Executive Assistant and Operations Lead
Act as the CEO's right hand by managing priorities, calendars, and coordinating projects across technology, real estate, and hospitality businesses. Oversee hospitality operations, manage staff and vendors, and handle light bookkeeping and administrative tasks.
- On-site
- Toronto, ON
- Posted Aug 24, 2026
- Apply by Feb 20, 2027
- 1 position
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Job summary
Overview We’re looking for a highly organized, resourceful generalist to become the CEO’s right hand across a growing group of businesses spanning technology, real estate, and hospitality. This is not a traditional Executive Assistant role. One day you may be organizing the CEO’s priorities and coordinating with lawyers; the next, you may be solving an operational issue at a hotel, managing hospitality staff, or pushing a project across the finish line. The right person is positive, adaptable, and energized by variety. You take ownership, anticipate what needs to happen next, and make life easier for everyone around you. Key Responsibilities Keep the CEO organized, focused, and ahead of commitments Manage calendars, priorities, tasks, deadlines, and follow-ups Turn ideas and conversations into clear action plans—and ensure they get done Oversee and support hospitality operations, including managing staff, vendors, scheduling, and guest-related issues Coordinate projects across U-Rite, Elsam Capital, and related businesses Liaise with lawyers, accountants, bookkeepers, partners, and service providers Assist with invoicing, expenses, reconciliations, and other light bookkeeping Organize documents, systems, and information Handle occasional personal tasks, errands, and last-minute problem-solving Identify gaps, improve processes, and bring order to moving parts Qualifications Exceptionally organized and strong at follow-through A natural problem-solver who acts without waiting to be told every step Comfortable managing people and holding others accountable Positive, calm, and professional—even when things get busy An excellent communicator with strong judgment and discretion Willing to roll up your sleeves and do what is needed Experienced in operations, hospitality, executive support, project management, or a similarly hands-on role Proficient with Microsoft Office and comfortable learning new systems
What you’ll do
Act as the CEO's right hand by managing priorities, calendars, and coordinating projects across technology, real estate, and hospitality businesses. Oversee hospitality operations, manage staff and vendors, and handle light bookkeeping and administrative tasks.
Requirements
Requires a highly organized professional with experience in operations, hospitality, or executive support. Must be a proactive problem-solver proficient in Microsoft Office with strong communication skills and the ability to hold others accountable.
Listed skills
- Problem solvingPreferred
- CommunicationPreferred
- Microsoft OfficePreferred
- Project managementPreferred
- BookkeepingPreferred
Other relevant skills
Identified from the job description. Confirm important requirements above.
- Executive Support
- Operations Management
- Project Management
- Calendar Management
- Hospitality Management
- Bookkeeping
- Vendor Management
- Staff Management
- Process Improvement
- Microsoft Office
- Communication
- Problem Solving
Job areas
- Administrative
- Management & Leadership
- Hospitality
- Sales
- Finance & Accounting
Additional details
- Minimum experience
- 2+ years
- Apply by
- Feb 20, 2027
- Posting language
- English
- Working hours
- 40 hours per week
- Seniority
- Mid-Senior level
- Application method
- Direct apply is available
