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.

EVP, Finance & Administration
Toronto | In-office | Real Estate
$220,000-$240,000 base plus 30% bonus and future LTIP

We are recruiting an Executive Vice President, Finance & Administration for a growing real estate investment company in Toronto. This is a newly created role, reporting directly to the CEO, and will be a key player in shaping the company’s financial and operational strategy as it scales.

The company specializes in acquiring and managing properties across Canada and the U.S. With strong financial backing and a growing portfolio, they are now building out their internal finance and administrative functions. The EVP will be responsible for establishing financial infrastructure, implementing systems and processes, and transitioning away from a third-party service agreement. The role will also oversee financial reporting, budgeting, forecasting, tax, treasury, risk management, IT, HR, and office operations.

In the near term, priorities will include:

  • Setting up financial systems and processes to support growth.
  • Managing the transition away from a third-party finance provider before their contract ends in 2025.
  • Refinancing a bridge loan as part of the company’s financial strategy.
  • Building relationships with external advisors, auditors, and lenders to ensure compliance and efficiency.

As the company scales, the EVP will play a strategic role in:

  • Supporting acquisitions and optimizing assets for long-term value.
  • Developing and implementing key financial metrics and KPIs to guide decision-making.
  • Providing financial leadership to the board and investors, ensuring transparency and strong governance.
  • Building and leading a high-performing finance team to support the company’s growth.

Who We’re Looking For

The ideal candidate is a proven finance leader with experience in real estate, asset management, or other recurring revenue business models. They should have a track record of scaling a finance function, leading financial strategy, and working closely with investors and boards. Strong analytical skills, business acumen, and the ability to balance strategic thinking with hands-on execution are essential.

Qualifications

  • CPA designation required
  • Experience in real estate, asset management, or private equity-backed companies is highly desirable.
  • Strong background in financial reporting, FP&A, treasury, and tax.
  • Experience with process automation and financial system implementation is a plus.
  • Ability to work effectively in a fast-growing, entrepreneurial environment.
  • Fluent French speakers will be prioritized.

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.

Accounts Payable Administrator
Located Downtown Toronto (3-4 days a week in office)
Salary between $60k – $70k plus discretionary bonus and benefits

Our client is a Toronto-based real estate development company and they are looking for an AP Administrator to join the team on a full-time basis. This position offers an excellent opportunity of learning and growth with an innovative developer and comes with perks such as hybrid work set-up, collaborative work environment, great work/life balance and benefits.

Responsibilities:

  • Receive and sort invoices, check invoices for accuracy and code invoices, and post invoices in     accounting system
  • Prepare for cheque and electronic payments
  • Prepare monthly HST reports
  • Reconcile accounts payable transactions
  • Check batch list at month end to ensure invoices are entered correctly and resolve discrepancies
  • Subcontract invoices – check accuracy of each progress billings – contract value, previously billed, and holdback matches to our records. Review invoice package for documents required under each contract
  • Reconcile vendor accounts including subcontractors’ final settlement at the end of project and holdback reconciliations
  • Main contact for vendor inquiries
  • Maintain tracking for invoices that are on hold
  • Banking duties, deposits and administrative duties as required

Requirements:

  • Minimum 2 years of previous experience – experience within the real estate field is preferred
  • Must be able to do 3-4 days a week in the downtown Toronto office
  • Experience using Yardi voyager is an asset
  • Strong communication skills

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 an interview will be contacted.

Corporate Controller
Downtown Toronto, Ontario – hybrid
$130,000-$150,000 base plus bonus and benefits

Our client is a growing diversified real estate company in downtown Toronto, Ontario, Canada.

This established company has been in business for more than 20 years and continues to grow with a number of exciting projects coming up. The CFO is looking for a Corporate Controller to join the team working in the corporate office, located in Toronto, Ontario. The Corporate Controller will lead the corporate accounting and financial reporting functions of the department. You will manage the accounting and control functions and report results of operations ensuring compliance with IFRS standards.

