Senior Associate - Diligence (Chicago)

About the role

Diligence Analyst/Associate - Specialty Finance

HDS Job Description

Locations: Greater Chicago, IL (Hybrid)

Hilco Diligence Services

Hilco Diligence Services (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.

Position Overview

This Senior Associate will join HDS' Specialty Finance team in Chicago. 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.

The role 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.

Relevant prior experience may include

• Audit or assurance work for financial services, leasing, lending or specialty finance clients.
• Field exams, collateral audits, ABL diligence or borrowing base reviews.
• Securitization, structured finance, loan / lease portfolio analysis or lender due diligence.
• Large data-set analysis, file testing, credit and collections testing or operational control reviews.

Key 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.

Ideal Candidate Profile

• Approximately 4-5 years of experience in audit, assurance, transaction services, field examination, due diligence, commercial finance or related lending work.
• CPA qualification preferred but not essential.
• 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.
• An 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.
• Market contacts or prior competitor experience would be a significant plus, but business development is not a core responsibility of the role.
• The ability to effectively manage multiple workstreams and competing priorities in a fast-paced environment. Strong time management and organizational skills are essential for success in this role.

Working Model and Travel

• This role will primarily support US Specialty Finance engagements, with opportunities to collaborate with the European team on cross-border or global assignments.
• Hybrid working model, with 2-3 days in the office on non-travel weeks as the expectation.
• Travel is expected to be approximately 10-20%, depending on client location and engagement requirements.
• The Specialty Finance group operates as one integrated team across geographies, so candidates should be comfortable working with colleagues and clients in different time zones. You will be part of a collaborative, high-performing team and will work closely with colleagues at all levels of the organization across multiple locations.