Vice President, Corporate Strategy

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

Benefits offered by this job

Competitive compensation

Health & Dental Benefits

RRSP with company match

SOAR share ownership

Employee share purchase plan

Continuous learning

Diversity and inclusion

Job summary

Sienna Senior Living is seeking a Vice President, Corporate Strategy to act as a trusted advisor to the Executive Team. You will lead strategic initiatives, build business cases, assess risks, and create implementation roadmaps that drive growth and value across the organization.

You will collaborate with business leaders to advance innovation, growth, and operational excellence while supporting the annual strategic planning cycle and enterprise-wide transformation efforts.

Qualifications

• Bachelor’s degree in a related field.
• MBA strongly preferred.
• Postgraduate education in Strategy/Finance is an asset.
• 10–15 years of progressive experience in corporate strategy, management consulting, or related executive roles.

Responsibilities

• Identify and evaluate high-priority strategic growth opportunities across the organization.
• Develop business cases with rigorous analysis and actionable recommendations.
• Lead executive-level discussions to assess growth, innovation, and efficiency opportunities.
• Partner with senior leaders to evaluate new services, operating models, and revenue streams.
• Develop implementation roadmaps with milestones, risks, and governance considerations.
• Conduct market research, competitive analysis, and scenario planning.
• Establish consistent frameworks for evaluating strategic initiatives.
• Support pilots, proof-of-concept projects, and early-stage implementations.
• Prepare executive-level reports and briefings for the Board.

Skills

Strategic thinking

Analytical reasoning

Structured problem-solving

Executive communication

Stakeholder management

Financial modeling

Education

Bachelor’s degree in Business Administration, Economics, Finance, Engineering, or related field

MBA

Postgraduate education in Strategy or Finance

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:

• 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.