There is also a senior enlisted staffer at USNA Admissions who is the go-to person for enlisted applicants. Call the general Admissions number, and they can steer you to him/her, if you need specific help.
For your package going up the chain to your CO, I suggest consulting the admin experts in the front office on how to prepare it, as well as working with your immediate chain of command for their support and advice on staffing your package. I reviewed many of these when I was in command, and I was always impressed when an enlisted commissioning package arrived with everything clearly laid out as to what was being asked for, when it was needed, required format, and suggested draft recommendation for my review. This whole initiative should not be a surprise to your immediate leadership. Their support and recommendation to the CO will be key.
Have you sought out any USNA grads amongst the junior officers to ask for their insight and mentoring?
Don't be surprised if you land on the CO's schedule for a visit. I never signed these blindly. It was my signature on a document stating the applicant was a worthy candidate for commissioning and had my trust and confidence. Be prepared for questions about your motivation to become an officer, why USNA is your preferred route, the role of an officer versus a senior enlisted leader, etc. I recall an applicant who replied "because it pays better," when I asked him why he wanted to be an officer. I did not sign off on his package at that time. I did send him on some "instructional rounds," and he stepped up to the plate.
And - good luck!
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