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.

Director – Third Party Vendor Management 
Downtown Toronto (Hybrid)
$190,000 – $210,000 (plus 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. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted. 

Director, Underwriting – Remote Opportunity
$120,000 – $140,000 base plus up to 25% bonus and benefits
Growing Commercial Real Estate Lending Brokerage

Are you a professional in commercial, multifamily, or construction mortgage financing? Do you thrive in leadership roles, mentoring teams, and driving successful outcomes? If so, this fully remote position may be your next career step.

This organization, a leader in the mortgage financing space across Canada, is looking for a Director of Underwriting to join their team. With licensing in multiple provinces and an expanding reach, they are dedicated to delivering excellence in commercial, multifamily, and construction mortgage solutions.

As the Director of Underwriting, you’ll play a critical role in analyzing mortgage opportunities, managing client relationships, mentoring your team, and driving the success of mortgage deals.

Responsibilities

  • Analyze and prepare financing proposals, review mortgage applications, and liaise with CMHC, lenders, and third-party providers to ensure accurate and consistent application processes.
  • Lead client calls, address inquiries, and build relationships with third-party providers such as appraisers and cost consultants.
  • Oversee work distribution, provide coaching and feedback, and lead team meetings. Actively support hiring and onboarding processes for new team members.
  • Propose and implement process enhancements to improve efficiency and team capacity.
  • Stay informed on real estate and mortgage trends and foster a culture of continuous learning within the team.
  • Other ad hoc projects and tasks

Requirements

  • At least 7 years of experience in commercial, multifamily, or construction real estate roles, with 5 years directly focused on mortgage lending.
  • A minimum of 5 years in a managerial or supervisory role within the mortgage industry.
  • Expertise in CMHC-related processes and financial modeling using tools like Excel.
  • Proven ability to mentor and train team members while managing multiple priorities in a fast-paced environment.
  • Strong understanding of underwriting principles, including rent rolls, operating statements, debt service ratios, and valuation models.

If you are interested in learning more about this opportunity, please apply now by sending a resume to [email protected] . 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)

This massive organization based in Downtown Toronto is seeking a charismatic Director to work on all 3rd party vendor issues, contract negotiations and vendor performance.  This is in a project environment where results matter and vendors need to perform. 

The ideal candidate will come from a Procurement, Sourcing, Vendor or Contracts Management background from either the Public or Private Sector.  Stakeholder and Vendor communication is vital, so you must have a strength in building trust and rapport.  You must also be a strong leader, to manage the team working under you.

This large organisation offers great opportunities for growth and development.

As the ideal candidate you will have:

  • 10+ years’ Procurement, Strategic Sourcing, Vendor Management or Contract Management experience
  • 4+ years’ Management experience
  • Exceptional communication skills
  • Excellent relationship building skills

If you would like to find out more about the role, please email Neil Drew ([email protected]) with your resume. Unfortunately, due to the high volume of applicants, only those individuals chosen for an interview will be contacted. To receive updates on new job postings regularly, follow us on LinkedIn.

 

Associate – Real Estate Development
Downtown Toronto – hybrid (Fridays from home)
$100,000-$110,000 base plus 10% bonus and a lucrative profit-sharing piece

Our client is a growth-oriented real estate development firm in downtown Toronto. The company is adding this brand-new position to the team where you will own the proformas for 10+ mid- and high-rise projects in the GTA. Post acquisition, the project will move to your division and you will have full financial responsibility for a number of interesting projects.

Responsibilities:

  • Take charge of development models and proformas for ongoing real estate projects, ensuring proactive management from acquisition to project completion to mitigate risks and maximize returns.
  • Oversee monthly updates on proformas, equity requirements, property tax payments, loan renewals, and insurance expirations.
  • Run various proforma scenarios to evaluate different project outcomes (e.g., sales launch date, additional height, unit mix) and determine the best approach.
  • Provide regular updates to the investment committee on project budgets, incorporating feedback from finance, construction, development, sales, and consultants.
  • Participate in critical decision-making and project management meetings throughout the entire development cycle (planning, design, sales, permits, construction, and delivery phases).
  • Review and assess legal documents (e.g., LOI, DM Agreements, JV Agreements, loan documents, fee proposals) and ensure financial models accurately reflect the agreements.
  • Monitor market conditions to identify opportunities to maximize returns or mitigate risks.
  • Manage the forecasting process, ensuring financial models remain aligned with market realities and departmental input.
  • Critically analyze progress draw reports.
  • Consolidate and organize project information, including financial summaries, for quarterly or monthly investor reporting.
  • Maintain high financial modeling standards, focusing on prudent leverage and minimizing exposure to risks.
  • Identify and address project risks (e.g., budget overruns) and provide operational insights to resolve issues.
  • Mentor and support the Senior Analyst.

