Interviews

Interview: Ben Coltrin, Founder of Remote Tech Jobs On Freelancing As A Programmer

Ben Coltrin interview

Coding or programming is one of the hottest industries in the freelancing market.

Coding is also one of the highest paying freelancing jobs right now.

I reached out to Ben Coltrin, the founder of the new tech jobs board Remote Tech Jobs, to pick his brain about what it’s like to work as a freelancer in the tech industry. As well as to talk about the best ways to get started as a freelance coder. He also shared valuable advice on how to impress your clients as well.

Even though Ben is now the CEO of Custody X Change, he’s a coder at heart. He started programming for fun in his high-school years and worked as a programmer at a local company before achieving so many great things.

His new startup, Remote Tech Jobs, aims to help fellow programmers by providing a curated board full of jobs in the industry.

Read the interview below for the full conversation.

Could you tell us a little bit about yourself and how you got started in the industry?

I started programming when I took a class in my final year of high school, and then spent that summer of 1999 programming a game for fun.

I studied computer science in college, and after my first year was lucky enough to land a job at a local company as their sole programmer, rewriting their system from DOS to Windows (using Delphi Pascal).

My dad has always worked for himself, and a number of his siblings have as well, so it always seemed normal to me to try to work for yourself. I tried a few different business ideas, and in 2004 decided to pursue working on Custody X Change. A family law attorney had approached me with the idea the previous year, and after thinking about it, I decided it was something I could feel good working on.

What’s it like to go from being a programmer to running your own company?

It started out really slow and difficult, as is to be expected. However, I didn’t expect that at the time. After I graduated from college, I took a break from Custody X Change and got a job for about six months, and then spent two years at MIT Sloan getting an MBA, from 2006-2008.

For various reasons, the partnership fell apart and I ended up acquiring my partner’s half of the business at the end of 2006 while I was in grad school. The business wasn’t really earning any money at that point, but I still wanted to work on it.

I had put a lot of programming time and effort in creating it, and I was hoping I could work on it longer. I continued to work on it through grad school, when I likely should have been doing an internship, making connections, and other MBA-type stuff. And even after all of that, it likely would have failed, or been mediocre at best, were it not for my wife.

I got married in early 2009 and we decided to give this business six months before likely having to give up on it. My wife started doing article writing and SEO work, and that immediately started improving the business. That’s a part of the business that I am not good at and really not interested in, but without it, there wouldn’t be a business, just a product.

After those six months, we decided to extend it another six months, and by that point the business looked viable, and I’ve worked on it ever since.

In 2012 I set up a physical office and hired a couple people, but didn’t experience the growth I was hoping for, and shut the office down after not being able to find the technical talent I needed. I tried a software consultancy shop to do my programming work, but that was an overpriced mistake.

Do you have any experience hiring remote workers?

In 2015 I decided to try to hire remotely. I had resisted it for a long time because I thought there was some benefit to sitting in the same room together for talking and brainstorming. But I didn’t have any other choice, so I thought I would just try it. Well, I’m glad I did, because hiring remote has been transformational to my business.

I had so many more people apply to my job post when it was remote compared to local, which makes sense. And I had my first successful tech hire, a programmer in Brazil named Andre. He was the most talented person I had found from that round of interviews, and it started me on a path toward exclusively hiring remote.

By 2019 I had hired a number of people remote, and it had thoroughly convinced me that remote was the best way to hire and to work. I had also noticed that it’s an underserved market; there are so many more job seekers wanting remote work than available positions. I wanted to help close this gap — and specifically help fellow programmers, because tech work lends itself so easily to remote work.

Is that why you started Remote Tech Jobs?

So we started work on Remote Tech Jobs in January 2020. We spent about a year programming it before the initial launch. The job board currently scrapes from eleven different sources, only takes the remote jobs, and parses the jobs to determine which programming language or languages the candidates need to have for each job.

Then we apply the tech labels to each job, so that the job seeker can just look at the jobs in the languages that they would actually like to apply to.

The trouble with most other job sites is that remote work is already a “niche”, so you often can’t accurately say I’d like a remote programming job in a certain language. But that’s exactly what you can do with Remote Tech Jobs.

If you only want to see remote JavaScript jobs, great, you won’t see the remote PHP jobs, and vice-versa. Or if you really would like to get a remote Python job that has SQL along with it, you can find that too.

I still think remote work is the future, and with so many other people having recently got a taste of remote work, the trend toward remote work is accelerating. I think that means there will be an uptick of freelance work as well as traditional work. Aside from the about one-year stint when I had a physical office, I’ve been working from home for about fifteen years now, and I’ve really enjoyed it.

Have you ever had a bad experience with a freelancer?

The first programmer I hired remotely was a real bust. I hired someone who understood the language (JavaScript / Angular) but didn’t have any experience in it.

That would have been alright, but I didn’t test his capabilities, and it ended up that he really didn’t know how to do much, and I had to find someone else pretty quickly.

The next time I posted, I really liked this guy I was interviewing. He was a really friendly person and we seemed to click. I was excited to have him on the team.

Around this time I was reading about doing technical interviews (I really like some of the old Joel on Software essays on the topic) and decided to give him a basic programming test. Unfortunately, he failed it pretty bad, and I was fortunate enough to avoid that hire.

So how do you avoid hiring bad freelancers?

I do a basic short programming interview first, and then a longer language-specific interview second. It’s helped me immensely in finding the right people.

