Gayle was struggling with picking a name for her first child, so she created JustPickAName.com to help with this. This webapp lists the most popular baby names, but merges alternate spellings of names. This allows parents to more easily see what are really the most popular names. The site also allows favoriting of names, sharing lists of favorites, and adding custom alternate spellings.

For many years, Wharton's 2nd Year MBA students had a tradition where, just prior to graduation (and all-class trip to Miami), people would list their "top 5 crushes." If there's a "match" between two people, they are notified of this. Prior to the class of 2010, this "system" was managed through an assistant in India, who would do this semi-manually. This was, not surprisingly, very messy and problematic. For the Class of 2010, Gayle built a website to run this whole system. Students enter the email addresses of their crushes during a designated week and are notified at the end of the week of how many matches they had (and how many other people listed them). This system has now been used by four graduating MBA classes at Wharton, and by several other top MBA programs, including INSEAD and Kellogg.

Noticing that so many young professionals faced the so-called “Seattle Freeze” -- a term referring to Seattlites being friendly but never welcoming - Gayle founded “Seattle Anti-Freeze” in 2007. Together with her business partner Scott, they plan and organize social, athletic and community service activities for young professionals in Seattle. Seattle Anti-Freeze uses a custom ticketing system, built by Gayle. This offers a number of advantages, including increased profits (by cutting out the margins of other ticketing platforms) and custom features (such as public guest lists, reselling tickets, and custom waitlist management).

Gayle created PictureMash to help her manage pictures. PictureMash helps you organize and manage your pictures better with its many features. It can group your pictures logically – and automatically with its Smart Folder feature, merge your albums from other photo hosting sites, lets you add tags and related links, and even lets you create one feed for all your friends!