Tech Leadership: My Journey from Developer to CTO

When I transitioned from being a developer to CTO, I expected that leadership would be about making everything run smoothly, ensuring there were no mistakes, and focusing on growth and stability. The reality, however, has been quite different. The most valuable lessons I’ve learned didn’t come from the successful projects but from the mistakes, the downtimes, and the daily challenges of balancing competing priorities. Leadership, as it turns out, is less about preventing issues and more about how you handle them when they inevitably happen.

Here’s a look at some of the surprising lessons I’ve learned along the way, from system failures to dealing with sales teams who sometimes think engineers have it easy.

1. System Failures Are Inevitable

Early in my journey as a CTO, I believed it was my job to create systems that never failed. Of course, this was an unrealistic expectation. No matter how well you plan, downtime will happen, and when it does, it’s often at the worst possible time. I experienced this first-hand when a critical system went down during peak hours, resulting in significant disruption.

This taught me that failure is part of the process. Every time the system crashed, we learned something new about the weaknesses in our architecture and improved our incident response strategies. The real lesson wasn’t about preventing failure but about how quickly and effectively we could recover from it and communicate during the crisis.

What also became apparent during these times was the need for transparency. Sometimes it wasn’t the downtime that frustrated clients; it was the lack of communication during those incidents. A well-handled downtime, with clear updates and quick recovery, leaves a far better impression than an uncommunicated disruption.

Lesson Learned: Failure is inevitable. What matters most is how you handle it—having a plan, communicating effectively, and learning from the experience.

2. Failed Deployments Shape Resilience

Failed deployments are part of the journey, and they’re often where the most learning happens. I remember one particular deployment that seemed routine but ended up crashing a critical payment module. The team and I spent the night trying to fix the bug and recover from the mistake. It was stressful, and the impact on the users was immediate.

But the real value of that experience wasn’t just in fixing the problem. It taught us that we weren’t properly stress-testing features in real-world conditions. It also made us realize that our deployment processes lacked the safety nets they needed, like easy rollback mechanisms and better disaster recovery planning. That failure helped shape a more robust and resilient deployment process for the future.

Lesson Learned: Embrace failures as opportunities to build stronger systems and processes. Every failed deployment highlights gaps that can be improved for the long term.

3. Scaling Too Fast Can Reveal More Than Growing Slowly

There’s a lot of advice about scaling your product and team carefully, but in my experience, scaling too fast is sometimes the only way to see where the real issues lie. At one point, we experienced rapid growth and rushed to meet the demand by adding features and expanding the team. It seemed like the right move at the time, but soon after, we faced technical debt, performance issues, and a burnt-out engineering team.

While it wasn’t easy, that rapid growth exposed inefficiencies we hadn’t anticipated. It forced us to rethink our processes, improve our infrastructure, and re-prioritize our development efforts. Slowing down after the fact gave us the space to catch up, but without that initial push, we wouldn’t have seen where the true limits were.

Lesson Learned: Sometimes, scaling too fast is necessary to uncover underlying weaknesses in your system. You won’t always know the breaking points until you push past them.

4. Dealing with Sales: It’s a Different Kind of Challenge

One of the unexpected challenges I faced as CTO was managing the day-to-day friction with the sales team. Salespeople often have a different perspective on what it takes to run a technology product. From their side, they’re on the front lines, dealing with clients, sweating it out to close deals, and facing constant pressure. Many times, this leads to the perception that engineers are sitting comfortably behind their desks, “chilling” while they do all the hard work.

But the reality is far from that. The engineering team is often deep in the trenches, working through complex problems, resolving incidents, maintaining infrastructure, and trying to build stable systems that can support the ambitious promises made by sales. There’s a constant push and pull between delivering features quickly to meet customer demands and ensuring those features are built in a way that doesn’t compromise the long-term stability of the product.

I’ve had to regularly explain that while it may seem like the engineering team isn’t moving as fast as sales would like, every technical decision we make is about ensuring the system can handle what’s being sold. That tension is part of the job—balancing short-term business goals with long-term technical sustainability.

Lesson Learned: Navigating the relationship between sales and engineering requires clear communication and understanding. Sales needs to appreciate the complexity of what’s happening under the hood, while engineering needs to understand the pressure sales is under to deliver.

5. Innovation Can Be Risky, and That’s Okay

In technology, there’s always a temptation to jump on the latest trends and tools. I’ve been guilty of this—pushing for the adoption of cutting-edge technology to stay ahead of the curve. But I’ve also learned that new technology can bring new problems.

In one instance, we adopted a new database technology that was supposed to revolutionize our processing speeds. Instead, it introduced bugs that slowed down our system and required significant resources to fix. It was a humbling experience, and it reminded me that stability should always be a priority when it comes to critical infrastructure.

However, I wouldn’t say it was a mistake. The lessons we learned from that failed experiment pushed us to be more cautious with future innovations while still keeping the spirit of experimentation alive. Sometimes, you need to take risks to grow, but you also need to be ready to deal with the fallout.

Lesson Learned: Innovation is important, but stability is key. When experimenting with new technology, always weigh the risks and have a plan for when things don’t go as expected.

Conclusion: Leadership is Defined by How You Handle the Unexpected

As I look back on my journey from developer to CTO, I realize that the most valuable lessons came from the challenges, the failures, and the unexpected friction points. Leadership isn’t about avoiding mistakes—it’s about being ready for them and responding with resilience, transparency, and the willingness to learn.

Whether it’s managing system failures, navigating the tension between sales and engineering, or learning from failed innovations, the road to leadership is full of surprises. And while I used to think the goal was to prevent things from going wrong, I’ve come to understand that real leadership is about how you grow and improve when things inevitably do go wrong.

For anyone stepping into a leadership role, remember that the true test of your capabilities will come in those moments of difficulty. How you handle failure, how you manage expectations across teams, and how you push forward through the challenges will define your success as a leader.