Careers in the Cloud – E38: Go From IT Contractor to Employer | Legal & Hiring Tips

Описание: Thinking about hiring your first employee or contractor? In this episode of Careers in the Cloud,
we're joined by Emily Kroboth, Employment & Labour Lawyer and Associate at Dentons Canada LLP, to unpack the real-world journey from being a solo IT contractor to running a growing consultancy. Discover the legal, financial, and operational essentials every tech professional needs to know before expanding their business.

We explore employment law, compliance challenges across regions, and the tax implications of scaling your cloud or IT practice. Whether you’re a seasoned freelancer or just starting to build your team, this conversation will help you avoid costly mistakes and set up for sustainable success.

What you’ll learn:
How to transition from self-employed contractor to employer
Legal and HR basics when hiring staff or subcontractors
Payroll, taxes, and compliance across different jurisdictions
Structuring contracts and protecting your business legally
Common pitfalls IT professionals face when scaling

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Chapters:
00:00 – Introduction & Disclaimer
01:15 – The natural progression from contractor to business owner
05:40 – When and why to hire your first employee
10:25 – Legal frameworks: incorporation and compliance
16:10 – Employment law vs. contracting law
21:45 – Tax implications of hiring across regions
27:30 – Payroll, benefits, and managing remote workers
33:50 – Avoiding common legal and HR mistakes
39:10 – Building a sustainable IT consultancy
44:00 – Final advice for contractors scaling up
46:30 – Wrap-up & key takeaways


Looking to hire or work as an IT contractor? Visit us at www.montrealassociates.com.


Links:
Follow us on LinkedIn -   / montreal-associates  
Connect with Emily on LinkedIn:   / emilykroboth  
Connect with Maurizio (Host) on LinkedIn -   / mauriziogioffre