Head of Revenue and Growth, Canada

Stripe•Toronto, ON

About The Position

Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. The Canada Sales team is focused on driving revenue across the full spectrum of Stripe's customer base in Canada — from high-growth startups to some of the largest enterprises in the country. Stripe helps these businesses build new business models and drive innovation and modernization across industries. As the Head of Sales - Canada, you will be a critical part of the Americas go-to-market leadership team, owning the end-to-end sales strategy and execution for the Canadian market and driving accelerated adoption and revenue growth across Stripe's customer base in the region.

Requirements

5+ years of people management experience, ideally leading sales teams in Canada or broader North American markets
Experience leading Sales organizations in a high-growth technology environment
Experience building and scaling high-caliber teams, including launching or growing market presence in new regions
Ability to hire, train, and coach a high-performance sales team
Demonstrated quantitative and analytical skills with a strong command of pipeline and forecast management
Deep understanding of the Canadian business landscape, including key industries, regulatory environment, and enterprise customer dynamics

Nice To Haves

Prior experience at a growth-stage internet or software company
Prior experience in enterprise sales, partnerships, and/or business development in Canada
Prior experience in the payments industry, card issuing, or financial services
Established executive-level network within the Canadian business community
Bilingual (English/French) is an asset, particularly for engaging customers in Quebec

Responsibilities

Serve as the senior Stripe leader and executive sponsor for key customer and partner relationships across Canada, engaging C-suite stakeholders at Stripe's most strategic accounts.
Own and drive sales growth across Canada through strong leadership, organizational planning, and outstanding execution of all sales programs.
Oversee the expansion and satisfaction of Stripe's existing Canadian customers while aggressively pursuing new logo growth.
Develop and refine Stripe's Canada-specific go-to-market strategy, guiding investment and resource decisions in partnership with Product, Engineering, Marketing, and other supporting teams.
Make hiring decisions, shaping the ideal candidate profile and onboarding strategy to build a world-class Canadian sales organization.
Create structure and focus for GTM ideas and product sales campaigns relevant to the Canadian market. Drive execution, measurement, and timely analysis with clear recommendations for action.
Define key sales support mechanisms, processes, and programs to meet the rapid growth of the Canadian business and achieve revenue attainment and market development objectives.
Build and develop a high-performing organization and help write the playbook for enterprise and commercial sales in Canada.
Lead a senior, experienced team of Account Executives and indirectly lead the supporting roles and resources surrounding the accounts those AEs support across Canada.
Develop the long-term vision and strategy for the Canadian market, scaling day-to-day operations to support growth.
Champion and influence Stripe's sales methodology and process, driving best practices on selling, forecasting, and pipeline management across the team.
Develop best practices that enable the Canadian organization to rapidly scale, deliver on revenue targets, and support KPIs for growth.
Engage personally on large strategic opportunities, leading executive relationships and helping the team win and expand key customers.
Effectively work cross-functionally across the organization to represent Canadian customer needs and help shape Stripe's product roadmap accordingly.
Act as Stripe's market presence in Canada, engaging with the local business community, partners, and industry stakeholders to build brand awareness and strategic relationships.