Underdog Fantasy Customer Support Jobs (NOW HIRING)

As Underdog's first dedicated tax hire, you will own and scale the company's tax function across our diverse and evolving business. You will oversee external tax advisors while taking direct ownership of key filings, calculations, and processes performed in-house. You will manage tax compliance and reporting and partner cross-functionally to incorporate tax requirements into Underdog's products, systems, and operations.

• 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
• Directly oversee and prepare 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 applicable requirements and products evolve
• Partner with Product, Engineering, and Data to develop and maintain customer-facing tax capabilities and validate the completeness and accuracy of tax calculations and reporting
• Coordinate the annual tax provision process under ASC 740, serving as the primary liaison with external tax advisors and auditors 
• Coordinate the company's R&D tax credit analysis and support the collection and documentation of qualifying activities and expenses
• Research and communicate the tax implications of new products, markets, and business initiatives in partnership with external advisors and internal stakeholders 
• Build scalable tax processes, documentation, reconciliations, and internal controls that can grow with the business
• Monitor changes in tax law and information-reporting requirements and proactively identify risks, opportunities, and operational impacts
• Manage relationships with external tax advisors, auditors, and tax authorities

• 5+ years of progressive tax experience, ideally including experience in public accounting and an in-house corporate tax environment
• CPA with a strong technical foundation in federal and state income tax; Big Four experience is strongly preferred
• A versatile tax professional comfortable working across a broad range of tax matters, including income tax, industry-specific taxes, and customer information reporting
• Comfortable overseeing outside advisors while remaining hands-on and accountable for the underlying work
• Experienced in reviewing complex datasets, reconciling tax calculations, and identifying data or process issues
• Able to collaborate with cross-functional stakeholders on tax-related business and product needs 
• Skilled at translating complex tax requirements into clear operational and technical requirements for non-tax stakeholders
• Comfortable being the only tax professional in the room, without a large internal team or established playbook to rely on
• Detail-oriented and pragmatic, with sound judgment about risk and what to prioritize in a fast-moving environment
• Able to manage multiple deadlines and competing priorities without dropping the ball
• Excited to build systems and improve processes, not simply administer existing ones

• Experience at a high-growth startup or as part of 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 the related documentation requirements
• Experience implementing tax software, data workflows, or other tax infrastructure

Our target starting base salary range for this position is between $128,000 and $160,000, plus target equity. Final compensation will be determined based on a variety of factors including relevant experience, skills and expertise, interview performance, and other market considerations.

• Unlimited PTO for full-time employees (we're extremely flexible with the exception of the first few weeks before and into the NFL season)
• 16 weeks of fully paid parental leave
• Home office stipend
• A virtual-first culture, but we come together a few times per year in person for offsites, trainings, hackathons, and more
• Slack reactions for every occasion
• 401k with up to 5% employer match
• Company paid health, dental, vision plan options for employees and dependents, FSA, and more
• Opportunity to celebrate your favorite sports teams through local meetups and company-sponsored events
• Claude and ChatGPT enterprise accounts

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