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Our Winchesters Accounting and Finance team has extensive experience recruiting professionals across Ontario. Whether you are seeking a role as a Senior Accountant, Project Accountant, Accounts Payable, Property Accountant, Construction Accountant, Financial Controller, Senior Financial Analyst, Director of Finance, or VP Finance, our team can help you find your next career opportunity!

The Winchesters Team will help you find your next opportunity, whether you are looking to fill permanent, short-term, or project-based positions.

Below are current Accounting and Finance opportunities available through Winchesters. We also have exciting career opportunities related to procurement, tax, and audit, so please check our website regularly for new opportunities! To receive updates on new job postings regularly, follow us on LinkedIn.

Mortgage Analyst
$70,000 base plus 40% bonus, great benefits
Downtown, Toronto (5 days in office)

Our client is one of Canada’s best institutional mortgage brokerage and advisory firms. The company originates and structures unique financing solutions for real estate companies in the form of CMHC, mezzanine, construction, bridge and term loans. They are actively looking to find a new analyst for the mortgage underwriting team. If you have some experience in real estate deal underwriting and commercial mortgage underwriting, apply now!

Key Responsibilities:

  • Collaborate with mortgage professionals to assess commercial mortgage investment opportunities.
  • Analyze financial documents, including operating statements, rent rolls, and market data, alongside third-party reports such as appraisals and engineering assessments.
  • Develop proformas, cash flow models, and detailed project underwriting documents.
  • Research and share market insights, including brokerage reports, and cost consultancy findings, with the team.
  • Maintain an up-to-date database of market trends and comparable, including lease rates, vacancy rates, and construction costs.
  • Review and summarize external reports such as appraisals, environmental studies, and building condition assessments.
  • Organize and manage documentation, ensuring accurate and efficient record-keeping.
  • Assist in structuring mortgage opportunities that align with diverse investment criteria.
  • Prepare polished Mortgage Investment Brochures and commitment letters for team and client review.
  • Build and maintain relationships with third-party providers, including appraisers, engineers, and consultants.

Required Qualifications:

  • Bachelor’s degree in Commerce, Finance, Economics, or Math (MBA is a strong asset).
  • 1-3 years of experience in commercial real estate (preferred).
  • Strong knowledge of financial modeling, including IRR, NPV, and cash flow analysis.
  • Willingness to obtain a provincial mortgage license within six months if not already licensed.
  • Strong understanding of cash flow statements and financial analysis.
  • Advanced proficiency in Excel, including functions, pivot tables, and charting.
  • Familiarity with the real estate or finance sectors is an advantage.

If you are interested in learning more about this opportunity, please apply now or email your resume in confidence to [email protected]. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted

Senior Analyst – Acquisitions and Asset Management
Toronto, Ontario (3 days per week in office)
$100,000-$120,000 base plus 20% bonus

With this company being one of the fastest growing real estate companies in the GTA/Toronto, you will get experience and insight into the multifaceted operations and execution of high-profile real estate development projects and income-producing property portfolios. The company is looking to add a new person as a Senior Analyst or Associate of Acquisitions / Asset Management.

You will be responsible for the day to day duties of managing real estate models, acquisitions, monitoring project performance, planning/analyzing budgets, asset management, presentations, corporate analysis and identifying investment opportunities. If this new position sounds like a fit for you, do not hesitate to apply.

