Country Lead Canada

Linkup

17h•$200,000 - $400,000•Remote

About The Position

Linkup is seeking a Country Lead to open and own its Canadian market. As the first person on the ground in Canada, the Country Lead will work closely with the founders and the go-to-market team, splitting time between Canada and Linkup’s New York City and San Francisco hubs. The company already has Canadian customers, traction, and relationships; the role will build on this foundation to deepen and scale the business and make Linkup a default choice for Canadian AI teams. This is a builder role combining sales with development of the market playbook, network, and local presence. The Country Lead will own Canadian market strategy, pipeline, revenue, and expansion; lead sales from outreach through close; build relationships across the AI ecosystem; represent Linkup locally; and connect Canadian insights and US momentum across teams and deals. The role will partner with Product and Engineering to tailor solutions and inform the roadmap, and develop repeatable sales playbooks for AI-native teams and enterprise innovation groups. The role is central to Linkup’s go-to-market expansion, partners closely with the founders, and reports to the US GTM team. The work will shape Linkup’s growth beyond its first two markets and could lead to building and leading the Canada team. Linkup offers a flexible remote-work policy, and regular travel between Canada, NYC, and SF is expected.

Requirements

At least 5 years of experience in B2B SaaS or technical sales.
A strong network in the Canadian tech and AI ecosystem.
Experience closing high-value, multi-stakeholder deals, ideally with technical buyers.
Comfort working with founders, CTOs, engineers, and data teams.
Willingness to travel regularly between Canada, NYC, and SF.
Excitement about helping build Google for AI agents.

Nice To Haves

Experience in AI, developer tools, or data infrastructure.
Experience opening a market, launching an office, or serving as an early go-to-market hire.

Responsibilities

Own Canada end to end, including market strategy, pipeline, revenue, and expansion.
Run the full sales cycle, from outreach and discovery through demo, negotiation, and close.
Build relationships across the Canadian AI ecosystem, including startups, scale-ups, enterprises, research labs, and investors.
Represent Linkup locally by hosting events, speaking at meetups, and building visibility in Toronto, Montreal, and Vancouver.
Bring Canadian market insight to the US team and bring US momentum and customers into Canadian deals.
Partner with Product and Engineering to tailor solutions and feed field insights into the roadmap.
Build repeatable playbooks for selling to AI-native teams and enterprise innovation groups in Canada.