This is Gwynne Shotwell's
title at SpaceX, and is a strong indication that actual operational leadership
of the organization rests with the COO. A "Vice President", by analogy, is
someone who helps out the President with the details of their duties. In the
U.S. government there's only one Vice President, but many corporations have
dozens.

Google's tripartite leadership, with Eric as President & CEO, Larry as
President of Product, and Sergey as President of Technology, was a way of
showing that _all 3_ of them were in charge, and actual leadership rested with
the triumvirate. If Larry had been VP of Product (a title actually held by
Jonathan Rosenberg), it would've put him subservient to Eric, which is not how
Google's leadership was actually structured.

The reason most companies don't do this is that it's usually a really bad
idea: having multiple bosses typically results in the destruction of the
organization. Google could get away with it because they were _so_ far ahead
of the competitors and _so_ profitable that having Larry & Sergey running
around sponsoring crazy innovative products did not seriously impede the
running of its normal business. It also speaks extremely well to the working
relationship among the triumvirate, and Eric's humility in leadership.

~~~
lioeters
Very insightful. I had the same question why it's always the VP of Engineering
but rarely does one hear of a _President_ of Eng/Product/Sales, etc.

Thank you for providing historical context in explaining these roles and how
they worked at Google.

> the working relationship among the triumvirate, and Eric's humility in
> leadership

Respect!

------
thecupisblue
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.

~~~
fredley
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.

~~~
bartread
This is where roles like VP of Engineering _can_ be helpful[1]. However, I
have to admit, I can't immediately list a ton of technical founders I've met
who'd be happy to be called VP of Engineering rather than CTO.

And just because they have a job title that you can theoretically hire above
doesn't mean they're going to like it. And if they don't like it they'll
probably quit (might be a good thing) - I know I would.

There are other options though:

1\. Put in place a development plan for your founding CTO, and other C-levels,
so they can actually grow with their roles. Again, this isn't something that
will work in all cases, but it can certainly help. My CEO has been through
something similar, from a tiny 2 person startup, to now successfully running a
200+ person company.

2\. Transition them into a new role. Tricky, and not going to work for a lot
of people, but possibly an avenue worth considering.

 _[1] Not only can you bring in a CTO above this, but also SVP and EVP roles._

~~~
Ididntdothis
In the companies I have seen I never understood the difference between CTO and
VP Engineering. Some had only one of them, some both. I understand that
somehow the CTO sets the technological vision and the VP executes but I have
never seen this really work. Especially in tech companies where a lot of
people spend their whole time on developing the vision.

In a small company CTO seems more like a cool title than actually a real role.

~~~
derefr
All C-suite roles are meaningless outside of large companies.

In large companies, C-suite roles all mean “someone who comes up with company
strategy given a particular set of incentives.” E.g.:

• A CEO is the voice of the Board of Directors within the company hierarchy,
and—because they can be _fired_ by the Board—is incentivized to strategize in
the direction that will give shareholders value and address their demands.

• A COO is ultimately responsible for the company’s operations, both its
operational expenses (e.g. product sitting in warehouses depreciating) and
operational revenue (liabilities incurred for income unmatched by
deliverables); and is on both sides incentivized to strategize in the
direction of making the operations pipeline “leaner”—in est, getting other
parts of the supply chain to “hold the bag.”

• A CTO (or CIO, depending on the type of company) is ultimately responsible
for any IP assets on the balance sheet; and for any expenses that go into
producing such IP. As such, they’re incentivized to create and fund R&D
efforts (but also to make them lean), and to push to acquire companies with
valuable IP (but to be a miser in the M&A negotiations.) They’re also
incentivized to find new ways to exploit any technological resources on the
balance sheet, in order to increase their liquid value.

• A CPO (Chief Product Officer—not that many stable, large companies have
anyone by that name) is ultimately responsible for _exploiting_ developed or
acquired IP assets by building operational revenue sources “around” them, and
is measured by the new revenue sources they create. This is what a startup’s
“business founder” really is, most of the time, except when they’re raising
(during which they’re more playing the CEO role.)

I would liken a company’s C-suite to a Congress: it’s a bunch of people with
mostly equivalent _responsibilities_ (define top-level strategy and delegate
out the execution) but different _constituencies_ driving their beliefs and
preferences.

If you’re actually doing anything in your job that a “corporate Congressman”
wouldn’t do, then you’re not really in a C-suite role; or, at least, you have
multiple roles within the company, and your C-suite role is just a part-time
gig.

(I would highly encourage the latter POV: if a technical cofounder is _both_ a
CTO and a Head of Engineering, then later they can give away or delegate one
of those titles while retaining the other. I say “delegate” because, as a
cofounder, they’re a shareholder on the Board, so ultimately they’re “above”
whoever the CTO is, through the office of the CEO, even if they don’t
_personally_ end up holding any C-suite title in the end.)

~~~
NikolaNovak
>>A CTO (or CIO, depending on the type of company)

I have seen companies that have both. Purposefully before Googling it
myself;), my personal experience in such cases CIO would be more business
oriented and have a more software/data oriented view; whereas a CTO would be
more implementation, technology, infrastructure, enforcement of standards and
policies orientation.

Edit, after Googling, other disagree with my experience: _CIO is for internal
operations, CTO is for external business_ :

[https://www.linkedin.com/pulse/difference-between-cio-cto-
ra...](https://www.linkedin.com/pulse/difference-between-cio-cto-rahul-singh)

[https://www.telegraph.co.uk/business/ready-and-
enabled/cio-v...](https://www.telegraph.co.uk/business/ready-and-enabled/cio-
vs-cto/)

~~~
derefr
If your company’s IP is in the form of technology, the CTO drives R&D strategy
and the CIO is a purely-tactical role; if your company’s IP is in the form of
information (e.g. a GIS or other data-product company), the CIO drives R&D
strategy and the CTO is the purely-tactical role.

------
mooreds
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
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
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
VP Eng should report to CEO, not CTO.

~~~
marcinzm
Which makes a technical inward facing CTO somewhat pointless to me and less
impactful than a chief architect reporting to the VP of Eng.

~~~
khalilravanna
I've seen the CTO report to the VP of Eng and I think it was exactly this.
They were essentially the chief architect. VP of Eng handled talent and
strategy. It was essentially a transition for the CTO who just didn't like the
people side of it but was a baller at the technical side of it so they went
from reporting to CEO to VP. It seemed to work out very well.

I imagine it only works if you have a CTO who's doesn't let the change in
reporting structure bother them (i.e. someone who isn't egotistical or vain).

------
reggieband
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
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.

------
cik
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.

------
mrits
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.

------
simonebrunozzi
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
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
Thanks! One day I'll write a book about everything :)

------
jgrahamc
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.

------
methodover
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.)

------
juris-ws
Shameless plug: Reminds me of [https://www.about.wiserstate.com/post/startup-
cto-many-hats-...](https://www.about.wiserstate.com/post/startup-cto-many-
hats-outside-comfort-zone).

