Grading for a New Generation: A Look Back at Gradescope’s Path to Acquisition

By Wayee Chu

For many entrepreneurs, the path to success isn’t linear. It’s marked by serendipitous events, big wins and countless failures. For Gradescope, it was their heads-down, product-driven mentality that led them to an unexpected yet fortuitous acquisition and partnership with Turnitin, an edtech leader focused on plagiarism detection and writing improvement.

Gradescope is an AI-assisted grading tool used by teachers at 500+ universities across the country. Educators are initially attracted to the tool to solve the immediate pain point of grading, but they soon learn the power of Gradescope goes far beyond making grading more efficient, it actually improves the learning process and provides a clear feedback loop to students.

The company roots began as a prototype called Pandagrader, a collaboration between Arjun Singh, his AI professor at Berkeley, Pieter Abbeel, and fellow teaching assistant, Ibrahim Awwal. The tool streamlined the tedious part of grading lessons and homework assignments and became an instant hit among TAs and instructors. The homegrown tool was quickly adopted by renowned institutions including the CS departments at MIT and Stanford.

In 2014, Arjun met Sergey Karayev, a fellow PhD student, while co-TAing an AI graduate course at Berkeley. They started to hear from educators across the country that they were grading their coursework in half the time. Given this growing demand, they asked themselves an important question: Should they open source the platform or create their own startup? They decided to go all-in on building a better product, and Gradescope was born.

Today, Gradescope is used by over 13,000 instructors across 500+ universities, including Georgia Tech, UC San Diego, UCLA, University of Washington, Carnegie Mellon University and University of Michigan.

I met Arjun and Sergey in 2016 when we were introduced by one of their earliest investors, Manu Kumar of K9 Ventures. Looking back, it’s easy to remember what made us excited about Gradescope — they had an ambitious mission to understand how students learn and even improve their learning experience with higher quality, more responsive grading and feedback, we also saw an exciting market opportunity that went beyond higher ed, and, most importantly, they had a unique dual perspective. It was a company being built by students who were also educators, founders who deeply understand the pain points from both sides of the equation.

With Gradescope, teachers can save time grading and are armed with real-time student data to assess how well they are teaching. The robust data analytics engine that drove this personalized feedback loop is one of the most unique aspects to the Gradescope platform. Students are able to receive timely, accurate feedback on their work, while educators in return received granular levels of data in better understanding how their students learn, thus improving their own teaching process. The grading process becomes a more reliable, trusted and consistent process for all.

Our mission at Reach Capital is to support tools that enable more thoughtful and meaningful connections between students and instructors. We invested in Gradescope early and were excited to support this exceptionally scrappy team of incredible technical talent, a team that was applying a smart use of AI with a very targeted application, supercharging people, not replacing them.

We believe our vertically-focused fund and our network of education entrepreneurs, advisors and funders contribute to an ever-growing supportive edtech ecosystem, a pay-it-forward community that specifically supports each other, from offering tactical support for education sales strategies, to user and customer success engagement with teachers and students.

Time and again, we see our edtech community make meaningful and successful connections. Chris Caren, CEO of Turnitin, met Sergey two years ago at a Reach-hosted networking event right on Sand Hill Road. Turnitin provides instructors with the tools to prevent plagiarism, engage students in the writing process, and provide personalized feedback. Clearly, the opportunities for potential partnership were already brewing given the two company’s common goals of providing personalized feedback, yet the differentiation (and complementary business offerings) was Turnitin’s focus on writing and Gradescope’s strong usage across STEM subjects.

Last year, Chris was a guest speaker at our Reach Capital Founders’ Day and spoke about his experience in scaling a company culture of growth. Chris was pivotal to Turnitin’s path from what started as a graduate student’s project on text pattern matching to a comprehensive suite of writing tools adopted widely across the US and internationally. It’s safe to say the conversations and connections over the last few years between Chris, Arjun and Sergey resulted in more than small talk and yielded an exciting new partnership.

We’re confident that with Turnitin’s trusted brand, comprehensive product and distribution platform and deep expertise in the education space, Gradescope can pursue its vision and continue to scale for years to come. We see a logical extension to Gradescope’s grading and feedback capacity unleashing new product opportunities for Turnitin, particularly in the STEM disciplines. Importantly, many of the machine learning capabilities of Gradescope are leverageable across other Turnitin products. We are confident this partnership will continue to make a meaningful impact on how students learn and how teachers teach for years to come. At Reach, we’re excited to support Arjun and Sergey and the entire Gradescope team as they embark on this new journey. Congratulations to the Gradescope and Turnitin teams on this new chapter.