I used to be a developer, but I never became am excellent one, because I was interested in so many aspects, including (dev)ops, qa, product management, and most importantly the business side of things. At some point someone else (which is a bit embarrassing in hindsight) realized I might have what it takes to be a CTO, and I was brave enough to do that step.

Now since about four years, I'm a freelance interim CTO and help companies that struggle inside and around the product development department.

I'm glad you found your calling :)

Now I'm really intrigued by what it takes to get "freelance interim CTO" jobs - and whether this is with tiny one-person shops (where the CTO is also "the developer"), middle-size businesses (10-50), or enterprises that lost an executive to poaching or illness and need someone to plug the gap until their headhunter's got a new one lined up.

In my case, most engagements came from head hunters, and only some from my network. Also, I have a somewhat nice looking vita, which helps.

Right now, it's mid size businesses with 50-75 FTE product development departments, but when I will be 50+, I want to get also projects at bigger companies :)

Very interesting to read this. I am currently working as a UX designer, but notice I also have a very broad interest and knowledge in all parts of product development.

What was the hardest hurdle to take when making the transition?

I don't know, I think I was very lucky. I just went from job to job (I'm 47 btw, and started working in the field ~20 years ago), and it all just came to me.

The switch to freelancing also sort of came naturally - a permanent job stopped very abrupt, and a headhunter that helped me find developers before approached me with the idea, because he had a customer who needed help.

I guess you also have to be "management material". Either you can do it or not. To a certain degree, you can learn management stuff, but honestly you have to be that kind of person.

> you have to be that kind of person.

Jus out of curiosity, what exactly do you mean by that kind of person.

that sounds like me. I love developing tho, but other aspects of work interest me aswell (qa, devops, leading the team, communicating with a customer etc...) I am slowly growing in the company where I work to cover some of the roles listed. But how do you go on to become freelance interim CTO ? (as in chief technology officer)?

As described above, to me it came sort of naturally. But generally, you just have to find your first project :)

I used to be a developer until I took an arrow to the knee.

I realized at some point that 'coding for answers' was more interesting to me than applications. That discovery spurred a shift into analytics in the financial sector, followed by a post-crisis stint in government service. In the latter role sql and python were secret weapons.

I now analyze public policy for hedge funds.

This is so much me. I can whip out quick scripts to do simple tasks. But really don't enjoy other dev aspects such as polishing apps to looks and behave nicer, unit tests, etc. I need to look into this. Thanks for great morning motivation!

Any tips on making that switch? What types of jobs would you search for?

TLDR: look for 'analyst' or 'analytics' jobs where the challenges are less mathematical and more organizational.

Personal connections (even tenuous) make all the difference. One approach is to pick a vertical in which you have a secular interest that is unlikely to flag (e.g. finance for me), and be open to making the most of opportunities that might have non-obvious embedded call options. Then look for opportunities to be informally helpful to people working in that vertical (if starting at 0, look for a meetup or other public event to attend).

This can often look like a lateral or downward move to a job at which your outperformance is likely. In most analytics or adjacent roles there is still plenty of low-hanging fruit for automation, which frees up your time to add value on domain problems.

YMMV, but I found it helpful to not highlight the automation work (in fear of being pegged the "tech" guy). Instead, using the earned time to do exploratory analyses on root causes (or sensitivity or whatever) paid real dividends. Adding that kind of value has its own gravity, and my experience was that it opened other opportunities.

I'm getting pretty close to pulling the pin and retiring. I won't really need the money but will probably do a bit of consultancy now and then. Since 2003 I've been writing a memoir on living in Thailand - I hope one day to actually get around to finishing it! :D

A friend of mine recently bailed out of software and is now a qualified mountain leader.

Product Management. I do miss being an individual contributor but I'm learning quite a bit about the 'biz'

That's actually a great move. Ex-devs as Product Managers / Product Owners are the best.

I slightly disagree there. Currently have an ex-dev product owner. Who takes away the thinking of individual developers and is unable to provide enthusiasm to the team.

Having technical knowledge, yes. Very big plus. Not every developer has the other aspects of a Product owner or Product manager though.

VP of Customer Analytics at a financial institution.

I was a decent software engineer to boot but never really got into the super technical side of things. I enjoyed working with people and speaking to them about how technology can help solve their problems - hence, the role switch.

To scratch my itch, I do a bit of dev/machine learning work.

I expected a lot more people to say a blue collar career path like Construction or Plumbing, a la Office Space. Color me a bit disappointed.

Those people are out there, just not posting on HN at 2pm EST cuz they're not at a desk, they're working 10 hours on a site job.

One of my buddies was a linux admin, but now he blows glass and does custom stained-glass windows. Still has a website and does other techy stuff but mostly just playing w/ fire and sand last I heard.

Based on people I know that have bailed - its either management, or craft beer brewers