If Hallmark’s business model were a Hallmark movie, the logline would be straightforward: Tired of the monotonous dating landscape, a hardworking woman is ready to try something different. As she opens herself up to new experiences, she envisions a future that no one saw coming.

At Hallmark Media, executives know it’s a turbulent time in the entertainment business, with thousands of layoffs and budget cuts being made across the industry. They also recognize that for Hallmark’s business to thrive, they have to surprise audiences with new ideas. Heading into its busiest season, Hallmark is rolling out a series of initiatives encompassing elaborate fan experiences and a new app, a massive NFL deal and the first-ever holiday cruise.

“We have to go where the consumer goes. People want to do things, not have more stuff. How do we create this?” That’s something Lindsey Roy, senior VP of...