Toronto’s Tailscale planning to expand engineering, product, and sales teams

What’s going on at Tailscale?

After securing $230 million during its latest financing round, Tailscale, a Toronto-based virtual private network (VPN) technology provider, is planning to expand its 150-person workforce.

According to news outlets, including The Globe and Mail, CEO Avery Pennarun said the company is looking to grow its engineering, product, and sales teams.

“Our sales team never has to do cold outreach to new customers,” Pennarun claimed.

Founded in 2019, Tailscale recently surpassed 10,000 paying business customers — which includes Telus, Motorola, Instacart, and SAP AG.

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If you’re thinking about working for Tailscale in Canada, here are a few things that non-unionized employees need to keep in mind.

Review your employment contract carefully

If you’re offered a job at Tailscale, don’t sign your employment contract before seeking legal advice.

These agreements often reduce the legal protections of non-unionized employees in Ontario, Alberta, and British Columbia — especially when it comes to severance pay or workplace changes.

ADDITIONAL RESOURCES
• Can my employer make changes to my job in Ontario?
• Job changes in Alberta: What employees need to know
• Changes to your employment in B.C.: Your rights

WATCH: Employment lawyer Lior Samfiru explains what you should know about employment contracts on an episode of the Employment Law Show.

Common clauses to watch for:

• A termination clause limiting severance to just a few weeks’ pay.
• A provision allowing your employer to make significant job changes without your consent.
• A “probation clause” that could affect your job security.

You don’t have to accept an agreement immediately. An experienced employment lawyer at Samfiru Tumarkin LLP can review the contract and ensure that your workplace rights are properly protected.

LEARN MORE
• Starting a new job? Here’s how an employment contract could limit your rights
• ’60 days or more’: Is it an enforceable termination clause?
• Employment Law Show: Things to never do before seeking legal counsel

You might have complete a probationary period

Most employment contracts require staff to complete a “probationary period” — often lasting three to six months.

If you’re fired or let go during this time, and the requirement isn’t clearly stated in your agreement (i.e. no probation clause), you might be owed severance pay.

Our firm can assess your legal options and advise you of potential next steps.

LEARN MORE
• Employment Law Show: Probationary periods and termination
• Car dealership fires worker during probation for violating office dress code
• Wrongful dismissal in Canada: Employee rights

Think about severance before changing jobs

Before leaving your current role for a new one, consider the severance implications.

Non-unionized employees in Canada, including those at Tailscale, can receive up to 24 months of pay when they’re let go without cause. If you quit your job voluntarily, you’re likely not entitled to a severance package.

However, if you were forced to resign due to unwanted changes to your job, contact an experienced employment lawyer at Samfiru Tumarkin LLP.

We can help you determine if you have grounds for a constructive dismissal claim.

ADDITIONAL RESOURCES
• How to calculate severance pay in Canada
• Should I negotiate my own severance package in Ontario?
• What Albertans need to know about negotiating severance
• Negotiating severance in B.C.: What employees need to know

Length of service matters

The amount of severance pay you’re owed is heavily influenced by how long you’ve worked for your employer.

• Example: If you leave a job you’ve held in the Greater Toronto Area for 15 years to join a new company, and you’re let go a few months after your start date, your severance package might be minimal — unless you were induced to leave your previous employer (see “Inducement” below).

A short amount of service at a business doesn’t automatically mean meager compensation. Many short-service employees are entitled to significant severance packages.

If you’re let go after a short time with a company, don’t sign anything before speaking with our team. You could be owed much more than your employer offers.

🕒 IMPORTANT: You have up to two years from the date of your termination to pursue full severance pay — as long as you haven’t accepted the offer in writing.

SEE ALSO 
• I already accepted a severance package, what should I do?
• Do I have to look for a new job after getting fired?
• Employment Law Show: Facts about the termination process

Lost your job after being recruited?

In some cases, non-unionized workers in Canada leave their current job after being actively recruited by another company.

If your new employer took documented steps to entice you to take up employment with them, this will likely be considered inducement.

ADDITIONAL RESOURCES
• Recruited by another company in Ontario: Employee rights
• What workers in Alberta need to know about inducement
• Inducement in B.C.: What employees need to know

In the event that the company decides to terminate you shortly after pulling you away from your previous employer, the inducement should be taken into consideration when determining your severance entitlements.

• Example: Tailscale entices you to leave your current job in Ottawa to come work at its office in Toronto. If you’re terminated shortly after making the switch, the company may be on the hook for enhanced severance pay because of the pressure it placed on you to leave your previous employer.

If this situation applies to you, don’t sign your severance offer until it’s been reviewed by a member of our team.

We can confirm that the inducement has been properly factored into your severance package and help you secure the compensation you deserve if it isn’t.

Got a job offer? Contact us before signing

Before signing an employment contract, have the experienced employment law team at Samfiru Tumarkin LLP review the agreement to make sure your workplace rights are protected.

Our lawyers in Ontario, Alberta, and B.C. have successfully represented tens of thousands of non-unionized individuals.

We can help you better understand the terms of the contract and advise you on how best to navigate the situation.

Disclaimer: The materials above are provided as general information about the rights of non-unionized employees in Canada. It is not specific to any one company and SHOULD NOT be read as suggesting any improper conduct on the part of any specific employer, or a relationship between Samfiru Tumarkin LLP and a specific employer.