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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.

Commercial Real Estate Financing Associate
Location: Vancouver, BC or Calgary, AB
Compensation: Competitive base salary plus uncapped commissions and excellent benefits

Are you ready to take your career in commercial real estate finance to the next level? We’re hiring an Associate, Commercial Real Estate Financing to join our dynamic client in Vancouver or Calgary. The office is fully hybrid and will offer unparalleled growth opportunities because the company is focused on Western Canadian expansion and is allocating 50% of its marketing budget to these two provinces (Alberta and BC). This is a role that offers the chance to work on diverse, high-impact transactions while building strong relationships across the real estate industry.

This is a role where you can join at the senior analyst / associate level and within several years move your way up within originations to have your own book of business and be earning $400K+ per year, $600K+ for top performers. Apply now!

Key Responsibilities:

  • Analyze and structure competitive transactions for various mortgage product types, including land loans, construction loans, servicing loans, inventory loans, and term loans.
  • Collaborate with the origination team to prepare high-quality Term Sheets/Deal Summaries for credit and investor approval, contributing to overall profitability.
  • Assist in preparing and issuing Letters of Intent and internal credit applications for new financing opportunities.
  • Build relationships with borrowers, understanding their needs, and ensuring timely, superior customer service to meet funding deadlines.
  • Work closely with underwriting and portfolio management teams to ensure accurate Term Sheets/Deal Summaries for funding transactions.
  • Stay informed about industry trends and proactively identify opportunities for growth and development.
  • Represent the company at industry events, collecting market intelligence and networking to establish a strong brand presence.
  • Conduct research to support market and new client pursuits.

Requirements:

  • Strong analytical and underwriting skills with a focus on real estate finance.
  • Knowledge of various mortgage products and commercial real estate transactions.
  • Preference will be given to individuals with a competitive sports background, but is not mandatory.
  • Exceptional communication and relationship-building abilities.
  • Proficiency in financial modeling and quantitative analysis.

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

Director of Finance
Downtown Toronto, ON (hybrid)
Competitive compensation with excellent benefits – commensurate with experience

Our client is a growing Real Estate development and management company in Toronto, ON. They are looking for an experienced director who is coming from real estate development. This position will support the current CFO and will ultimately move up to lead a significant portion of the business. As it stands now, the position will be very hands-on but will oversee a team of five accountants. Individuals with hands-on Yardi experience will be given preference.

Reporting to the CFO, the Director of Finance will be responsible for oversight of all finance, accounting and analysis for a portfolio of real estate development assets. The Director will aid in all corporate accounting, including yearly reviews and tax planning, and reporting for certain legal entities, assist with financings for new and existing assets and be a key liaison with lenders. The majority of this position will be to lead development accounting for certain key projects, including monthly draw process. The role will provide significant exposure to senior executives and help chart the strategic growth for the organization.

Responsibilities:

  • Prepare financial statements with notes in accordance with accounting standards on a monthly/quarterly/semi-annual/annual basis as per company requirements.
  • Perform cash flow analysis on an individual entity and portfolio basis
  • Perform monthly analysis of hospitality portfolio, including benchmarking
  • Assist in the preparation of detailed year end working paper files for audit or review purposes.
  • Manage and prepare all lender reporting along with internal debt schedules
  • Assist with new and existing financings including review, drafting and negotiations of credit agreements and working with legal counsel
  • Produce portfolio metrics looking for opportunities for improvement of margins
  • Manage banking relationships and assist with wire transfers and cash management
  • Assist in preparing budgets and forecast as required
  • Assist in reviewing due diligence materials, review of asset purchase & sale agreements for the acquisition of hospitality and real estate assets.
  • Lead project accounting and monthly draw process for key projects
  • Work with tax consultants and CFO for tax review and planning for entities
  • Additional duties and responsibilities as required

Requirements:

  • University degree
  • Minimum 6 years of experience
  • Exposure to financing; due diligence; acquisitions/divestitures, project accounting and year-end financials
  • Strong computer skills, specifically in Excel
  • Excellent communication and leadership skills

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.

Chief Financial Officer
North York, ON – onsite
Competitive compensation package

Are you ready to lead the financial strategy for a growing organization? We’re seeking a results-driven CFO 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. We are looking for an individual who can be flexible with longer hours, especially as this role will require some restructuring and overhaul of processes and procedures.

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
  • Manage FP&A functions
  • 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. Unfortunately, due to the high volume of applicants, only those selected for an 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].

 

Director of Mortgage Underwriting
Toronto, ON – hybrid
High paying with great benefits/bonus

Are you a driven, detail-oriented professional with a passion for commercial mortgage underwriting? We’re on the hunt for a dynamic Director, Underwriting to join a fast-paced and entrepreneurial team and supervise three underwriters. If you’re ready to lead and thrive in a high-energy environment, this role could be your perfect match.

What’s in it for you?

