There are three Zwift academies running each year.
Each of those contains a number of workouts that you need to complete in a certain time. Completing those in any shape or form will unlock a whole load of ingame goodies, such as kit, hats/helmets, shoes.
If you are one of the top performers you will get shortlisted and enter an in person competition where in the case of run and tri a team is selected which will be trained up for a specific event (i.e. New York marathon or iron man worlds). Run and Tri are pretty much at an Amateur/Elite level.
Ride on the other hand is a different type of thing. The best will get shortlisted for a 1 week in person competition where the gents compete for an actual professional contract on Team Alpecin Deceuninck and the ladies for a professional contract on Team Canyon//Sram. The gents do have an age restriction while I believe the ladies do not. Generally speaking: If you are in a shape to compete with Mathieu Van Der Poel you might have a shot at winning the Zwift academy … hence the comment was more tongue in cheek.
The helmet in question however cannot get earned and will instead get assigned to members of the professional Canyon\Sram team, hence the only way of getting that helmet is to be a woman and winning the Zwift academy or get recruited onto team Canyon\Sram in another way.
You have to be a member of the Canyon//SRAM professional team to get that helmet in-game.
Zwift Academy is an annual program that identifies exceptionally talented riders from the Zwift community. Those competing for the top prize (for women) earn a contract with the Canyon//SRAM Racing team.
I have updated my game version today to 1.44.2. I completed three of these rides last week in the hopes I will receive the jersey. After the update I have logged in and out a number of times, still no Jersey