Tax Manager

Responsibilities

• Own Underdog’s overall tax function and serve as the primary internal resource for tax matters across the business.
• Manage federal, state, and local income tax compliance, including coordinating with outside preparers, reviewing filings, and ensuring timely and accurate submissions.
• Prepare and oversee key in-house filings and reporting, including state fantasy sports tax filings, customer tax information reporting, and equity-related tax reporting.
• Lead the company’s approach to tax information reporting for prediction market customers as requirements and products evolve.
• Partner with Product, Engineering, and Data to develop and maintain customer-facing tax capabilities and validate tax calculations and reporting.
• Coordinate the annual tax provision process under ASC 740 with external tax advisors and auditors.
• Coordinate the company’s R&D tax credit analysis and document qualifying activities and expenses.
• Research and communicate tax implications of new products, markets, and business initiatives.
• Build scalable tax processes, documentation, reconciliations, and internal controls.
• Monitor changes in tax law and information-reporting requirements and identify risks, opportunities, and operational impacts.
• Manage relationships with external tax advisors, auditors, and tax authorities.

Requirements

• 5+ years of progressive tax experience, ideally including public accounting and in-house corporate tax experience.
• CPA with a strong technical foundation in federal and state income tax; Big Four experience strongly preferred.
• Experience across income tax, industry-specific taxes, and customer information reporting.
• Experience overseeing outside advisors while remaining hands-on and accountable for the underlying work.
• Experience reviewing complex datasets, reconciling tax calculations, and identifying data or process issues.
• Ability to collaborate with cross-functional stakeholders on tax-related business and product needs.
• Ability to translate complex tax requirements into clear operational and technical requirements.
• Strong judgment, attention to detail, prioritization, and deadline-management skills.
• Willingness to build systems and improve processes.

Nice-to-haves

• Experience at a high-growth startup or within a lean finance team.
• Experience in fantasy sports, gaming, fintech, financial services, prediction markets, or another highly regulated industry.
• Significant multistate tax and nexus experience.
• Experience with high-volume customer or payee information reporting.
• Experience partnering with technical teams to build tax calculations or customer-facing tax products.
• Experience with equity compensation tax matters, including ISOs, NSOs, RSUs, Forms 3921, and Section 83(b) elections.
• Familiarity with R&D tax credits and related documentation requirements.
• Experience implementing tax software, data workflows, or other tax infrastructure.

Compensation and Benefits

• Target starting base salary: $128,000–$160,000, plus target equity.
• Unlimited PTO.
• 16 weeks of fully paid parental leave.
• Home office stipend.
• 5% 401(k) match.
• FSA and company-paid health, dental, and vision plan options for employees and dependents.
• Remote-first work culture with periodic in-person gatherings.