When I joined GreatPages, the platform was already supporting a rapidly growing customer base, and its monolithic infrastructure struggled to keep up. Although the core idea—creating websites and landing pages with ease—was strong, frequent crashes, performance bottlenecks, and limited system visibility underscored the need for a major overhaul.

The goal was clear: scale the platform without disrupting service. This meant restructuring the architecture while keeping everything live—a classic “changing the airplane’s wings midflight” scenario.

Gaining Trust and Taking Ownership

Early on, I navigated internal dynamics between two co-founders who were both deeply involved in development. One embraced my new ideas; the other—cautious by nature—needed assurance before committing to large-scale changes. I believed actions would speak louder than words.

To prove the viability of my proposals, I rolled out optimizations in parallel. I identified critical weaknesses in database queries and built a separate, improved version of key functionalities—rather than forcing an immediate overhaul.

This approach was tested sooner than expected. A failure in the customer charts reporting triggered a cascade of issues, impacting support response times. Amid the turmoil, I deployed my optimized solution—restoring stability and laying a stronger foundation for rapid growth. This highlighted the power of foresight and parallel planning.

Architectural Transformation: From Monolith to Microservices

With trust established, we undertook a massive effort to convert our monolithic system into microservices. This allowed us to:

• Handle rapid scaling without degrading performance.
• Reduce operational costs while improving reliability.
• Implement comprehensive monitoring for faster, targeted issue resolution.

SSL Certificates: The Critical Infrastructure Challenge

Another major hurdle emerged around SSL certificate management. GreatPages was issuing and renewing a large volume of certificates—originally via Let’s Encrypt, which required renewal every three months. As the number of custom domains skyrocketed, manually extending our quota and managing these renewals became cumbersome.

Seeking a more streamlined approach, we engaged a renowned British provider who promised they could handle expiring certificates in large batches, meeting our ambitious schedule. Initially, it seemed like the perfect fit: they pledged to complete a full migration in about a day.

However, partway through implementation, they requested we drastically slow our request volume, stretching the migration to six days. This was far off from the original agreement and would have left thousands of pages offline if we complied. We even sent fixes via pull requests to help stabilize their Kubernetes environment, but the delays persisted.

Meanwhile, we’d also considered another provider in India. Their sales pitch was intriguing but hadn’t fully earned my confidence. Fortunately, I'd already developed a Plan C leveraging Cloudflare’s APIs. Although it was slightly pricier, we had trimmed enough costs elsewhere to absorb it. More importantly, it gave us direct control over certificate provisioning and renewals.

When the British solution faltered, we swiftly pivoted to Cloudflare. This seamless backup plan prevented downtime and highlighted the importance of contingency planning—especially in security and infrastructure matters.

Growth, Leadership, and the Future

With the microservices architecture in place and a reliable SSL strategy secured, GreatPages continued to expand at a remarkable pace. Over two years, we evolved from a constrained monolith into a platform supporting billions of visits across a wide-ranging client base. Office environments were scaled up multiple times to accommodate the growing team, solidifying a culture of innovation and collaboration.

Throughout this transformation, I remained focused on engineering excellence and empathic leadership, guiding the company toward long-term scalability instead of short-term patches. The end result is a stable, adaptable platform poised for future challenges—no matter how big they may be.

Ultimately, GreatPages’ journey illustrates the value of anticipating challenges and maintaining flexible options—ensuring that growth and stability go hand in hand.