Senior Tax Manager (Richmond)

Senior Tax Manager

Location: Richmond, VA

Reports to: COO

About Cookie Finance

Cookie Finance is a rapidly growing accounting and tax technology startup for content creators. We work exclusively with creators and influencers on platforms like YouTube, Instagram, Twitch, and TikTok, supporting everyone from up-and-coming creators to digital megastars. We're looking for a Senior Tax Manager to lead our tax practice as we grow and to help us rethink how accounting is done.

About the Role

This is not a traditional firm role. You'll own the technical quality of our tax work for a client base of creators and entrepreneurs with complex, fast-moving financial lives: multi-state income, brand deals, S corporations, and rapid business growth. You'll review and sign off on complex 1040 and 1120S returns, guide a team of tax professionals, and advise clients on strategy with clarity and confidence.

You'll also help shape how we work. Cookie is building technology, including AI, that changes how tax gets prepared and reviewed, and you'll have a real voice in designing those processes. If you want to build something rather than inherit a playbook, this role was made for you.

Who This Role Is Perfect For

You're a deeply technical tax professional who is just as energized by building and improving as by the work itself. You're comfortable with ambiguity, you take ownership without being asked, and you get excited about the idea of doing tax differently. You can untangle a complicated S corporation basis question in the morning and explain it plainly to a client in the afternoon. You want to grow with a startup and have a real impact on how it develops.

What You'll Own

• Review and finalize complex individual (1040) and S corporation (1120S) returns, ensuring technical accuracy, quality, and timely delivery
• Lead, coach, and develop our team of tax associates and senior associates, providing clear feedback and career growth
• Meet with clients to develop proactive tax strategies, including entity structuring, S corporation elections, reasonable compensation, retirement planning, and multi-state planning
• Serve as the technical escalation point for the tax team on research, notices, and complex client situations
• Manage tax season workflow and capacity, keeping a high volume of returns moving accurately and on schedule
• Partner with Bookkeeping, Payroll, Product, and Client Services to deliver a seamless client experience
• Help design and improve tax processes, tools, and AI-assisted workflows that make our work faster, more accurate, and more scalable
• Contribute to building the standards, checklists, and training that define how Cookie does tax

What We're Looking For

• 5+ years of tax experience, preferred 2+ years in a review or management role
• Deep, hands-on experience preparing and reviewing 1040 and 1120S returns, including multi-state filings and shareholder basis
• Familiarity with partnership (1065) returns preferred
• CPA or EA strongly preferred; Bachelor's degree in Accounting, Finance, or a related field
• Experience leading and developing tax staff
• Proficiency with tax preparation software and QuickBooks
• Strong client communication skills and the ability to explain complex tax concepts simply
• An entrepreneurial mindset: comfortable with change, eager to take initiative, and excited to help build a company
• Interest in the creator economy and in using technology and AI to improve how tax work gets done

Cookie Finance is an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law.

E-Verify Notice: Cookie Finance participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S.