US Tax Advisory Manager

This is a unique opportunity to join a fast-growing, well-funded firm in a Senior US Tax Accountant capacity, reporting directly to the CEO. The role is ideal for someone with strong US individual tax experience who enjoys working in a dynamic, entrepreneurial environment with meaningful visibility and impact.

Beyond traditional tax work, this position offers the opportunity to be involved in helping shape and build out the firm’s AI capabilities, making it a great fit for someone excited by innovation and process improvement. The role is fully remote, highly collaborative, and offers strong long-term growth potential within a rapidly scaling organization.

Senior US Cross-Border Tax Professional (Canada)

Remote — Canada | Full-time

Venture-backed, AI-native tax firm helping individuals meet their US tax filing obligations. We specialize in expats, US citizens, green card holders, and anyone required to file US taxes while living outside the United States.

Founded recently and backed by significant investment from both the US and Israel, we are headquartered in Israel and currently serve clients across Israel and Canada. Our mission is to build AI agents that automate the end-to-end work of tax professionals, from client communication, data gathering and tax prep - so that every member of our team operates as a reviewer of AI-produced work rather than a manual preparer.

The Role

We are looking for a senior cross-border tax professional to prepare and review US individual tax returns for Canadian residents who must file with the IRS. This is a remote, individual-contributor role with significant autonomy and trust.

Beyond preparing returns, you will be a client-facing point of contact in the Canadian time zone. You will engage prospective and existing clients, answer their questions, and help convert leads into clients.

You will play an active part in shaping how we build and use AI. This is the core of the role, not a side project: you will review the work our AI agents produce, feed your corrections back into the system, and help design and improve the AI agents that automate tax preparation - including deciding which capabilities we build next.

Key Responsibilities

• Review US individual tax returns for Canadian residents with US filing obligations and sign off on accurate, compliant returns.
• Apply cross-border tax expertise to expat and dual-filing situations, catching and correcting errors in AI-prepared work.
• Serve as a client-facing contact for Canadian clients and prospects
• Engage with leads, answer questions, and help convert prospects into clients.
• Work independently, manage your own workload, and consistently deliver high-quality work.
• Train, evaluate, and improve Waypoint's AI agents: feed your review corrections back into the system and help design the agents that automate end-to-end tax preparation and client communication.

Qualifications

Must-Have

• CPA or EA (Enrolled Agent) - an active credential that allows you to sign US tax returns.
• Hands-on experience with cross-border tax preparation, specifically US returns for Canadian residents.
• Focused on individual tax - not business/corporate tax.
• Trustworthy and highly self-directed, with the ability to understand tasks and work independently when needed.
• Strong interpersonal skills and comfort engaging directly with clients and prospects.
• The willingness to make a big impact on the future and shape how AI agents will automate tax work.

Nice-to-Have

• Interest in growing into a managerial role as the Canadian team expands.

What We Offer

• Competitive compensation - we pay strong salaries for the right people; level set to your expertise and experience.
• Equity / stock options in the company.
• 20 days of paid vacation.
• Fully remote role - no commute, work from anywhere in Canada.
• A venture-backed, high-growth environment with the opportunity to grow into a leadership role and help shape our mission to automate tax work with AI agents.