Finance

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.

Vice President, Finance – Real Estate Development & Family Office

Concord, ON – onsite

$190,000-$210,000 base plus bonus

 

We are working with a dynamic and growing real estate development company that also operates a family office. They are searching for an eager, motivated, and strategic finance leader to join their executive team.

 

As Vice President, Finance, you’ll report directly to the President and play a vital role in shaping the financial direction of the business. This is a hands-on leadership role with oversight of all core financial functions, including accounting, forecasting, strategic planning, cashflow management, budgeting, deal structuring, investor relations, and compliance. You’ll be the financial voice at the executive table, offering insight and analysis to support both day-to-day operations and long-term growth.

 

You will also have exposure to ancillary businesses and personal financial matters through the family office, so we’re looking for someone with both the technical expertise and discretion to operate at the highest levels.

 

What You’ll Be Doing:

  • Leading the finance and accounting teams across all divisions
  • Developing and managing budgets, forecasts, and job costing systems
  • Partnering with executives to drive strategic decisions and long-term planning
  • Managing financial reporting, cashflow, and financing for various development projects
  • Supporting deal negotiations, investor communications, and partnership agreements
  • Ensuring proper internal controls and compliance with financial regulations
  • Overseeing systems implementation and technology improvements

 

What We’re Looking For:

  • CPA designation and/or MBA preferred
  • 10+ years in a senior financial leadership role, ideally within real estate development, property management, construction, or a family office environment
  • Strong understanding of job costing, financing structures, and complex reporting
  • Excellent leadership and communication skills, with the ability to work closely with executives and stakeholders
  • A proactive and strategic thinker who is also happy to roll up their sleeves when needed

 

How to Apply:

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.

Property Accountant

Mid-town Toronto, ON

$65,000 – $75,000 base, bonus and great benefits

 

Our client is a real-estate company based in North York, ON. They develop and provide residential properties in North America. They are looking for a Property Accountant to join the team on a full-time basis. This position offers an excellent opportunity to work in a company that manages a diverse real estate portfolio while being a key member in the business.

The successful candidate will be a responsible for providing timely and accurate management reporting for commercial real estate. If you are a highly motivated individual with a passion for real estate, this could be an exciting opportunity for you. In the role, you will be responsible for the following tasks:

  • Handling full cycle accounting functions
  • Oversight and management of bank accounts, record of cash inflow, payable invoices and payments
  • Ensure data on accounting system is up to date
  • Oversee accuracy of tenant’s ledgers and resolve billing differences
  • Assist Property Management and necessary departments with accounting information when requested
  • Work with property accountants concerning accounting, reporting, and property management activities
  • Handle enquiries from tenants
  • Prepare and review reporting packages; monthly and quarterly
  • Prepare tenant operating and tax reconciliations
  • Handle treasury functions
  • Prepare quarterly board requirements
  • Ad hoc duties as required

Requirements:

  • CPA designated or enrollment in the program
  • Post-secondary accounting education or equivalent accounting qualification
  • Proficient in Excel, Microsoft Word, and accounting software packages
  • Knowledge and experience in property management accounting
  • Good attention to detail

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

Office Manager – Real Estate

North York (On-site) – on the transit line

$80,000–$100,000 base plus bonus and great benefits

 

We’re looking for a smart, organized, and humble Office Manager to join a busy real estate office in North York. This is a full-time, in-office position—just steps from the subway line—and it’s ideal for someone who’s as comfortable reviewing legal documents as they are managing calendars for a busy CEO.

You’ll be the go-to person for keeping the office running smoothly, and your work will touch everything from legal paperwork and administration to office supplies and team support.

What you’ll be doing:

  • Managing the day-to-day operations of the office
  • Reviewing, organizing, and tracking real estate contracts and legal documentation
  • Handling administrative tasks like scheduling, calendar management, and correspondence
  • Keeping digital and physical files up to date and easy to access
  • Liaising with external consultants, lawyers and all 3rd party stakeholders
  • Making occasional supply runs (yes, you might be the one doing a Costco haul)
  • Supporting the team with anything they need to keep things moving

What we’re looking for:

  • Someone detail-oriented, proactive, and unflappable
  • Experience in real estate or legal admin is a strong asset
  • Strong organizational and tech skills (Excel, Google Workspace, etc.)
  • Comfortable juggling many moving parts with a great attitude
  • A true team player who doesn’t view any task as “beneath them”

 

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

Financial Controller

North York, ON – in-office

$90,000-$120,000 base plus 15% bonus and great benefits

 

Our client is a pension-backed real estate company seeking a Financial Controller to join their growing team. Established within the last five years, this company focuses on acquiring and managing high-quality commercial assets across North America. They pride themselves on building strong relationships and delivering value-add projects, all while maximizing returns and driving stakeholder value.

 

Reporting directly to the CFO, the Financial Controller will play a key role in building a top-tier accounting function. This role is ideal for someone with solid commercial property accounting experience who’s just as comfortable handling day-to-day accounting entries as they are contributing strategically. You should enjoy wearing multiple hats and thrive in a lean, hands-on environment. In this position you will not supervise any staff.

