The Canada Country Manager will lead TaxGPT's market entry in Canada, merging roles of sales and tax expertise to drive growth and product development in AI-driven tax solutions.
Canada Country Manager — Revenue Closer & Tax Subject Matter Expert
About TaxGPT
About the Role
What You'll Do
What We're Looking For
Required Qualifications
Preferred Qualifications
How We Define Success in This Role
Why Join Us
Remote — Canada | Full-Time | Competitive Base + Uncapped Commission + Equity
TaxGPT is revolutionizing the tax and accounting space with AI-driven solutions tailored for accountants, tax professionals, and SMBs. We are building an AI co-pilot to transform tax workflows, drive efficiency, and simplify compliance. Recently named one of Business Insider's 30 Early-Stage Startups Most Likely to Become Tech's Next Unicorns, we would love for you to join our growing team.
This is the rarest, most consequential hire we'll make in Canada this year. We're combining two roles — Account Executive / Country Lead and Senior Canadian Tax Subject Matter Expert — into a single seat for one extraordinary person who can do both. If you're a CPA (or seasoned tax practitioner) who happens to be a phenomenal seller, or a top-tier AE with real Canadian tax depth in your background, keep reading. This role was written for you.
You will own Canada. End-to-end. From the first cold call to the closed-won deal, from the first product gap you flag to the workpaper logic our AI uses to reason about a T2 return — this is your domain. You'll be our face in the Canadian market, our voice inside the building, and the technical authority that gives every customer conversation credibility most AEs can only dream of.
You'll knock down doors as a founding seller and country manager. You'll also be the in-house Canadian tax brain that shapes the product, validates the AI's outputs, and translates CRA, Department of Finance, and provincial nuance into something our models can actually reason about.
This is not a normal AE role. It's not a normal SME role either. It's a founding seat with real ownership, real equity in the outcome, and a clear path to building and leading the Canadian team.
- Open the Canadian market. Operate as a founding commercial leader. Establish TaxGPT as the leading AI platform for Canadian tax professionals, accounting firms, and finance teams.
- Source and close your own pipeline. This is a hunter role. Some inbound will come your way, but you'll primarily generate pipeline through outbound prospecting, referrals, events, LinkedIn, and strategic outreach across the Canadian tax ecosystem.
- Run the full sales cycle. Prospecting, discovery, demos, trials, procurement, negotiation, close, expansion. You own it all.
- Sell like the expert you are. Walk into a demo with a CPA partner, a CFO, or a Big Four alum and hold your own on T2s, GST/HST nuances, provincial allocation, permanent establishment questions, and cross-border treaty issues.
- Be the Canadian tax brain inside TaxGPT. Prepare, review, and validate Canadian tax documentation and datasets — federal and provincial corporate income (T2), personal income (T1), GST/HST, provincial sales tax, and beyond.
- Shape the Canadian product. Work directly with engineering, data, and product to translate complex Canadian tax concepts into structured, machine-readable formats.
- Provide expert feedback on AI model outputs. Improve precision, context, and realism so customers trust what they see.
- Build the ecosystem. Develop trusted relationships with firm partners, tax leaders, CFOs, finance executives, and operations teams across Canada.
- Operate like a country manager. High ownership, high autonomy, high initiative. You'll help define how we sell, position, localize, and grow TaxGPT in Canada.
Required Qualifications
- 3–6+ years of sales experience in SaaS or technology, ideally within AI, fintech, tax, accounting, or financial services.
- Proven ability to prospect and generate pipeline independently.
- Strong closing record — you've carried and exceeded quota.
- Demonstrated success running consultative discovery and high-quality demos.
- Excellent communication: written, verbal, and on video.
- Disciplined operator with clean pipeline hygiene.
- Comfortable working autonomously in a fast-moving startup environment.
- Fluent in modern GTM tools — HubSpot, Apollo, LinkedIn Sales Navigator, etc.
- 5+ years of experience in Canadian tax compliance and consulting (or equivalent depth gained through a CPA + advisory career).
- Proven track record preparing and reviewing federal and provincial corporate income (T2), personal income (T1), GST/HST, provincial sales tax, and other Canadian tax returns for individuals, small businesses, and mid-sized entities.
