Director of TaxDepartment: Finance
Employment Type: Permanent - Full Time
Location: Chicago
Compensation: $160,000 - $200,000 / year
DescriptionThis is a hands-on leadership role, not an oversight seat. You will be the company's in-house tax authority: setting strategy, managing one direct report, and directing a network of external advisors across multiple jurisdictions. You will own the answer, and you will often be the person who builds it.
The work spans a multi-entity international structure, a SaaS revenue model with complex indirect tax exposure, an active M&A agenda, and private-equity ownership. We are looking for someone with strong technical judgment, the initiative to get ahead of issues rather than react to them, and the pragmatism to decide with incomplete information. If you want breadth and ownership rather than a narrow specialty, this role is for you.
Key ResponsibilitiesTax Provision & Reporting- Own the quarterly and annual income tax provision under ASC 740 - current and deferred taxes, valuation allowances, uncertain tax positions, return-to-provision, and effective tax rate analysis and forecasting.
- Prepare tax disclosures for financial statements and lender reporting, and serve as the primary point of contact for external auditors on all tax matters.
- Maintain tax account reconciliations, provision-to-return true-ups, and supporting documentation that is complete and audit-ready.
- Build and maintain tax controls and process documentation aligned with the broader finance control environment.
Global Compliance & Controversy- Own the global tax compliance calendar across U.S. federal, state and local, and international jurisdictions - ensuring accurate, timely filings and no missed obligations.
- Manage external advisors relationships: define scope, review deliverables, control fees, and hold providers to deadlines.
- Manage tax audits, notices, and inquiries end to end, developing positions and negotiating resolutions with taxing authorities.
- Monitor legislative and regulatory change across the jurisdictions where we operate and assess the impact on the company.
Transfer Pricing & International Structure- Own the global transfer pricing framework - intercompany service, IP, and cost-sharing arrangements - including policy design, annual documentation, local files, and country-by-country reporting.
- Calculate, book, and monitor intercompany charges and true-ups; ensure legal agreements, invoicing, and actual cash movement are consistent with policy.
- Advise on international structure and cross-border flows: entity rationalization, cash repatriation, withholding taxes, treaty positions, and permanent establishment risk from remote and travelling employees.
- Model and manage U.S. international tax positions (GILTI, FDII, BEAT, Subpart F, foreign tax credits) and their effect on the global effective tax rate and cash taxes.
M&A and Tax Planning- Serve as the tax lead on M&A transactions from diligence through integration - identifying exposures, quantifying risk, and recommending deal structure and purchase agreement protections.
- Partner with Accounting on acquisition accounting for tax: opening deferred taxes, attribute carryover and limitations, and integration of acquired entities into the provision and compliance processes.
- Develop and execute the tax planning agenda - cash tax optimization, credits and incentives including R&D credits, legal entity structure, and post-acquisition integration planning.
- Support executive leadership and sponsor stakeholders with modelling and analysis on structuring, financing, and transaction-related tax considerations.
Indirect Tax & SaaS Nexus- Own indirect tax globally - U.S. sales and use tax, VAT/GST, and digital services taxes - including registrations, filings, and reverse charge and place-of-supply determinations.
- Determine taxability and nexus for a multi-jurisdiction SaaS and data business, spanning software, hosted services, data feeds, and professional services.
- Own tax engine and system configuration (e.g., Avalara or similar) in partnership with finance systems and revenue operations, ensuring correct rates and treatment at the point of invoicing in NetSuite.
- Manage exemption certificate processes, customer tax inquiries, voluntary disclosure agreements, and remediation of historical exposure.
Leadership & Cross-Functional Partnership- Manage and develop one direct report, building a function that scales through process and automation rather than headcount.
- Act as a strategic partner to Legal, FP&A, Accounting, Revenue Operations, People, and the business - bringing tax into decisions before they become tax problems.
- Translate complex tax positions into clear, decision-ready recommendations for senior leadership and sponsor stakeholders.
Skills, Knowledge and ExpertiseEssential Skills & Experience- CPA and/or advanced tax degree required.
- 15+ years of progressive corporate tax experience, including meaningful time in a multinational in-house tax function.
- A strong blend of public accounting and industry experience; Big 4 or large regional firm foundation preferred.
- Deep, hands-on ASC 740 expertise - able to own the provision and defend it to auditors without outsourcing the judgment.
- Demonstrated ownership of transfer pricing and U.S. international tax in a multi-entity global structure.
- Practical experience with indirect tax for software or SaaS: nexus, taxability, and multi-jurisdiction compliance.
- Hands-on M&A tax experience across diligence, structuring, and integration.
- Proven success managing external advisors and co-sourced compliance - scoping work, controlling cost, and reviewing quality.
Desirable Skills & Experience- Experience in a technology, SaaS, or financial technology company.
- Private equity or sponsor-backed environment, including lender and Board reporting requirements.
- Experience with NetSuite, a tax engine such as Avalara, and tax provision software.
- Exposure to EMEA and APAC compliance regimes and multi-currency consolidations.
- Familiarity with SOX or SOX-adjacent internal controls frameworks.
- Excellent communicator - able to translate complex tax topics for non-finance audiences and executive stakeholders.
- Highly organized, proactive, and comfortable operating in ambiguity with competing priorities.
BenefitsCompetitive Benefits & Perks We offer a comprehensive benefits package designed to support your well-being, growth, and work-life balance.
- Health & Financial Security:
- Medical, Dental, and Vision insurance
- Flexible Spending Accounts (FSA) & Health Savings Accounts (HSA)
- 401(k) retirement plan
- Pre-tax transit and parking benefits
- Time Off & Flexibility:
- Enjoy the best of both worlds: the energy and collaboration of in-person work, combined with the convenience and focus of remote days. This is a hybrid position requiring three days of in-office collaboration per week, with the flexibility to work remotely for the remaining two days. Our hybrid model is designed to balance individual flexibility with the benefits of in-person collaboration, enhanced team cohesion, spontaneous innovation, hands-on mentorship opportunities and strengthens our company culture.
- 22 days of Paid Time Off (PTO) per year, with the option to roll over unused days.
- One dedicated day per year for volunteering.
- Two professional development days per year to allow uninterrupted professional development.
- An additional PTO day added during milestone anniversary years.
- Robust paid holiday schedule with early dismissal.
- Generous parental leave for all parents (including adoptive parents).
- Work-Life Support & Resources:
- Budget for tech accessories, including monitors, headphones, keyboards, and other office equipment.
- Backup child and pet care, as well as tutoring services.
- Milestone anniversary bonuses.
- Wellness & Lifestyle Perks:
- Stipend and subsidy contributions toward personally-owned cell phones
- Contributions for gym memberships and health/wellness initiatives.
- Discounted healthcare premiums.
- Healthy meal delivery program subsidies.
