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Nichelle HubleyNichelle Hubley 

Best workflow to merge custom object fields into a word template, render to pdf, attach to record and email to contact?

I don't know if this is the right place to post this but I thought it is worth a shot. I am looking for a solution to do the following steps:
  1. merge custom object fields into a template (currently a word document but could be changed)
  2. render to pdf
  3. attach to record
  4. email to contact
I was hoping to use mail merge to accomplish as least part of this but it doesn't look possible on Mac OS. I also tried using a VF email template with pdf attached but it doesn't allow the option of previewing the pdf attachment before sending.

Any other suggestions to do this within Salesforce?