 

Responsibilities:

  • Review and assess monthly accounting reports from third-party property management—rent rolls, accruals, turnovers, utilities, AR, and management fees.
  • Prepare timely and accurate quarterly reporting packages for properties.
  • Review monthly financial variance analyses for both commercial and residential portfolios.
  • Support budget preparation and review for residential and commercial properties.
  • Ensure proper accounting standards are followed, including accruals, prepayments, and refinancing entries.
  • Handle year-end financials for external auditors.
  • Prepare CAM and tax reconciliations.
  • Play a lead role in improving and implementing financial systems and reporting processes.
  • Work on enhancing current templates to create more efficient reporting practices.

 

Requirements:

  • At least 5 years of relevant accounting experience.
  • Experience with commercial property accounting is a requirement.
  • Strong skills in Microsoft Excel and PowerPoint.
  • A strong communicator, both written and verbal.
  • Ability to work 5 days per week in the office near York Mills mall.

 

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

Project Accountant

$95k – $105k all in plus benefits

Mid-Toronto (in office)

 

Our client, a respected real estate developer, is looking for a Project Accountant to join their team. You will be responsible for managing the full cycle of accounting for a mix of high- and low-rise developments in a dynamic environment with a very competitive salary.

 

Key Responsibilities

  • Monitor the financial position of the projects – recommend financing alternatives, calls for funds, and distributions as appropriate;
  • Verify and approve payments, journal entries, invoices, remittances and lot sale transactions;
  • Review monthly trial balances and costing reports;
  • Update various tracking schedules needed for reporting and analysis;
  • Partner with Financial Analysts to review proforma budgets, cashflow forecasts and budget variance analyses;
  • Generate draw requests for financing and prepare monthly bank reporting packages;
  • Review legal agreements that govern joint venture partnerships and fee structure and interpret financial statement impact;
  • Prepare year end working papers, financial statements and stub period reporting for select projects;
  • Drive continuous improvement and assist with the documentation of the company accounting processes
  • Ensure and enforce compliance to all company and legislated Safety policies and procedures;
  • Other duties/projects as assigned from time to time.

 

Requirements

  • Ideally 2-3 years experience in project accounting
  • Advanced level computer skills, particularly Excel (i.e. pivot tables, lookups and advanced formulas);
  • Excellent verbal and written communication skills;
  • University degree or college diploma in accounting / financial management required;
  • Development industry experience preferred.

 

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

Manager, Corporate Accounting

Downtown Toronto – in-office role with some flexibility

$120,000 – $140,000 base plus bonus and generous benefits

 

Our client is a growing real estate organization that develops residential properties in North America. They are looking for a Manager of Corporate Accounting to join the team on a full-time basis. This position offers an excellent opportunity to work for an organization that delivers a significant social impact to communities across Canada.

The successful candidate will be a responsible for the oversight of corporate financial reporting, budgeting, forecasting and treasury. Ideally you will come with previous or current experience working in an accounting firm. Real estate sector experience is a must-have.

 

Responsibilities:

  • Supporting projects surrounding the corporate accounting and development accounting
  • Key lead in quarterly and annually budgeting and forecasting
  • Handle treasury functions
  • Prepare quarterly board reports
  • Liaise with auditors and communicate with development staff for tax returns/financial audits
  • Oversee accuracy of internal controls and accounting procedures through documentation
  • Review processes for efficiency of operations and reporting
  • Provide necessary leadership, guidance to corporate finance team
  • Ad hoc duties as required

 

Requirements:

  • CPA designated coupled with degree
  • Experience in full cycle accounting and ideally previous experience in public accounting
  • Impeccable communication and relationship building skills – both written and verbal
  • Proficient in Microsoft Excel
  • Ability to manage stressful situations and provide guidance to team members
  • Ability to continuously improve and implement efficient processes for development

 

How to Apply

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.

Senior Property Accountant

Scarborough, ON – 5 days per week in the office

$90,000-$100,000 base plus bonus and great benefits – excellent work/life balance

 

Our client is a well-established property management and real estate investment company with over 30 years of success and a 5+ million square foot portfolio across Canada. They’re known for their strong relationships with tenants and a fast-paced, dynamic work environment.

 

We’re looking for an experienced Accounting Supervisor or Senior Property Accountant to oversee property and corporate accounting functions. This role involves supervising a team, driving financial accuracy, and supporting key business decisions.

 

Responsibilities:

  • Review month-end reports and variance analysis – ensure accuracy and work with auditors as needed.
  • Manage fixed asset accounting and recoverable amortization schedules.
  • Oversee monthly recurring journal entries and ensure recovery accuracy.
  • Manage accounts payable, including weekly payment runs.
  • Maintain general ledgers and support financial reporting and analysis.
  • Lead the budget process, including preparing property tax budgets and recovery assumptions.
  • Oversee MPAC reporting and annual recovery reconciliation.
  • Monitor daily bank activity and manage fund transfers.
  • Provide financial planning insights based on cash flow timelines.
  • Lead and mentor junior team members and senior accountants.
  • Improve internal controls and update systems to meet business needs.
  • Handle vendor management and corporate HST returns.
  • Manage payroll and government remittances (T4s, ROEs, etc.).
  • Support stakeholders with financial advice and problem-solving.

