Create Searchable PDFs with Table of Contents on Mac (Office 2011)

How to create a searchable PDF on a Mac with Office 2011, including table of contents.

Requires/assumes access to the following software:

1) Microsoft Office 2011 (In particular, Word 2011)
2) Adobe Reader (free download)
3) PDFOutliner (free, also paid $5 PRO version available)