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Freelancer Classification Checklist

For companies hiring more than 100 freelancers, misclassification is a mistake that can bankrupt you. This checklist is a quick guide to make sure you have the right foundation.

Matthew MottolaMatthew MottolaFebruary 21, 20231 min read
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Classification Checklist

For companies hiring more than 100 freelancers, misclassification is a mistake that can bankrupt you.  

While classification rules and implications vary regionally, the  main impact is back taxes or lawsuits. 

Classification is as simple as, “should this person be a full time employee (W2) or independent contractor (1099)”. Countries, and even states like California, have different rules and tests to determine.  

If on the wrong side, you can owe years of back taxes, or class action lawsuits like Microsoft’s $97m ‘permatemp’ case

DISCLAIMER: This is not legal advice. Classification is ever-changing, and this does not replace advice from employment lawyers.

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Matthew Mottola

Matthew Mottola

CEO, Human Cloud

Matthew Mottola is the CEO of Human Cloud, the leading sourcing platform for companies to scale their future workforce. A serial entrepreneur, angel investor, and author of The Human Cloud book, published by HarperCollins; Matthew has been at the forefront of workforce tech for 15+ years. With an extended passport, Matthew has lived, led companies, and spoken across 50 international stages, while leading and advising global brands from Microsoft, to Novo Nordisk, to G7 Governments. On any given day you can find Matthew fighting his IDE in Singapore, San Francisco, or his hometown of Newburyport, Massachusetts.

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