And it helps to know that your programmers are smart and qualified when they’re remote, because projects always take longer than you’re expecting — but I’m still able to trust their skills, rather than wonder then if I made a mistake in hiring.

What kind of skills, experience, or characteristics do you look for in coders when hiring?

Apart from programming abilities, I have to make sure the candidate can communicate clearly in English, as that’s the only language I’m fluent in. I also personally want to hire people who are looking for remote work for a better work-life balance, because it suggests that they’ll stay a long time.

I let all my employees set their own hours and I’m really flexible with that, and so I like to find people who appreciate that. But even if a candidate simply had a super long commute when applying (2-3 hours round trip daily), working remotely for me is something they’d want to stick with long-term.

The other skill that I really value is someone who is a good listener. I personally don’t like to have to repeat myself, so anyone who already takes detailed notes is helpful.

I think it’s especially beneficial remote, since we have few interactions, and if tasks and ideas don’t get written down they’ll get forgotten. But this is a fairly easy skill to pick up on, so I don’t worry about the person having it or not having it, I just include it as part of the training.

Is it difficult to manage a team of remote workers who live in different countries?

I have had little to no difficulty in managing a team of remote workers. I’m not a micromanager in any way. Unless you’re taking a week off, I don’t need to hear about it. I want people to have a happy lifestyle, and work can be a part of that.

At the same time, I evaluate people solely based on the results of their work, and if someone is doing a poor job I have to fire them (it usually comes out fairly early after getting hired).

What I look for generally are people who can work independently, really without any supervision. Unless there’s something to talk about, there’s no need to have a call. An employee can go a month without talking to me sometimes.

Other times we’re talking every day. It really just depends on what each person is working on at the time. I think it averages out to about one call per week for each person I’m managing.

Also what kind of tools and strategies do you use to manage your teams?

For tools, we use mostly Slack and Skype. I like Slack because it’ll ping me on my phone and I can respond to people pretty quickly, even if I happen to not be at my computer.

Skype’s a bit old-school, but I don’t mind it because I can just ring people (I don’t setup predetermined meeting times ahead of time). Being able to video call and screen share are all I really need, and Skype does both of those good enough.

Of course, we use other tools for programming-related tasks, like Jira for issue tracking. Jira is helpful because I can organize all of the customer feedback with proposed solutions, and then order the issues and assignments to set a timeline.

I also don’t set deadlines on anything, which helps a ton with managing. My opinion is that if you set a deadline, the product quality is going to suffer (bugs) or your employees are going to suffer (burnout).

What kind of advice would you give to someone who’s looking to get started as a freelance developer or coder?

As a freelancer, I think it’s important to study the most popular languages. Right now I think that’s Android (Java), iOS (Swift) and Web (JavaScript). We do all of our coding in Angular and TypeScript, and I think they’re really great languages.

Other languages are still very helpful — I think it’s important to have a basic understanding of a few languages though, because you can have more opportunities for work. However, having a really solid understanding in one to three languages seems like a must.

SQL and noSQL can’t be overlooked though. SQL is really easy to learn and is used in so many applications. It pays to know how to write your own queries and structure a database in normal form. And considering the ease of SQL, it’s worth the time and the energy to learn.

Which areas in the tech industry offers the best opportunities right now?

If you’re really just getting started, the most important project is going to be your first one. It sets you on a path to become an expert in a language because you’ll be spending so much effort working in that language. So if you’re still looking for your first opportunity, I would suggest doing some hobby projects in one of the popular languages and try to springboard that into a gig.

However, without experience, if you can land an entry-level job, after a year or two of experience it will make freelancing in that language so much easier.

That’s what I did — I got about a year of experience in Delphi (Pascal) and then wrote Custody X Change in that same framework and language (we’ve since rewritten it).

But that year of paid experience made it so much easier for me to freelance. I even picked up a little bit of side work, and because I had experience with that language, I was able to get that side work done really easy.

With the pandemic, many businesses switched to remote working systems. Do you think more businesses should adopt this strategy? What do you think the future of freelancing will look like?

I definitely think more businesses should adopt a remote-first strategy. There are so many benefits to everyone in doing so. Companies can find more qualified people because they don’t have to restrict hiring to just the cities where they have offices. Employees can stop wasting so much time in traffic, which also helps the planet.

There are a lot of flexible arrangements that companies can do — such as partial remote, where people come in less frequently. Or even a completely remote team that has an annual retreat.

The pandemic has shown a lot of companies that their employees are just as productive (or even more so) when working remotely, and so many employees are going to want to stay remote, it’s going to force companies to accelerate their remote working plans.

Meeting in person is overrated for so many types of positions, especially for tech work, which is why I’m focusing on remote programming jobs for a job board.

This shift will definitely help the future of freelancing. As more companies are open to hiring remote, they will naturally be more open to contractors and freelancers who are remote, which will provide more work opportunities for freelancing.

I see this decade as really a great opportunity for freelancing and remote work.

Thank you, Ben for taking the time off of your busy schedule to answer my questions.

Did you find this article useful? Then you should check out my book Freelance Like A Pro. It includes 21 lessons and 5 secrets from my freelance career to help you supercharge your journey as a freelancer. Click here to learn more.

Roshan Perera
I’m Roshan Jerad Perera, a freelance writer/blogger and the founder at FreelancingHacks.com. My goal is to help other people get started in freelancing and guide them toward a successful career and financial freedom.
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