If you want to become more attractive to the more casual rider I could sympathize with the idea (of @AlphaDogCycling) of hiding all complexity around numbers, terms and dates and have a simple wizard. Maybe that could also be combined with the simple workout card system for those that don’t like the calendar
Also something to advertise could be audio guiding through the workouts (Would Audible Narration be a good idea? I think so - #22 by chad).
BUT…on the other hand you fill a bit of a niche for us competitive or structure/periodization needing or number crunching cyclists. And in that you shine (and should definitely stay focused in my opinion)!
Another promotion slogan you cannot emphasize enough (if that is still valid):
“As long as you keep your subscription active we will never ever rise your rate”.