Responsibilities:

  • Conduct due diligence and feasibility studies to analyze acquisitions
  • Technical analysis and ensure proper accounting for acquisitions and deal disposition
  • Underwrite new development deals and create intricate proforma budgets
  • Conduct project budget review with focus on actual vs budget proformas monthly to meet company and project objectives
  • Analyze project cash flows and prepare sensitivity analysis to study impacts on overall project
  • Prepare equity and investment IRR waterfall analysis to ensure KPI’s are met
  • Continuously Monitor and update all project proformas, cashflows and IRR models in conjunction with project accountants, controller, and CFO
  • Create monthly project financial reports to present to LP partners, CEO, CFO and COO.
  • Participate, collaborate and give recommendations on projects and identify efficiencies for continuous improvements
  • Assist with execution of development portfolio strategy related to investments and supporting executive team on execution of transactional activity

Requirements:

  • Must have at least two (2) or more years’ experience in financial/investment analysis in real estate
  • Completed a university degree
  • Are analytical and have ability to produce analysis in appropriate language and style
  • Possess excellent communication (both written and verbal) and presentation skills
  • Have strong process management/improvement skills with a mindset for continuous improvement
  • Have ability to manage your time, with strong organizational skills and ability to prioritize tasks within a demanding environment
  • Are proficient in Microsoft Office suite some modeling software (Word, Excel, Project, Outlook)

If you are interested in learning more about this opportunity, please apply now or email your resume in confidence to [email protected]. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Portfolio Operations Manager
Toronto, ON – hybrid
Flexible compensation with huge upside

We are seeking a highly skilled and experienced Portfolio Operations Manager to help our client in managing a portfolio of a combined AUM of $100M for some prominent family offices. This role offers a unique opportunity to optimize operational processes, help an experienced portfolio manager, and work closely with top-tier family offices. Currently the wealth management firm is waiting to get approved by the OSC and this role will be pivotal to that. We are seeking someone with several years of experience working for an investment fund manager. We are also potentially open to individuals with a strong fund accounting background.

Key Responsibilities

  • Manage investments across Fixed Income, Money Market, and Real Estate portfolios.
  • Oversee and coordinate back-office administrative operations.
  • Enhance efficiency by streamlining processes for fund mergers and closures, utilizing strategies such as weekly rebalancing, capital calls, and fund-of-funds (FOF) initiatives.
  • Extract and analyze daily trade data using SQL to provide actionable insights for the Fund Accounting and Trading teams.
  • Collaborate effectively with custodian banks, portfolio managers, and traders to resolve portfolio discrepancies and ensure smooth operations.
  • Verify and report transactions, including domestic and foreign bond/equity purchases, derivative trades, term loans, and margin movements.
  • Coordinate the settlement of Short-Term Notes (STNs) through close interaction with trading desks, brokers, and internal custodians
  • Develop macros and automated tools to optimize workflows

Requirements:

  • Designed and implemented process improvements, including automation of trade settlement workflows and enhanced client reporting templates.
  • Successfully supported large-scale fund integrations and operational initiatives, contributing to the growth and efficiency of the portfolio management process.
  • Proven experience in fund operations, portfolio management, or a similar role.
  • Expertise in Bloomberg Terminal, SQL, and financial reporting tools.
  • Exceptional organizational and problem-solving skills with a focus on process optimization.
  • Adept at building relationships with internal and external stakeholders, including portfolio managers, custodians, and trading desks.

If you are interested in learning more about this opportunity, please apply now by sending your resume to [email protected] Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of Finance – Accounting (12-18 month contract)
Downtown Toronto, ON – Hybrid
Competitive salary

We’re seeking an experienced Director of Finance to join a dynamic Toronto-based client. This role is pivotal in overseeing the financial reporting processes – monthly, quarterly, and annually – for the Core Accounting team. You’ll support operations, including acquisitions and dispositions, and play an integral role in working cross-functionally with senior leadership, investment, asset management, and property finance teams.

If you’re passionate about leadership, problem-solving, and continuous improvement, this role is tailored for you. We’re looking for a solutions-oriented, accountable team player who thrives in a fast-paced environment and enjoys mentoring and building cohesive teams.

