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Peloton Search Partners

Associate

Toronto, ON, Canada

Job type: Full-time
Apply by: Oct 29, 2026
Posting language: English
Posted: Sep 29, 2026

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Original job description

Overview

Our client is a well-established investment firm providing structured debt and equity capital solutions to mid-market and growth companies.

The firm’s long track record includes raising committed capital from third-party investors, including pension, institutional and family-office investors. The team has considerable expertise in real estate and infrastructure.

The Role

The Associate will be a key member of the team, supporting the evaluation, structuring, execution and ongoing management of bespoke debt and equity financings. This is a highly analytical, hands-on role with meaningful exposure to senior investment professionals, management teams, external advisors and the firm’s investment committee.

Working closely with senior deal team members, the Associate will assess new investment opportunities, build and review financial models, conduct diligence, prepare investment committee materials and support transaction execution from initial screening through to closing. The Associate will also assist with monitoring portfolio investments and identifying opportunities to support existing portfolio companies.

The opportunity is well suited to a motivated, detail-oriented professional with strong financial analysis and modelling skills, sound commercial judgment, and a genuine interest in private credit, structured capital and principal investing. The successful candidate will be comfortable working across multiple transactions in a fast-paced, entrepreneurial environment and will take ownership of workstreams while benefiting from close mentorship and development.

Key Responsibilities

Transaction Evaluation and Underwriting

Evaluate opportunities against the firm’s mandate, return thresholds and risk appetite.
Build, review and maintain detailed financial models, including integrated operating models, cash-flow forecasts, debt schedules, returns analyses and downside scenarios.
Conduct industry, market, company and competitive research to support underwriting and investment thesis development.
Analyze historical financial performance, liquidity, leverage, collateral value, covenant capacity and key business drivers.
Assist in assessing and recommending appropriate capital structures, including senior and subordinated debt, mezzanine, asset-backed facilities, bridge financings and special-situations equity capital.
Support the preparation of term sheets, preliminary investment recommendations and internal screening materials.

Execution and Investment Committee Support

Coordinate transaction workstreams through diligence, documentation and closing.
Assist with financial, commercial, legal, tax, accounting and technical diligence, working with management teams and external advisors as required.
Prepare investment committee memoranda, presentation materials and supporting analyses; clearly articulate key risks, mitigants, return drivers and structural protections.
Support the negotiation and review of transaction terms, including pricing, covenants, security packages, conditions precedent and other downside protections.
Maintain data-room materials, diligence trackers, transaction models and execution timelines.
Assist with closing mechanics and funding processes alongside internal stakeholders and external counsel.

Portfolio Monitoring and Value Creation

Monitor assigned portfolio investments, including operating performance, liquidity, leverage, covenant compliance and reporting requirements.
Prepare periodic portfolio-monitoring materials, lender updates and internal reporting.
Identify emerging risks, financing needs and potential follow-on investment opportunities.
Support senior team members in maintaining constructive relationships with management teams, sponsors and other stakeholders.

Candidate Profile

The firm seeks to hire individuals who are highly motivated, intellectually curious and who have demonstrated excellence in prior endeavours.

The successful candidate should have:

Approximately 3–6 years of relevant experience in specialty finance, mezzanine or subordinated debt, leveraged finance, corporate banking, investment banking, restructuring, transaction advisory or a related structured-finance discipline.
Strong financial modelling, valuation and analytical skills, with the ability to build and interrogate detailed models independently.
Foundational credit judgment and an understanding of cash-flow and asset-based underwriting, leverage, liquidity, covenants, security packages and downside scenario analysis.
Experience supporting the execution of complex financing or M&A transactions, including diligence, investment or credit memoranda, documentation and closing processes.
Strong attention to detail, organization and ability to manage multiple priorities while meeting tight timelines.
A proactive, accountable and entrepreneurial approach; willingness to take ownership of workstreams and operate effectively in a lean team environment.
Strong interpersonal and communication skills, both written and verbal, with the ability to synthesize complex information into clear, decision-useful materials.
An undergraduate degree in business, finance, economics, accounting, engineering or a related discipline. An MBA, CFA, CPA or CBV designation, or progress toward one, is considered an asset.

Location

Toronto, Canada (in-office)

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More about this job

Responsibilities

Evaluate, structure, and execute bespoke debt and equity investments by building financial models, conducting diligence, assessing risks and returns, and preparing investment committee materials. Monitor portfolio companies’ financial and operating performance, identify emerging risks and financing opportunities, and support relationships with management teams and other stakeholders.

Requirements

Candidates should have approximately 3–6 years of relevant experience in specialty finance, leveraged finance, investment banking, restructuring, transaction advisory, or a related field, along with strong financial modeling, valuation, and credit analysis skills. A relevant undergraduate degree is required; an MBA, CFA, CPA, or CBV designation, or progress toward one, is considered an asset.

Skills

Financial Modeling
Credit Analysis
Investment Underwriting
Valuation
Cash-Flow Analysis
Downside Scenario Analysis
Transaction Due Diligence
Transaction Execution
Capital Structure Analysis
Covenant Analysis
Portfolio Monitoring
Financial Research
Risk Assessment
Communication
Project Management

Visa sponsorship

Not detected in the job text

Keywords

Private Credit
Structured Capital
Principal Investing
Mezzanine Debt
Subordinated Debt
Leveraged Finance
Corporate Banking
Investment Banking
Restructuring
Transaction Advisory
Financial Modeling
Integrated Operating Models
Cash-Flow Forecasts
Debt Schedules
Returns Analysis
Downside Scenarios
Credit Underwriting
Asset-Based Underwriting
Liquidity Analysis
Leverage Analysis
Covenants
Security Packages
Due Diligence
Investment Committee Memoranda
Term Sheets
Portfolio Monitoring
Real Estate
Infrastructure
Special-Situations Equity
Transaction Closing

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