Qualifications:

  • Minimum of 2-3 years of relevant experience with real estate finance, development or project management
  • Experience conducting asset management and financial analysis for development projects using advanced models in MS-Excel
  • Experience developing and maintaining budgets, project proformas, cash flow projections and financial reports
  • Strong understanding of development financing (typical financing structures at various stages of development) and land economics.

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.

Finance Manager
Windsor, ON (in-office)
Salary is between $100k – $125k plus bonus and benefits

Our client, one of the largest CPA firms in Canada, is looking for a Finance Manager to join their dynamic, collaborative team. This office is one of the fastest growing firms in the area and offers the unique opportunity of access to significant resources and mentoring while simultaneously enjoying an exceptional work-life balance.

Responsibilities:

  • Working closely with the CFO to support the internal operations of the firm, including
  •  Financial Reporting/Budgeting, Payroll, and administrative operations.
  • Managing the day-to-day accounting operations including financial reporting, general
  • ledger maintenance, receivables, payables, account analysis and cash management
  • Conduct financial analysis and provide insights into senior management for decision-
  • making and budget forecasting
  • Oversees payroll (semi-monthly), issues ROES as needed, Creates and prepares T4s
  • Collaborates with HR to ensure payroll deductions and activities are compliant
  • Process Improvements: Assist in developing, documenting, and implementing internal
  • controls. Assist in identifying inefficiencies and revamping processes.
  • Supervision of Finance and administrative resources.
  • Other duties as required.

Qualifications:

  • University degree in Business/Accounting, along with their accounting designation
  • 5 or more years of experience, including management of personnel; a mix of public
  • accounting and private company experience is considered an asset.
  • Advanced knowledge of MS Office and Excel. Familiarity with PowerBI and Dynamics
  • 365 is a strong asset.
  • Strong ability to analyze problems, problem-solving and negotiation
  • Ability work on a complicated group of companies is an asset.
  • Strong ability to handle multiple projects with tight deadlines in a fast-paced environment
  • Excellent attention to detail.
  • Project management experience

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, Finance
Welland, Ontario – hybrid
Competitive base plus bonus and benefits

Join a growing company dedicated to excellence in their multiple service lines. We are seeking an individual who wants to join a fast-growing and dynamic group of companies with a head office in Welland, ON. The company’s top line revenue has grown tremendously over the past few years. The VP Finance will be instrumental to lead the finance and accounting team and provide strategic oversight to the company’s financial operations. You will report directly to the President of the company with a small accounting and finance team.

Responsibilities:

  • Manage all QuickBooks accounting for several manufacturing plants
  • Handle daily sales reports, journal entries, payables, and bank reconciliations
  • Monitor cash flow and prepare monthly P&L reports
  • Manage quarterly WSIB and HST filings
  • Oversee accounting for multiple four different entities unrelated to the manufacturing business lines
  • Issue monthly rent invoices, handle mortgage payments, and bank reconciliations
  • File quarterly HST returns
  • Oversee bank reconciliations, intercompany invoicing, inventory adjustments, and month-end closes for parent company
  • Handle payroll for multiple divisions and process cash receipts
  • Submit covenant calculations to the bank and manage accounts receivable insurance
  • Prepare working paper files for year-end, maintain fixed asset subledgers, and process T5s
  • Analyze and manage Visa statements for employee charge approvals

Qualifications:

  • Undergraduate degree in Accounting, Finance, Business, or related discipline, with a Chartered Professional Accountant (CPA) designation
  • Intermediate to advanced proficiency in Microsoft Office, with the ability to present data and findings effectively.
  • Self-starter with strong motivation to take ownership of tasks, while also excelling in a team environment.
  • Strong ability to manage multiple priorities in a fast-paced environment.
  • Ability to work extended hours to meet tight 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 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.

Vice President Finance
Toronto, Ontario – Hybrid
Competitive Base Salary Plus 30% Bonus, Excellent Benefits & Vacation

A leading company in downtown Toronto is seeking a VP of Finance to oversee financial operations, reporting, and compliance. This role will manage corporate financial functions, including reporting, fund management, and investor relations. If you are looking to make a significant impact in a growing company and have expertise in real estate investments/asset management, this is the role for you.

Key Responsibilities:

  • Lead and manage financial reporting (P&L, balance sheet, cash flow) and variance analysis.
  • Oversee budgeting and forecasting, aligning with business goals.
  • Coordinate financial audits and ensure regulatory compliance.
  • Manage fund accounting, reporting, and investor communications for multiple investment vehicles.
  • Analyze portfolio performance, including key metrics such as loan composition and yield.
  • Lead payroll and benefits administration in collaboration with HR.
  • Oversee tax compliance, ensuring timely preparation of tax forms for investors.
  • Collaborate with the investment team to evaluate performance trends and provide strategic insights.
  • Supervise a finance and accounting team
  • Ad-hoc duties and special projects

Qualifications:

  • CPA designation with 10+ years of progressive experience, including leadership roles.
  • Strong understanding of real estate investments, fund accounting, and portfolio performance.
  • Previous external audit firm experience.
  • Proven ability to manage corporate financial reporting, budgeting, and audits.
  • Excellent leadership and communication skills, with experience managing teams.

