Executive Assistant (Chief Operating Officer)

Perennial; Toronto; Hybrid; CAD 60,000 - 75,000; Full time

Benefits offered by this job

Competitive salary

Benefits

Leadership access

Growth opportunities

Job summary

Perennial in Toronto is seeking an experienced Executive Assistant to support the Chief Operating Officer and the leadership team. This hybrid role combines high‑level administrative work with strategic coordination across the organization, ensuring priorities are clear and deadlines are met.

You will manage the COO's calendar, coordinate travel to Oakville, prepare materials, take notes, maintain confidentiality, and help drive projects.

Qualifications

• 5+ years of administrative or executive assistant experience, ideally supporting a senior executive or leader in a fast-paced environment.
• Experience supporting a COO, CEO, VP, or other senior leader is an asset.
• Experience managing a complex calendar and multiple competing priorities.
• Strong organizational skills and exceptional attention to detail.
• Strong follow-through. You don't let things fall through the cracks.
• Comfortable tracking deliverables, following up with stakeholders, and keeping people accountable to timelines.
• Strong judgment and discretion when dealing with confidential or sensitive information.
• Highly resourceful and able to figure things out independently.
• Comfortable working in a dynamic, rapidly changing environment where priorities can shift quickly.
• Strong business acumen and an understanding of how organizations operate.
• Proficiency with Google Workspace.
• Post-secondary education in business, administration, communications, or a related field is considered an asset. Equivalent professional experience will also be considered.

Responsibilities

• 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.
• 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.
• 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.
• Support presentations, reports, spreadsheets, communications, and other business materials.
• Coordinate cross-functional meetings and follow-ups.
• Support special projects and organizational initiatives as required.
• Take on other administrative responsibilities as needed to help the team operate effectively.

Skills

Calendar management

Administrative support

Communication

Discretion

Organizational skills

Problem solving

Education

Post-secondary education in business or related field

Tools

Google Workspace

Job description

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 initiatives as required.
• Take on other administrative responsibilities as needed to help the team operate effectively.

What We're Looking For

• 5+ years of administrative or executive assistant experience, ideally supporting a senior executive or leader in a fast‑paced environment.
• Experience supporting a COO, CEO, VP, or other senior leader is an asset.
• Experience managing a complex calendar and multiple competing priorities.
• Strong organizational skills and exceptional attention to detail.
• Strong follow‑through. You don't let things fall through the cracks.
• Comfortable tracking deliverables, following up with stakeholders, and keeping people accountable to timelines.
• Strong judgment and discretion when dealing with confidential or sensitive information.
• Highly resourceful and able to figure things out independently.
• Comfortable working in a dynamic, rapidly changing environment where priorities can shift quickly.
• Strong business acumen and an understanding of how organizations operate.
• Proficiency with Google Workspace.
• Post‑secondary education in business, administration, communications, or a related field is considered an asset. Equivalent professional experience will also be considered.

The Person We're Looking For

You are someone who:

• Anticipates rather than reacts. You think ahead and are always looking for what the COO or team will need next.
• Takes ownership. You don't need to be reminded twice and are comfortable driving things forward independently.
• Is resourceful. When you don't know the answer, you know how to find it.
• Is highly organized. You can manage multiple priorities without losing sight of the details.
• Understands business. You appreciate the bigger picture and understand why priorities and deadlines matter.
• Communicates clearly. You know when to provide an update, when to follow up, and when to escalates.
• Has good judgment. You can operate with discretion and navigate sensitive situations professionally.
• Thrives in ambiguity. You enjoy being part of a growing organization where things are evolving and you're helping build the processes along the way.
• Brings energy and ambition. You're excited by the opportunity to work alongside a senior leader and contribute to a growing organization.

Why Join Perennial?

• Genuine impact - your work directly shapes the experience of the clinicians caring for 10,000+ patients
• A foundational role with broad ownership and a clear line to leadership
• A growth‑stage company where you'll build, not just maintain
• Competitive salary, benefits, and more

Perennial is a fast‑growing healthcare operator at the intersection of primary care and senior living. You'll join a small, ambitious leadership team, work directly with the executive team, and have meaningful ownership over how care is delivered to thousands of residents across Canada.

Perennial is an equal opportunity, affirmative action employer. All qualified applicants will receive consideration for employment without regard to race, colour, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or any other characteristic protected by law.

If you are an individual with a disability and require a reasonable accommodation to complete any part of the application process, or are limited in the ability or unable to access or use this online application process and need an alternative method for applying, you may contact [e-mail] for assistance.

We thank all applicants in advance for their interest in this position, however, only those selected for an interview will be contacted.