Purpose-Driven Learning: How I became CTO of room2learn

By Ryan Leaf

“You have to choose between taking a business path or a technical one. You can’t do both.”

This was the advice that a mentor gave me while in my Freshman year of college. I was struggling in my Computer Science program; I often felt like I was missing a significant portion of what was being taught in the classroom. As I took each successive required CS class, I felt more and more lost. My grades fell from A’s to B’s and then to C’s.

Despair set in. It felt like my dream of studying Computer Science and starting a business was coming to an end. I loved technology and the idea of being able to build products through code. But, somehow I was getting more lost as time went on.

What crushed me the most during this time was the lack of encouragement and support by those around me. My friends and professors didn’t believe I could overcome my challenges in the classroom and actually be able to write code and build a business. They encouraged me to take the easy path: focus on graduating and getting an “average” job. While I knew this path wasn’t true to myself, I began to believe them.

Learning for myself

I had tried learning to code many times in the past, but failed every single time. After college, I picked up Michael Hartl’s Ruby on Rails Tutorial and began to follow every section, step-by-step. In a few short weeks, I had built my first web application.

Since I was learning with the purpose of building a product for a business I was starting, staying committed to the journey became a lot easier. I wasn’t simply learning for the sake of learning; I was learning to create something valuable to the world. Learning shifted from being all about me to serving a greater purpose.

Accelerating that Growth

Student founders hard at work at the Harvard Innovation Lab.

In 2017, I joined a startup at the Harvard Innovation Labs. There, I found a supportive community that encourages everyone to do their best work. In contrast with my college experience, my peers demonstrated persistence, commitment and perseverance. They readily shared their experience, knowledge and insights with me.

Shortly after arriving at the iLab, I had a highly transformative conversation with one of my mentors. She recommended I read Nail it, then Scale It by Nathan Furr and Paul Ahlstrom as it changed her way of thinking about building startups. In reading the book, I began to reflect on many of the mistakes I had made in my own journey.

My audio library of books on business, leadership, and personal development.

For some, mistakes would spell defeat, but I was more driven than ever. I began looking for more books to read on business, leadership, and personal development. I did this haphazardly in the past, but now I had a dogmatic approach to reading books and incorporating the learning.

For the first time, I had an immediate feedback loop. The knowledge in the books I read could be directly applied to many of the immediate issues the startup was facing as it scaled. I was grew as quickly as the company did. I learned more in the past 6 months than I did in the 4 years I spent in college. The stakes are higher too: successfully accomplishing a task was now a matter of survival for the company

Joining room2learn

These experiences led me to join room2learn as the Chief Technology Officer. I met Jane during my last months at the iLab, and we bonded over the importance of the right environments for learning.

While my technical skills were certainly an important factor in joining the team, even more important was my ability to develop relationships and apply my business acumen to technical issues. According to a 2013 NACE study, technical skill is the 7th most important factor companies consider when considering a candidate for a position. The rest are “soft” skills.

I spend a large chunk of my time on non-technical topics. As the company grows and the scope of the product increases, my ability to find, recruit, lead, and manage a team of people to build the room2learn platform becomes more essential. A successful CTO brings not only deep technical knowledge but inspires and directs others to do great work.

One recent project I worked on that bridged technology and people at room2learn is the new and improved search feature.

The new room2learn search function allows teachers to find relevant content more easily.

The focus of the new search implementation is to make discovering content easier, helping teachers find designs for specific learning and teaching styles. At room2learn, we’re committed to helping teachers make the most of their learning spaces to help their students find purpose in their learning journey.

Looking for layouts and DIY hacks for “collaboration” or “personalized learning”? Check our our new and improved search feature at room2learn.org today! What do you think? Let us know on Twitter, Facebook, or Instagram!

Ryan Leaf is an entrepreneur, technologist, and software engineer who is passionate about the intersection of technology and education. At room2learn, Ryan leads product development and technical strategy. Previously, Ryan was a software architect at Doorbell and founded Minsilo. Ryan received his B.S. in Management Information Systems from Worcester Polytechnic Institute.

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