Trust Associate (Tax)

Wintrust Wealth Management serves the financial needs of private clients, including high net worth individuals, business owners, and institutions. Since our founding in 1931, we have been helping clients meet their increasingly complex financial goals with the highest standards of service and integrity. Through our four companies, Wintrust Investments LLC, Wintrust Private Trust., Great Lakes Advisors LLC, and The Chicago Deferred Exchange Company LLC, we offer comprehensive wealth management solutions, including investment, trust, and asset management services. Wintrust Wealth Management is a division of Wintrust, a financial services company with more than $66 billion in assets.

Why join us?

• An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years)
• Competitive pay and discretionary or incentive bonus eligible
• Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few
• Family-friendly work hours
• With 200+ community bank locations, we offer opportunities to grow and develop in your career
• Promote from within culture

Position Overview:

The Trust Tax Associate provides fiduciary tax and trust administration support to the Trust Tax Liaison, Trust Officers, and Trust Administration teams. This position is responsible for assisting with fiduciary tax reporting/tracking, tax document coordination, tax payment processing, account onboarding and closing, and communication with internal partners and external tax vendors. In addition, the Trust Tax Associate performs traditional trust administration support functions, including account maintenance, transaction processing, document management, account reviews, and client service activities.

The successful candidate will possess strong organizational and analytical skills, exceptional attention to detail, a foundational understanding of trust administration and fiduciary taxation, and a commitment to providing superior client service.

What you’ll do:

Fiduciary Tax Administration (Primary)

• Assist the Trust Tax Liaison with the administration and monitoring of fiduciary tax reporting processes for trusts, estates, charitable entities, guardianships, and agency accounts.
• Coordinate with tax service providers, Trust Officers, and Trust Administrators to gather information required for the preparation and filing of fiduciary, individual, charitable, and grantor tax returns.
• Track fiduciary tax return deadlines and monitor timely completion of tax filings.
• Assist with review of account activity and supporting documentation for tax reporting, including income, expenses, sales transactions, cost basis information, and account classifications.
• Monitor and track the timely distribution of tax reporting documents, including Forms 1099, K-1, 1099-R, 5498, Grantor Tax Letters, and related tax information statements.
• Process federal and state tax payments and estimated tax payments.
• Assist in resolving tax notices, penalty assessments, IRS correspondence, and other communications from taxing authorities.
• Coordinate tax fee processing and related account billing activities.
• Assist in reviewing newly established accounts to ensure accurate tax coding, taxpayer setup, and collection of required tax documentation.
• Support account-closing reviews to ensure tax filing requirements, final tax obligations, and fees have been addressed.
• Maintain tracking logs and reports for annual filings, registrations, tax reporting obligations, and compliance requirements.
• Research and reconcile missing or incomplete tax information and assist in resolving discrepancies between trust accounting systems and tax preparation platforms.
• Support monitoring of foreign beneficiary accounts and related reporting requirements.

Trust Administration Support (Secondary)

• Provide administrative support to Trust Officers and Trust Administrators in managing fiduciary relationships, including personal trusts, estates, guardianships, agency accounts, and custody relationships.
• Assist with account openings, account maintenance, account closings, and asset transfer activities.
• Execute administrative account transactions, including distributions, bill payments, wire transfers, ACH transactions, and cash receipts in accordance with established procedures.
• Respond to routine client, beneficiary, advisor, and internal partner inquiries and provide timely follow-up.
• Create, maintain, and organize electronic account records and documentation, ensuring account coding and records are accurate and complete.
• Monitor daily account activity and notify Trust Officers of overdrafts, unusual transactions, or significant cash balances.
• Coordinate incoming and outgoing correspondence, client documentation, and related administrative functions.
• Prepare materials for client meetings, account reviews, fiduciary committees, and internal presentations.
• Assist with special projects, audits, compliance reviews, and process improvement initiatives.
• Provide back-up support for other Trust Associates and administrative personnel as needed.
• Maintain confidentiality and ensure compliance with fiduciary standards, regulatory requirements, and company policies.

Knowledge, Skills, and Abilities:

• Working knowledge of trust administration principles and fiduciary account structures.
• Basic understanding of fiduciary income taxation, trusts, estates, and charitable entities.
• Strong organizational and time-management skills with the ability to manage multiple priorities and deadlines.
• Exceptional attention to detail and accuracy.
• Strong analytical and problem-solving skills.
• Ability to communicate effectively with clients, beneficiaries, attorneys, accountants, tax preparers, and internal business partners.
• Excellent written and verbal communication skills.
• Ability to work independently while contributing effectively within a collaborative team environment.
• Strong client service orientation and commitment to quality.
• Ability to identify process improvements and support operational efficiency initiatives.
• Proficiency in Microsoft Office applications, including Excel, Word, PowerPoint, and Outlook.
• Ability to maintain confidentiality and adhere to the highest ethical standards.

Education and Experience:

Required

• Bachelor's degree or equivalent work experience in Accounting, Finance, Business Administration, or related field.
• 2 to 5 years of experience in trust administration, fiduciary operations, tax administration, accounting, financial services, or a related field.
• Experience working in a deadline-driven environment while managing multiple priorities.
• Proficiency in Microsoft Office applications, particularly Excel and Word.

Preferred

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

Benefits:

Medical Insurance

• Dental
• Vision
• Life insurance
• Accidental death and dismemberment
• Short-term and long term Disability Insurance
• Parental Leave
• Employee Assistance Program (EAP)
• Traditional and Roth 401(k) with company match
• Flexible Spending Account (FSA)
• Employee Stock Purchase Plan at 5% discount
• Critical Illness Insurance
• Accident Insurance
• Transportation and Commuting Benefits
• Banking Benefits
• Pet Insurance

Compensation:

The estimated hourly rate for this role is $20.20 - $26.50, along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.

From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.