Senior Associate - Diligence (Chicago)

Locations: Greater Chicago, IL (Hybrid)

About the role

This Senior Associate will join Hilco Diligence Services' (HDS) Specialty Finance team in Chicago. HDS provides due diligence services, including transaction services and field exams for traditional and complex transactions across many different industries. Our services include borrowing base development, inventory and accounts receivable performance metrics, and comprehensive collateral analysis. Our reports are used by lenders, advisors, and investors to provide a reliable basis for structuring and monitoring loans and other transactions.

The Specialty Finance team focuses on lending businesses and structured transactions where collateral is typically made up of receivables, loans, leases, or other financial assets rather than traditional inventory or fixed assets.

The role is intended for a candidate with approximately 4-5 years of audit, assurance, transaction services, diligence, field examination, commercial finance, or related experience. It combines portfolio analysis, operational diligence, collateral testing, and report writing. The successful candidate will manage meaningful workstreams, review supporting analysis, interact with borrowers and lender clients, and help translate detailed findings into practical conclusions for banks, private credit funds, institutional investors, and securitization participants.

Responsibilities

• Lead workstreams within specialty finance diligence and manage interactions/project management with lenders and borrowers.
• Review and validate lender reporting, borrowing base calculations, servicer reports, and securitization performance reporting.
• Assess underwriting, servicing, collections, cash management, and operational controls.
• Analyze loan, lease, and receivable portfolio performance metrics and identify key collateral trends.
• Perform and review sample-based file testing, data validation, payment testing, and documentation analysis.
• Prepare clear client-facing conclusions, exception summaries, and recommendations.
• Manage information requests, borrower/servicer interviews, and day-to-day engagement execution.
• Review work prepared by Analysts or Associates and support coaching on fieldwork, analysis, and report drafting.

Requirements

• Approximately 4-5 years of experience in audit, assurance, transaction services, field examination, due diligence, commercial finance, or related lending work.
• Direct field exam, lender due diligence, securitization, ABL, or specialty finance experience is preferred.
• Bachelor's degree in accounting, finance, economics, or a related discipline.
• Strong Excel, data analysis, and financial reconciliation skills.
• Eagerness to embrace innovation and leverage new tools and technologies to drive efficiency and continuous improvement.
• Strong report writing skills and ability to present findings clearly to lenders, investors, and management teams.
• Ability to effectively manage multiple workstreams and competing priorities in a fast-paced environment.
• Strong time management and organizational skills.

CPA qualification preferred but not essential. Market contacts or prior competitor experience would be a plus, though business development is not a core responsibility of the role.

Schedule

• Hybrid working model, with 2-3 days in the office on non-travel weeks.
• Travel is expected to be approximately 10-20%, depending on client location and engagement requirements.
• Opportunities to collaborate with the European team on cross-border or global assignments.

Benefits

Hilco Global offers a comprehensive, competitive benefits package, including:

• A variety of medical and dental plans, vision coverage, disability, and life insurance.
• 401(k) plans.
• A robust suite of personal well-being benefits to support mental health.

Available benefits are based on eligibility.