Executive Assistant & Office Manager

Executive Support | Office Operations | Technology & AI Enablement

The Opportunity

We are seeking a highly resourceful, tech-forward Executive Assistant & Office Manager to join a privately held, entrepreneurial organization in North Toronto.

This is a dynamic, hands-on “jack of all trades” position for someone who enjoys being at the centre of the action. The successful candidate will provide executive support to two principals, oversee the day-to-day operation of the office, administer technology and software platforms, and take ownership of a wide range of operational projects.

The organization operates in a sophisticated, paperless and AI-enabled environment. The right person will be highly adaptable, genuinely comfortable with technology and eager to explore how AI can make work faster, smarter and more efficient.

This is a fully onsite position with on-site parking. A valid driver’s licence and reliable personal vehicle are required.

Key Responsibilities

Executive and Personal Support

- Manage complex calendars, meetings, appointments and competing priorities for two principals
- Coordinate domestic and international travel, including itineraries, accommodations and supporting documentation
- Draft, organize and manage correspondence, documents and follow-up items
- Coordinate document signatures and maintain accurate electronic records
- Support personal, family, charitable and event-related administration with discretion
- Anticipate needs, identify potential conflicts and ensure commitments are followed through
- Act as a trusted point of coordination between the principals, employees, vendors and external partners

Office Management

- Oversee the smooth day-to-day operation of a professional office
- Manage office supplies, equipment, services, telecom providers and vendor relationships
- Maintain service agreements, subscription records and renewal schedules
- Coordinate team meetings, events and office initiatives
- Support employee onboarding and offboarding, including accounts, devices, permissions and office access
- Liaise with building management, service providers and contractors as required
- Identify operational gaps and implement practical solutions before they become escalations

Technology and Software Operations

- Serve as the first point of contact for day-to-day technology questions and basic troubleshooting
- Triage more complex issues to the organization’s managed IT provider and monitor them through resolution
- Administer Microsoft 365, SharePoint and other business software platforms
- Manage software and AI subscriptions, including user access, renewals and monthly spending
- Maintain established low-code automations, scheduled workflows and AI-supported processes using existing documentation




- Keep internal technology resources, operating procedures and quick-start guides current
- Support document organization, information management and digital process consistency
- Help ensure the organization’s technology environment remains secure, organized and dependable

AI Enablement and Process Improvement

- Use tools such as ChatGPT, Claude, Microsoft Copilot or similar platforms to improve administrative and operational workflows
- Identify repetitive work that could be simplified through AI, automation or better processes
- Create and maintain practical AI-supported workflows, templates, reports and administrative tools
- Provide patient, one-on-one support to colleagues using approved technology and AI platforms
- Stay curious about emerging capabilities and assess how they could create practical business value
- Adapt quickly as systems, software and ways of working continue to evolve

Projects and General Operations

- Take ownership of miscellaneous projects delegated by the principals
- Research products, services and potential vendors
- Obtain and compare quotes, coordinate purchases and follow up on delivery
- Visit properties, suppliers or service locations when required
- Track multiple workstreams and ensure deadlines, decisions and commitments are not missed
- Step into unfamiliar assignments confidently, determine what is needed and bring the work to completion

Qualifications

- Minimum five years of experience in an Executive Assistant, Office Manager, Operations Coordinator or similarly broad role
- Experience supporting senior executives, business owners or principals in a small or mid-sized entrepreneurial organization
- Advanced proficiency with Microsoft Outlook, Teams, Word, Excel and SharePoint
- Robust working knowledge of AI tools such as ChatGPT, Claude, Microsoft Copilot or comparable platforms
- Demonstrated ability to create a functional AI-supported workflow, automation, recurring report or process that continues to be used
- Experience coordinating vendors and holding external service providers accountable
- Robust digital file management and documentation skills
- Comfort learning software, working with administrative settings and troubleshooting basic technology issues
- Coding experience is not required
- Valid driver’s licence and reliable personal vehicle
- Ability to work onsite in North Toronto

Core Competencies





- Exceptional judgment, maturity and discretion
- Strong prioritization across multiple people, businesses and deadlines
- High degree of technological confidence and AI adaptability
- Resourcefulness and practical problem-solving
- Excellent written and verbal communication
- Strong attention to detail and documentation discipline
- Ability to manage confidential personal, family and business matters
- Comfortable holding vendors and service providers accountable
- Patient and supportive when assisting less technical colleagues
- Able to work independently without waiting for continuous direction

The Ideal Candidate

You are smart, grounded and highly capable. You enjoy variety and are comfortable moving between executive calendars, office operations, technology questions, vendor coordination and unexpected projects—sometimes within the same hour.

You do not simply identify problems; you investigate, recommend a solution and close the loop. You understand that being responsive is important, but being proactive is even more valuable.

You are naturally curious about technology and AI. You have moved beyond occasionally using an AI chatbot and can provide a specific example of something useful you have created with AI—such as a saved workflow, automation, scheduled report, reusable assistant or recurring business process.

Most importantly, you are a dependable finisher. People trust that when something is placed in your hands, it will be handled thoughtfully, discreetly and completely.

What Success Looks Like

Within the first year:

- The executives experience a meaningful reduction in administrative and operational demands
- Calendars, correspondence, personal administration and follow-up commitments are exceptionally well managed
- Office operations run smoothly with minimal escalation
- Technology and AI-supported systems continue operating reliably
- Software access, subscriptions, renewals and spending are accurately monitored
- IT requests are documented, followed through and resolved promptly
- Recent employees have the accounts, devices, information and access they need from day one
- Operational projects are completed without repeated reminders
- The organization continues identifying practical ways to use technology and AI more effectively

Additional Information

Finalists will be asked to complete:

- A criminal record check
- A driver’s abstract
- Education verification
- Professional reference checks, including at least one direct manager

Candidates may also be invited to complete a workplace personality assessment as part of the interview process. This assessment is intended to support team alignment and working-style discussions and is not used as a pass/fail test.

📌 Executive Assistant (Ontario)
🏢 Robert Half
📍 Ontario