By the time she left, in May 2017, Merriam-Webster’s account had about 445,000 followers. Ms. Naturale won three Webby awards for her work and was featured in Entertainment Weekly’s Best of 2016 list.

By bringing the dictionary into line with other playful brand accounts in industries as disparate as fast food, tires and telecommunications, she succeeded at what she says her boss, Lisa Schneider, the dictionary’s first chief digital officer, had asked her to do: Get people to pay attention on Twitter. Other dictionaries took note.

But not everyone at Merriam-Webster appreciated Ms. Naturale’s Trump-trolling tweets. Even as the account drew a surge of positive attention from the media, Ms. Naturale was barred, for months, from publicly revealing that she was behind it. When she did begin to grant interviews, they were conducted by email so that the message could be carefully controlled.

She said Ms. Schneider told her multiple times that a change in the direction of the feed was needed and implied that Ms. Naturale was trying to advance her own personal political agenda. She quit in part because, she said, Ms. Schneider was upset by the idea that Merriam-Webster was being seen as a politically progressive dictionary.

“Every time we were in the news it was a new crisis,” Ms. Naturale said. “It was treated like it was a disaster for the company.”