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The paper researches and discusses the strategy of Chegg in the past and future with regards to what was taught in UNL’s MNGT 495H course. The data was compiled from online resources including the company’s website and financials along with insights learned during an internship and interviews done in the Summer of 2016 and Spring of 2018. The insights of how Chegg went from a textbook rental company to the student learning hub it is today include experienced leaders, acquisitions and mergers, and being ahead of the curve in the industry. The final recommendation for Chegg’s strategy is to widen its market to actuarial science exam takers as part of the general test prep solution.