The Call That Changed Everything
It started with a simple phone call from one of my former General Assembly students.
"We're in over our heads," Ran admitted. "We landed Google as a client, but we don't have the technical expertise to deliver what they need."
I remembered Ran Craycraft and Kevin Ng well from my coding class in Santa Monica. They were ambitious, creative, and determined to build something exceptional. After graduating, they'd started Wildebeest — a design and development agency with bold visions but limited technical capabilities.
And now they had a client whose name carried weight: Google.
This wasn't just another freelance opportunity. This was two founders reaching out for help at a critical inflection point. Their entire business, their reputation, and their future client relationships were on the line.
What had started as a small design shop had gained impressive traction with some of the biggest brands in the world. But with those opportunities came technical challenges that far exceeded what two only-recently-graduated developers could handle alone.
That call marked the beginning of a journey that would evolve from technical consultant to tech lead to Head of Product — a transformation that would shape not just my career but the entire trajectory of Wildebeest as an agency.
From Teaching to Building
My relationship with Wildebeest was unique from the start. I wasn't just another hire — I was the teacher who had given them their technical foundation, who understood their capabilities and limitations.
This created both challenges and opportunities:
The Challenge: How do you transition from being someone's teacher to their technical leader? How do you help founders level up their technical skills while simultaneously delivering high-stakes projects for major clients?
The Opportunity: The chance to build something from the ground up with founders who already trusted me implicitly. To create not just code, but processes, culture, and standards that would define a growing agency.
In those early days, I spent long hours working directly with Ran and Kevin, often late into the night. We weren't just building applications — we were building a shared understanding of what great software development looks like. Every line of code was a teaching opportunity. Every architecture decision was a chance to elevate their thinking.
What made this relationship special was the mutual respect. They knew design and client relationships and business. I knew design and technology and development processes. Together, we could build something truly remarkable.
Scaling Under Pressure
As word spread about our work, our client roster expanded to include industry giants:
• Disney • Google • Spotify • GoodRx • Hulu •
Each new client brought more complex technical challenges. I remember sitting in a meeting with Disney executives as they described their vision: a personalized experience that would match users' Spotify listening habits with Disney characters. The creative concept was brilliant, but technically intimidating:
"We need to analyze users' listening history, match musical characteristics to character traits, and generate personalized playlists — all at scale, with enterprise-grade reliability."
The room looked to me for an answer. Could we deliver?
The honest truth was: I didn't know. Machine learning wasn't my expertise. But I knew we could learn.
That night, Kevin (the CTO) and I started teaching ourselves machine learning algorithms. We spent weekends experimenting with data analysis techniques. We read academic papers on recommendation systems. We failed repeatedly until we understood enough to architect a solution that would work.
This pattern defined our growth:
- Face challenges beyond our current capabilities
- Make a commitment to learn what was needed
- Dive deep into new technologies
- Deliver exceptional results
Building a Team That Delivers
As projects grew more complex, I realized we needed more than just technical skills — we needed to build a true engineering organization with a culture of excellence and growth.
I created structured mentorship programs that balanced technical growth with psychological safety:
- Daily code reviews that focused on learning, not criticism
- Friday learning sessions where we explored new technologies together
- Paired programming that transferred knowledge naturally
- Documentation standards that made codebases approachable for everyone
What I discovered was that investing in people was as important as investing in technology. The junior developers we hired were talented and eager to learn — they just needed structure, guidance, and psychological safety to thrive.
One junior developer had been struggling with a complex React component for days. When I sat down with her, I noticed she was afraid to ask questions, worried it would make her look incompetent.
"You know," I told her, "I spent three days last week figuring out a problem with our authentication flow. I had to completely rewrite it twice before I understood what was happening."
The relief in her eyes was immediate. She wasn't failing — she was learning, just like the rest of us.
That developer later became our frontend lead, mentoring new hires with the same empathy she had experienced. This was the culture of growth and support I wanted to build.
Technical Transformation
When I started at Wildebeest, the technical foundation was primarily Ruby on Rails — the framework I had taught Ran and Kevin. But as client demands grew more complex, we needed to evolve while continuing to deliver.
I led the technical transformation across several dimensions:
Frontend Revolution
We transitioned from server-rendered templates to React and Next.js, enabling us to build more interactive, performance-optimized experiences that major clients expected.
Backend Modernization
We moved from monolithic applications to a microservices architecture based on Node.js, allowing us to scale different parts independently and deploy changes more frequently.
