Sr. Manager Investment and Development; Seniors Housing

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
• Location: Markham Ontario
• Working Arrangement: 100% On‑Site

Reporting to the Vice President, Investments, the Senior Manager, Investments & Development (Seniors Housing) will support the structuring and execution of development opportunities across the organization, predominantly within the long‑term care division of Sienna. This role works cross‑functionally with all areas of the organization to deliver value‑added analysis and actionable recommendations.

The Senior Manager, Investments & Development (Seniors Housing), plays a pivotal role in the execution of the organization’s development strategy to support long‑term financial sustainability and growth, by leading underwriting, financial modelling, due diligence coordination and investment committee materials related to development opportunities.

• Support the commercial structuring and execution of development opportunities, including the evaluation and negotiation of key deal parameters, economic terms, and financing considerations to optimize risk‑adjusted returns.
• Collaborate closely with internal legal counsel and external advisors throughout the transaction lifecycle, supporting the drafting, negotiation, and execution of Letters of Intent (LOIs), Purchase and Sale Agreements (PSAs), and other transaction‑related documentation.
• Develop, maintain and continuously improve comprehensive financial models to forecast project costs, timelines, and expected returns for development opportunities.
• Lead the preparation of investment memoranda, business cases, and development summaries for Investment Committee and Board review, synthesizing complex financial, operational, and due diligence information into clear, actionable recommendations.
• Build and maintain redevelopment models to project cash flows and calculate returns under various operational and financing scenarios.
• Coordinate transaction execution activities, ensuring adherence to critical timelines, approval requirements, and closing deliverables while facilitating communication among internal stakeholders and external partners.
• Lead reporting requirements and oversee procurement process for development projects and contracts.

• Coordinate and manage due diligence process across cross‑functional teams.
• Review, interpret, and synthesize third‑party reports, including appraisals, environmental assessments, engineering studies, and legal documentation, incorporating key findings into underwriting assumptions and investment recommendations.
• Partner with senior leaders across the organization to align development opportunities with strategic objectives, operational capabilities, and long‑term portfolio goals.
• Support portfolio and pipeline reporting activities, providing analysis and insights on development status and strategic opportunities.

• Build and maintain strong relationships with operational leaders across business segments to ensure a deep understanding of the underlying business model and drivers of performance.
• Partner with Operations and Finance leaders to develop Net Operating Income (NOI) forecasts for new developments.
• Act as a trusted business partner to internal stakeholders, providing financial analysis, strategic insights, and…