Cowboy in the desert.

My First Year Working at Octopus

Rob Pearson
Octopus Deploy logo

This week, I hit my one year anniversary at Octopus and I thought it would be great to share what it's like to work at here and talk a bit about our culture. I previously wrote about my first impressions on my personal blog but I'd like to dig a bit deeper.


First and foremost, Octopus has a culture of shipping! I joined Octopus just as the team was preparing to ship Octopus 3.0. This was a huge milestone and it was exciting to watch the last bugs get bashed and get the release out the door. That said, I actually started out working on improvements to including enhancements to our sales and licensing plumbing as well as building the Super Upgrade Page to make it easier for customer to upgrade and renew their existing licenses.

Soon after, I started working on Octopus Deploy doing bug fixes and enhancements as well as contributing to the larger feature releases. It's been great to see big new features like Channels, Elastic Environments and Multi-tenancy take shape and get into customers hands. I love the fact that we post RFCs (requests for comments) for new features and the community provides feedback that helps shape the product. Another thing I love is the fact we regularly ship new releases as soon as they're ready (sometimes a few times per week) instead of longer release cycles. This is a great way to the latest features and fixes to our customers sooner rather than later.

We even automated our release process so that it could be done easily by anyone at anytime. This greatly reduced the friction to shipping! It's also fun to note that we indeed do ship Octopus with Octopus!

We're on the eve of shipping Octopus 3.4 and starting some really cool new work too. It's a very exciting time to be at Octopus Deploy!


We ship regularly and we strive to ship high quality releases! Trust is the key to making this happen. The entire team trusts and supports each other in everything we do. From our founder to the newest team member, everyone is willing to share or help at any time. This is very important because Octopus is a remote friendly company and we don't have a deep hierarchy of management. Most of the team works from home except for times when we need to collaborate. Octopus is based in Brisbane, Australia and we have an office in the central business district, or downtown area, where we can work and collaborate. It's a great balance of focused remote work and face to face communication.

We are Octopus!

Building on trust, Octopus has built a great team of people who care about what they do. Everyone has strengths and weaknesses but we're all willing to share and help others. It's amazing to be surrounded by great people. My colleague Damian Brady pointed out is that we refer to Octopus as we instead of saying it or the company. We are all comfortable talking about Octopus and representing it. We are all trusted. We are a team. We are Octopus!

This was reinforced when Octopus started attending conferences and we started talking to people in person. We are representing the company to help people understand the problems we solve and value we provide.

Working Remote

The shift to working remotely has been fun and rewarding. I definitely don't miss my daily commute to work and it's given me a lot more time at home with wife and two young sons. It can be challenging at times with family interruptions but the benefits far outweigh the costs. I regularly tweet how about my work life balance and I've never had it better.

Last time I wrote the following and it's still very true.

I get to see my wife and kids a lot more, we have lunch together and I’m around if we need to run family errands. This has helped improve my relationship with my wife and kids immensely and I don’t think I could go back.


I joined Octopus as employee number 12 and our team page now has 19 people with 2 more joining soon. We've outgrown our office so the team has shifted from Wednesday sprint reviews with everyone in the office to collaborating on different days. We've also started doing a weekly remote friendly TL;DR short demo session on Wednesdays that is recorded w/ deeper sessions at other times. Overall, the changes have been positive but we're still learning and adapting.

The biggest change from our growth is that we're transition to an open allocation management style where all team members have a lot of freedom in what we do day to day. Paul helps to set the overall direction but we're free to pitch new features and select the team/task force that we feel we can contribute the most to.

New Octopus team members are paired up with a buddy and they work together in the office for a week or until they're comfortable working from home. I've been a buddy for a couple of new team members and it's a wonderful way to get to know new team members and get them up and running quickly. We also held a two day mini Octopus University bootcamp to help a couple of our less-technical team members understand the challenges of software development and the pain of manual deployments. It was a lot of fun and everyone learned a lot!

Wrap up

I loved my first year at Octopus and I'm really looking forward to many more! Again, it's safe to say I'm a happy Octopus and the future is very bright.

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