We have a user that is currently using Outlook 2010 and we use a Hosted Exchange 2010 platform for our baseline. This user has built up a list of contacts into groups in Outlook. This user sends emails to these contacts on a daily basis always using BCC to keep the recipients discreet while getting bids for a current project. This has been working well for months for this user but the Outlook Contact Groups are getting to a point where they are starting to fuss about the size. The contacts have a bit of details inside of them like the signatures pasted in (pictures included) and details copied into the appropriate fields so they are not so tiny anymore.
My question has to do with trying to find a better way to send emails to these large lists of people. Keeping the contacts inside of Outlook isn't the problem but more the problem concerns the number of contacts inside of a Group. He has some Groups and we talked about breaking them out alphabetically and creating multiples next to each other but that would get less organized and confusing overall. I thought about using software like Infacta's GroupMail which acts as a mailer but I don't know if this would simplify the grouping of contacts any better. I also thought about using Constant Contact (with Outlook Sync options) but that isn't really the strong point for CC either. I am looking for some software that can synchronize up with an Outlook Address Book (Contacts) and make it easier to send emails to a bunch of users without having all the limitations of the Outlook Contacts' version of Groups which appears to be a smaller scale version of what we need.
Any thoughts are welcome. Thanks.