Responsibilities:

  • Lead monthly, quarterly, and annual reporting deliverables, ensuring accuracy, timeliness, and ASPE compliance for a portfolio of funds.
  • Review and verify monthly forecasts to maintain compliance with covenants, manage liquidity, and provide accurate projections for acquisitions and dispositions.
  • Oversee the quarterly board reporting process, ensuring all inputs are accurate for board presentations.
  • Manage quarterly compliance reporting to lenders.
  • Direct the annual budget process, validating the accuracy and reasonableness of all assumptions.
  • Serve as the primary point of contact for the annual audit.
  • Oversee investor transactions, including capital calls, returns, preferred returns, and gain distributions.
  • Address investor inquiries promptly and professionally.
  • Lead and mentor a team of four, providing guidance and fostering professional growth.

Requirements:

  • Undergraduate degree in Finance or Business; CPA designation required.
  • Real estate experience is a major plus.
  • 8+ years of experience
  • Supervisory experience
  • Strong written and verbal communication abilities.
  • Preference will be given to individuals with prior audit firm experience
  • A collaborative team player with high ethical standards and integrity.

If you are interested in learning more about this opportunity, please apply now by sending your resume to [email protected] Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Vice President, Real Estate Development Finance
Oakville, ON – Hybrid
$200,000 – $300,000 base plus generous bonus

Are you an ambitious real estate development professional with a strong background in real estate private equity? Do you thrive on strategic financial analysis and have a proven ability to oversee complex portfolios with a focus on high-rise developments? This is an exciting opportunity to step into a leadership role where you’ll drive performance and maximize returns across a dynamic portfolio.

As the Vice President, you will be responsible for managing multiple private equity real estate portfolios, primarily focused on transit-oriented urban high-rise developments. This role requires a proactive leader who can develop robust business plans, oversee portfolio performance, and communicate effectively with investors.

Responsibilities:

  • Develop and execute strategic business plans to maximize investment returns and mitigate risks.
  • Conduct market research to identify trends and opportunities impacting urban high-rise developments.
  • Oversee portfolio financial models, including cash flow projections, valuations, and sensitivity analyses.
  • Monitor KPIs and benchmark performance against industry standards.
  • Evaluate new investment opportunities and provide insightful recommendations.
  • Lead the asset management team in forecasting, reporting, and day-to-day operations.
  • Collaborate with Development Managers to assess progress and address challenges.
  • Recommend capital structure strategies and oversee asset-level financing.
  • Conduct site visits to ensure compliance with development objectives.
  • Prepare comprehensive reporting packages for investors and stakeholders.
  • Deliver clear, professional, and transparent updates to build long-term trust.
  • Respond to investor inquiries with insights into portfolio strategies and outcomes.
  • Ensure adherence to all legal, regulatory, and financial requirements.
  • Proactively identify and mitigate risks associated with portfolio assets.
  • Maintain meticulous documentation for all portfolio activities.

Requirements:

  • Bachelor’s degree in finance, real estate, business, or a related field; MBA, CFA, or CPA designation preferred.
  • 7–10 years of experience in asset management or real estate private equity, with a focus on high-rise developments.
  • Expertise in financial modeling and portfolio management tools.
  • Strong understanding of market trends and urban development dynamics.
  • Exceptional communication and relationship-building skills.

If you are interested in learning more about this opportunity, please apply now by sending your reume to [email protected]. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Corporate AP/AR Specialist
Located Mid-Toronto (4 days/week in office)
Salary between $60k – $65k plus discretionary bonus and benefits

Our real estate client is looking for a Corporate AP/AR Specialist to join their dynamic team to support with the day-to-day AP/AR functions and to contribute to the overall success of the team. 

