Senior Tax Manager in Winnipeg

Meridia Recruitment Solutions has partnered with Waypoint, a venture-backed, AI-native tax firm, to recruit a Senior Tax Manager to lead its US cross-border individual tax practice. Waypoint is helping US citizens, green card holders, and expats meet their US tax filing obligations. 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:

• AI AND PROCESS
  • Work with product and engineering to design, evaluate, and improve our AI agents, turning review findings into concrete improvements.
  • Identify bottlenecks in our tax workflow and help automate them.
• TAX OPERATIONS
  • Own the engagement lifecycle from intake to electronic filing, including filing season deadlines and extensions.
  • Track KPIs such as turnaround time, accuracy, and client satisfaction.
  • Maintain firm tax positions, review checklists, and quality control standards, and keep the team current on IRS changes.
• TEAM LEADERSHIP
  • Lead, mentor, and manage our senior tax accountants across Israel and Canada, from hiring and onboarding to performance reviews.
  • Allocate workload and balance capacity, especially during filing season.
  • Build a culture of ownership, accuracy, and continuous improvement.
• CLIENT OWNERSHIP AND GROWTH
  • Own a portfolio of our most complex and high-value clients as their year-round trusted advisor.
  • Lead prospect meetings, scope and price engagements with sales, and write proposals that turn leads into long-term clients.
• TECHNICAL REVIEW AND ESCALATIONS
  • Act as final reviewer and signer on complex US individual returns for clients living abroad.
  • Handle escalations, IRS notices and correspondence, and amended returns.

QUALIFICATIONS:

• 8+ years of US individual tax experience, including at least 2 years as a Tax Manager leading a team of expat tax preparers and reviewers.
• Deep expertise in international individual tax, including Forms 1040, 2555, 1116, 8938, 8621, 3520, 5471, and FinCEN 114 (FBAR).
• Proven track record running tax operations through busy seasons, including workflow design, capacity planning, and quality control.
• Experience owning client relationships and growing a practice.
• Hands-on experience with professional tax software such as CCH Axcess.
• Excitement about leading a practice where AI agents prepare and people review.
• Ability to work independently in a fully remote environment.

KEY SKILLS & CHARACTERISTICS

• Strong leadership and communication skills, and comfort leading a remote team across time zones.
• Background in business tax.
• Background in bookkeeping.
• Familiarity with current AI agents such as Claude Cowork and ChatGPT.

This is a current vacancy; the salary range is $120,000 - $150,000 USD. The position includes equity/stock options, 20 days of paid vacation, and the flexibility to work from anywhere.

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.

We appreciate your interest in this opportunity.