Our client, a Canadian family enterprise requires an Executive Assistant to join their team. This is not just an administrative job. It is a high-impact role supporting the CEO and helping ensure his time is focused on the areas where it matters most. Today the group spans four business platforms: an auto dealership operation with three locations across the Greater Toronto Area; a national leasing division, Canada’s largest independently owned fleet leasing and management company; a ventures arm, the group’s investment platform focused on mobility technology; and a real estate division, which owns and develops the group’s property holdings. The group is in an active growth phase - recent acquisitions, a new operating model, and a national brand build.
The role involves working across multiple business units, with a variety of priorities and responsibilities that can shift quickly throughout the day. The successful candidate will need to be comfortable managing competing demands, staying ahead of priorities, and ensuring nothing falls through the cracks.
The North Star is simple: the CEO is focused, informed, connected, and spending time where it matters most; not reactive, overloaded, or chasing details.
Two key areas of responsibility will move off the CEO’s plate and onto yours: the meeting loop: agendas, notes, recaps, and action items, and follow-through: tracking commitments and projects through to completion.
You will be the filter, the memory, and the forcing function. You will help manage priorities, keep things moving, and ensure accountability across the business. This is a role for someone who is proactive, highly organized, comfortable taking ownership, and able to operate with sound judgment and discretion.
CORE RESPONSIBILITIES
- The meeting loop: own it end to end. Agendas and pre-reads out before every meeting the CEO hosts, with background research on the people and organizations in the room. Notes captured in the meeting. Recaps issued afterward with decisions, action items, owners and dates. Working with AI notetakers to make this fast and consistent.
- Follow-through and project management. Track every commitment made by and to the CEO across the businesses and chase them to close. Maintain the executive team’s open issue lists and project status. Prepare and circulate recurring reports. The standard: nothing is asked for twice, and nothing sits for two weeks because no one owned it.
- Calendar management. Own the annual planner and the daily calendar as a strategic instrument: protect focus blocks, enforce booking caps and buffers, match meeting type to energy level, and run a proactive daily review and 1–2 week look-ahead. Hold the scheduling guidelines; bring exceptions to the CEO proactively.
- Email and communications. Own inbox triage end to end: filter, summarize, respond, delegate, draft, and escalate only what genuinely requires his judgment. Build response templates for recurring inbound and route it to the right leader.
- Relationships, culture and events. Track birthdays, anniversaries and milestones. Surface wins worth recognizing. Learn names and faces across 400+ people. Plan leadership offsites, dealership events and group gatherings including venue, format, budget, logistics.
- Stand in for the CEO. Attend designated internal and operational meetings on their behalf, representing their position accurately, and report back - freeing time for the external work only they can do.
- Documents and brand. Keep OneDrive and Teams in order. Prepare presentations and Canva assets. Support the CEO’s external presence: LinkedIn, curated content, speaking and media opportunities, and coordination with the PR and agency partners.
- Personal and family coordination (roughly 10–15% of the role). Travel research and booking, personal appointments, gifts, expense reporting, household and family logistics. This is a genuine part of the job, not an afterthought. If it isn’t for you, this isn’t the right role, and that’s completely fair.
WHO YOU ARE
- 8+ years supporting a senior executive. Ideally a CEO or founder in a multi-entity, owner-led or family business.
- A project manager, not just a coordinator. You hold dozens of open threads across unrelated workstreams and you close them. This is what separates a good candidate from the right one.
- Exceptional judgment and absolute discretion. You know what to handle, what to escalate, and when to say nothing. You will sit close to family, financial and personnel matters.
- AI-curious. Not an expert but the kind of person who reaches for a new tool to make the work better. The company is actively adopting AI and you will help lead it in the CEO’s office.
- Direct and warm. You will be asked to challenge, remind, nag and tell the truth, with humour and care.
- Calm at pace, and strong across Microsoft 365, Teams and Canva. Priorities shift and days run long around events and travel. You bring order rather than absorbing the chaos.
ADDITIONAL INFORMATION
– Location: North GTA, across the CEO’s office and the group’s locations in Thornhill, Woodbridge, Markham, and Aurora.
– Hybrid: Roughly 50/50 in-person and remote, weighted to in-person, flexible rather than fixed days. On-site for events and key meetings; occasional evenings. Must have driver's license and access to a reliable vehicle.
– Reports to: CEO
– Compensation: $120-130k base salary + discretionary bonus, benefits
TDS Personnel is an equal opportunity employer committed to fostering an inclusive and accessible workplace in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act (AODA). Accommodations are available upon request for candidates participating in all stages of the recruitment and selection process.
