Job Title

Executive Personal Assistant High-Trust, High-Impact Role This is a rare opportunity for an exceptional Executive Personal Assistant to work in close partnership with a founder and senior executive in a fast-growing, high-performance organization. The Executive Personal Assistant plays a pivotal role in enabling the CEO to operate at the highest level, ensuring focus, momentum, and clarity across both professional and personal priorities. This role extends well beyond traditional administrative support. You will act as a trusted extension of the CEO, managing complexity, anticipating needs, and creating the conditions for strong decision-making. Your presence allows the executive to remain focused on strategy, growth, and leadership, while you ensure that details, timing, relationships, and transitions are handled seamlessly. The Executive Personal Assistant also serves as a stabilizing force for the organization. By managing flow, priorities, and sensitive interactions, this role reduces friction, protects time, and reinforces professionalism across internal and external relationships. You will represent the executive with discretion and confidence across high-net-worth, executive, family, and social networks, often serving as the first point of contact and a trusted gatekeeper. The right individual brings confident positive energy, exceptional emotional intelligence, impeccable judgment, a resourceful approach to problem solving, and a strong sense of ownership. You are naturally anticipatory, highly adaptable, and calm under pressure. Trustworthiness, loyalty, and discretion are essential, as this role sits at the intersection of leadership, business operations, and personal life. Why this opportunity is different Unmatched exposure and learning Former assistants consistently describe this role as one of the most accelerated learning experiences of their careers. You will gain direct insight into executive leadership, strategic decision-making, and entrepreneurial growth, positioning you for long-term professional development. Executive-level benefits Comprehensive executive health coverage that exceeds standard plans, including access to leading physicians globally and meaningful coverage for critical illness or injury for both the employee and their family. Compensation and participation Competitive base salary in the range of $70,000$100,000, based on experience, benefits, and participation in the company''s equity plan. Work environment Fully in-office role, working closely with Executive five days per week in a downtown Toronto office, minutes from Union Station. Typical hours are approximately 9:30am5:30pm, with flexibility required for occasional evenings, extended days, or travel-related support. Additional perks Daily lunch provided What to expect This is a high-trust role with meaningful responsibility and close partnership with the CEO. The work is engaging and dynamic, with occasional flexibility required to support travel, urgent matters, or time-sensitive priorities. For the right individual, this is more than a position. It is a long-term partnership and a career-defining opportunity to work closely with a founder, contribute to important decisions, and play a visible role in the continued growth and success of the organization.