Apply on Kit Job: kitjob.ca/job/2g8ptv

Overview 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

Location: Markham Ontario

Working Arrangement: 100% In office

What You’ll Be Doing Reporting to the Chief Financial Officer & Executive Vice President, Investments, the Vice President, Investments will lead the initiation, structuring and execution of acquisitions across the organization. This role will act as the primary point of contact for external stakeholders and lead transactions from initial outreach to the execution of definitive agreements.

The Vice President, Investments will partner with the Vice President, Finance as it relates to underwriting, financial modeling, due diligence coordination and investment committee materials.

How You’ll Succeed

Lead the proactive sourcing and development of acquisitions and other investment opportunities through long-standing industry relationships with senior housing owners and operations, developers and builders, brokers, and advisors.

Develop and sustain a strong pipeline of proprietary and intermediate opportunities.

Act as the primary external relationship lead for prospective transaction counterparties, ensuring consistent engagement and strategic alignment.

Represent the organization at industry conferences, meetings and sector events to strengthen brand presence and generate new business opportunities.





Lead the commercial structuring of transactions including: deal parameters and economic terms, partnership and joint venture frameworks as well as purchase price methodologies and closing conditions.

Work closely with in house legal counsel on the drafting, negotiation and execution of: Letters of Intent (LOIs), Purchase and Sale Agreements (PSAs).

Partner with Legal Counsel and external advisors to manage negotiation process and mitigate contractual risks.

Act as the transaction lead, driving momentum and oversight from signed LOI through to closing.

Support and coordinate the exchange of information between external stakeholders and internal teams.

Partner with the Vice‑President, Finance to provide transaction context, commercial rationale and key business assumptions.

Identify, assess and support the resolution of commercial, operational and/or regulatory concerns that arise during the transaction lifestyle.

Collaborate with Senior Operational Leaders to evaluate strategic fit within the existing portfolio, operation model compatibility and integration considerations and transition risks.

Review high-level operational and strategic synergies, without leading detailed financial modeling.

Support post‑close integration planning in partnership with operations and other internal stakeholders.

Serve as a senior organizational representative in all external transaction‑related interactions.

Provide market intelligence on acquisition trends, valuation benchmarks and competitive dynamics to inform investment strategy.





Deliver transaction updates, insights and strategic recommendations to the Senior Executive Team as required.

Set direction and establish priorities for key department initiatives as assigned.

Actively demonstrate our leadership commitments and model the appropriate leadership qualities.

As part of the senior leadership team, provide input into the overall business strategy of the organization and help set the strategic direction.

Who You Are

Bachelor’s degree in Business, Finance or a related field.

MBA or relevant graduate degree preferred

20+ years’ experience in acquisitions, development or strategic partnerships within Long‑Term Care, Retirement Living, Senior’s housing or Healthcare Real Estate.

Exceptional ability to build strong relationships with key stakeholders and manage complex stakeholder dynamics.

Ability to apply a deep understanding of market trends, financial drivers and business risk.

Strong executive presence and the ability to communicate complex information in a concise and persuasive manner, enabling informed decision‑making in high‑impact environments.

Ability to manage complex transactions without direct underwriting responsibility.

Highly collaborative mindset, fostering teamwork, transparency and shared accountability.

What You Need To Know

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.

#J-18808-Ljbffr

Apply on Kit Job: kitjob.ca/job/2g8ptv

📌 Vice President, Investments (Markham)
🏢 Sienna Senior Living
📍 Markham