Regional Director of Operations - Retirement at Sienna Senior Living in Markham, ON, CA. This Full time on site position offers great opportunities for career growth.

Location: Markham, ON, 302 Town Centre Blvd.

Category: Management.

Job ID: REGIO079111. Full time. Sep 21 2026.

At Sienna, we empower our team members across Ontario, British Columbia, Saskatchewan and Alberta to help our residents live the life they desire and deserve.

Our purpose is simple: to cultivate happiness in daily life!

What Sienna Offers

A competitive compensation and vacation package

Employer Paid Health & Dental Benefits

RRSP with Company Match

Share Ownership and Reward Program (SOAR)

Employee Share Purchase Plan with Company Match

Continuous learning and growth so you have the skillset needed to succeed and take on new challenges A welcoming culture that values diversity and differing perspectives, experiences and beliefs

What You’ll Be Doing

This position is located in British Columbia.

Analyze and define an operational plan for each home and the overall region to improve growth and performance, elevate quality of care and strengthen team member engagement

Shape and champion new initiatives to anticipate current & future needs of seniors and their families

Actively engage with colleagues, community partners and regulatory bodies to consistently achieve results

Drive organizational change to effectively anticipate and respond to the needs of residents and their families, leaders, team members and community stakeholders/partners

Align and build an effective leadership team by articulating expectations and inspiring commitment & performance





Attract and select the best leadership talent

Who you are

Education and experience should come from the health sector where you have led large teams, worked in a fast-paced environment and worked with multiple internal and external stakeholders.

A university graduate, with 3-5 years’ experience in a leadership role.

An exceptional leader with operational knowledge, strong business acumen and has a demonstrated track record of delivering results and continuously improving performance.

Possess strong financial judgement, including P&L; experience in developing, monitoring and reporting on annual operating and capital budget.

Sound knowledge of Long-Term Care Communities Provincial Regulatory Framework.

A strong bias for customer service, specifically a passion for seniors and senior living.

A collaborative senior leader that seeks diverse input from multiple sources and can flex their leadership style when faced with obstacles.

Powerful communication and executive presentation skills.

What you need to know:

Any offer of employment will be conditional upon a criminal background and references check.

Extensive Travel within British Columbia based on Operational/Business requirements.

This posting is for an existing vacancy.

Sienna Senior Living may utilize artificial Intelligence to screen or assess applicants for this position.

Sienna Senior Living is committed to employment equity, diversity, and inclusion in the workplace.

In accordance with provincial regulations, upon request, support will be provided for accommodations throughout the recruitment, selection, and assessment process.

📌 Regional Director of Operations - Retirement at Sienna Senior Living (Winnipeg)
🏢 Sienna Senior Living
📍 Winnipeg