Hiring Independent Contractors in Canada: A Complete Guide for Businesses
Learn how to hire independent contractors in Canada. Understand legal rules, tax responsibilities, and how to avoid misclassification with this guide.
Remote work has matured from a post-pandemic trend into a permanent fixture of high-performing businesses. For companies managing 10 or more employees, the ability to hire remote workers efficiently and legally has become a must-have. Understanding how to hire a remote team involves more than logistics. It’s a long-term strategic move that opens your company to international remote workers, reduces overhead and creates access to top-tier talent from a truly global talent pool.
But hiring remote employees also introduces new complexities — from navigating local labor laws to managing a remote work environment across multiple countries and time zones. This guide is built to help you master every aspect of remote hiring, so you can scale confidently and sustainably.
To scale your remote workforce effectively, you first need a clear and intentional hiring model. One option is to bring on full-time remote employees, which works best for core team roles that require long-term investment, such as those in engineering, operations or leadership. These hires can grow with the company and contribute to building a strong internal culture.
Alternatively, you might consider working with freelancers, especially for short-term or highly specialized projects. Platforms like Upwork1 make it easy to source skilled remote talent quickly and on demand.
If you’re expanding into multiple countries, partnering with an Employer of Record (EOR)2 can help simplify the process. Services like Deel,3 Remote4 and Oyster5 enable you to legally hire international remote workers without having to establish a local entity in each country.
Don’t skip internal preparation. A solid remote hiring strategy includes clearly documented policies, structured workflows, and the right mix of project management software and communication tools. These elements create a stable remote work environment where new hires can integrate quickly and contribute effectively from day one.
Your job descriptions should serve as a remote-ready blueprint. Beyond listing qualifications and responsibilities, they must reflect the nature of the remote work environment you're offering.
Candidates should immediately understand the time zones your team operates in and whether schedule overlap is required. Clear expectations around communication rhythms and participation in virtual team meetings are essential, particularly if you're running a fully remote team.
You should also outline the remote work tools and platforms your remote team members will rely on daily — whether it's Slack, Zoom, Notion or project management software like Asana or Trello. This helps remote workers assess how well-equipped your team is to support productive remote employees and whether your systems align with how they prefer working remotely.
Include perks that appeal specifically to remote workers: tech stipends, flexible hours, home office setup support and emphasis on work-life balance. These signals show you’re serious about building a high-performing remote workforce.
Remote hiring processes should be optimized for distributed, asynchronous collaboration. That means replacing informal “gut feeling” interviews with structured, standardized assessments designed to reflect real-world remote challenges.
Here’s how to conduct effective remote interviews:
Great remote workers aren’t just technically skilled, they also excel at navigating ambiguity, prioritizing tasks independently and collaborating without supervision.
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Hiring remote employees in multiple countries adds legal complexity you can’t afford to ignore. Each country has its own labor regulations, tax obligations and mandatory benefits that affect how you structure remote contracts.
To stay compliant, it’s essential to thoroughly understand and follow local labor laws before drafting or sending any employment agreements. For companies looking to scale quickly or avoid the hassle of setting up legal entities in each country, partnering with an Employer of Record is often the smartest move. EOR services like Deel, Remote or Oyster handle everything from payroll processing and tax withholding to benefits administration and contract compliance.
First impressions matter. Remote employees working from day one without proper onboarding can easily feel disconnected or unsure of expectations.
A successful onboarding process starts with a clear playbook — covering tech access, company policies and introductions — paired with regular check-ins to ensure alignment and support.
Assigning a buddy or mentor helps new hires integrate faster, while early participation in team meetings reinforces communication norms and company culture. These steps lay the foundation for productive remote employees who feel empowered to contribute.
Retention also requires investing in career growth, learning resources and regular feedback cycles. A great remote work environment doesn’t just focus on output, but also supports the long-term success of each team member.
Jumping into remote hiring without a structured plan can lead to costly missteps. Many companies, especially those transitioning from in-office to distributed models, struggle with predictable but avoidable problems. Here’s what to watch for:
One of the most common mistakes in hiring remote employees is publishing job listings that lack clarity. When expectations for working remotely aren’t clearly communicated, you risk:
To hire the right remote team members, your job descriptions must explicitly outline responsibilities, required remote work tools, preferred time zones and communication rhythms.
