Senior Manager, Investments and Development

Sienna Senior Living; Markham; On-site; CAD 97,000 - 121,000; Full time

Job summary

Sienna Senior Living is seeking a Senior Manager, Investments & Development in Markham to drive underwriting, financial modelling and due diligence for development opportunities. You’ll prepare investment memos and board materials and coordinate cross-functional teams to align deals with portfolio goals.

Reporting to the VP Investments, you’ll help structure transactions, manage LOIs and PSAs, and analyze returns under various market scenarios, contributing to long-term financial sustainability

Qualifications

• Minimum 5–7+ years in real estate investments, development, asset management, or corporate finance.
• Strong analytical skills with data synthesis across finance and other functions.
• Experience building dynamic financial models for development scenarios.
• Ability to assess third-party reports with commercial judgment.
• Proven ability to present to boards and Investment Committee.

Responsibilities

• Support commercial structuring and negotiation of deal parameters and terms.
• Lead underwriting, financial modelling, and due diligence coordination.
• Prepare investment memoranda and board materials.
• Develop redevelopment models to project cash flows and returns.
• Coordinate transaction execution and closing deliverables.
• Oversee procurement and due diligence processes for development projects.

Skills

Real estate investments

Financial analysis

Financial modelling

Cross-functional collaboration

Presentation to board

Education

Bachelor’s degree in finance, accounting, mathematics, or real estate

CPA / CFA / MBA designation (asset)

Tools

Microsoft Excel

Microsoft Word

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 Vice President, Investments, the Senior Manager, Investments & Development will support the structuring and execution of development opportunities across the organization. This role works cross functionally with all areas of the organization to deliver value-added analysis and actionable recommendations.

The Senior Manager, Investments & Development, 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.

How You’ll Succeed:

• 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.

Who you are:

• Bachelor’s degree in finance, accounting, mathematics, or real estate preferred.
• 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
• 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.
• Strong business acumen with an interest in real estate development, seniors housing, and AI applications.
• Proven capability to develop high-quality presentation materials for Board and Investment Committee review
• Collaborative team player who works effectively across departments and stakeholders.
• Strong work ethic and exceptional attention to detail with a focus on accuracy in dynamic environments.
• Advanced knowledge of Microsoft Office applications (Excel, Word, PowerPoint).

What you need to know:

• The salary range for this position is: $96,655.00-$120,818.50
• 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 an existing 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.