Senior Executive Assistant

Swim Recruiting; Toronto; Hybrid; CAD 90,000 - 105,000; Full time

Benefits offered by this job

Health & dental benefits

Unlimited PTO

RRSP match

Flexible work schedule

Job summary

Swim Recruiting is seeking a highly proactive Senior Executive Assistant to support key leadership in a Toronto-based organization known for its innovation and growth. The ideal candidate should thrive in a fast-paced, high-growth environment and possess excellent judgment and decision-making skills.

Responsibilities include managing complex calendars, coordinating executive travel, and enhancing operational efficiency through AI tools. The role offers competitive compensation of $90,000 – $105,000 CAD, flexible work arrangements, and a strong benefits package.

Qualifications

• 8+ years of experience supporting senior executives in complex organizations.
• Comfortable operating with urgency and shifting priorities.
• Experience in SaaS, technology, fintech, or e-commerce preferred.

Responsibilities

• Manage complex, multi-time-zone calendars.
• Coordinate end-to-end executive travel.
• Prepare materials for meetings and attend to capture notes.
• Support leadership events and manage executive communications.
• Drive operational efficiency and process improvements.

Skills

Proactive mindset

Strong decision-making

Organizational discipline

AI fluency

Tools

AI tools

Automation platforms

Job description

The Company

Our client is a well-established, high-growth organization with a strong global footprint and an exceptional leadership team. Headquartered in Vancouver, BC, they operate in a specialized, high-impact sector and are known for innovation, collaboration, and thoughtful leadership. This is the kind of environment where strong EAs are trusted, respected, and given room to grow.

What - the Role

This is a well-rounded Senior Executive Assistant role supporting key senior leadership within the organization (including senior revenue and commercial leadership and associated executive stakeholders). The position operates in a high-velocity, highly ambiguous environment and requires an EA who is able to operate independently, anticipate needs, and stay ahead of rapidly changing priorities.

Key responsibilities include

• Complex, multi-time-zone calendar management in a high-volume, constantly shifting environment
• End-to-end executive travel coordination (domestic and international)
• Scheduling, preparing materials for, and supporting in-person and virtual meetings
• Attending meetings to capture high-quality notes and drive follow-ups to completion
• Managing executive inboxes and communications with strong judgment and prioritization
• Supporting leadership offsites, executive summits, team dinners, and large-scale events
• Coordinating high-value event budgets and cross-functional logistics
• Supporting multiple senior leaders across Sales, Revenue Operations, Partnerships, and Strategy functions
• High-level stakeholder management across internal and external partners
• Creating executive-level presentations, documentation, and communications
• Driving operational efficiency, process improvement, and automation opportunities
• Leveraging AI tools and technology to streamline and improve execution quality

This is not a reactive support role. It requires a proactive operator who identifies issues before they arise, brings forward solutions, and executes with minimal direction.

Who - the Candidate

Our client is seeking a highly proactive, fast-moving, and self-directed Senior Executive Assistant who thrives in high-performance, high-growth environments. The ideal candidate has a strong track record of supporting senior executives in complex organizations and is comfortable operating with ambiguity, urgency, and shifting priorities.

This role is best suited to someone who demonstrates:

• A “proactive by default” mindset (anticipates needs before they are expressed)
• Strong decision-making ability and brings recommendations, not questions
• High processing speed and strong judgment under pressure
• Comfort supporting multiple senior stakeholders simultaneously
• Minimal need for direction or oversight
• Confidence working with senior leadership and pushing back when needed
• Strong organizational discipline and follow-through (“done, confirmed, completed”)

A major requirement for success is strong AI fluency. The ideal candidate is:

• AI-native or highly AI-curious
• Comfortable using modern AI tools and automation platforms
• Actively experimenting with technology to improve workflows
• Continuously looking for ways to streamline and improve execution

Candidates with traditional EA experience are welcome, but success in this role is more strongly defined by mindset, speed, and initiative than tenure alone.

While 8+ years of experience is preferred, strong candidates with fewer years will be considered if they demonstrate exceptional capability in fast-paced, high-growth environments.

Industry background is flexible. Strong preference for experience in SaaS, technology, fintech, e-commerce, or similarly scaled organizations where the EA function operates at a high level of complexity.

How Much

Highly competitive compensation in the range of $90,000 – $105,000 CAD + equity, depending on experience and qualifications. The total compensation package includes health & dental benefits, RRSP match, unlimited PTO (minimum 20 business days), flexible work arrangements, and a strong track record of rapid compensation growth and internal promotion for high performers.

Where

Toronto-based headquarters with a hybrid work schedule requiring a minimum of 2 days in-office per week for candidates within commuting distance. Occasional flexibility required for early morning or evening meetings to accommodate global time zones.