The Bundle is a direct-to-consumer product, so you would need to subscribe and self-pay if you'd like to take part in the bundle. You can reach out to your insurance provider to see if they'll reimburse you part or all of the cost though!
In addition, our understanding is that HSA's and some FSA's typically do cover test strips as an OTC allowable without the need for a prescription. However, you may need to have a prescription simply for the purposes of if you were to be audited, you would need to prove you had a medical need for the subscription.
My suggestion would be that you need to call your benefits manager first to confirm that they will reimburse for the monthly subscription since it will be providing test strips to you, rather than you going to a pharmacy to get them.