Principal US Tax AI Specialist
Remote
Reference # AC-7517
Meridia Recruitment Solutions has partnered with Waypoint, a venture-backed, AI-native tax firm, to recruit a Principal US Tax AI Specialist. This opportunity is ideal for an experienced US tax professional who combines deep technical expertise in cross-border individual tax with an interest in shaping the future of tax preparation through AI.
Waypoint is a venture-backed, AI-native tax firm helping US citizens, green card holders, and expats meet their US tax filing obligations. Headquartered in Israel and backed by US and Israeli investors, Waypoint serves clients across Israel and Canada and is expanding into the United Kingdom. The firm builds AI agents that automate the end-to-end work of tax professionals, so every member of the team reviews AI-produced work instead of preparing it by hand.
RESPONSIBILITIES:
TECHNICAL REVIEW AND CLIENT OWNERSHIP
• Review, correct, and complete US individual tax returns prepared by AI agents, with the ability and credentials to sign returns as the preparer.
• Own a client portfolio from intake through filing, serving as the primary tax expert for client matters.
• Handle complex US cross-border individual tax matters, including foreign tax credits, FEIE, FBAR and FATCA reporting, PFICs, Forms 5471 and 5472, GILTI and Subpart F, Section 962 elections, dual-status returns, EITC, and relevant tax treaties.
• Manage filing deadlines and extensions while maintaining a high standard of accuracy and quality.
AI DEVELOPMENT AND PROCESS IMPROVEMENT
• Manage and train AI agents to perform tax preparation and review work to the standard expected of experienced junior and senior tax professionals.
• Work closely with the R&D team and AI engineers to improve agent performance, providing structured feedback on corrections and review findings.
• Help define and maintain the firm's tax positions, review standards, and quality control processes that guide AI-generated returns.
• Identify opportunities to automate additional parts of the tax workflow and collaborate with the team to implement improvements.
QUALIFICATIONS:
EDUCATION & EXPERIENCE
• Active CPA or Enrolled Agent (EA) credential, with the authority to sign US tax returns.
• Current experience at the Tax Senior or Tax Manager level in US individual tax, with a track record of reviewing returns, training junior staff, and handling complex tax matters.
• Deep expertise in US international individual tax, including foreign earned income exclusions, foreign tax credits, FBAR and FATCA reporting, PFICs, Forms 5471 and 5472, GILTI and Subpart F, Section 962 elections, dual-status returns, EITC, and tax treaties.
• Experience with professional tax software such as CCH Axcess.
• Ability to manage a client portfolio independently and meet filing deadlines in a fully remote environment.
• Genuine interest in working with AI agents and helping improve how tax work is completed.
KEY SKILLS & CHARACTERISTICS
• Exceptional attention to detail, sound technical judgment, and a strong commitment to accuracy.
• Ability to work independently, take ownership of client matters, and manage competing priorities.
• Strong analytical and problem-solving skills, with the ability to translate tax review findings into clear, structured feedback.
• Collaborative approach and interest in working closely with AI engineers and product development teams.
• Experience with US business tax is an asset.
• A UK tax qualification, such as ATT or CTA, is an asset.
• Familiarity with AI tools such as Claude and ChatGPT is an asset.
This is a current vacancy; the salary range is $90,000 - $120,000 USD.
The position includes equity/stock options, 20 days of paid vacation, and the flexibility to work from anywhere.
To express interest in this opportunity, please click on the "Apply Now" button below.
For more information, please contact Adam Creaghan, Partner, at acreaghan@kbrs.ca or 647-336-1416 or Lauren MacDonald, Recruitment Specialist, at laurenmacdonald@kbrs.ca or 902-407-1427. If you require accommodation to participate in the recruitment process, please let Lauren know.
Meridia Recruitment Solutions connects leading organizations with top talent by building strong relationships and creating ideal matches with candidates because we are only successful when you are.
We appreciate your interest in this opportunity. To learn more about Meridia Recruitment Solutions, our job opportunities, and our services, please visit our website.
