If you're seven years out from Stern then your GMAT will matter much more than your GPA. However, the GPA is a measure of your ability to maintain interest on a long, challenging task. Your GPA is far below the average at even a very modest MBA, so you'd need to be above the average on other factors.

Stern is a top school for your career, and perhaps doing your MBA there is a good option. I think they would ease in their own alumni. Otherwise you'd perhaps consider Wharton, Booth, Kellogg or Harvard, which are also well placed for insurance operations MBAs - partly because of their scale. For those schools, you'd need to emphasise that you're not a career changer (your GPA would make them worry about your lower chances with consulting firms, for example).

Stern allows some alumni to take up to three credits a semester after graduation. Maybe taking come course work part time and getting a high GPA would also strengthen your hand?

Stern allows some alumni to take up to three credits a semester after graduation. Maybe taking come course work part time and getting a high GPA would also strengthen your hand?

^This. Showing that you are a more responsible student now, and a strong GMAT will greatly improve your chances. Otherwise I believe you will have a tough time with that GPA.

Agreed. And a main goal in your personal essays should be trying to explain your low GPA, and how you've made progress in your professional life to make up for it.

And an above-average GMAT score is a necessity.