If what you have isn't a spreadsheet but a folder of PDF certificates, upload the folder. Each certificate is read, matched to a contractor by the name on it, and filed — creating the contractor record if there isn't one yet.
This is the fastest way to move off a shared drive, because the roster and the documents arrive in the same step.
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Zip the certificates
Zip the folder of PDFs. Up to 50 files per archive — split a bigger folder across a few runs.
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Open the import screen
Tools → Data Import, then choose Certificates of Insurance rather than Contractors.
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Upload the archive
Drop the ZIP in. Each PDF is read in turn — insurer, insured name, coverages, limits and dates — which takes a few seconds per file, so a full archive takes a few minutes.
You don't have to wait on the page. Progress shows under Recent Activity (the bell, top right), and you'll get an email when the certificates are ready to review. The import also waits under Your certificate imports on the Data Import screen for 7 days.
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Review what was read, then import
The preview lists what was found in each certificate and which contractor it will attach to. Where the insured name matches an existing contractor, it attaches; where it doesn't, a new contractor is created from the name on the certificate.
Check that column especially. "Rodriguez Electric LLC" on the certificate and "Rodriguez Electric" on your roster are different strings, and you'd rather notice now than end up with two records.
Note
What happens next
Spot-check a few of the imported certificates against their PDFs — Review and correct a parsed COI. Bulk imports are where a wrong date is most likely to slip past, because nobody looked at any single one of them.