Working remote as a Fractional CTO

Hey,

I'm Sergio Pereira, and this is the Remote Work newsletter 👋

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Last week I told you about the two biggest mistakes I see in remote job applicants, and a big pool of opportunities most are missing out on.

Today, I'll make it a more personal edition of this newsletter, and I'll tell about how Remote Work gave me the opportunity to work as a Fractional CTO.

In fact, this path is being followed by many others in different roles, because it brings added freedom when compared to full time jobs. On the other hand, it's very challenging to stick to this "non-fulltime" lifestyle long term.

Follow me through the ups and downs:

1/ How my Fractional CTO career started

In early 2014, I left a “traditional” big consultancy career at Accenture to join as co-founder & CTO at Clickly, a friend’s startup in the AdTech space. That’s how I became a Startup CTO in the first place. We got early traction and joined the StartupBootcamp accelerator, in Amsterdam, in 2015.

We had mentorship sessions and Founder’s “braintrusts” which resulted in my network growing quite fast during those months. That’s where my first fractional CTO clients eventually came from.

During the accelerator program, I became a go-to person for other startup Founders that didn’t have a technical co-founder.

They’d ask for my help with things like interviewing their first engineer hires, integrating with a tech partner, or sorting out some AWS issue or some bug in the code. I did not charge them anything in those early days, but a couple of these "ask for help" continued over time and we made it an "official" agreement. That's how it all started.

While I met them during this in-person accelerator in Amsterdam, these startups were from all over Europe, and once I moved back to Portugal I had was doing these gigs remotely, in parallel to my Startup CTO job.

2/ How that career is going

I've been a Fractional CTO on and off. There are great things about this lifestyle, but also major drawbacks (more about that below).

I did it in parallel to my full time jobs for a few years in those early days. Mostly advisory stuff, or interim work that I'd sprint on during nights and weekend for a month or two. It was fun and brought in some extra income.

I failed when I tried going full time at it the first time. I went back to a full time job within a year. It was very tempting to just accept the offer the one of my fCTO clients extended me to join full time.

Recently I went on for a second time of going full time at being a Fractional CTO, and I feel I'm being quite successful.

3/ The bad parts of being a Fractional CTO

Not all is great about non-full time work. The biggest challenge is dealing with the variable nature of revenue. One month I’m juggling 5 clients and earning record revenue. Another month I have no clients and see no new opportunities coming in. Earnings can be unpredictable and seemingly random at times.

This is what led me to return to full time employment a few years ago. The determinism and comfort of a full time job's salary is unmatched!

Another challenge is to manage my time. It's so easy to commit to more work than I can handle. And sometimes I committed to unpaid work as an entryway for potential new clients. There were times I was badly under water.

Recently I became much better at preventing this. One key aspect is to set hard boundaries that are contractually agreed upon. Number of hours committed per week or month is a good framework that has worked well for me.

4/ The good parts of being a Fractional CTO

Obviously there are good parts, and that's the reason I've been trying to make it work for a few years now.

The absolute best part of working in a non-full-time capacity is the freedom. Mostly, the feeling that no one owns my calendar. I won't see random meetings dropping in my calendar with a feeling that it's my duty to show up. I can also take time off without asking for permission. I simply tell my clients that I won't be available at certain dates, and I don't bill those days.

There are also some more nuanced upsides, such as experiencing a broader range of industries, founder personalities, business models, team compositions, tech stacks and so on. I gain so much perspective about business areas I'd never have thought of. It's quite exciting for my personality, and would be impossible with a full time job.

5/ Can you work on such a Fractional capacity too?

Well, it depends on your skills and personality.

You need to have very distinct hard skills that makes a company want to hire you on this capacity. Fractional C roles and freelance gigs are usually created out of a specific need that's burning hot for the company. You must have the skills, independence and ownership to come in and solve it. That takes seniority, and that usually means very significant and verifiable professional experience in your field.

The personality part is more nuanced, and that's where most people get tripped up. Fractional gigs aren't posted in job boards, like full time roles. In fact, most companies I work with didn't realise they could benefit from a Fractional CTO before they spoke with me. It's a sales process, and you need to have that personality in you. Building yourself a deterministic sales process is key to succeed as a freelancer or Fractional executive.

The common case of struggle is that very senior and capable people fail to get clients. They get seriously anxious about the lack of consistent income, and go back to a full time job. I know dozens of such profiles. 

Many have reached out to me in Twitter DMs, and some have joined the Remote Jobs Braintrust. For all these I'm considering to add an extra live session about Fractional/freelance roles in Cohort 4, from January onwards. In case you're interested or have further thoughts, feel free to reply to this email with your questions.

Thanks for reading this newsletter until the end. You can read all past editions here. Make sure to share the link with your friends and colleagues so they can read it too.

See you next Friday,

Sergio Pereira, 
Startup CTO & Remote Work Lover