I'm considering purchasing Job Roller to use for the next four months while I build out a bigger, more interactive jobs site. Will I be able to transfer client information and job information over to the new site when we launch or will this be a complicated process?
Transition efficiency will really depends on the target website database structure and you coding knowledge. Jobroller is a wordpress theme and so you need to keep in mind the wp db structure for your future migration on other system.
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