Executive Assistant; Chief Operating Officer

Position: Executive Assistant (Chief Operating Officer)
Position:  Executive Assistant to the Chief Operating Officer (COO)

Location:

Toronto
- Hybrid (3 days onsite per week)

Occasional Travel:  Oakville

Salary Range:  $60,000-$75,000 annually

Status:  Full-Time Permanent

Reports to:

Chief Operating Officer

About Perennial
Perennial brings primary care to where people live. We embed on-site nurse practitioners, physicians, and allied health professionals directly into senior living and long-term care communities, so residents get continuous, high-quality care without leaving home. Today we operate across 30+ communities in Ontario, Alberta, Manitoba, Saskatchewan and Quebec, with more than 500 clinicians serving 10,000+ patients and we're growing quickly into new regions and new lines of service.

We are looking for an ambitious, highly organized and resourceful Executive Assistant to support our Chief Operating Officer (COO) and the broader Perennial leadership team.

This is a high-impact role for someone who thrives in a fast-paced environment, enjoys working alongside senior leaders, and can anticipate what needs to happen before being asked. You will be a trusted partner to the COO, helping keep priorities organized, commitments moving, and the day-to-day operating rhythm of the team running smoothly.

If you are someone who brings energy, sound judgment, discretion, attention to detail, and a strong understanding of how businesses operate, we would love to hear from you.

The Opportunity
As Executive Assistant to the COO, you will provide high-level administrative and organizational support while helping the COO and Perennial leadership team stay focused on the priorities that matter most. This is a varied role where no two days will look exactly the same. You will be expected to manage competing priorities, stay ahead of deadlines and communicate effectively across the organization.

You will work closely with the COO, leadership team, and other members of the organization and will have visibility into a broad range of operational and business priorities.

What You'll Do
Executive & Administrative Support

Provide proactive day-to-day support to the COO, including managing priorities, scheduling, correspondence, meetings, and administrative tasks.

Manage a complex and changing calendar, ensuring meetings are appropriately prioritized, scheduled, and prepared for.

Help the COO stay organized and prepared for meetings, presentations, deadlines, and key commitments.

Prepare meeting materials, agendas, and other documents as required.

Take clear, concise meeting notes and ensure action items and follow-ups are captured and communicated.

Maintain a high level of confidentiality and discretion when handling sensitive information.

Deliverable & Priority Tracking

Track key deliverables, deadlines, and follow‑up items for the COO and Perennial leadership team.

Proactively follow up with stakeholders and provide updates on outstanding items.

Help maintain visibility into priorities, commitments, and timelines.

Identify potential gaps or delays and flag them proactively.

Bring structure and organization to projects and initiatives as needed.

Travel & Logistics

Coordinate travel arrangements for the COO and Perennial leadership team.

Book flights, accommodations, ground transportation, and other travel logistics.

Coordinate team meetings, off‑sites, events, and other business activities.

Manage itineraries and ensure logistical details are communicated clearly and in advance.

General Business & Team Support

Support the Perennial leadership team with administrative and organizational needs.

Assist with presentations, reports, spreadsheets, communications, and other business materials.

Coordinate cross‑functional meetings and follow‑ups.

Support special projects and organizational…