From writing code to running a company of 300+ employees

By Zheng Li | Posted Jan 29, 2025 | 6 min. (1180 words)

Today we break down another exciting edition of Founders and Friends, the podcast we’ve created to hold conversations with visionary leaders shaping the tech industry. Today’s conversation features Paul Stovell, co-founder and CEO of Octopus Deploy, and of course, JD Trask, co-founder and CEO of Raygun. Together, they explore the realities of running software businesses, from the evolving nature of agile practices to scaling software teams efficiently.

What’s in this article

The origins of a visionary tool

JD kicked the episode off by asking Paul about the inception of Octopus Deploy and the transition from developer to CEO:

Paul: “So, around 2010, I started shipping the first versions of Octopus and had it on my blog. People started following it. They got excited about the problem space I was working in. And they started downloading it and giving feedback.”

Paul shared how his consulting days shaped his understanding of deployment challenges and inspired Octopus Deploy:

“The challenge with consulting is, you get exposed to a wide range of problems, but you don’t get to take ownership of them in the way you do when building a product.”

He explained how Octopus began as a side project to address frustrations with deployment processes, emphasizing the lack of tools for automation:

“Octopus was born out of that frustration… it should be as easy as it was to set up Git for source code, as easy as it was to set up TeamCity for my builds. I want something that I can set up to do my deployments.”

Paul’s journey highlights how necessity often drives innovation, especially when existing tools fail to solve persistent problems. His ability to identify gaps in deployment automation laid the foundation for Octopus Deploy’s success.

Agile: Beyond the buzzwords

The conversation shifted to agile practices, and Paul provided a clear definition of what agile means to him:

“Our highest priority is to satisfy the customer through the early and continuous delivery of valuable software. And to me, that’s agile.”

He critiqued surface-level implementations of agile:

“If that truly is the highest priority of your software organization, then you’re doing agile. And if it’s not, but you’re doing daily standups, planning poker, and all the artifacts associated with people that claim to do agile, you’re not being agile.”

JD added his perspective on leadership and the CEO’s role in setting the pace:

“I always find that an interesting dynamic… the CEO, the founder does set the tempo.”

Paul elaborated on aligning leadership priorities with team goals:

“If you’re, as CEO, waking up thinking about, like, gosh, it would be so much better if we could ship something in this space soon because our customers are desperately asking for it, and the software team… isn’t waking up thinking the same thing. That’s the gap to close.”

Agile is not just a methodology but a mindset. For Paul and JD, the core of agile lies in delivering meaningful outcomes that address customer needs promptly, rather than simply adhering to rituals or processes. Consider reading this article to delve deeper into the essence of agile practices and their evolution.

The challenges of scaling

Paul has experienced incredible growth during his time leading Octopus Deploy, starting out as a side hustle in 2010; it wasn’t until 2012 that it became a full-time position for him. Now, in 2025, the team of Octonauts (employees) is over 300 and has passed $50M in revenue. So, what are the challenges that come with growth at such a rate?

Paul: “Every year, it’s like, okay. We can hire thirty more software engineers this year. But what are they going to work on? The question we’ve never been able to figure out is, when does that sort of stop being effective?”

JD pointed out inefficiencies that arise with large engineering teams:

“We’re scaling product companies as though they are services companies. Why are we adding in all these people? If WhatsApp and Instagram have twenty or fifty people, what’s your excuse?”

Paul acknowledged these pitfalls and emphasized a thoughtful approach to growth:

“Octopus is a place where, if you want to come and self actualize and feel proud of the contribution you make to society and, your craft and just the enjoyment that comes with that. We want to be that workplace.”

Scaling effectively requires balancing growth with efficiency. Both leaders agree that the goal should not just be to hire more engineers but to ensure those engineers contribute meaningfully to the product.

The role of open source and venture capital distortion

Paul and JD discussed the impact of open source and venture capital (VC) on the software industry. Paul reflected on open source’s evolution:

“I think in the early days of open source, that was generally a good thing. Nowadays, the whole thing is flipped.”

He critiqued big tech’s role in dominating the ecosystem:

“Almost all open source software is done by a giant advertising company as a way to make it cool to work there.”

JD highlighted similar concerns about VC-backed companies:

“A lot of modern VCs, particularly when it plays into open source, is actually how a startup behaves nefariously as an antitrust player.”

The rise of open source as a strategic tool by big tech has shifted the dynamics of innovation. Smaller companies face increasing pressure to compete against free software backed by massive marketing budgets, distorting the playing field. For more about responsible engineering practices, check out this blog post.

Building teams and leadership

Both leaders touched on fostering accountability and creating a positive work culture. JD emphasized the importance of peer accountability:

“It is far better for the peer group to hold people accountable than for accountability to be driven top down.”

Paul added his thoughts on cultivating a motivated team:

“The goal is to bring together a diverse group of people who are going to produce things that they’re proud to have done.”

JD also shared how trust and clear communication are essential for effective leadership:

“You need to understand this to help you figure out how many things you have to say no to. It simply zeros you in on what matters.”

Leadership is about creating an environment where teams thrive, take ownership, and align with the organization’s goals. Building trust and empowering teams is at the heart of effective leadership. Check out this post about building high-performance teams.

Closing thoughts

We hope this candid conversation between two tech leaders gives insight in to what it takes to build and grow a successful software company. To hear more from these two experienced founders, check out the full episode of Founder & Friends - The Truth About Leadership: From Writing Code to Running a Company of 300+ Employees.

About Paul

Paul Stovell started Octopus Deploy in 2010. It was an after-hours and weekend side-project that has now become a category-defining company. Octopus Deploy now assists thousands globally with automated and consistent deployments.