  • Comprehensive extended health benefits
  • Educational assistance for professional development and accreditation
  • RRSP matching program
  • Huge promotional opportunities

What You’ll Be Doing:

  • Managing and developing the Underwriting & Portfolio Management team, including training new hires.
  • Overseeing the underwriting and funding process.
  • Managing resource allocation and prioritizing deals.
  • Ensuring the timely submission of loan applications and funding documents to institutional and private investors.
  • Performing quality control on all loan applications and fundings (you’ll be the second signature).
  • Conducting thorough risk assessments and ensuring consistency.
  • Acting as a key contact for investors, addressing questions, and ensuring timely loan adjudication and funding.
  • Building and maintaining relationships with institutional and private investors.
  • Staying up to date with industry knowledge, competition, and market trends.
  • Collaborating closely with support staff and the executive team.

What You’ll Bring to the Table:

  • A post-secondary degree in Commerce, Business Administration, Economics, or Finance, with a focus on Real Estate or Land Development.
  • 5+ years of related experience in the real estate lending industry.
  • Management and supervision experience required.
  • Exceptional communication skills, both written and verbal, with acute attention to detail.
  • Proven leadership, organizational, and time management skills.
  • Bonus points for an MBA or CFA designation!

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.

Senior Property Accountant
Located Downtown Toronto (in office role)
Salary between $90k – $100k plus discretionary bonus and benefits

Our client, a multifamily asset management firm, is looking for a Senior Property Accountant to join their team. The firm has an expanding portfolio of over $700 million in AUM and the overall role for this candidate will be to manage the day-to-day financial operations of a portfolio of residential properties.  

Responsibilities:

  • Prepare monthly, quarterly, and annual financial statements for the residential multifamily property portfolio.
  • Accurately record all financial transactions, including rent collections, operating expenses, and
  • capital expenditures, ensuring compliance with internal controls.
  • Monitor and reconcile bank accounts, balance sheets, and general ledgers for assigned
  • properties.
  • Lead budgeting and forecasting processes, providing variance analysis and actionable insights
  • into financial performance.
  • Prepare and review detailed financial reports, including property-level profit and loss
  • statements, cash flow projections, and budget comparisons.
  • Coordinate the preparation and submission of year-end working papers for external auditors,
  • responding to audit queries in a timely manner.
  • Evaluate financial performance, identifying opportunities for optimization to improve
  • profitability and operational efficiency.
  • Collaborate closely with property managers, asset managers, and senior leadership to align
  • financial strategies with operational goals.
  • Mentor and guide junior accounting staff, fostering a collaborative and productive work
  • environment.
  • Assist with special projects and ad hoc reporting as assigned by senior leadership.

Qualifications

  • Bachelor’s degree in Accounting, Finance, or a related field.
  • CPA designation or working towards a CPA is preferred.
  • Proficiency in accounting software such as Yardi, MRI, or similar property management systems.
  • Advanced Microsoft Excel skills (pivot tables, v-lookups, etc.).
  • Strong understanding of IFRS and Canadian GAAP accounting principles.
  • Exceptional attention to detail, analytical capabilities, and ability to manage multiple priorities in a fast-paced environment.
  • Bilingual skills (French and English) would be an asset.
  • Ability to work independently and collaboratively with cross-functional teams.

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. 

VP of Mortgage Origination
Calgary, Alberta – remote
$400,000-$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 VP 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.

We are seeking a Vice President, Origination to lead and grow relationships with real estate developers, property owners, and key stakeholders across Alberta and British Columbia. This critical role will drive business development, enhance market presence, and advance strategic growth.

Key Responsibilities

Marketing/Strategic Planning:

  • Collaborate with senior executives to refine the brand strategy and increase market visibility.
  • Develop plans to meet business goals and identify opportunities in existing and new markets.
  • Promote brand awareness through business development initiatives (e.g., events, thought leadership).

Relationship Management:

  • Build and maintain strong relationships with clients and lending partners, understanding their risk appetites and needs.
  • Mentor junior originators and provide guidance to the Origination Team.
  • Monitor project progress, ensuring processes align with objectives.

Mortgage Origination:

  • Originate and adjudicate transactions for a range of mortgage products, including land loans, construction loans, bridge loans, and term loans.
  • Partner with lending teams to negotiate terms and provide detailed transaction feedback.
  • Stay informed on market trends, client needs, and competitor offerings.

Deal Management and Funding:

  • Oversee due diligence with the Mortgage Investments Analyst(s) and structure transactions to present to Investment Committees.
  • Negotiate and secure commitments through Letters of Intent and term sheets.
  • Support funding processes, ensuring clear communication with investors and lending partners.

Requirements:

  • 8+ years in loan origination with strong relationships in Alberta and British Columbia.
  • Extensive experience in credit adjudication, underwriting, and commercial real estate finance.
  • Proven track record of successfully originating deals in the $15M+ range.
  • Strong sales, marketing, and relationship-building skills.

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.

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.