Jason Posel
Founder & CEO, Greenlight.ai

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Episode Overview


Jason Posel, Founder & CEO of Greenlight.ai, is a recognized leader in the Future of Work. He is an expert in managing contingent workforce payroll programs and associated contractor classification, tax, and labor law issues. This conversation explores the topic of worker classification and its impact on the freelance economy and provides timely insights into the potential impact of the recent updates by the U.S. Department of Labor on worker classification. Risk of misclassification is by far one of the leading blockers for freelance adoption, at scale, due to the massive implications of not getting this right. Jason emphasizes the need for a robust process to evaluate and engage contractors and helps companies adapt to these changes, ensuring compliance and fostering a fair and transparent work environment. 


  • Having a robust process to evaluate and engage contractors is crucial for larger enterprises.

  • Recent changes in classification legislation have made it harder for businesses to classify workers as independent contractors.

  • Companies have traditionally used internal processes, employer of record services, or staffing companies to manage classification.

  • The rise of freelance work has introduced new challenges in classification, particularly in terms of compliance and risk management.

  • Companies should pay attention to this issue and implement programs to mitigate risks.

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Follow the link to learn more about Greenlight.ai : https://www.greenlight.ai/# 


00:00 – Introduction and Overview of Greenlight
01:12 – Understanding Worker Classification
03:01 – Historical Approaches to Classification
09:17 – Traditional Strategies for Managing Classification
14:43 – The Rise of Freelance Work
23:47 – The Impact of Classification on Greenlight’s Business
24:20 – Recent Changes in Classification Legislation
32:08 – Overview of the New Classification Rules
43:32 – Summary and Conclusion
44:50 – Legislation and Uncertainty
45:20 – Impact on Companies
46:01 – Hiring as W2 vs 1099
46:27 – Robust Process for Engaging Contractors
47:01 – Where to Find Greenlight.ai
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