Tax Planning and Strategy SME

Role Description

We're seeking a Tax Planning and Strategy Expert with extensive experience in tax advisory and complex planning scenarios. You'll play a critical role in developing and validating the tax data and documentation that power our AI systems. This position is ideal for someone who thrives on complexity, balancing deep technical knowledge with strategic thinking, and is eager to shape the next generation of intelligent tax technology.

You'll collaborate closely with our product and engineering teams to ensure our AI models reflect the nuances of real-world tax planning—from entity structuring and transaction planning to wealth transfer strategies and cross-border considerations. This is your chance to apply your expertise beyond client work, impacting how thousands of professionals use AI to navigate sophisticated tax planning and decision-making.

What You’ll Do

• Technical Advisory & Subject Matter Expertise
  • Serve as the technical resource for complex tax questions involving transactions, entity restructuring, business succession, M&A, and wealth transfer strategies.
  • Guide product and engineering teams on feature development, ensuring tools meet the needs of sophisticated tax professionals.
• Evaluation and Quality Assurance
  • Create tax planning content, case studies, and decision trees for AI training and user education.
  • Document methodologies, workflows, and strategic frameworks for internal knowledge bases.
  • Develop fact patterns and scenarios that stress-test AI capabilities across diverse planning situations.
  • Compile question lists and create answer keys to support continuous evaluation of products and features.
  • Monitor tax law changes and advise on policy and procedural updates.

Qualifications

• 5+ years in tax planning and strategy with expertise in complex advisory scenarios.
• Bachelor's or Master's degree in Accounting, Finance, or Taxation.
• CPA, CFP, EA, or JD preferred.
• Deep knowledge across multiple areas including:
  • Corporate and personal tax planning strategies.
  • Entity selection and optimization.
  • Partnership and S-corporation taxation.
  • M&A structuring and business succession.
  • Estate planning and wealth transfer.
  • Cross-border transactions.
• Excellent communication skills—ability to explain complex tax concepts clearly to diverse audiences.
• Collaborative approach and comfort working cross-functionally with non-tax professionals.

Preferred Qualifications

• Experience in SaaS, fintech, or startup environments.
• Combined Big 4, national firm, or law firm and technology industry experience.
• Prior experience developing tax technology solutions, training materials, or educational content.
• Experience serving high-net-worth individuals or closely held businesses.

Benefits

• Medical insurance.
• Dental.
• Vision.
• 401k + 3% match.
• Life insurance.
• Equity.
• Travel: Once a quarter to the San Francisco headquarters.