Sr. Manager Investment and Development (Seniors Housing)

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Sienna Senior Living is hiring a Senior Manager, Investments & Development (Seniors Housing) to lead underwriting, financial modelling, due diligence, and investment committee materials for development opportunities. Based in Markham on-site, you will partner with Legal, Operations and Finance to evaluate deal terms, draft LOIs and PSAs, maintain development cash flow models, and translate due diligence into clear recommendations for the Investment Committee. The ideal candidate has 5-7+ years in real estate investments, development or corporate finance; CPA CFA or MBA a plus, along with strong analytical and presentation skills. To apply, tailor your resume to show end-to-end deal experience, NOI forecasting, cross-functional collaboration, and board-ready materials; expect background checks and AI screening; salary range 96,655 to 126,859; Markham onsite.

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.

What You’ll Be Doing:   

Development Support & Reporting

• 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.

Strategic & Operational Alignment

• 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.

Relationship Management

• 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 expertise to support development decisions across the portfolio.

Who you are:

• CPA, CFA and/or MBA designation a strong asset.
• 5-7+ years of relevant working experience in real estate investments, development, asset management, or corporate finance. 
• Strong analytical skills with the ability to gather and synthesize data across Finance and other functions to support ad hoc analyses and strategic initiatives.
• Experience building and maintaining dynamic financial and development models across multiple operating, development, and financing scenarios
• Ability to critically assess and summarize third-party reports with sound commercial judgment.
• Proven capability to develop high-quality presentation materials for Board and Investment Committee review, with guidance from senior leadership.
• Experience coordinating due diligence processes, with sound judgment on information relevance and sensitivity.

What you need to know:

• Any offer of employment will be conditional upon a criminal background and references check.
• We will review applications as they are received. Only those candidates selected for an interview will be contacted.
• Sienna Senior Living may utilize Artificial Intelligence to screen or assess applicants for this position.
• Salary Range: $96,655 - $126,859 **Please note that individual salary is determined by factors such as job-related knowledge, skills and experience, as well as internal equity**
• This posting is for a new 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.