Remote
Reference # AC-7517
Meridia Recruitment Solutions has partnered with Waypoint, a venture-backed, AI-native tax firm, to recruit a Principal US Tax AI Specialist. This opportunity is ideal for an experienced US tax professional who combines deep technical expertise in cross-border individual tax with an interest in shaping the future of tax preparation through AI.
Waypoint is a venture-backed, AI-native tax firm helping US citizens, green card holders, and expats meet their US tax filing obligations. Headquartered in Israel and backed by US and Israeli investors, Waypoint serves clients across Israel and Canada and is expanding into the United Kingdom. The firm builds AI agents that automate the end-to-end work of tax professionals, so every member of the team reviews AI-produced work instead of preparing it by hand.
RESPONSIBILITIES:
TECHNICAL REVIEW AND CLIENT OWNERSHIP
• Review, correct, and complete US individual tax returns prepared by AI agents, with the ability and credentials to sign returns as the preparer.
• Own a client portfolio from intake through filing, serving as the primary tax expert for client matters.
• Handle complex US cross-border individual tax matters, including foreign tax credits, FEIE, FBAR and FATCA reporting, PFICs, Forms 5471 and 5472, GILTI and Subpart F, Section 962 elections, dual-status returns, EITC, and relevant tax treaties.
• Manage filing deadlines and extensions while maintaining a high standard of accuracy and quality.
AI DEVELOPMENT AND PROCESS IMPROVEMENT
• Manage and train AI agents to perform tax preparation and review work to the standard expected of experienced junior and senior tax professionals.
• Work closely with the R&D team and AI engineers to improve agent performance, providing structured feedback on corrections and review findings.
• Help define and maintain the firm's tax positions, review standards, and quality control processes that guide AI-generated returns.
• Identify opportunities to automate additional parts of the tax workflow and collaborate with the team to implement improvements.
QUALIFICATIONS:
EDUCATION & EXPERIENCE
• Active CPA or Enrolled Agent (EA) credential, with the authority to sign US tax returns.
• Current experience at the Tax Senior or Tax Manager level in US individual tax, with a track record of reviewing returns, training junior staff, and handling complex tax matters.
• Deep expertise in US international individual tax, including foreign earned income exclusions, foreign tax credits, FBAR and FATCA reporting, PFICs, Forms 5471 and 5472, GILTI and Subpart F, Section 962 elections, dual-status returns, EITC, and tax treaties.
• Experience with professional tax software such as CCH Axcess.
• Ability to manage a client portfolio independently and meet filing deadlines in a fully remote environment.
• Genuine interest in working with AI agents and helping improve how tax work is completed.
KEY SKILLS & CHARACTERISTICS
• Exceptional attention to detail, sound technical judgment, and a strong commitment to accuracy.
• Ability to work independently, take ownership of client matters, and manage competing priorities.
• Strong analytical and problem-solving skills, with the ability to translate tax review findings into clear, structured feedback.
• Collaborative approach and interest in working closely with AI engineers and product development teams.
• Experience with US business tax is an asset.
• A UK tax qualification, such as ATT or CTA, is an asset.
• Familiarity with AI tools such as Claude and ChatGPT is an asset.
This is a current vacancy; the salary range is $90,000 - $120,000 USD.
The position includes equity/stock options, 20 days of paid vacation, and the flexibility to work from anywhere.
To express interest in this opportunity, please click on the "Apply Now" button below.
For more information, please contact Adam Creaghan, Partner, at acreaghan@kbrs.ca or 647-336-1416 or Lauren MacDonald, Recruitment Specialist, at laurenmacdonald@kbrs.ca or 902-407-1427. If you require accommodation to participate in the recruitment process, please let Lauren know.
Meridia Recruitment Solutions connects leading organizations with top talent by building strong relationships and creating ideal matches with candidates because we are only successful when you are.
We appreciate your interest in this opportunity. To learn more about Meridia Recruitment Solutions, our job opportunities, and our services, please visit our website.