Responsibilities:

  • Match invoices to backup documents (e.g., pay orders, quotes, receipts, etc. and obtain proper approvals for invoices
  • Monitor corporate invoice inbox and communicate with vendors in a professional manner
  • Address any invoice discrepancies with the vendors 
  • Reconcile vendor statements/ledgers to AP subledgers, research and correct discrepancies with analysts
  • Process invoices into Yardi using the scanner/labeler. 
  • Manage credit card reconciliations process with card users and prepare chargeback invoices as required
  • Prepare fee billings for applicable entities in a timely manner.
  • Process payments and cheque batches for controller review in a timely manner 
  • Process payments and cheque batches for controller review in a timely manner
  • Prepare deposits for bank using deposit scanner and prepare manual deposits as necessary. 
  • Maintain files and documentation thoroughly and accurately 
  • Assist with any inquiry by pulling copy of invoices as needed.
  • Ensure all banks are reconciled on a weekly basis by clearing cheques, deposits and fees. Communicate when entries are missing
  • Centralize all HST filings and payments for corporate entities through the online tax filing system monthly
  • Direct chargebacks to other entities in the Group for payments processed directly by corporate.
  • Liaise/coordinate with other inter-company AP contacts and vendors as required, and manage reconciliation processes for the Group
  • Adhoc reports as required

Qualifications

  • College degree in related field
  • A minimum of 3 years experiences in accounts payable/ receivable functions.
  • Experience using Yardi voyager
  • Superior interpersonal and problem-solving skills, with a customer service focus. Portrays a
  • professional image
  • Detail-oriented, process-driven, and take responsibility for your work

If you are interested in applying for this opportunity, please email your resume to [email protected]. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Vice President of Finance
Toronto, ON – Onsite
$175,000-$220,000 base plus bonus and great benefits

Are you ready to lead the financial strategy for a growing organization? We’re seeking a results-driven VP of Finance to work closely with the President in shaping the financial vision and streamlining operations. If you thrive in fast-paced environments and have a passion for process improvement and strategic leadership, this is the role for you.

Responsibilities:

  • Develop and implement financial strategies to optimize efficiency and scalability
  • Streamline processes, implement new systems and maintain a strong controls environment
  • Lead and mentor the finance team, ensuring peak performance
  • Collaborate with external partners, including banks, auditors, and consultants
  • Oversee reporting, internal controls, budgeting, and compliance
  • Review the current finance team and hire/fire if needed
  • Other ad hoc responsibilities

Requirements:

  • Bachelor’s degree in business or a related field along with CPA certification
  • Experienced in financial leadership
  • Proven ability to innovate, strategize, and deliver results
  • A natural mentor and leader who can inspire a team
  • Demonstrated success in establishing cooperative working relationships both internally and externally
  • Strong verbal and written communication skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to [email protected]. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of Mortgage Origination
Calgary, Alberta – hybrid
$300,000-$600,000 (base + bonus) plus excellent benefits

Are you an experienced commercial real estate professional with a passion for structuring innovative mortgage solutions? We are looking for a Director of Mortgage Origination to join a high-performing team in Western Canada. This is an exciting opportunity to contribute to a growing portfolio of mortgage investments while leveraging your deep knowledge of real estate markets across Canada.

As a Director, your focus will be to identify, structure, and manage mortgage investment opportunities. You’ll work closely with brokers, developers, and lenders to build a robust pipeline while overseeing detailed analysis and presenting opportunities to an investment committee.

Responsibilities

  • Build and maintain a strong pipeline of mortgage investment opportunities aligned with the company’s objectives.
  • Develop and nurture relationships with industry stakeholders, including brokers, developers, and service providers.
  • Conduct preliminary reviews, site visits, and due diligence for potential investments.
  • Recommend deal structures, negotiate term sheets, and lead the preparation of investment proposals.
  • Present and advocate for investment opportunities at committee meetings.
  • Collaborate with underwriting teams to structure and close transactions while adhering to policies.
  • Represent the organization at industry events and conferences to strengthen market presence.
  • Act as a resource to identify and refer opportunities across various product lines within the organization.

What You Bring

  • 7-10 years of experience in commercial real estate, ideally in an origination or similar role.
  • A university degree in business or a related field.
  • Expertise in real estate investment analysis, financial structuring, and transactional risk management.
  • Strong negotiation, critical thinking, and communication skills.
  • Familiarity with complex lending agreements and the ability to navigate financial and contractual challenges.

