Managing Tech Debt and Building Scalable Systems

Sandeep Chellani, CIO of Teach for America, and Grant Ingersoll, CTO of Wikimedia Foundation, discuss how they build systems that scale for billions of users, but maintain their personal touch.
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Grant serves as Chief Technology Officer of the Wikimedia Foundation, a non-profit devoted to keeping open-source content free and accessible to billions of people worldwide. Sandeep is Chief Information Officer of Teach for America, helping connect Teach for America corps and alumni to make an impact in underserved schools across the country.

Sandeep Chellani, CIO of Teach for America, and Grant Ingersoll, CTO of Wikimedia Foundation, build systems designed to scale. Whether they’re hosting a few billion page views a month or processing tens of thousands of applications efficiently, Grant and Sandeep are focused on streamlining systems. On this episode of CIO Classified, we unpack how they’re doing just that.

Key Takeaways

  • The role of the CIO is intertwined with the role of the CTO. To build efficient processes, you have to have the right tech stack in place in addition to the right systems for leveraging that tech stack. 
  • Tech debt piles up when you’re moving too fast. When a project’s finish line is in sight, don’t sprint to it and gloss over dependencies that could bog down your engineering organization for years to come. Be smart, not impatient. 
  • Design information systems for your users to share information easily, and effortlessly. Information silos can lead to coworkers repeating their colleague’s work, slowing down your company and taxing your employees. 

Key Quotes

  • “I look at the experience as we can deliver. Our participants are inundated with different people like schools, giving them directions, certification partners, they need coherence.They need information real time. They need tools that are created and available to them to do their work.” – Sandeep Chellani
  • “What is our core value proposition? What are the things we absolutely have to be really good at? Let’s be thoughtful. Let’s try to do them in a way that we can create experiments that allow us to build upon successes allows us to make incremental changes.” – Grant Ingersoll
  • “You really need to be set up in a different way of working than the old hierarchical way of thinking. But in addition to that, the pressures from outside to innovate are really large. I think the bar just keeps getting higher and higher when it comes to what people expect from you.” – Sandeep Chellani
  • “We have a very complex ecosystem. Of course, I would love to have more speed, but we have a dynamic as well with our community. We’re very much with the community. So, there are times where for us, it makes a whole lot more sense to actually slow down.” – Grant Ingersoll


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