Executive Assistant

CanadaVisa; Toronto; Hybrid; CAD 62,000 - 78,000; Full time

Job summary

CanadaVisa is seeking an Executive Assistant to serve as the operational backbone for our office, CEO and COO. This role will keep the office running smoothly, protect leadership's time, and support growth as the business scales.

Based in Toronto, the position is hybrid with in-office days at least two days per week. You will own calendars, travel, expense handling, and run office projects while collaborating with legal, sales and client support teams.

Qualifications

• 2+ years in executive assistant, office manager or admin role.
• Strong calendar and scheduling skills, supporting multiple executives.
• Clear written and spoken English.
• Comfort with technology and tools like Microsoft 365, Notion and Claude.

Responsibilities

• Manage the CEO and COO calendars and book meetings.
• Coordinate travel, expenses, documents and ad hoc requests.
• Organize office events, vendor management and facilities.
• Lead office projects like expansions or moves, sourcing vendors and quotes.

Skills

Calendar management

Communication

Technology proficiency

English proficiency

Tools

Microsoft 365

Notion

Claude

Job description

Location: Toronto (hybrid, at least 2 days a week in office; in-office days flex with team schedules, events and executive needs)

Compensation: C$62,000–78,000

We're looking for an Executive Assistant to be the operational backbone for our office, CEO and COO. You'll keep the office running smoothly and protect leadership's time so they can focus on growing the business.

What we're building

Six months ago, we pivoted toward building an AI-native legal technology company. Since then, we've grown fivefold.

AI has changed the economics of legal services, enabling us to scale faster while providing better client experiences. We're using that opportunity to serve substantially more people and expand beyond immigration into other areas of consumer law. Our ambition is to become Canada's largest consumer law business.

We've already built AI-native technology across client portals, case-management systems and public-facing tools. We're using it to reduce manual work, give people personalized guidance and improve how they access and experience legal services.

Who we are

CanadaVisa brings together nearly 50 years of legal experience through Cohen Immigration Law, thousands of client matters each year and a national audience. Millions of people visit our websites each month, and our immigration community has roughly one million members.

We're a profitable family business with a history of using technology to change how people find and access immigration services.

We operate like a startup: small teams, broad ownership, fast decisions and close involvement from leadership. Our colleagues bring experience from Wealthsimple and Clio, alongside startup and growth experience. You'll join a company with an established business and substantial room to shape what it becomes.

What you'll Own

You'll own the day-to-day running of the executive office:

• Manage the CEO and COO calendars. Book meetings, prevent conflicts, and send a weekly look-ahead so both leaders know what's coming.
• Handle leadership team admin. Take care of travel, expenses, documents and ad hoc requests, and book company events, dinners and meetings within a given budget.
• Run the office and build a friendly workplace. Manage supplies, vendors and facilities, and organize regular team events and touchpoints.
• Lead one-off office projects. Coordinate projects like office expansions, moves and fit-outs. Source and manage vendors, get quotes, and keep projects on time and on budget.

You'll work directly with the CEO and COO on their priorities and schedules, and closely with our legal, sales and client support teams to keep work moving.

Who will thrive here

• You're service minded. You're warm, patient and clear with everyone you work with.
• You stay calm under pressure. You stay steady when priorities compete and plans change.
• You're self-directed. You spot what needs doing and act without being asked.
• You're organized and accurate. You juggle many requests, prioritize well and get the details right.
• You have a can-do attitude. You own problems and find a way to get things done.

What you'll bring

• 2+ years in an executive assistant, office manager or admin role
• Strong calendar and scheduling skills, ideally supporting more than one executive
• Clear written and spoken English
• Comfort with technology and tools like Microsoft 365, Notion, Claude, etc.
• Experience in a law firm or a high growth startup is a plus

Why CanadaVisa

The promise of AI is to make people's lives better. We're applying it to legal services that matter to individuals and families: helping them navigate complex processes, make informed decisions and achieve better outcomes.

You'll be part of that work by making sure every leader can focus on what matters most. You'll join a profitable, growing business where your work is visible every day and there are many career growth opportunities as the business scales.