Vice President, Corporate Strategy

Sienna Senior Living; Markham; On-site; CAD 180,000 - 260,000; Full time

Benefits offered by this job

Health & dental benefits

RRSP with company match

Share Ownership and SOAR

Employee Share Purchase Plan

Continuous learning

Diversity & inclusion culture

Job summary

Sienna Senior Living seeks a Senior leader to drive corporate strategy, growth and transformation. You will partner with the CEO, CFO, and Executive Team to shape opportunities, build robust business cases, and deliver implementation roadmaps that advance residents' experience and organizational value.

Lead cross-functional initiatives, oversee market analysis, and provide actionable insights to support decision-making, budgeting, and strategic planning in a multi-site senior living environment.

Qualifications

• MBA or equivalent with strong business acumen.
• 10–15 years in corporate strategy, management consulting or executive leadership.
• Experience partnering with C-suite and leading cross-functional teams.

Responsibilities

• Lead enterprise strategy and growth initiatives across the organization.
• Develop business cases, roadmaps, and implementation plans.
• Coordinate with CEO/CFO and executives to align on priorities and governance.
• Provide executive insights on trends, risks, and opportunities.

Skills

Strategic thinking

Executive communication

Stakeholder management

Financial modeling

Leadership

Problem solving

Market analysis

Education

MBA

Bachelor's in Business/Finance/Engineering

Tools

Excel

PowerPoint

Job description

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:

We aspire to cultivate an environment and culture where team members feel valued, heard and empowered to do meaningful work. We offer a number of programs and benefits that support team members' financial, personal and professional needs:

• 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:

Reporting to the Chief Financial Officer & Executive Vice President, Investments, the Vice President, Corporate Strategy serves as a trusted advisor to the Executive Team and senior leaders across the organization. The role is responsible for accelerating Sienna's most important growth, innovation, and business improvement opportunities by bringing structure, analytical rigor, and cross-functional leadership to strategic initiatives.

Working in partnership with business leaders, the Vice President leads the evaluation of strategic opportunities, development of business cases, assessment of risks and market dynamics, and creation of implementation roadmaps that support informed decision-making and successful execution. Strategic initiatives remain owned by the appropriate operating or functional leader, with Corporate Strategy providing the dedicated capacity and expertise required to move opportunities from concept to execution-ready plans.

This hands-on role provides leadership in enterprise strategy, innovation, market intelligence, and growth opportunities. With the support of an analyst, the role also supports the annual strategic planning cycle.

How You'll Succeed:

• Identify, evaluate, and advance high-priority strategic growth and business improvement opportunities aligned with Sienna's long-term objectives.
• Transform early-stage concepts into well-defined strategic initiatives supported by rigorous analysis and actionable recommendations.
• Partner with executive leaders to assess opportunities related to growth, innovation, workforce transformation, new services, ancillary revenue streams, operational excellence, and business model innovation.
• Lead comprehensive assessments of strategic opportunities through market research, customer insights, competitive analysis, operational feasibility reviews, financial modeling, and risk evaluation.
• Develop robust business cases that clearly articulate value creation opportunities, investment requirements, implementation considerations, risks, and anticipated returns.
• Conduct scenario analysis and evaluate strategic alternatives to support executive decision-making.
• Establish consistent methodologies and frameworks for evaluating strategic initiatives and growth opportunities across the organization.
• Create and implement a disciplined approach to evaluating, prioritizing, piloting, and scaling new business opportunities.
• Develop recommendations regarding market entry, service innovation, customer experience improvements, and long-term growth strategies.
• Evaluate strategic opportunities through the lens of resident experience, team member engagement, operational effectiveness, and shareholder value creation.
• Monitor industry trends, demographic shifts, consumer preferences, competitive activity, policy developments, regulatory changes, and emerging market opportunities affecting the seniors living, healthcare, and hospitality sectors.
• Assess external market dynamics and competitive developments to identify opportunities and risks affecting Sienna's strategic direction.
• Provide executive leadership with actionable insights regarding emerging trends and strategic implications for the organization.
• Establish clear accountabilities, deliverables, timelines, and decision-making frameworks for strategic initiatives.
• Develop implementation roadmaps outlining resource requirements, milestones, risks, economic impacts, governance considerations, and measures of success.
• Support the design and launch of pilots and proof-of-concept initiatives.
• Support business leaders through the early stages of implementation before transitioning ongoing accountability to operational ownership.
• Partner with the CEO, CFO, Executive Team, on key enterprise strategic priorities.
• Support the development and execution of Sienna's long-term strategic plan, ensuring alignment with corporate objectives, growth priorities, and financial goals.
• Support annual and multi-year strategic planning activities.
• Prepare executive-level reports, presentations, and recommendations for senior leadership and Board discussions.

Who you are:

• Bachelor's degree in Business Administration, Commerce, Economics, Finance, Engineering, Public Policy, Healthcare Administration, or a related field.
• MBA from a leading business school strongly preferred.
• Additional postgraduate education in Strategy, Finance, Economics, Organizational Leadership, Healthcare Administration, or related disciplines is considered an asset.
• 10 to 15 years of progressive experience in corporate strategy, management consulting, business transformation, operations, corporate development, or related executive leadership roles.
• Significant experience within a leading strategy consulting firm or an equivalent strategic advisory environment.
• Demonstrated experience partnering directly with executive leadership teams and influencing senior business leaders.
• Proven success developing and evaluating strategic growth opportunities, enterprise business cases, and investment decisions.
• Demonstrated success identifying and advancing enterprise-wide growth and innovation initiatives within complex organizations.
• Experience working within a complex, multi-site operating environment.
• Experience within senior living, healthcare, hospitality, consumer services, retail, or other service-oriented sectors is considered an asset.
• Exceptional strategic thinking, analytical reasoning, and structured problem-solving capability.
• Advanced business case development and strategic assessment skills.
• Exceptional ability to translate ambiguous business challenges into clear workplans and actionable recommendations.
• Excellent executive communication, presentation, and stakeholder management skills.
• High intellectual curiosity and the ability to rapidly understand new business challenges and opportunities.

What you need to know:

• This is an on-site position at our Shared Support office in Markham
• Any offer of employment will be conditional upon a criminal background and references check.
• This posting is for a new position
• 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.