DevOps & Reliability
I implemented CI/CD pipelines, automated testing, and deployment strategies that turned deployments from anxiety-inducing events into routine operations.
Data & Machine Learning
We built capabilities in data processing and machine learning that allowed us to tackle projects like the Disney-Spotify collaboration.
Each of these transformations required careful planning. We couldn't stop delivering client work while we modernized. We had to evolve the technical foundation while simultaneously building on it — like replacing the foundation of a house while people were living in it.
From Technical Leader to Product Leader
As Wildebeest continued to grow, my role evolved beyond technical leadership. Ran and Kevin approached me about taking on a new challenge: becoming Head of Product.
This wasn't just a new title — it was a fundamental shift in responsibilities. I would now be directly responsible for client relationships, product strategy, and technical execution alignment with business goals.
The transition demanded new skills:
- Translate client visions into technical roadmaps our team could execute
- Manage expectations when client requests exceeded technical feasibility
- Balance innovation with reliability to deliver both creative and stable solutions
- Guide junior product managers as they learned to bridge business and technical considerations
This evolution enabled us to take on even more ambitious challenges, as I could now oversee projects from initial concept through technical execution, ensuring alignment between client needs and team capabilities.
The Ultimate Test: Enterprise-Scale Challenges
With my new role as Head of Product, we tackled two massive projects that pushed our capabilities to their limits:
Enterprise Hardware Company – Multi-Language, Thousands of Pages
This multi-million dollar project required building a corporate website with thousands of pages across multiple languages. The challenge wasn't just technical — it was organizational. We needed to coordinate with teams across global offices while ensuring consistent performance.
Three weeks into development, I discovered our initial architecture couldn't handle the scale. Page load times were already unacceptable with just a fraction of the content.
I called an emergency meeting with client leadership. With complete transparency, I explained the technical issues and presented a revised architecture.
"This will require two weeks of refactoring," I told them, "but it will save months of optimization later."
They appreciated the honesty. The revised system delivered sub-second page loads across their massive content library, even in markets with slower connections.
Custom Community Platform – Forums, Courses & Live Events
Another client needed a real-time community platform combining forums, workshops, and live events. The technical complexity centered on real-time features — showing who was online, enabling live discussions, and delivering instant notifications.
I assembled a focused team and created a phased approach that balanced technical excellence with business needs:
- Core community features
- Course delivery system
- Live events platform
- Integrated analytics
This strategy allowed earlier launch while building more complex features, reducing risk while maintaining client confidence.
The Human Element of Technical Leadership
Throughout my journey at Wildebeest, I discovered that technical challenges were never just about technology. They were fundamentally human challenges:
- Helping founders grow beyond their technical comfort zones
- Building confidence in junior developers
- Creating psychological safety for teams to innovate
- Understanding client needs beyond what they explicitly stated
- Balancing perfectionism with practical delivery timelines
I learned that empathy was as important as technical expertise. That listening often revealed solutions that technical analysis missed. That understanding the human context of technical problems led to better solutions.
This approach transformed how our team worked. Instead of treating client requests as specifications to be implemented, we treated them as starting points for deeper conversations about what they were truly trying to achieve.
Technical Leadership That Transforms
What began with a desperate call became a journey of transformation. Under my leadership, Wildebeest evolved from a small Rails shop into a technical powerhouse delivering enterprise solutions for global brands.
This journey taught me that exceptional technical leadership requires:
- Technical Excellence with Human Understanding — Building systems that scale while growing the people who build them
- Vision Through Action — Leading by example, from hands-on coding to high-level strategy
- Learning Agility — Turning new challenges into opportunities for growth
- Trust Through Transparency — Building confidence by sharing both successes and struggles
- Balanced Innovation — Delivering creative solutions while maintaining reliability
The impact of this approach was transformative:
- We rebuilt our technical foundation with React, Next.js, and microservices—not for trend, but for scale
- We created an engineering culture where junior developers became technical leaders through structured mentorship
- We developed a strategic vision that turned technical capabilities into business advantages
Ready to Transform Your Technical Organization?
If your organization is facing similar challenges—whether it's scaling technical capabilities, evolving engineering culture, or bridging the gap between vision and execution—I bring a unique combination of technical depth, strategic vision, and team building expertise.
Because the best technical leaders don't just build systems—they build capabilities. They transform organizations. They create lasting impact.
Let's talk about how we can do that together.