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Does anyone have any recommendations as to mass mailing software I can get? Yes, I know you can do it manually, but I'd rather even pay some $$$ to make this process easier. Specifically, I've done research and found it is difficult to do a mail merge with DOCUMENTS attached. I.e. template cover letter. Also, I know I could use a cover letter as the body of my email, however I don't think having a three paragraph block of text is gonna help.

I had good luck with Easy Mail Merge. http://www.emailaddressmanager.com/mail_merge.html

Its about $40 and lets you specify which files (such as individualized cover letters) to attach to each line of your mail merge in Outlook. I found it to be worth the money.

If you use a professional version of adobe acrobat, there's a way to have Word print each mail merged cover letter as a different .pdf document. You can then use a spreadsheet to match the file names to the right firm and blast out the mail merge all at once.

thank you, that was super helpful! looks like im gonna splurge on acrobat professional..

OutoftheWoods wrote:thank you, that was super helpful! looks like im gonna splurge on acrobat professional..

Before splurging on an Acrobat upgrade simply to split PDFs automatically, try some of the free online tools (like http://www.splitpdf.com/) that can do the same thing. SplitPDF creates a zip of individual PDFs and numbers them in order "originalfilename.1.pdf, originalfilename.2.pdf, etc.)

Make sure it doesn't put a watermark on there, but I'm pretty sure it doesn't (I've used one before and I'm pretty sure this was it. Some online PDF tools add watermarks).

You can split pdfs on Preview in Mac too.