In this role you will supervise an experienced team of 5 individuals, while having the full support of an excellent and experienced CFO. Accounting is not just seen as a back-office cost in this company, you are well-respected and lead on a number of special projects and initiatives. Ideally you will come with at least a few recent years in real estate and have supervisory experience.

Responsibilities

  • Respond to all investor questions, information requests, ad hoc reporting requirements on a timely basis
  • Oversee the preparation of quarterly financial statements and annual audited financial statements for each fund or segregated mandate
  • Prepare quarterly cash flow updates for the funds and segregated mandates.
  • Ensure development and construction budgets are updated quarterly within the accounting system along with approved PO, contracts and change orders
  • Monthly, quarterly and annual corporate accounting and financial reporting
  • Maintain internal controls over invoice entry, approval and ultimately payment to vendors.
  • Review and comment on quarterly project cash flows providing insight into financial costs such as interest, insurance, property taxes, cash flows, etc.
  • Prepare and present the annual budget for the management company
  • Re-forecast the annual budget quarterly, investigate all actual to forecasted variances
  • Prepare timely distributions to the Partners
  • Manage and maintain the company’s fee schedule ensuring all fees are charged on a timely basis
  • Manage a team of accountants and accounts payable coordinators

Requirements

  • College diploma or University degree coupled with the CPA completed
  • 8+ years of accounting experience
  • Working knowledge and understanding of the real estate sector
  • Working knowledge of inter-company accounting
  • Excellent communication skills, both oral and written
  • Ability to work effectively in a team environment as well as independently
  • Hands-on approach to accounting and management

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.

Bookkeeper
Concord, Ontario – onsite
$60,000-$75,000, no bonus, but great benefits paid by the company

Our client is a real-estate company based in Concord, Ontario. They are looking for a passionate bookkeeper 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 business has been around for several decades and offers excellent work/life balance.

The successful candidate will be a responsible for providing timely and accurate management reporting for commercial and residential real estate.

Responsibilities:

  • Handle day-to-day accounting duties including Accounts Receivable, booking journal entries, banking (including making deposits), reconciling bank accounts and preparation of HST returns;
  • Ensuring accuracy of tenant’s ledger and the timely resolution of receivable or billing differences;
  • Assist Property Management and other departments as requested with providing accurate/timely accounting information;
  • Liaise with property accountants or other counterparts in respect of various accounting, reporting, and property management activities;
  • Provide assistance in dealing with tenant enquiries;
  • Other projects as required.

Requirements:

  • Post-secondary accounting education or equivalent accounting qualification
  • Proficient in Excel, Microsoft Word, and accounting software packages
  • Good communication and relationship building skills – both written and verbal
  • Good attention to detail

How to Apply

We would like to thank all applicants for your interest in working as part of our team. Please send all job applications to [email protected] Only those applicants selected to move forward in the recruitment process will be contacted.

Manager, Investment and Corporate Accounting
Markham, ON – onsite
$100,000-$120,000 base plus discretionary bonus and great benefits

Are you an experienced accounting professional with a passion for investment and corporate accounting? This is your chance to join our client which is a growing family office, working closely with the executives and owners to oversee critical financial operations and lead tax and compliance strategies for their diverse portfolio.

The Role

As the Manager, Investment and Corporate Accounting, you will report to the Director of Finance and play a pivotal role in managing the accounting for the Group’s family office investments and corporate entities. This position requires a highly organized professional with strong technical expertise in investment and corporate accounting.

Key Responsibilities

  • Oversee accounting for the Group’s investment portfolio, including publicly traded securities, derivatives, venture capital, and private equity fund investments across Canada, the US, and globally.
  • Ensure the accurate and timely recording of investment transactions, including capital calls and distributions for private equity funds.
  • Prepare and maintain monthly investment tracking reports.
  • Reconcile accounting records with external investment statements, capital account statements, and transaction histories.
  • Monitor cash positions in brokerage accounts and lines of credit to ensure optimal cash management.
  • Lead tax compliance, reporting, and planning for the investment portfolio in collaboration with external advisors, ensuring compliance with Canadian and US regulations.
  • Assist in preparing and reviewing month-end closings and financial statements for the Group’s corporate entities.
  • Support tax compliance efforts, including the preparation and/or review of corporate tax returns and filings.
  • Collaborate with external accountants to ensure timely completion of year-end audits, serving as the primary liaison for specific corporate entities.
  • Handle ad-hoc tasks and projects as required.

