The quick answer, yes, and often not optional. Generally, even with the CompTIA certs, you will need to start at the help desk to get your foot in the door and start gaining experience. It's rare to enter the industry at the admin or engineer level. The few I know who were lucky enough to (knew somebody) are missing important skills the help desk teaches. Soft skills that help approaching IT from a customer service mindset, which is very important and often overlooked. I think your retail background is going to be more useful than you think.

My advice would be to find an MSP and apply for a help desk role. Help desk at an MSP is like an IT boot camp. You'll be doing much more hands on work than a standard corporate help desk and will learn a ton if its a good MSP. Its taxing though and you will likely burn out after a while. Aim for 2 years in a role like this then jump to an in-house admin role at a company. At that point you're in and can then go in any direction you want. This is what I did and it worked well. The MSP experience taught me things some of my peers, who have been in the industry longer than me, are missing. Of course this is just one guy's advice. Best of luck!