Senior Director, Indirect Tax

Metropolis•Chicago, IL

1d•$225,000 - $245,000•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 includes building and mentoring an indirect tax team of approximately five tax team members; overseeing tax preparation, review, and filings across the United States and Canada; managing tax determination, payments, and balance sheet reconciliations; overseeing audits and disputes; establishing controls and policies; and improving tax operations through automation, analytics, and technology implementations. Metropolis follows an office-first model requiring corporate team members to work onsite at least four days per week.

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, with 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 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.

Nice To Haves

Exposure to regulated parking industry tax 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, evaluating talent and designing an agile department built for 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 oversee 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 activities 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.