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The single most important thing you can do to retain your rankings is to make individual 301 redirects from as many old old pages as you can to the equivalent new pages.
Make sure that Old Page will redirect to Equivalent New Page with a single step ... no chains of redirects.
They MUST be 301 redirects, so keep an eye on what the techies are doing. Sometimes they think any old redirect will do the job.
It's a lot of work to set up individual redirects, so focus first on pages that have inbound links from external sources, then do as many of the rest as you can.
Once the new site is launched, invest some time to get external links updated wherever possible.
I was involved in a massive site makeover late last year, where only a handful of pages kept the same URLs. The techies lost count of how many individual redirects they made (hundreds!) but the site got through the update with its rankings intact. Within a week after launch, new URLs were starting to replace old URLs in Google SERPs; it took about a month for all three search engines to fully switch to the new URLs. Traffic is better now than last year because the site is better optimized all around, and internal pages are getting a lot more long tail traffic than the old version ever got.
I've just been through your situation with a smaller ecommerce site. Everything went well, so just take your time and make sure you have things setup right before you implement this change.
And when you said.... "First, we're going to make sure each new page is correctly optimized for the equivalent old page. I want to make sure these new pages will maintain their position in the SERPs for the targeted keywords. No one specifically told me to do this, but it seems like the logical thing to do."
I was wondering specifically how you "optimized" each new page to be the same as the old pages? If each page has the same text/body content, what else can be done do 'optimize' the new ones?
For exmaple, should I make sure that the <title> tags are exactly the same, or does that not matter?
Thanks!
It would really be bad to see your rankings dip b/c the new site wasn't optimized the same way as the original pages.