WOW! I love your profile! I don't mean this to come off the wrong way, but I see so many applicants with 700+ GMAT scores and not much interesting about them that I get excited when I see someone who's in the opposite situation!
I love your work experience, your involvement in undergrad, and your community involvement. All terrific stuff, and all the stuff of students in top-10 business schools. Also, having targeted CPG jobs myself while in b-school, I can tell you that your current professional experience will make you very marketable to potential employers while you're in school (and adcomms do think about this sort of thing), whether or not you actually want to go back to CPG. So, I think you're in great shape overall.
And now on to the GMAT... At first glance, my advice would be to aim for Round 2 and start studying / enroll in a class ASAP to try to get your score at least closer to the mid-600's. Don't stress about meeting each target school's avg. GMAT score, but do try to get inside their middle-80% GMAT range (most schools publish that on their sites). Don't worry about making a tradeoff by applying for Round 2... All other things being equal. your odds of success are just as good in R2 as they are in R1. And I'd recommend aiming at top schools in R2 with a (hopefully) better score than aiming at lower-ranked schools in R1 just to get your apps in by R1.
I think your profile is very strong, so I really encourage you to keep aiming at top-10 schools. You *can* get into a top-10 school with a 590 GMAT (esp. since your undergrad GPA is strong; did you have a lot of quant classes?), but I'd recommend not rolling the dice. Hustle to take the GMAT again and apply by the R2 deadline.
Veritas Prep | GMAT Prep | MBA Admissions Consulting | Co-author, Your MBA Game Plan
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