Employers of Remote Workers Are Unsure They Are Remitting Taxes Correctly

Due to COVID-19, employees are spread throughout the country and moving around. This is a challenge for employers who are obligated to pay taxes in the jurisdictions their employees are working. Remote native companies and companies that support a growing remote workforce will continue to face this challenge.

See also:

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    The new law turns enables a tourist visa for up to one year with proof of stable income and medical insurance. This is meant to attract digital nomads to spend more time in Costa Rica and thus spend more money there.

  • Startups Oscillate Between Operating Ignorance and Normalization

    As companies grow their operations become more complex and they must constantly make changes. Startups prioritize speed and solving the most important problem, even if it is in exchange for future liability. A useful framing is to think of it as moving between two states—operating ignorance and normalization.

  • Trailing Tax Liability

    When employees move around they generate trailing tax liabilities for the time spent in a particular jurisdiction. This includes employment taxes and reporting as well as personal tax issues (for example, shares vested while in California will need to pay taxes once a gain is realized).