Career Contacts is a fractional human resources and recruitment consulting firm, supporting companies throughout Canada and the US.We provide support with permanent placements, temporary staffing, executive searches, HR consulting, and payroll management. We manage all phases of sourcing, screening, selection, and onboarding and retaining.

Career Contacts is recruiting on behalf of our client, a leading private investment and advisory firm, seeking an experienced, tech-forward Executive Assistant to provide direct support to the Principal/CEO.

This is a hands-on opportunity for an experienced Executive Assistant who thrives in a fast-paced environment and understands the level of organization, responsiveness, discretion, and judgment required to support a busy CEO.

The successful candidate will serve as a trusted partner to the CEO, managing complex schedules, communications, travel, digital workflows, and select personal and family-related responsibilities. This position requires someone who is equally comfortable coordinating executive meetings, troubleshooting technology, managing personal appointments, and anticipating needs before they arise.

We are looking for someone who has experience supporting a CEO directly and enjoys taking ownership of the full scope of executive support responsibilities. Less ideal for someone that is used to supporting in a large enterprise environment or supporting a full executive team. The ideal candidate is resourceful, highly organized and comfortable working independently without relying on a larger administrative support team. This is a fully in-office position requiring a high degree of professionalism, executive presence, flexibility, and confidentiality.

Start Date: ASAP

Hours: Monday to Friday, fully on-site (5 days per week)

Job Type: Full-time, Temporary (possibility of extension or permanency for the right fit)

Salary: $40.00 - $55.00 per hour (based on experience)

Location: Toronto, ON

Responsibilities

Executive Support & Digital Workflow Management

● Provide comprehensive, one-on-one executive support to the Principal/CEO, managing competing priorities across professional and personal commitments

● Manage complex calendars, coordinate meetings, resolve scheduling conflicts, and proactively anticipate the CEO's daily and longer-term needs

● Serve as a central point of contact for internal and external stakeholders, ensuring qualified and timely communication on behalf of the CEO

● Coordinate domestic and international travel arrangements,



including transportation, accommodations, detailed itineraries, and last-minute changes

● Prepare meeting agendas, briefing materials, presentations, correspondence, and follow-up documentation as required

● Track outstanding action items, deadlines, and commitments to ensure timely follow-through.

● Leverage Microsoft 365 and other digital tools to improve scheduling, communication, document management, and overall executive efficiency

● Manage confidential information and sensitive communications with professionalism and discretion

Personal & Lifestyle Coordination

● Provide personal administrative support to the CEO, ensuring professional and personal commitments are coordinated effectively

● Assist with family scheduling, appointments, travel arrangements, and other personal logistics.

● Coordinate personal errands, including prescription pickups, deliveries, and other time-sensitive requests

● Liaise with personal contacts, service providers, vendors, and external stakeholders as required.

● Assist with planning and coordinating private events, family engagements, and philanthropic initiatives

● Anticipate scheduling conflicts between professional and personal commitments and proactively identify solutions

Office & Operations Support

● Coordinate the CEO’s individual office and administrative needs, including personal office supplies, vendor arrangements, hospitality, and other day-to-day requirements specific to the CEO

● Manage digital filing systems, contact databases, expense reporting, and administrative tracking processes

● Identify opportunities to streamline administrative workflows and implement practical improvements

● Coordinate special projects and ad hoc requests with minimal oversight

● Provide hands-on support wherever needed, demonstrating flexibility and a willingness to take ownership of tasks both large and small

Requirements

● Minimum 5 years of progressive Executive Assistant experience, including direct, one-on-one support to a CEO, Principal, or senior executive with a demanding schedule





● Demonstrated experience independently managing the full scope of executive support responsibilities, rather than working within a larger executive administrative team.

● Expert-level proficiency in Microsoft 365, particularly Outlook, Teams, Word, Excel, PowerPoint, SharePoint, and OneDrive

● Strong technical aptitude and confidence troubleshooting everyday technology challenges, improving digital workflows, and learning new systems

● Experience managing complex calendars, coordinating travel, preparing executive communications, and maintaining organized digital systems

● Previous experience providing a combination of executive and personal administrative support, including family scheduling, appointments, and personal logistics

● Strong executive presence, communication skills, and the ability to interact professionally with senior leaders and external stakeholders

● Exceptional organizational skills, attention to detail, and the ability to manage competing priorities in a fast-paced environment

● Demonstrated ability to anticipate needs, exercise sound judgment, and work independently with minimal direction

● High degree of discretion and confidentiality, with the ability to handle sensitive professional and personal information

● Must be willing to sign a non-disclosure agreement (NDA)

● Comfortable working fully on-site, five days per week, in Toronto

● Ability to reliably travel to the office and coordinate occasional local errands, using a personal vehicle, rideshare, or public transportation as appropriate

Application Process

Please submit your resume in a Word document and let us know why you are the right fit for this role. Career Contacts is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment.

We look forward to hearing from you!

Your privacy and confidentiality are of utmost important to us; all applications to Career Contacts are kept confidential. We will not share your personal or professional information with anyone without your prior expressed approval. While we will only be considering qualified applicants for this position, we encourage you to visit our Job Board at www.careercontacts.ca for opportunities that fit your profile.

Pay: $40.00-$55.00 per hour

Experience:

- executive assistant: 5 years (preferred)
- Microsoft Office: 5 years (required)

Work Location: In person

📌 Executive Assistant (Toronto)
🏢 Career Contacts
📍 Toronto