Director of Tax

Department: Finance

Employment Type: Permanent - Full Time

Location: Chicago

Compensation: $160,000 - $200,000 / year

Description

Key Responsibilities

• 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.

• 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.

• 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.

• 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.

• 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.

• 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 Expertise

• 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.

• 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.
  
  

Benefits

• 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.