Splitting and moving site to two domains - How to redirect
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This is a great question and not easy. I would love to hear some others chime in. My guess is that splitting the pages immediately would be the best. Yes, you would lose the ability to do the change of address, but that really isn't essential. At the beginning, I would keep the content as similar as possible if not identical after the transfer (of course with different internal links).
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Thanks EGOL. Unfortunately they are committed to a full rebranding and want a new domain.
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I like this idea too

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OK... thanks for the details.
In that case. I would build newretaildomain.com. Any pages that have equivalent or near-equivalent content on currentdomain.com would 301 direct page-by-page to newretaildomain.com.
All existing wholesale pages on currentdomain.com would 301 redirect to a new page on newretaildomain.com that explains your new wholesale website and has one outlink to newwholesaledomain.com. This page will keep all of the power of the wholesale pages on your new retail site, which must be competitive in the SERPs.
This maximizes power of newretaildomain.com and directs anyone who follows links to old pages on currentdomain.com to your new wholesale website.
This would be accompanied by multiple email and snail mail announcements to all wholesale clients. Sales agents would be trained how to transition.
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My first thought was exactly what EGOL suggested. However given the decission that they are dead set on rebranding I would suggest the following.
Split the wholesale site off first, leaving the current domain in place for a transitional period. After a pre-dertmined period of time (however long they feel it necessary for wholesale buyers to get used to the new website), then change the retail side to the new brand, and take full advatange of 301 and change of address.
My thoughts hope it helps,
Don
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Interesting. At first I thought that it isn't a great experience for wholesale customers, but what if we added a meta refresh so that page has a message like... "The content you are looking for has moved. You will be redirected to the new location automatically in 5 seconds. Please bookmark the correct page at newwholesaledomain.com"
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Personally. I would not use metarefresh. I don't know how Google will treat it.
If I wanted to keep as much power as possible on the retail site I would have a plain page with my full internal navigation on it. It would also have a very clear message for wholesale visitors, that gives them as much time as they need to read, change their directories, and leave by their own action.
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It would also be a good idea to plan and announce the move. This can be done by:
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email and mail to important retail and wholesale clients.
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before redirecting pages the old domain could include obvious messages to retail and wholesale clients, thanking them for their support, letting them know about the schedule of the move, and asking them to bookmark the new site.
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inserts in retail shipments
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special advertising before the move
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special advertising and email after the move that gives old customers a nice discount when they make their first purchase on the new website.
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I might also send out some... "Tell a Friend" email messages to past clients. They can then forward these to friends who may or may not have purchased in the past, but it will get them nice savings on their first purchase from your new domain.
I would make these offers so good that I don't make much money on them. This is just to get new people to the new domain. I would send them out in batches so my employees filling orders will not be so swamped that they will have trouble giving their normal fast service.
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Your points about communicating as much as possible offline and by email, etc, are well taken.
I would still like to redirect existing wholesale pages to newwholesaledomain.com, primarily due to a desire to make everything as easy as we can for both types of customers. They want to emphasize the retail side but don't want to make it a pain for wholesale customers in the process.
So I'm inclined to redirect retail pages to newretaildomain.com and wholesale pages to newwholesaledomain.com. All page by page of course. Since the currentdomain.com home page will redirect to newretaildomain.com, we would put a notice on the new home page for our wholesale customers, pointing them to newwholesaledomain.com.
How does that sound? I think you are all correct that I should avoid redirect chains and meta refreshes.
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You can do that. No problem. It will be best for wholesale customers.
My comments are designed to be best for retail rankings. If my connections to wholesale customers are poor then I would use your method. If my connections to wholesale customers are strong them I would do what's best for retail rankings. It is simply a matter of choice.