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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.

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.

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.

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.)

>>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.telegraph.co.uk/business/ready-and-enabled/cio-v...

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.

In a very large company I see that role. But what's a CTO in a 20-50 people company that also has a VP Engineering which is something I have seen quite a bit.

It's just a name. That's what happens when a three person startup where each person took one C level role grows a bit. A CTO at a 50 person company has fewer people under them than a middle manager at a big company.

um you mean direct reports? here

They probably mean the whole pyramid. Using the ten-is-a-lot metric for direct reports, as a middle manager in a large org I can pretty easily have 8 people report to me who each have 8 people report to them on average. So that’s already more people than the entire headcount of the 50 person company, and I’m only a 2nd tier manager, and may still have a half dozen roles between me and CTO (some of whom will have fewer directs, probably)

Could be skip levels in there if the organization is extremely hierarchical.

VP Engineering isn't a technical role, it's purely management, though usually someone with an engineering background so they can talk to engineers.

VP Eng configures engineering's organizational structure, sets processes, and manages engineering managers.

VP Eng doesn't make architectural or technology decisions.

VP Eng is a good hire for many startups that start out with a CTO who isn't a specialist in management (which will be most founding CTOs).

What does the CTO do? Who makes architectural or technology decisions?

CTO title makes sense when the company is growing big. Apart from managing engineering leaders, CTO's approve decisions to share the trajectory of the company. For eg. should go with aws or gc or azure. How it helps to future of our company. We need to invest in ML or AI or xyz because we see that is the future. The day today engineering/architecture will be driven by Architects OR engineers close to the problem.

Do tech companies have CTOs? I can see that role more in a company that doesn't focus on tech. In a tech company I can see that role quickly devolving into something like the "architects" in IT departments who do pretty diagrams and presentations the whole day but are totally out of touch with what's really happening.

CTO sets the technical and architectural vision, also security and toolchain being used etc. You can think of it as CTO is leading the technical vision, while a VP of E is helping out managing the team on a daily basis, organizing the product work, managing sprint resourcing etc.

If your actually a Director its not just a cool title.

hahaha this post is funny in so many ways.

Why you are aware of the duties of a "director" of a company I take it.

> 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.

How I might explain this to a very technically-inclined audience (the way I would explain this to an executive would be "lay out the management realities of what is expected of a CTO", then sit back and wait for any follow up questions).

It may depend upon how you sell the CTO role. If you get board backing, then the technically-inclined will tend to sort themselves out if you present the CTO role evolving into one that needs someone who no longer codes 20% of the time, but instead only in their limited personal time.

Instead, the role evolves into one more akin to a sell-side investment banker, with lots of communicating between lots of different stakeholders. Endless PowerPoints, traveling road shows to meet investors, if you haven't learned yet then taking etiquette classes so you can concentrate on the conversation around the table instead of stressing over being the only one to not know what they're doing at a table in a Michelin starred establishment, prepping your tech teams on how to present to due diligence teams at customers and investors, meeting with tech teams to get high-level presentations on product technical direction while translating board and CEO strategy into those teams' terms, meeting with the board and CEO to set strategy, researching and talking with analysts about industry direction before deciding what you believe that direction will be and defending your analysis, hashing over the same topics with the board and CEO and other C-levels in a nearly infinite number of permutations, learning golf if you have to, learning how to socialize from actual professional trainers if you have to, "have to" defined by the board and investors on any number of other areas, learn how to read and parse financial statements if you haven't already, hashing out share dilution events between C-levels and your technical teams, setting leadership examples for your technical teams, mediating between engineering/technical department heads if you're in a small enough company, recruiting for such department heads, working with a mentor on how to distill and package complex technical details into salient and succinct framing for leadership, take lessons from PR professionals on talking with the media, and on, and on, and on.

Faced with such hardcore managerial demands acting as a translating layer between the technical and investor/C-level layers, and clear expectations that the board and investors want someone who dives into them without a backward glance at firing up Emacs in Javascript mode at work, most sane early founder CTO's who love the technology for its own sake would leap at the opportunity to take the reins of a VP/EVP/SVP type role depending upon the size of the company, where there is a clear expectation they would still be doing some pull requests, pair programming, etc.

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.

>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.

What's the difference?

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.

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).

if the CTO is inexperienced, you can hire a mentor for the CTO. nominally the CTO still makes the decisions, but can fall back on the mentor for advice.

a good leader also listens to his team and doesn't make decisions against the teams judgement. so it's not always necessary to replace an inexperienced CTO. you can also give the CTO the opportunity to get the experience they need in order to continue.

I totally agree! And if you really need someone on a CTO aka management/board level, you can hire an experienced person part-time.

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.

> 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.

> Well that was a predictable outcome.

Which was probably a blessing in disguise.

Absolutely!

As a CTO I’d probably hire the guy. OTOH I probably would not let prod be touched in the first place.

Will you hire me :-)

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.

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)

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.

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?

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

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.

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.

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

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.