About You

  • Education: Bachelor’s degree in accounting, finance, or a related field. CPA designation preferred; CFA (or in progress) is an asset.
  • Experience: Minimum of 4-5 years’ experience with a solid understanding of private equity investments and their tax implications.
  • Skills: Proficiency in Excel with a proven ability to develop templates and models, along with excellent organizational and communication skills.
  • Attributes: Detail-oriented, proactive, and comfortable collaborating with internal teams and external advisors.

Why Join this company?

This is more than just a role; it’s an opportunity to contribute to a thriving organization while developing your expertise in investment and corporate accounting. You’ll work in a dynamic, collaborative environment that values innovation and excellence.

Interested? If this sounds like the right fit for you, please apply now to Casey La Russa.

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.

Manager, Land Development Accounting

North York (In-office role)

$100k – $110k plus discretionary bonus and benefits

Our client, a leader in land development, is seeking a Manager, Land Development Accounting to join their team. The successful candidate will oversee financial operations for a diverse portfolio of land development projects, providing key insights and leadership.

Responsibilities:

  • Oversee accounting and financial operations for assigned portfolios, including land purchase and sales, cost recoveries, trial balance reviews, account reconciliations, and job costing.
  • Provide accurate and timely monthly, quarterly, and annual reporting, including variance and cost analysis for Senior Management and Project Managers.
  • Prepare and maintain detailed project budgets in collaboration with Project Managers and the Finance Team, focusing on construction costs and fee analysis.
  • Monitor and manage cash flow for development projects, including cash flow forecasting, funding draws, and loan utilization.
  • Review invoices, manage change order processing, and oversee invoice coding.
  • Prepare and reconcile internal and external loans, including interest calculations.
  • Supervise and provide oversight to the land development accounting team.
  • Assist in year-end financial statement preparation in compliance with accounting principles and audits.
  • Document and maintain accurate financial transaction records.
  • Lead ad hoc projects and analyses to support company objectives.

Requirements:

  • CPA designation
  • Bachelor’s degree in business or accounting.
  • Several years of experience in full-cycle accounting within land development or property accounting.
  • Proficiency in cash flow analysis, budgeting, and understanding joint business arrangements (e.g., JVs, partnerships).
  • Strong problem-solving skills with attention to operational and financial impacts.
  • Advanced proficiency in Microsoft Office, particularly Excel

 

If you are interested in applying for this opportunity, please email your resume to [email protected]. Due to the high volume of applicants, only those selected for interviews will be contacted.

 

Junior Accountant
North York (In-office role)
$60k – $70k plus discretionary bonus and benefits

Our client, a leader in land development, is looking for a Junior Accountant to join their team. This role is ideal for someone highly motivated, detail-oriented, and ready to thrive in a fast-paced environment. The successful candidate will take on accounting tasks for a diverse portfolio of land development projects.

Responsibilities:

  • Perform monthly bank reconciliations and manage accounts payable for multiple entities.
  • Track and reconcile lot discharges, house closings, and loan balances with external statements.
  • Set up and maintain accounts receivable invoices and process internal and external cash calls.
  • Reconcile intercompany accounts and create/post journal entries.
  • Prepare HST returns (monthly, quarterly, or annually).
  • Manage and reconcile letters of credit for all projects.
  • Maintain accounting records in compliance with Canadian GAAP and company policies.
  • Support auditors with accurate and timely documentation.
  • Participate in special projects and back charge processing.

Requirements:

  • Bachelor’s degree in Business or Accounting; CPA designation or equivalent is an asset.
  • 1-2+ years of experience in accounting
  • Excellent communication skills and a collaborative team player.

If you are interested in applying for this opportunity, please email your resume to [email protected]. Due to the high volume of applicants, only those selected for interviews 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.