 

Requirements:

  • 5+ years of accounting experience in real estate or property management.
  • Strong skills in accounting software and advanced EXCEL.
  • Excellent problem-solving and analytical skills.
  • Strong communication skills – able to engage with stakeholders and team members.
  • Detail-oriented with the ability to manage multiple deadlines.

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, Commercial Mortgage Loan Funding
Toronto, ON (hybrid)
Competitive, commensurate with experience

Are you a seasoned professional in commercial mortgage funding with a proven track record of success? Are you ready to step into a leadership role where you’ll drive operational excellence and foster key relationships? We’re seeking a Vice President of Commercial Loan Funding to join a high-performing team in Toronto.

Why This Opportunity?

  • Be a pivotal leader in a thriving organization.
  • Work in a dynamic and fast-paced environment with growth potential.
  • Enjoy a competitive compensation package, including robust benefits and professional development opportunities.

Key Responsibilities:

  • Lead and manage the commercial mortgage loan funding operations, ensuring timely and accurate execution of funding processes.
  • Hire, train and manage a high-performing team, providing guidance, mentorship, and training to drive exceptional performance.
  • Establish and maintain strong relationships with institutional and private investors, ensuring confidence in funding processes and outcomes.
  • Collaborate with underwriting, origination, credit and portfolio management teams to ensure seamless deal execution and adherence to service standards.
  • Monitor and refine funding workflows and quality control measures to enhance efficiency and accuracy.
  • Ensure compliance with all regulatory requirements and company policies.
  • Serve as the primary point of contact for complex funding issues, resolving them with speed and precision.
  • Stay informed on industry trends, competitive practices, and market conditions to inform strategic decisions.

What You’ll Bring:

  • A minimum of 8+ years of experience in commercial mortgage lending or funding, with at least 3–5 years in a senior leadership role.
  • A post-secondary degree in Finance, Business Administration, or a related field.
  • Comprehensive knowledge of commercial real estate lending, funding processes, and risk management.
  • Superior communication and interpersonal skills to build relationships with stakeholders at all levels.
  • Exceptional attention to detail, organizational skills, and the ability to manage multiple priorities in a fast-paced environment.
  • Advanced proficiency in Microsoft Office (Word, Excel, PowerPoint).
  • MBA or CFA designation is an asset but not required.

What Success Looks Like:
You’ll thrive in this role if you’re a natural leader who can balance strategic thinking with hands-on execution. You’re passionate about delivering exceptional results, building high-performing teams, and fostering strong relationships with stakeholders.

How to Apply:
If you’re ready to elevate your career and make an impact in the world of commercial mortgage funding, we’d love to hear from you. Please email your resume to [email protected].

 

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.

 Vice President Capital Markets  – Capital Raising
Toronto, ON – downtown hybrid
Competitive compensation made up of base plus bonus

Our client is a growth-oriented, Toronto based real estate investment firm primarily focused on multi-residential development in the Greater Toronto Area.

The VP of Capital Markets is a newly created role and will be an important role in the Company’s platform growth including fund raising, corporate development and product development. This is a broad role with significant responsibility, well suited to an individual with significant fund raising and client management experience, now looking to apply it in a hands-on, entrepreneurial and platform building environment. The company is seeking an individual who can leverage their pre-existing institutional and private client relationships to lead the capital raising initiatives.

With established expertise in capital raising and investment structuring, the incoming VP of Capital Markets will be an instrumental figure in establishing fundraising channels for the various investment mandates being undertaken by our client. The key area that you will be focused on will be HNW and family offices. The company has a great track record with an existing investor pool, but will like this person to join and help grow the investor base.

Roles & Responsibilities

  • Build and maintain strong relationships with prospective and current investors, with a focus on HNW and Family Office segments.
  • Maintain technical knowledge of the company’s offerings to provide the best solutions for investors.
  • Clearly communicate the offerings and assist investors with due diligence questions and investor subscription process, where appropriate from a legal and regulatory perspective.
  • Use CRM software to track business development efforts and progress achieved.
  • Assist in marketing efforts such as creating investor presentations, webinars, and educational materials.
  • Assist in structuring and successfully launching new investment mandates for the investors.
  • Establish, maintain, and engage with industry relationships including advisors, lenders, brokers, legal counsel, and accountants.

Qualifications & Experience

  • 7+ years of investment sales experience, with a proven track record in developing and growing Assets Under Management.
  • Intimate understanding of financial products that serve the interests of institutional and high-net-worth investors.
  • Experience in raising capital from family offices, UHNW individuals and HNW families or institutional avenues.
  • A self-starter who can manage individual responsibilities and maintain overall awareness of management priorities.
  • Excellent communication skills and ability to work in a team setting.

Our client is passionate about investing, community building, and the collective success of the team and their partners. Compensation is highly competitive and commensurate with experience. Please apply now if you are interested. Unfortunately, due to the high volume of applicants, only those individuals chosen for an interview will be contacted.