- Expertise developing Canadian tax workpapers — provincial allocation schedules, permanent establishment and nexus analyses, jurisdiction-specific adjustments.
- Strong background conducting Canadian and cross-border tax research across federal, provincial, and treaty contexts.
- Hands-on experience with multi-jurisdictional Canadian tax obligations.
- CPA, J.D./LL.B., CPA Canada In-Depth Tax Course (Levels I–III), or equivalent credential strongly preferred.
- Experience selling to accounting firms, tax professionals, or financial services organizations.
- Experience with legacy tax and research platforms (CCH, Thomson Reuters, TaxPrep).
- Background as an early-stage or founding sales hire.
- Quebec tax depth (TVQ, Revenu Québec practice) and/or bilingual English/French.
- Prior exposure to AI or data-driven tax innovation projects.
- Experience with indirect tax automation tools.
How We Define Success in This Role
- Builds a credible Canadian book from zero. In the first 3 months, lands first 8–15 mid tier to enterprise logos across accounting firms, tax practices, and corporate finance teams — through self-sourced pipeline, not handed leads. Establishes TaxGPT as a recognized name in the Canadian tax community by month 6.
- Earns trust in the room that most AEs can't. Walks into a discovery call with a CPA partner or CFO and gets treated as a peer, not a vendor. Closes deals because prospects can see that the product works for Canadian tax — and believes it because the person across the table proved it does.
- Translates Canada into the product. Ships measurable improvements for the Canadian Product to include: handling of T2s, GST/HST, provincial allocation, and CRA-specific reasoning by working directly with engineering and product. Becomes the internal source of truth on every Canadian tax question that touches the roadmap.
This is the seat that will scale TaxGPT's Canadian business — the person in this role won't just sell into the market, they'll shape what we sell, how the product reasons about Canadian tax, and who joins the team next. You'll have the autonomy of a country manager, the technical authority of a senior tax advisor, and the upside of an early hire at a company Business Insider has flagged as one of the most likely next unicorns in tech.
Similar Jobs
.png)
Blockchain • Fintech • Analytics • Financial Services • Cryptocurrency • Web3
As a Junior Crypto Trader, you will perform basic trading operations, analyze market trends, and work under a mentor to develop trading skills.
Top Skills:
Analytical ToolsMarket DataTrading Tools
Artificial Intelligence • Productivity • Software • Automation
The Senior Fullstack Engineer will build and manage enterprise authentication systems, improve user session management, ensure security compliance, and support internal API usage across services, while enhancing performance and reliability.
Top Skills:
Ci/CdDjangoFastifyKubernetesNode.jsPythonTerraform
Artificial Intelligence • Productivity • Software • Automation
Lead and develop a Mid Market Account Executive team to drive new logo acquisition and expansion. Hire, coach, and ramp quota-carrying AEs; oversee pipeline, forecasting, and deal reviews; collaborate cross-functionally to drive adoption, retention, and product-informed go-to-market strategies; and scale repeatable playbooks for horizontal AI orchestration and automation sales.
Top Skills:
AIAPIsAutomationHubspotIntegrationsZapier
What you need to know about the Montreal Tech Scene
With roots dating back to 1642, Montreal is often recognized for its French-inspired architecture and cobblestone streets lined with traditional shops and cafés. But what truly sets the city apart is how it blends its rich tradition with a modern edge, reflected in its evolving skyline and fast-growing tech industry. According to economic promotion agency Montréal International, the city ranks among the top in North America to invest in artificial intelligence, making it le spot idéal for job seekers who want the best of both worlds.
Key Facts About Montreal Tech
- Number of Tech Workers: 255,000+ (2024, Tourisme Montréal)
- Major Tech Employers: SAP, Google, Microsoft, Cisco
- Key Industries: Artificial intelligence, machine learning, cybersecurity, cloud computing, web development
- Funding Landscape: $1.47 billion in venture capital funding in 2024 (BetaKit)
- Notable Investors: CIBC Innovation Banking, BDC Capital, Investissement Québec, Fonds de solidarité FTQ
- Research Centers and Universities: McGill University, Université de Montréal, Concordia University, Mila Quebec, ÉTS Montréal
