Senior Director, Indirect Tax
Metropolis Technologies
Chicago, IL · $225k–$245k a year · Posted October 21, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about finance jobs
- Best cities for finance jobs #1 New York (1,932 openings)
- Best cities for finance pay after cost of living #1 San Mateo ($162k)
- Most requested AI skills in finance jobs #1 AI tools in daily work (4.3%)
- AI tools named most often in finance jobs #1 Claude (0.55%)
- Employers with the most finance jobs #1 Amazon (475 roles)
How AI is used in this kind of work
AI use among tax examiners and collectors, and revenue agents is little observed so far. Measured exposure for tax examiners and collectors, and revenue agents: 3% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
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About the job
Who we are
The real world is the next frontier, and at Metropolis, we are creating the artificial intelligence to make it responsive. We are pioneering the Recognition Economy — a future where mundane repetition disappears and being known unlocks access, comfort, and belonging everywhere you go. From transforming parking into a seamless drive-in, drive-out experience for millions of Members to expanding our intelligence layer across retail and hospitality, we are building a world that feels instinctive and magical. The future isn’t coming; it’s here, and we need builders, innovators, and problem solvers to help us create it.
Who you are
Metropolis is seeking a Senior Director of Indirect Tax to architect, build, and scale our indirect tax and compliance operations during our next phase of rapid growth. Serving 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/use tax, VAT/GST, motor vehicle taxes, business licensing, and emerging regulatory obligations across new verticals.
What you'll do
Build and mentor a high-performing indirect tax team of approximately 5 tax team members, evaluating talent and designing an agile indirect tax department built for scale
Oversee the preparation, review, and timely filing of indirect tax returns, including sales and use tax, parking tax, VAT/GST, excise taxes, and other applicable indirect tax filings across all 50 states and Canada
Ensure accurate tax determination, tax payments, and monthly balance sheet account reconciliations of prepaid and accrued sales and use tax accounts to support financial statement reporting
Oversee indirect tax audits, notices, assessments, appeals, hearings, and dispute resolution activities while working closely 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
Leverage data analytics with proficient knowledge of AI to create reporting tools and dashboards to monitor compliance performance, identify exceptions, and support strategic decision-making
Lead the implementation and optimization of indirect tax technology, including tax engines (e.g., ONESOURCE, Vertex), enterprise resource planning (ERP) integrations, and automated compliance solutions
What we're looking for
12+ years of progressive indirect tax leadership experience in fast-growing, high-volume tech, mobility, or marketplace companies
Bachelor's degree in Accounting, Taxation, or a related field
CPA required
Expert technical command of 50-state U.S. sales/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 (e.g., ONESOURCE, Vertex) integrated into existing ERP Systems'
Advanced expertise or high capability in utilizing AI platforms (e.g., Claude AI) and data tools (e.g., Quad) for tax modeling, liability reporting, and operational automation
Executive presence, strategic visionary mindset, and high-energy leadership capable of driving organizational change and presenting directly to executive leadership
While not required, these are a plus:
Exposure to regulated parking industry tax and SOX Controls
Master's degree in taxation
Other relevant professional qualifications
4 Days in Office: Metropolis values in-person collaboration to drive innovation, strengthen culture, and enhance the Member experience. Our corporate team members hold to our office-first model, which requires employees to be on-site at least four days a week, fostering organic interactions that spark creativity and connection
When you join Metropolis, you'll join a team of world-class product leaders and engineers, building an ecosystem of technologies at the intersection of parking, mobility, and real estate. Our goal is to build an inclusive culture where everyone has a voice and the best idea wins. You will play a key role in building and maintaining this culture as our organization grows. The anticipated base salary for this position is $225,000.00 USD to $245,000.00 USD annually. The actual base salary offered is determined by a number of variables, including, as appropriate, the applicant's qualifications for the position, years of relevant experience, distinctive skills, level of education attained, certifications or other professional licenses held, and the location of residence and/or place of employment. Base salary is one component of Metropolis' total compensation package, which may also include access to or eligibility for healthcare benefits, a 401(k) plan, short-term and long-term disability coverage, basic life insurance, a lucrative stock option plan, bonus plans, and more. #LI-WT1 #LI-Onsite
Metropolis may utilize an automated employment decision tool (AEDT) to assess or evaluate your candidacy for employment or promotion. AEDTs are used to assist in assessing a candidate’s application relative to the required job qualifications and responsibilities listed in the job posting.
As part of this process, Metropolis retains data relevant to your candidacy, including personal information, for a period that is reasonably necessary for the use of the tool. If you are hired for the position, your data may become part of your employee records.
Metropolis Technologies is an equal opportunity employer. We make all hiring decisions based on merit, qualifications, and business needs — without regard to race, color, religion, sex (including gender identity, sexual orientation, and pregnancy), national origin, disability, veteran status, or any other protected characteristic under federal, state, or local law.
We are committed to providing a welcoming, accessible hiring experience. If you need a reasonable accommodation for any part of the application or interview process, please reach out to us at recruiting@metropolis.io .