Sales Manager, Enterprise (Canada)

WinsAbove; Toronto; Hybrid; CAD 180,000 - 240,000; Full time

Job summary

Stripe is seeking a First Line Manager to lead a team of 6 Account Executives focused on the Enterprise segment in Toronto, Ontario. You will coach, hire, and develop top talent while shaping strategy to grow revenue and deepen product adoption.

You will partner with Customer Success, Product, and Partnerships to surface insights, manage forecasts, and drive multi-product expansion across Canada.

Qualifications

• 10+ years of sales experience including 5+ years of people management.
• Demonstrated experience leading an Enterprise sales team in a high-growth technology environment.
• Ability to hire, train and coach a high-performance sales team.
• Ability to build strategic executive relationships with customers and industry thought leaders.
• Demonstrated passion for helping to scale new technology businesses.
• Ability to understand and articulate technical concepts, and translate them into industry- or business-relevant terms.
• Prior experience at a growth stage technology company.
• Prior experience in the payments industry

Responsibilities

• Recruit, develop, and lead a high-performing team of Existing Business Account Executives focused on the Enterprise segment, driving expansion and retention within Stripe’s largest customers.
• Define and execute the long-term vision and strategy for the team, ensuring alignment to revenue growth, renewal, and multi-product adoption goals.
• Manage day-to-day operations and performance, including forecasting, pipeline management, and attainment against key metrics such as net revenue retention and product penetration.
• Coach and enable the team to lead consultative, solution-oriented conversations that identify new opportunities within existing relationships and deliver measurable customer impact.
• Partner cross-functionally with Customer Success, Product, and Partnerships to surface customer insights and deliver a unified Stripe experience across accounts.
• Build and maintain strong executive relationships with key customers to deepen engagement and uncover new areas for growth.
• Inspire, develop, and mentor team members through regular coaching, feedback, and structured career development plans to elevate individual and team performance.
• Represent Stripe at industry events and customer forums to drive brand advocacy and market awareness.

Skills

People management

Enterprise sales leadership

Forecasting & pipeline mgmt

Executive stakeholder engagement

Job description

Who we are

About Stripe

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. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

About the team

The Velocity Sales team engages with some of the largest and fastest-growing businesses in the world to unlock revenue potential through Stripe’s platform. Today, over 55,000 Canadian accounts represent an exceptional, untapped opportunity—previously managed remotely or unserviced locally. We are building out our dedicated Canadian footprint to put local leaders and Account Executives in front of local customers, driving substantial growth across the region. As a First Line Manager leading a team of 6 Account Executives focused on portfolio expansion ("Grower" roles), you will serve as a key strategic builder, shaping our team, expanding our Canadian presence, and leading one of our most exciting regional growth engines.

What you’ll do

Responsibilities

• Recruit, develop, and lead a high-performing team of Existing Business Account Executives focused on the Enterprise segment, driving expansion and retention within Stripe’s largest customers.
• Define and execute the long-term vision and strategy for the team, ensuring alignment to revenue growth, renewal, and multi-product adoption goals.
• Manage day-to-day operations and performance, including forecasting, pipeline management, and attainment against key metrics such as net revenue retention and product penetration.
• Coach and enable the team to lead consultative, solution-oriented conversations that identify new opportunities within existing relationships and deliver measurable customer impact.
• Partner cross-functionally with Customer Success, Product, and Partnerships to surface customer insights and deliver a unified Stripe experience across accounts.
• Build and maintain strong executive relationships with key customers to deepen engagement and uncover new areas for growth.
• Inspire, develop, and mentor team members through regular coaching, feedback, and structured career development plans to elevate individual and team performance.
• Represent Stripe at industry events and customer forums to drive brand advocacy and market awareness.

Who you are

We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

Minimum requirements

• 10+ years of sales experience including 5+ years of people management experience.
• Demonstrated experience leading and Enterprise sales team in a high-growth technology environment.
• Ability to hire, train and coach a high-performance sales team.
• Ability to build strategic executive relationships with customers and industry thought leaders.
• Demonstrated passion for helping to scale new technology businesses.
• Ability to understand and articulate technical concepts, and translate them into industry- or business-relevant terms.

Preferred qualifications

• Prior experience at a growth stage technology company.
• Prior experience in the payments industry