How to find work as a contractor: Learning from Rob Isenberg
Writing the best pitch and getting creative with platforms like Upwork
Rob Isenberg
London, UK
Worked as a professional magician before getting a tech job
Has been working as a developer for nearly two decades
Has been a freelancer since 2010
Author of The Pragmatic Programmer's Docker for Rails Developers
Behind the scenes
I met Rob (LI: @robisenberg) in 2022 while working for The Room, a London-based startup. As the acting CTO, he was the one who interviewed me. We did a live coding test together and I remember feeling very comfortable during our call.
It doesn’t matter how experienced you are. You’ll always feel nervous in a situation like this. A good interviewer knows how to get the best out of you.
So Rob, what's your backstory?
I studied computer science at uni, but I didn't end up getting a tech job straightaway. I actually worked as a professional magician for two or three years afterwards. And then I decided to start a business with this friend of mine. We wanted to help overweight teenagers lose weight.
We wrote a book, and of course, we made the mistake of writing the whole book before getting anyone interested in it. We were hopelessly naive.
In the end, we ended up building a website because we thought it was free and people could come to it. That's what got me back into tech. The business eventually failed, but I ended up working for this small agency in London using ASP.NET and PHP.
What do you do now?
I'm contracting for a startup based in New York called Qwoted. It's essentially a marketplace for journalists, PR professionals, and subject experts.
How did you get a US-based job from Europe?
I got it through Upwork. Most people think that Upwork is only for small tasks done by developers with really low rates, like $10 or $20 an hour. But you can also get ongoing work, and some contracts are offering really good rates like $100 an hour, or even higher sometimes.
And it's all paid through Upwork. You submit your timesheets and you get paid weekly, which is really good for cash flow.
How do you succeed on Upwork?
You need to write your profile and make it as good as you can. Then, you have to check frequently. If something comes up, you want to get there first with a pitch quite early on. I spend a lot of time on the pitch, tweaking it to be more appropriate for each place.
When they're reading it, it has to resonate with them.
For Qwoted, I did this really tailored pitch. It's over a thousand words and it's really targeted at them. They actually wanted someone based in the USA, with earnings of at least $10,000 on Upwork. But right up front, I said: “You know, I'm aware I don't meet these preferences of yours, but can I please just address that?”
What they want to verify, is not that you can earn that money on Upwork, but that they can trust you.
How do you find work as a contractor?
I think you need to reach a certain level in your career where you're confident, and you have things that you can point to and say, look, I've worked on this project, I've worked on that, and you can demonstrate an ability.
Then for years and years, when I needed a new role, I used to upload my CV to different job boards. And I'd have almost daily calls from recruiters, where I chose the roles that seemed the most suitable.
But now, it seems like this era has passed. Maybe the markets will pick up, but there seem to be very few contract roles at the moment. That's why I've been broadening to platforms like Upwork, trying to be a bit more creative. I'm asking:
How do I attract things to come to me, rather than me going out looking for them?
What's your plan?
I've worked for quite a few startups now, and I see some common problems that they fall into. Often the founders don't necessarily understand the technology or how to get the best from their tech teams. So I'm thinking of writing a book and a series of articles on things that early-stage startup founders would find useful.
I can then use this as a way of getting inbound leads from people who like what I have to say and might conceive uses for me at their company. I recently bought the domain TheStartupCTO.com for this as well. There’s nothing there yet, so watch this space.
Do you have any advice for someone starting out?
When you're early on, the experiences you get are the sort of things your career is going to be built on.
Optimizing for better experience and learning from really good people will help you grow so much faster than just trying to earn the most.
That’s a wrap!
If you have any questions for Rob, reply in the comments below.
See you next time ❤️