Tax Insights Associate

Overview

This role involves researching, drafting, and refining practitioner-facing articles for a growing US tax content library, covering the full breadth of US tax law and adding context and insights on high-demand topics. Work is supported by purpose-built AI tools.

The employer is primarily remote, with occasional in-person meetings at its Toronto office and possible rare travel for conferences. Candidates based anywhere in the United States are welcome to apply.

Responsibilities

• Tax research and writing: Research, draft, and edit multiple practitioner-facing US tax articles per week, covering areas such as:
  • corporate tax
  • individual tax
  • deductions and credits
  • S corporations, partnerships, trusts
  • exempt organizations and more
    Adapt quickly to researching, understanding, and summarizing questions across multiple areas of tax law; evaluate sources for accuracy and currency; analyze source documents to support analysis; and assess the quality and accuracy of AI-generated tax analysis. Take ownership of accuracy and quality before articles are submitted for manager review.
• Validation: Perform technical review on articles produced by other contributors, checking for accuracy, currency, and alignment with content standards.
• Process awareness: Apply knowledge of tax firm workflows to align product with real-world use cases and improve adoption.
• Teamwork and collaboration: Work with experienced tax professionals, and alongside analysts and data scientists to develop and improve AI tools. Build strong relationships across the tax research and data science teams.
• Strategic thinking: Help shape a new internal product function from the ground up by influencing quality, coverage, and continuous improvement.
• Evolving based on customer needs: Partner with tax professionals by addressing feedback, troubleshooting, and incorporating recommendations to consistently add value.

Requirements

• JD or CPA designation.
• 3–7 years of professional experience in US federal tax (at a firm, in-house, government, or a tax-focused research or content role).
• Strong writing skills, including the ability to clearly explain complex tax concepts for a practitioner audience.
• Comfort using AI tools as part of daily workflow, with real enthusiasm for integrating them into the work.
• Ability to work independently, manage competing priorities, and meet deadlines.
• Intellectual curiosity and genuine interest in how technology can improve the tax profession (prior tech experience not required).

Preferred Qualifications

• Experience collaborating with or using AI tools in a professional workflow (not required, but aligned with the role).

Compensation & Benefits

• Competitive base salary, stock options, and benefits designed to support you and your family.

Location

• Primarily remote.
• Occasional in-person meetings at the Toronto office (2–4 times a year) as needed.
• Possible rare travel for conferences.
• Candidates based anywhere in the United States are welcome to apply.

Interview Process

• Step 1: Chat with Bailey, Talent Acquisition Manager
• Step 2: Meet with members from the Legal Research Team
• Step 3: Meet with Kim, Director of Tax Research, and Susan, VP of Tax Research
• Step 4: Take Home Case Study Submission
• Step 5: Meet Ben, CEO

Additional Information

• Human review: Human talent team members review applications, and decisions are made by humans.
• Accessibility: The employer strives to create an inclusive and accessible hiring experience and provides reasonable accommodations upon request during the interview process.
• Equal opportunity: The employer is an equal opportunity employer and does not discriminate based on race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.