Location: North York, Ontario
Work Schedule: Full-time, 4 days in-office 1 day remote
About Trolleybus
Trolleybus Urban Development is a boutique land aggregator and real estate developer specializing in purpose-built rental, student housing, and seniors housing. We are builders of relationships where every project we undertake is grounded in creating genuine, long-term value for our partners, landowners, and investors.
Our active pipeline includes purpose-built rental and student housing developments near major Ontario universities — including Guelph and McMaster — alongside PBR housing projects across the Greater Toronto Area. It's a pipeline built one relationship and one site assembly at a time, not acquired in a single multi-billion-dollar transaction. Our operations are expanding into South Florida along with a vertical integration by opening up a Real Estate Advisory firm.
Position Overview
Reporting directly to the CEO, the position will lead investment analysis for new acquisitions and own the company's capital raise & partner retention function, while also owning investment reporting across the active project portfolio.
This is a rare seat for someone who wants ownership over the full financial narrative of a growing development platform and not a narrow lane within a larger team. The ideal candidate combines technical fluency in financial modelling for income-producing assets with strong investor relations instincts: someone equally comfortable underwriting a deal from scratch and standing in front of capital partners to advocate for it.
Key Responsibilities
Investment Analysis, Underwriting & Capital Strategy
- Work closely with the CEO and core team to identify, analyze, and thoroughly underwrite potential acquisitions and development projects.
- Design project investment structures, including distribution waterfalls and investor IRR schedules.
- Partner with the planning & acquisitions teams to understand and communicate key market trends and focus areas for acquisition activity.
- Prepare Highest and Best Use feasibility reports for our Advisory Services and acquisition pipeline
- Assist in the evaluation of near-campus PBSA opportunities, including market sizing, enrollment and demand analysis, competitive set review, and operating assumptions.
- Prepare investment committee materials, memoranda, and presentation content for internal approvals and senior management review.
- Prepare monthly market research, benchmarking analyses, and presentation materials to support investment strategy, capital markets activity, and broader real estate business development.
Due Diligence, Reporting & Portfolio Oversight
- Coordinate and complete the financial due diligence processes, including preparing professional investor grade decks.
- Present to landowners, developer partners, and key investors.
- Ensure the financial integrity of each project is sound and defensible; liaise directly with cost and market consultants to validate inputs.
- Work with the operating teams to analyze leasing, occupancy, rental rate, NOI, capital expenditure, and operational KPIs, and identify trends, risks, and value-creation opportunities.
- Assist with business planning and ad hoc strategic initiatives.
- Help coordinate data, reporting, and analyses required to support asset-level initiatives, pipeline reviews, and management decision-making.
Candidate Profile
- University degree in Finance, Business Administration, Real Estate, or a related field.
- Minimum of 4 years of experience in residential real estate development and related investment structures.
- Advanced financial modelling skills in Excel, with the ability to leverage AI tools to enhance investment reporting.
- Strong acumen on report presentations, sound problem-solving, and logical analysis.
- Proven ability to multi-task, prioritize, and meet deadlines across multiple concurrent projects.
- Demonstrated ability to build and maintain external relationships within the real estate community.
- A proactive, entrepreneurial drive and comfort operating without the guardrails — or the bureaucracy — of a large corporate structure.
Why Trolleybus
- Direct access to the CEO — not five layers of VP, Director, and Principal between you and the person making the call.
- Full deal lifecycle exposure — acquisition underwriting through entitlement, and capital raise, instead of one specialized function within a large platform.
- Outsized ownership and visibility — your analysis directly shapes what gets built and who funds it. Your name is on the work that goes in front of capital partners.
- Faster decision-making — a small, senior team means ideas move from whiteboard to underwriting in days, not committee cycles.
- Room to grow with the platform — as Trolleybus's pipeline scales, so does your scope and seniority. This is a seat to grow into, not a defined lane to stay within.
- Excellent Benefits – An insurance program designed to keep you healthy, active, and supported. We have an in-office gym with healthy snacks. Plus, a $1,500 annual wellness credit.
- Competitive Total Rewards – We offer a well-rounded package that includes competitive pay, paid time off, market friendly vacation time, and performance-based incentives.
- Compensation – We are committed to supporting your success and are offering a salary range of approx: $80,000 – 90,000 CAD for this position reflecting your work experience.
Artificial Intelligence (AI) Usage
Trolleybus, at times, uses AI tools on a limited basis to support administrative tasks for our recruitment process, such as organizing applications and identifying basic keywords. These tools do not make or influence hiring decisions, which are made entirely by people reviewing your resume and conducting the interviews.
Pay: $80,000.00-$90,000.00 per year
Benefits:
- Dental care
- Extended health care
- On-site parking
- Paid time off
- Work from home
Work Location: Hybrid remote in North York, ON M2N 6Y8
