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. 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 solid investor relations instincts: someone equally comfortable underwriting a deal from scratch and standing in front of capital partners to advocate for it.

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 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. Ensure the financial integrity of each project is sound and defensible; 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.

Help coordinate data, reporting, and analyses required to support asset-level initiatives, pipeline reviews, and management decision-making. 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. 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. 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.

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. 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.

📌 Sr. Manager, Development Finance & Capital Strategy (Markham)
🏢 Trolleybus Urban Development
📍 Markham