If you are interested in learning more about this opportunity, please apply now by sending your resume to [email protected]. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted. 

Project Accountant
Toronto, Ontario – hybrid
$75,000-$85,000 annual salary, 3 weeks of vacation, great health/dental benefits

Our client is a well-respected real estate company that is heavily involved in residential and commercial real estate development in the Greater Toronto Area. They are looking to hire a new Project Accountant to the team and this is a great opportunity for someone currently working in development accounting. This is a role within a CPA-accredited training company so if growing your career beyond just Project Accounting and Accounts Payable is a motivation of yours, apply now!

Responsibilities:

  • Create purchase orders and change orders within the accounting system using cost codes consistent with project budgets while complying to project specific workflows;
  • Prepare invoice packages for draw packages;
  • Review invoices, collect supporting backup, and facilitate approvals for the Development Department payment processing;
  • Conduct vendor progress billing, hold back and job cost reconciliations on an ongoing basis;
  • Generate variance reports to Project Managers and assist with quarterly project cost-to-complete reviews;
  • Provide support with mailing/couriering cheques as needed and filing paid invoices promptly and accurately;
  • Prepare project related accrual reports to support monthly draws for the Accounting Department;

Requirements:

  • Degree or diploma
  • Experience working in Accounts Payable within real estate development or construction
  • Knowledge of accounting and finance principles and practices, and the analysis and reporting of financial-related reports
  • Experience with Draws and/or large construction/consultant contracts
  • Proficiency in MS Office, including Word, Excel and Outlook
  • Ability to communicate effectively, both verbally and in writing

 

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Director – Third Party Vendor Management
Downtown Toronto (Hybrid)
$190,000 – $210,000 (plus benefits)

Join a leading Canadian real estate investment and asset management firm with over $1B in assets, encompassing more multi-family units, commercial units, and properties under development. This company prioritizes people, growth, and community impact, with over 15 years of success across Canada in multi-residential real estate investment. Known for a dynamic and supportive culture, they empower team members through personal and professional development opportunities. This role will start as a contract but will move to permanent, which to many people is no different than a probation period.

As a Senior Property Accountant, you’ll report to the Accounting Manager and manage full-cycle accounting responsibilities for a dedicated portfolio of properties. This role is integral to supporting both corporate and property financial functions in a fast-paced, growing team. You’ll handle the day-to-day accounting for a variety of real estate asset management operations, directly impacting the financial success of the business.

Responsibilities:

  • Manage full-cycle property accounting for a portfolio of properties and corporate consolidated entities.
  • Support monthly and quarterly financial reporting and management analysis.
  • Maintain the general ledger for the company’s various entities and properties.
  • Complete month-end entries, ensuring accuracy in transactions, subledgers, and corporate workbooks.
  • Post recurring entries such as mortgages, property taxes, accruals, and intercompany transactions.
  • Handle acquisition, mortgage, and disposition entries for property assets.
  • Reconcile balance sheet accounts, including bank and credit card accounts.
  • Manage Accounts Receivable, including payment processing, intercompany invoicing, and tenant transaction recording.
  • Assist with Accounts Payable related to property expenses.
  • Participate in accounting changes and process improvements.
  • Support ad-hoc projects and file HST returns for all corporations.

Requirements:

  • Bachelor’s Degree in Accounting, Finance, or a related field.
  • 3-5 years of experience in accounting, preferably within real estate or fund management.
  • Professional Accounting Designation (CPA) or ideally you will be enrolled (not mandatory)
  • Strong organizational skills with the ability to multitask in a fast-paced environment.
  • Team-oriented, adaptable, and committed to achieving results.

If you’re ready to take the next step in your career with a leading real estate company, send your resume to [email protected]. Please note that only candidates selected for an interview will be contacted due to the high volume of applications.