Senior Director, Indirect Tax

Metropolis•Chicago, IL

11h•Onsite

About The Position

Metropolis is seeking a Senior Director of Indirect Tax to architect, build, and scale indirect tax and compliance operations during a period of rapid growth. As a key advisor to the VP of Tax, this leader will own indirect tax strategy, system transformations, AI-driven tax analytics, and proactive risk management across sales and use tax, VAT/GST, motor vehicle taxes, business licensing, and emerging regulatory obligations across new verticals. The role leads a team of approximately five tax team members and works across jurisdictions, including all 50 U.S. states and Canada. This is an office-first position requiring employees to be on-site at least four days a week. The anticipated annual base salary is $225,000 to $245,000 USD. Compensation may also include healthcare benefits, a 401(k) plan, short- and long-term disability coverage, basic life insurance, a stock option plan, and bonus plans.

Requirements

12+ years of progressive indirect tax leadership experience in fast-growing, high-volume technology, mobility, or marketplace companies.
Bachelor's degree in Accounting, Taxation, or a related field.
CPA required.
Expert technical command of U.S. 50-state sales and use tax laws and regulatory compliance.
Working knowledge of global VAT/GST and international indirect tax.
Proven track record executing enterprise-grade tax engine implementations, such as ONESOURCE or Vertex, integrated into existing ERP systems.
Advanced expertise or high capability in using AI platforms, such as Claude AI, and data tools, such as Quad, for tax modeling, liability reporting, and operational automation.
Executive presence, a strategic visionary mindset, and high-energy leadership capable of driving organizational change and presenting directly to executive leadership.
Ability to work on-site at least four days a week.

Nice To Haves

Exposure to the regulated parking industry and SOX controls.
Master's degree in taxation.
Other relevant professional qualifications.

Responsibilities

Build and mentor a high-performing indirect tax team of approximately five tax team members; evaluate talent and design an agile department built to scale.
Oversee preparation, review, and timely filing of indirect tax returns, including sales and use tax, parking tax, VAT/GST, excise taxes, and other applicable filings across all 50 states and Canada.
Ensure accurate tax determination and payments, and monthly balance sheet reconciliations of prepaid and accrued sales and use tax accounts for financial statement reporting.
Oversee indirect tax audits, notices, assessments, appeals, hearings, and dispute resolution in collaboration with operations and compliance teams.
Collaborate with Legal, external tax advisors, and other stakeholders on significant indirect tax disputes.
Establish internal controls, indirect tax policies, and risk assessment methodologies across relevant taxing jurisdictions.
Drive automation, standardization, and simplification of tax processes to improve accuracy, scalability, and efficiency.
Use data analytics and AI knowledge to create reporting tools and dashboards that monitor compliance performance, identify exceptions, and support strategic decisions.
Lead implementation and optimization of indirect tax technology, including tax engines, ERP integrations, and automated compliance solutions.
Help build and maintain an inclusive culture as the organization grows.