My First Weeks at Teleport

Posted on May 22, 2022

At the start of May, I embarked on a new adventure: joining Teleport as a Software Engineer. It was a bittersweet moment, because I’d really enjoyed my work at Krystal and was worried that the culture of Teleport might not match that of Krystal, but I decided to take the jump because Teleport was a product that had me really excited. I’d trialled it a few years ago, and I really felt that Teleport would offer me the chance to get knuckles deep on a project that’s really pushing new ground.

My Fears

I had a few different fears, making it not much different from most big life changes I’ve gone through so far.

Imposter Syndrome

The first is probably familiar to most of us: imposter syndrome. The interview process with Teleport had involved a two week take-home task to develop a gRPC service for executing abritrary Linux processes, with the additional challenge of adding support for cgroups based resource usage limits. I’d felt this went pretty well, but I was worried it had given a misleading view of my skills. At my previous employer, I’d recently been working with cgroups, and I was worried that whilst I understand cgroups well, it wouldn’t be representative of my understanding of other Linux features.

What Teleport had achieved so far was really impressive to me, which further added to the feeling that it was a project that I was not “worthy” of working on. Would I be the same calibre of engineer as those already working on the project? Would I be able to add value to the team? All questions which haunted my mind.

Working Remotely, Globally

I’d worked for fully remote companies the past 2-3 years, but I’d never worked for one where the team was distributed across the globe. Whilst there are a few Europeans and Australians on the team, the vast majority of the engineers seemed to be based in America so I expected lots of difficulty with communicating across timezones, especially in my first few weeks where I’d be wanting to ask lots of questions about the codebase in order to come up to speed.

Cultural differences were also a concern. Teleport hires across a range of different cultures, all with their own idiosyncrasies; would my dry British humour risk offending someone? I’ve always taken pride in trying to bring a bit of fun into the workplace dynamic, and that’s something I wanted to be able to continue doing.

The Reality


My biggest concerns about timezone differences and communication were allayed almost immediately when my manager let me know which members of the team shared similar timezones with me. This meant I had contacts I could go to first with questions, and most of the time they were able to answer them or at least point me in the right direction. Most communication within the company is handled asynchronously, and this means I never worry about missing an important meeting where decisions are made, and that my voice is always heard if I want it to be.

The work

Teleport’s codebase is about as complicated as I expected, with a tonne of different modes of configuration. But my fear was overblown, because other engineers in the team acknowledge this complexity and are always helpful in pointing out things that could go amiss. Seeing that other engineers had questions like I had reassured me that I wasn’t a lesser engineer for not immediately understanding how all of the components fit together.

So far, I’ve found the work extremely satisfying. The codebase is maturing, but still moving quickly, and this presents a lot of opportunity for suggesting improvements. There’s definitely pain points (*psst* flaky tests), but there’s often already issues setup in GitHub with a plan for how we are going to tackle it, which gives me confidence that it’s something that as a team we can overcome. There’s been a lot of learning for me, but I’ve found this quite fun, and the product is easily setup on a machine for me to get hands on and try the different configurations.


Teleport handles this greatly. There’s an array of events designed to help you meet other people within the company, and some of them look pretty cool (think cooking classes and such). As well as having these events, the company seems to have a great approach to Diversity, Equality and Inclusion, and this has meant it’s somewhere I feel comfortable with being openly gay. People within the company seem to be friendly, and operate on assuming the best rather than the worst of others, which helps with feeling welcome.

There’s a great feeling of trust within the company, with less expectation on you being at your desk nine to five, and more on you picking the hours throughout the day that works for you as long as you continue to deliver. This has been super handy for popping to the shops or gym whilst it’s quiet, or even just going on a walk to think through a more challenging problem.


It would be remiss of me not to mention the great compensation package Teleport offered me. The salary for the role is well above what I would consider London market rates, and this also comes with a healthy chunk of equity. They are clearly looking to engage and retain the best engineers in the industry, which gives me confidence that I’ll continue to learn a lot from my colleagues.

Outside of the standard compensation package, there’s other benefits such as the Wellness Benefit, which appears can be spent on anything you consider as improving your productivity, from a gym membership to new equipment for your home office. There’s also all the various coverages you’d expect from an American employer such as health, life and income protection.

I’ve not been able to mention everything I wanted to, but I felt this was getting longer than my own attention span would allow, so I’ll end it on this note. All in all, it’s been a pretty busy few weeks, and whilst it’s early days, it really feels like I’ve made the right decision here. Teleport continues to hire, so let me know if you have any questions ! I’m always happy to give my honest answer on things.