Thinking about hiring your first employee or contractor? In this episode of Careers in the Cloud, we're joined by Emily Kroboth, 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🔔 Subscribe for more episodes of Careers in the Cloud!Chapters:00:00 – Introduction & Disclaimer01:15 – The natural progression from contractor to business owner05:40 – When and why to hire your first employee10:25 – Legal frameworks: incorporation and compliance16:10 – Employment law vs. contracting law21:45 – Tax implications of hiring across regions27:30 – Payroll, benefits, and managing remote workers33:50 – Avoiding common legal and HR mistakes39:10 – Building a sustainable IT consultancy44:00 – Final advice for contractors scaling up46:30 – Wrap-up & key takeawaysLooking to hire or work as an IT contractor? Visit us at www.montrealassociates.com. Links:Follow us on LinkedIn - https://www.linkedin.com/company/montreal-associates/Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilykroboth/Connect with Maurizio (Host) on LinkedIn - https://www.linkedin.com/in/mauriziogioffre/