Senior US Cross-Border Tax Professional

Position: Senior US Cross-Border Tax Professional )
Senior US Cross-Border Tax Professional (Canada)
Remote (Canada)
Reference # AC - 7203

Meridia Recruitment Solutions has partnered with Waypoint, a venture-backed, AI-native tax firm, to recruit a Senior US Cross-Border Tax Professional to join their growing remote team in Canada. Waypoint specializes in helping individuals meet their US tax filing obligations, with a focus on expats, US citizens, green card holders, and individuals living outside the United States.

Headquartered in Israel and backed by significant investment from both the US and Israel, Waypoint serves clients across Israel and Canada. The firm is redefining the tax services model by building AI agents that automate the end-to-end work of tax professionals, from client communication and data gathering to tax preparation, enabling team members to operate as reviewers of AI-produced work rather than manual preparers.

This is a senior-level role suited for a confident and self-directed professional seeking autonomy and the opportunity to contribute to the evolution of AI-driven tax services.

YOUR RESPONSIBILITIES:

• Review US individual tax returns for Canadian residents with US filing obligations and sign off on accurate, compliant filings.

• Apply cross-border tax expertise to expat and dual-filing scenarios, identifying and correcting errors in AI-prepared work.

• Serve as a client-facing contact for Canadian clients and prospective clients.

• Engage with leads, respond to inquiries, and support the conversion of prospects into clients.

• Work independently, manage your own workload, and consistently deliver high-quality results.

• Train, evaluate, and improve Waypoint’s AI agents by feeding review corrections back into the system.

• Contribute to the design and enhancement of AI capabilities supporting tax preparation and client communication.

YOUR REQUIREMENTS:

EDUCATION & EXPERIENCE

• CPA designation or Enrolled Agent (EA) credential with the ability to sign US tax returns.

• Proven experience in cross-border tax preparation, specifically US individual returns for Canadian residents.

• Strong focus on individual tax (corporate tax experience not required).

KEY SKILLS & CHARACTERISTICS

• Highly self-directed, with the ability to take ownership and work independently.

• Strong interpersonal and communication skills, with confidence engaging directly with clients and prospects.

• High level of accuracy and attention to detail in tax review and compliance work.

• Interest in innovation and contributing to the development of AI-driven tax solutions.

• Demonstrated ability to manage multiple priorities in a remote work environment.

• Interest in future growth into a leadership role as the Canadian team expands.

ADDITIONAL INFORMATION

Work Environment: Fully remote, high-growth, venture-backed company focused on innovation in tax services through AI.

Benefits:

• Competitive compensation aligned with experience and expertise

• Equity / stock options

• Fully remote role – work from anywhere in Canada

• Opportunity for career progression into leadership roles

• A collaborative environment shaping the future of AI-powered tax services