Director, Client Tax Reporting Operational Advisory Lead

BMO•Chicago, IL

12d•$200,000 - $250,000•Hybrid

About The Position

BMO Capital Markets is a leading, full-service North American-based financial services provider offering equity and debt underwriting, corporate lending and project financing, merger and acquisitions advisory services, securitization, treasury management, market risk management, debt and equity research and institutional sales and trading. BMO Capital Markets has over 2,700 professionals in 30+ locations around the world, including 20 offices in North America. BMO Capital Markets is a member of BMO Financial Group (NYSE, TSX: BMO), one of the largest diversified financial services providers in North America with US$1.1 trillion total assets and approximately 53,000 employees as of October 31, 2025. #bmocapitalmarkets Mandate: The Director is a senior technical leader responsible for BMO Capital Markets (CM) client tax reporting and withholding obligations. The role works in a highly matrixed organization providing technical tax decisions, oversight, and execution of more complex client tax matters. The role manages a small team performing tax due diligence on clients and syndicated loan buyers (where BMO is the paying agent). The role also plays a key role in leading and facilitating new products and new regulations related to client tax. This role involves extensive stakeholder process management and stakeholder engagement. Frequent interaction is required with internal LOBs, trade desks, Corporate Tax and Tax Governance and externally with auditors, clients and tax authorities.

Requirements

Minimum of 10+ years of U.S. information reporting and withholding tax advisory or operational experience within the financial services industry.
A Bachelor's degree, with a CPA license, Enrolled Agent (EA) certification, or active membership of the Bar preferred.
Deep knowledge of U.S. tax laws and regulations related to U.S. tax withholding and reporting (e.g., Chapter 3 and 4, Chapter 61, Section 3406).
Proven ability to work across global departments to build credibility and strong relationships.
Exceptional ability to independently manage multiple priorities and to proactively service multiple internal clients in a fast-paced environment
Ability to work a demanding schedule under limited supervision
Excellent attention to detail and ability to learn and adapt quickly
Ability to review, assess and provide detailed information daily
Strong analytical and problem solving skills
Strong conflict management/ resolution skills
Strong organizational and prioritization skills
Excellent verbal and written communication skills are essential to synthesize and explain complex regulations to non-tax professionals and senior management

Nice To Haves

Experience with Common Reporting Standard, Canadian non-resident withholding and international financial transaction taxes would be an asset
Relevant experience in the financial services industry preferred
Working knowledge of trading products across Capital Markets
Working knowledge of the competitive marketplace, institutional clients, market trends and regulations in the industry

Responsibilities

Oversee the preparation and timely filing of various U.S. and Canadian tax reporting forms (e.g., Forms 1099, 1042-S, NR-4, T5 and T5008) for CM and ensure strong internal controls are maintained within a high-volume processing environment.
Reconciliation of Forms 1042-S received from DTC to Forms 1042-S issued by CM
Oversee the preparation and timely filing of international financial transaction tax monthly declarations and annual returns filed by CM with tax authorities and remittance of foreign stamp duty payments.
Review, analyze, and interpret changes to U.S. IRS, Canadian and certain international operational tax withholding and information reporting requirements (e.g., laws, regulations, rulings, QI agreement) to determine the impact on the company's processes, procedures, and documentation.
Maintain oversight of the interest and dividend withholding rates and review systemic controls to ensure accuracy.
Serve as a subject matter expert, providing guidance to CM business units and operations teams on complex operational tax reporting and withholding matters, client tax documentation, source and character of payments, and operational changes for new product offerings and updates to tax rules, working with BMO Corporate Tax Group where required.
Define and execute the strategic direction for CM operational tax information reporting and withholding operations, provide oversight and mentorship to multiple teams of professionals, and foster a culture of continuous improvement.
Act as the primary liaison for CM tax operations with business partners, technology, and other operational teams.
Maintain documentation of CM end-to-end operational tax withholding and reporting processes and controls.
Oversee testing of controls with respect to CM operational tax withholding and reporting and track and resolve any deficiencies.
Assist with certifications to IRS and periodic review with respect to CM transactions in Qualified Intermediaries in BMOFG.
Maintain documentation of settings in Broadridge that drive CM tax withholding and reporting and approve any changes
Drive process improvements and automation initiatives using data analysis to enhance efficiency, accuracy, and scalability of CM tax withholding and reporting operations.
Develop and enhance relationships, at multiple levels, by providing exceptional levels of client service
Keep abreast of current and upcoming product and functional specific industry initiative related topics.
Navigate the BMO organization, across divisions, to deliver timely and accurate issue resolution to complex, business critical issues which may include communication with senior stakeholders