In March 2020, Twiddy & Company, a family-owned vacation rental company known for hospitality rooted in personal interactions, needed to adjust to contactless, remote customer service. With the upcoming vacation season thrown into chaos by the COVID-19 pandemic, president Clark Twiddy had a responsibility to the company’s network of homeowners who rented their homes through the company, to guests who had booked vacations, and to employees who had been recruited by Twiddy’s reputation for treating staff well. Who, if anyone, could he afford to make whole and keep happy?