Olaf Weckesser, CFO at The Pingry School in New Jersey, may come up with the best April's Fools jokes on campus, but for him, school strategy is no laughing matter. When Pingry leaders had the opportunity to acquire property from a nearby closing independent school, they seized it, even though they hadn't mapped out all the details. Now the former dorms provide housing for faculty who otherwise would be commuting long distances, while other spaces enrich the day-school and auxiliary program experience, helping Pingry stand out in a competitive market. Weckesser shares the collective efforts to shape the school's value proposition and the business strategy behind it.