Sr. Manager, Development Finance

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 w