Trust Associate (Tax)

Location: Chicago, IL; onsite

Estimated hourly rate: $20.20–$26.50 per hour, plus eligibility for an annual bonus.

Company

Wintrust Wealth Management provides investment, trust, and asset management services for private clients, business owners, institutions, and other high-net-worth customers.

What you will do

• Support fiduciary tax reporting for trusts, estates, charitable entities, guardianships, and agency accounts.
• Coordinate tax information, documentation, filings, deadlines, tax payments, notices, fees, and reporting documents with internal teams and external tax providers.
• Review account activity, tax coding, taxpayer setup, supporting documentation, and account-closing requirements.
• Assist with account openings, maintenance, closings, asset transfers, distributions, bill payments, wires, ACH transactions, and cash receipts.
• Maintain electronic account records, tracking logs, reports, and compliance documentation.
• Respond to routine client and partner inquiries and support audits, fiduciary reviews, committees, and process improvement initiatives.

Requirements

• Bachelor's degree or equivalent experience in Accounting, Finance, Business Administration, or a related field.
• 2–5 years of experience in trust administration, fiduciary operations, tax administration, accounting, financial services, or a related field.
• Working knowledge of trust administration principles and basic understanding of fiduciary income taxation, trusts, estates, and charitable entities.
• Strong organizational, analytical, communication, problem-solving, and client service skills with exceptional attention to detail.
• Proficiency in Microsoft Office, particularly Excel and Word, with the ability to manage multiple deadlines and maintain confidentiality.
• Ability to work onsite in Chicago, IL.

Nice to have

• Bachelor's degree in Accounting or Finance.
• Experience supporting trust, estate, or fiduciary accounts.
• Familiarity with fiduciary income tax reporting, tax return processes, IRS and state tax requirements, or platforms such as FIS/TrustDesk, OneSource, and Egnyte.
• Progress toward or interest in pursuing CTFA, CPA, EA, or another relevant professional designation.

Culture & Benefits

• Full-time employment with family-friendly work hours and opportunities for career development.
• Medical, dental, vision, life, disability, critical illness, accident, and pet insurance.
• Traditional and Roth 401(k) plans with company match, flexible spending account, and employee stock purchase plan.
• Parental leave, employee assistance program, transportation and commuting benefits, and banking benefits.
• Eligibility for discretionary or incentive bonuses and tuition reimbursement.