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.

Manager of Finance 
North Bay, ON – 35 Hours Per Week – 3 Days Per Week In Office 
$90,000 – $100,000 Base Plus 5 Weeks Of Vacation And Great Benefits Including Pension 

Our client is seeking a highly qualified Manager of Finance to join their team in North Bay. This role is integral to the continued growth and success of the organization. With a strong mission and positive values, our client offers excellent work/life balance and a supportive team culture. If you have your CPA and comprehensive accounting experience, we encourage you to apply. 

Responsibilities: 

Leadership Team Participation: Actively participate as a member of the Agency’s Leadership Team, contributing to the development of the strategic plan and annual divisional operating plans, including financial and human resources allocation. 

Financial Management: Oversee full-cycle accounting operations, including accounts payable, accounts receivable, general ledger, and payroll responsibilities. Ensure accuracy, timeliness, and compliance with organizational policies and regulatory requirements. 

Budgeting and Forecasting: Oversee and support the preparation of organizational and departmental budgets. Provide strategic insights into resource allocation, financial forecasts, and risk identification. Ensure adherence to budgets and report notable variances to the Divisional Director. 

Financial Reporting and Controls: Oversee financial statement preparation, Management Discussion and Analysis (MD&A), and other financial reports. Design, implement, and monitor internal controls to safeguard assets and ensure compliance with corporate policies. 

Operational Leadership: Provide guidance, mentorship, and professional development opportunities to the Finance team. Foster a culture of accountability and continuous improvement within the department. 

Audit and Compliance: Liaise with external audit teams for audit reviews and internal control purposes. Ensure the organization’s financial processes align with regulatory requirements and best practices. 

Requirements: 

  • Bachelor of Commerce (BComm) or Bachelor of Business Administration (BBA) in Accounting, Finance, or related programs. 
  • Chartered Professional Accountant (CPA) certification is required. 
  • Minimum of five (5) years of experience in financial analysis with a strong understanding of Canadian accounting standards and regulatory compliance. 
  • Experience in non-profit organizations or knowledge of Accounting Standards for Not-For-Profit Organizations (ASNPO) is an asset. 
  • Strong communication skills, including negotiation, conflict resolution, and professional business writing. 

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

Senior Analyst – Real Estate Development
Toronto, ON – Hybrid
$80,000-$110,000 Base Plus Bonus and Great Benefits

Our client is a very active condo and rental development company. Reporting to the VP of Investments and Asset Management, this key member of the team will play a crucial role in evaluating potential investment opportunities and providing insightful analysis to support informed decision-making. This position involves project modelling, analysis, tracking, thorough industry research, analyzing financial data, assessing market trends to identify promising investment prospects and reporting on all aspects of the development process to the Management Team. This will also include asset management duties for a portfolio of development projects in the GTA.

Responsibilities:

  • Gather and analyze financial statements, market data, industry reports, and other relevant information to assess investment viability in real estate development acquisitions
  • Perform sensitivity analyses and scenario planning to evaluate the impact of market fluctuations and economic variables on investment performance
  • Underwrite mid- and high-rise multifamily rental and condo development opportunities in the GTA
  • Perform due diligence on potential investment targets, including evaluating financial performance, competitive positioning, and growth potential
  • Financial modelling to forecast project budgets, equity requirements, and partnership returns for a portfolio of rental and condominium projects
  • Collaborate with Development, Construction, and Finance teams in strategic planning, regulatory research, and budget monitoring throughout the project lifecycle
  • Assist in capital raising/investor relations efforts through the preparation of investment materials, scenario analyses, investment reporting, and other ad hoc tasks as required
  • Lead monthly investment accounting reconciliations, equity/debt draw requests and cost monitor budget reviews to ensure timely and effective project management
  • Performed extensive financial modeling including cash flow projections, detailed development and rental proformas, DCF’s, capital structure optimizations, and equity waterfalls
  • Prepare investment memos and reports outlining findings, analysis, and recommendations for investment opportunities.

Requirements:

  • Minimum of 1-3 years of relevant experience with real estate finance, or development management
  • Experience conducting financial analysis for potential land/real estate acquisitions using advanced models in MS-Excel
  • Experience developing and maintaining budgets, project proformas, cash flow projections and financial reports
  • Strong understanding of development financing (typical financing structures at various stages of development) and land economics.

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