How do you get pass the ATS system and actually get an interview with a hiring manager for legal and/or quasi legal (e.g., contracts management, etc.) roles in Toronto, ON?

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Maybe try referral if you know anyone from the firm or company, if you purely rely on the software, then try to use a much key words as possible in your applications

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Yes, unfortunately that appears to be the case in the North American market. Without someone from within advocating for you it becomes irrelevant on how qualified you are or how much experience you have under the belt.

A referral is the way to go if you have any network at all that you can reach out to. It is hard to get yourself noticed without one.

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