Executive Assistant to Co-CEOs and Office Manager

Role overview

This is a full-time, on-site Executive Assistant position based in Toronto, Ontario, in the Yonge and Davisville area along the subway line. The role supports two Co-CEOs and also contributes to office management for a growing boutique, entrepreneurial business.

The successful candidate will act as a trusted long-term partner to the leadership team, handling both business and personal support needs. The company is looking for someone highly organized, detail-oriented, proactive, and comfortable balancing a wide range of shifting priorities in a fast-paced, collaborative setting.

Compensation is $100,000 to $112,000 per year, with a strong bonus, benefits starting immediately, three weeks of vacation, an additional week during the holiday season, and summer hours as a perk.

Core duties

• Manage incoming correspondence and inquiries for the Co-CEOs, responding appropriately and professionally.
• Coordinate two busy calendars, schedule meetings, and prepare meeting materials while protecting confidentiality and using sound judgment.
• Ensure documents, approvals, and related materials are completed and returned promptly to the correct internal or external contacts.
• Arrange travel for the Co-CEOs and prepare detailed itineraries for local and national trips.
• Plan and support office and team events such as socials, dinners, retreats, and weekly lunches to help build a positive workplace culture.
• Oversee corporate accounts and vendor relationships so the office operates efficiently.
• Work with vendors to resolve issues that may affect productivity or day-to-day office function.
• Keep both digital and physical filing systems organized and up to date.
• Track and handle invoices, expense reports, and benefit claims related to the Co-CEOs.
• Support personal tasks as needed, including banking, bill payments, appointment scheduling, and other ad hoc requests.
• Help with onboarding new employees and assist with offboarding coordination when required.
• Take on miscellaneous administrative needs that contribute to a smooth and productive office environment.

Profile sought

The employer is seeking an experienced Executive Assistant with a background supporting senior leadership in a boutique or entrepreneurial organization. This person should be known for professionalism, discretion, strong communication, and the ability to stay calm and effective when priorities change quickly.

The ideal candidate is resourceful, self-directed, capable of anticipating needs, and comfortable building strong working relationships across the organization and with outside partners.

Work environment and benefits

This position is based in the office four to five days per week. The office is accessible by subway. Benefits begin right away, and the role includes a bonus, summer hours, three weeks of vacation, and an extra week off during the holiday period.

Additional details

The company describes itself as a growing, entrepreneurial organization where the Executive Assistant will play an important long-term role supporting both executive leadership and office operations.