Remote teams span geographies, and mismanaging time zones can kill momentum. You’ll hit a snag if you fail to plan for:
If ignored, you’ll face delays, missed messages and fractured team cohesion. Successful remote workers thrive on structured communication. Without it, productivity suffers.
Hiring remote workers across multiple countries without understanding local labor laws is a major liability. Each jurisdiction has its own regulations for:
Neglecting compliance can result in fines, backpay or termination of contracts. You also risk reputational damage if international remote workers feel exploited or misclassified.
Build a comprehensive remote hiring strategy that addresses these risks from the start. This should include:
Avoiding these pitfalls not only protects your business, it also ensures your remote workforce is set up to thrive.
To build an efficient remote workforce, choose the tools that fit your business best.
| Purpose | Tools | Why It Matters |
|---|---|---|
| Communication | Slack, Teams, Zoom | Keeps remote team members connected daily |
| Project Management | Asana, Trello, ClickUp | Enables visibility and accountability |
| Time Tracking | Hubstaff, Clockify, Toggl | Tracks hours across multiple countries |
| Onboarding & Documentation | Notion, Confluence, Google Drive | Helps remote employees stay aligned |
| Virtual Team Meetings | Gather, Donut, Trivia | Boosts culture in a remote world |
Choose tools that scale and integrate well with each other and your remote team will be able to collaborate effortlessly, even if they’ve never met in person.
Hiring remote employees is just the start. If you want a team that actually performs, you need to shift from just doing remote work to running a remote-first company.
If you’re still half-in, half-out with hybrid workflows, it’s time to commit. Full-time remote workers can’t thrive if they’re always adapting to systems built for an office.
Start phasing out location-dependent processes. Set clear time zone expectations, switch to async communication and make decisions in writing — not in hallway conversations that only happen for some of your team.
Your remote team can’t guess how things work. If it’s not documented, it doesn’t exist.
Build out SOPs for every department: how to onboard a new client, request time off and report bugs. Put it all in a shared workspace your team can access anytime. Use tools like Notion6 or Confluence.7
This removes bottlenecks and gives every team member from Serbia to São Paulo what they need to move forward without asking.
Don’t drown your team in meetings, but don’t go silent either. Establish a clear, consistent rhythm that keeps everyone informed without overwhelming the team.
Start with weekly video updates from leadership, which can be asynchronous to accommodate different time zones. Supplement that with monthly team-wide meetings to highlight wins, share company goals and maintain a sense of unity. A shared planning document, accessible and editable by all team members, ensures transparency and encourages cross-functional collaboration.
This approach keeps your remote team connected, focused and aligned without draining hours on unnecessary calls.
Hiring people in multiple countries means playing by their rules, not yours. If you get lazy here, it will catch up with you.
Don’t wing it. Learn the local labor laws, or use an Employer of Record to handle it. Keep your contracts, tax documents, and benefit policies up to date.
Build your company to scale without borders. Hire the best people, wherever they are. Create systems that don’t fall apart when one person leaves. Keep your team focused, not just available. That’s how you build a remote-first company that lasts.
If you want to hire remote workers who actually deliver, you need more than a job post and a video call. You need a strategy that includes a system that brings in the right people, keeps you legally compliant and sets your remote team members up to perform at their best.
With a clear hiring model, the right tools, and a respect for local labor laws, you won’t just hire remotely, but you’ll build a company that’s designed to run that way.
Wise is not a bank, but a Money Services Business (MSB) provider and a smart alternative to banks. Wise makes it easy to send, hold, and manage business funds in currencies. You can get major currency account details for a one-off fee to receive overseas payments like a local. Simply add the local account details when billing international customers to receive international payments with no fees.
Account opening is 100% online, with no need to visit a branch or book appointments.
Once you’re set up, you can connect to software such as Wave, FreshBooks, and more. You can also withdraw funds from Stripe without currency conversion fees.
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We make no representations, warranties or guarantees, whether expressed or implied, that the content in the publication is accurate, complete or up to date.
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