If you’ve been following Octopus Deploy for a while, you’ll know we’re not big on buzzwords or empty programs. We like things that work, matter, and help us grow - not just as a company, but as individuals. Leadership has never been more important as we hit a new inflection point in our journey - scaling up fast, welcoming new Octonauts, and tackling bigger challenges.
This September, we invested significantly in our leaders: a 3-day, in-person LEAD program in Brisbane. For a remote-first company like ours, this was more than just another calendar event - it was space to learn and connect.
Why LEAD - why now?
When we started Octopus, leadership was simple: a handful of us, sleeves rolled up, figuring things out together. But as we’ve grown, the job of a leader has changed. It’s not just about making decisions or setting direction. It’s about building bridges, connecting strategy, fostering trust, and helping others do their best work - especially as our teams become more diverse and distributed around the world.
When you work remotely, it’s easy to forget the power of face-to-face connection. Zoom calls are great for getting things done, but they can’t replace the energy, trust, and creativity from being in the same room. That’s why we brought together 40 people managers and senior leaders worldwide two years in a row. Some of us met for the first time after years of working together online. Others reconnected and deepened relationships that had only existed in pixels and Slack threads.
What made LEAD relevant for us?
We didn’t want another leadership course straight off the shelf. LEAD is hands-on, immersive, and grounded in the realities of leading at Octopus today. Here’s how we built it:
- Peer learning (40%): We learn best from each other. LEAD was full of dilemma sharing, coaching, and cohort support. The candid conversations and collaboration with other leaders, including some of our ELT, were some of the most meaningful parts for participants.
- Practice (40%): Games, simulations, and real-world scenarios bring the theory to life. Whether it’s a high-energy (an outrageously high level of cheating) game like Grimsby’s Code, these activities help us see leadership in action — laughing at ourselves along the way.
- Psychology & neuroleadership based theory (20%): We ground everything in science but keep it practical. Tools like DiSC help us understand ourselves and each other, and feedback loops encourage us to keep collaborating beyond silos.
What did our leaders take away?
Participants of LEAD didn’t just learn - they evolved. They walked away with:
- A clear leadership identity, aligned to our Leadership CODE.
- The ability to empower others while managing outcomes.
- Skills to foster psychological safety and inclusion, especially in remote-first teams.
- The confidence to lead change, build resilience, and communicate effectively—even when things get tough.
But maybe the biggest takeaway is connection. Time and again, we heard from participants that the most valuable part was meeting peers from across the business, sharing real issues, and building honest, understanding, and supportive relationships. Leadership can be lonely; LEAD ensures it doesn’t have to be.
Some feedback that’s stuck with us:
- “I really got to connect with my peers in a way I haven’t been able to prior to now. The process encouraged us to be more vulnerable and dig into things that really matter.”
- “I’ve been able to build real honest connections in a way I don’t know if I could otherwise”
- “The DISC profile surprised me. I’ve been suspicious of models like this, but the value came from the discussion and activity—it helped me learn how I might be perceived by others.”
- “Meeting managers from other departments and sharing practical issues relevant for all Octopus.”
- “Learning about managing polarities really helped explain a lot of the pain we feel at the moment, that was a real ‘aha’ moment.”
- “Leaning into the leadership ‘tensions’ that exist and exploring them from all angles - was a weight off my shoulders. It’s not just me who worries about these things.
These aren’t just nice-to-haves. They’re the foundation for the leadership we need to scale and help our customers solve real issues.
The road ahead
The LEAD offsite in Brisbane was a big investment - in time, travel, jet-lag and energy, but the payoff is already clear, our leaders left with more confidence, stronger connections, and a renewed sense of purpose. They’re better equipped to lead with empathy, clarity, and courage—qualities that matter now more than ever.
Octopus has grown fast and profitably and has an awesome culture. Our leaders are the glue between strategy and execution, culture and performance. They’re the ones who carry our values forward, shape our culture, and help every Octonaut do their best work.
As we continue to grow, we’ll keep investing in our people and our culture. Because at the end of the day, leadership will take Octopus Deploy from where we are to where we want to be.
Here’s to leading together - wherever in the world we are.
Happy deployments!
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