1. Produce your document
2. Convert doc to PDF
3. Produce a cover sheet
4. Convert cover sheet to PDF
5. Merge cover sheet PDF and document PDF (requires not-free Acrobat Pro)
6. Send combined PDF with Ooma fax service
Or, produce the document and cover sheet, print them both to paper, and scan them to PDF? Ugh.
By contrast, prompting for recipient name, phone, and comments to produce a cover sheet on the fly would be a pretty easy feature to develop.
I hope this is helpful.
Now you can do it as the previous user said in his post, merge all the pdf's together and make it into one single pdf file, where the first page is the cover sheet followed by the rest... Vonage does it similar to Ring Central as well...Integrated Fax Cover Sheet. I will tell you it has been numerous times on OOMA where I would send the cover sheet first separately from the rest to a very busy fax line, and when I'm ready to send the rest of the fax body after the cover sheet has been received, I get stopped in my tracks with a busy fax line; at which point I forget it for an hour or two, get side tracked only to find out later and get a call from a customer, - "Hi, we received a cover sheet, but not the fax"
What a pain.
I'd like to write OOMA a letter to their corporate office regarding this necessary feature.