Senior Executive Assistant

A high-impact EA opportunity for someone who operates two steps ahead
This is an excellent opportunity for a strong Senior Executive Assistant to join a successful, fast-growing global technology company and partner with senior commercial and revenue leadership.
We're looking for much more than someone who can manage a complex calendar and coordinate travel.
The successful candidate will be a highly proactive operator and trusted partner who processes information quickly, exercises excellent judgment, anticipates what is coming next and takes ownership without waiting to be asked.
If you're the kind of EA who sees a problem developing and solves it before it reaches your executive, brings recommendations rather than questions, and is constantly looking for smarter ways to operate, this could be an excellent next move.

Who – The Company
Our client is a well-established, high-growth global technology company with a strong leadership team and an award-winning workplace culture.
The organization operates internationally and continues to grow rapidly, creating an exciting and highly dynamic environment for its Executive Operations team.
Strong Executive Assistants are viewed as trusted partners to leadership, with significant exposure to the business and opportunities to grow alongside the organization.

What – The Role
This is a highly visible Senior Executive Assistant position supporting senior leaders across the company's commercial and revenue organization.
You'll operate in an environment where calendars change quickly, information moves fast and executives need an EA who can independently assess what matters most and take action.
The role requires someone who can move seamlessly between traditional executive support and broader operational responsibilities – managing complex calendars and international travel one moment, preparing an executive for a critical meeting the next, and then identifying a process or technology solution that makes the entire team more effective.
This is not a reactive support role.
Success will come from understanding your executives, anticipating their needs, protecting their time and ensuring that priorities don't get lost as the organization continues to move quickly.
What You'll Be Doing

• Own complex, high-volume and multi-time-zone executive calendars, continuously assessing priorities rather than simply scheduling meetings.
• Anticipate conflicts and proactively recommend solutions before issues reach the executive.
• Coordinate complex domestic and international travel from planning through execution, including contingencies and last-minute changes.
• Prepare executives for important meetings by ensuring they have the right context, materials and information ahead of time.
• Attend selected meetings, capture high-quality notes and translate discussions into clear decisions, actions, owners and follow-ups.
• Drive follow-ups through to completion and ensure commitments don't disappear after the meeting ends.
• Manage and prioritize executive communications using strong judgment and discretion.
• Support executive offsites, leadership summits, team dinners and large-scale events.
• Coordinate event budgets, vendors and complex cross-functional logistics.
• Partner with senior stakeholders across Sales, Revenue Operations, Partnerships, Strategy and other functions.
• Prepare polished executive-level presentations, documentation, briefing materials and communications.
• Identify opportunities to improve executive workflows, processes and operating rhythms.
• Use technology, AI and automation to reduce administrative work, synthesize information and improve the quality and speed of execution.
• Handle highly confidential and sensitive information with discretion.

Who – The Candidate
We're looking for an EA with exceptional communication skills, strong executive presence and excellent judgment.
You don't need every answer handed to you. You're comfortable gathering information, processing it quickly, understanding the context and determining the appropriate next step.
You're also comfortable challenging an assumption, protecting an executive's time or respectfully pushing back when you believe there is a better approach.
Most importantly, you take ownership.
If something is assigned to you, your executive should be able to trust that it will be followed through to completion without repeatedly checking on its status.

You Will Likely Be Someone Who:

• Is proactive by default and naturally thinks several steps ahead.
• Processes large amounts of information quickly and identifies what actually matters.
• Communicates clearly, concisely and confidently.
• Exercises strong judgment when priorities compete or information is incomplete.
• Brings solutions and recommendations, rather than simply escalating problems.
• Has the confidence and executive presence to partner credibly with senior leadership.
• Can support multiple senior stakeholders without losing attention to detail.
• Understands how to protect an executive's time and attention.
• Operates effectively with ambiguity and rapidly changing priorities.
• Demonstrates exceptional organization and follow-through.
• Is comfortable working independently with minimal oversight.
• Is naturally curious and continually looks for better ways of working.

AI & Technology
Technology is an important part of how this organization operates, and AI fluency and curiosity will be important to success in this position.
We're interested in candidates who are already using – or are genuinely excited about learning to use AI and modern technology to make executive support more effective.
This could include using AI to:

• Synthesize information and create concise executive briefings.
• Turn meeting notes into decisions, actions and follow-ups.
• Support research and meeting preparation.
• Improve the speed and quality of written communications.
• Streamline recurring administrative workflows.
• Identify opportunities for automation.
• Help executives access the information they need more efficiently.

You don't need to be an AI engineer or technical expert. What matters is a curious, experimental mindset and the ability to apply technology thoughtfully, securely and practically while maintaining strong human judgment.

Experience
We're open-minded about exactly what your career journey has looked like.
Ideally, you will bring:

• Approximately 8+ years of progressive Executive Assistant or senior executive support experience, although exceptional candidates with fewer years will absolutely be considered.
• Experience supporting VP, SVP, C-suite or similarly senior executives.
• Experience managing highly complex calendars, travel and competing executive priorities.
• Exposure to fast-paced, rapidly changing or high-growth organizations.
• Strong experience partnering with senior internal and external stakeholders.
• Excellent written and verbal communication skills.
• Confidence using modern workplace technology and an interest in AI and automation.

Experience within SaaS, technology, fintech, e-commerce or another high-growth environment would be particularly relevant, but industry background is flexible.
We're ultimately more interested in how you operate – your judgment, communication, initiative, processing speed and ability to anticipate – than simply the number of years on your resume.

What Makes This Opportunity Different
This role will appeal to an EA who wants to be genuinely relied upon as a partner to their executives, rather than simply receiving and completing administrative tasks.
You'll have the opportunity to:

• Work closely with highly accomplished senior leaders.
• Gain meaningful exposure to a rapidly scaling global business.
• Influence how your executives operate and use their time.
• Introduce new processes, technology and ways of working.
• Work within an organization that values innovation and actively embraces AI.
• Continue developing your career within a growing Executive Operations function.

For the right person, this is an opportunity to become the kind of EA where the executive thinks:
“I don't need to ask – they've already thought of it.”

How Much
Highly competitive compensation in the range of $90,000–$110,000 CAD + equity, depending on experience and qualifications.
The total rewards package includes health and dental benefits, RRSP matching, unlimited PTO (minimum 20 business days), flexible work arrangements and strong opportunities for professional growth and internal progression.

Where
Toronto, ON or Vancovuer BC – Hybrid
The position requires a minimum of two days per week in the office for candidates within commuting distance.
Occasional flexibility will be required for early-morning or evening meetings to accommodate executives and stakeholders operating across global time zones.

When & How to Apply
If you're an accomplished Executive Assistant who thrives in a fast-moving environment, takes genuine ownership of your work and naturally thinks ahead of the people you support, we'd love to hear from you.
If you already have a Recruiter at SWIM, please reach out directly. If you do not yet have a contact at SWIM Recruiting, please hit 'APPLY' to send us your resume.
SWIM is presenting shortlisted candidates directly to the hiring team for review. We work discreetly and confidentially with currently employed and passive job seekers.

SWIM Recruiting works confidentially with all candidates.