Enterprise Sales Leader, Canada Financial Services

Amazon • Toronto, ON

1d • CA$176,000 - CA$293,900 • Onsite

About The Position

AWS Canada is seeking an exceptional sales leader to manage and grow the AWS Financial Services & Insurance (FSI) business in Canada. In this role, you will be responsible for driving the next wave of cloud and AI adoption across Canada's largest and most complex financial institutions and insurance companies, helping them harness the power of AWS's industry-leading AI/ML services, AI capabilities (including agentic AI), and purpose-built cloud solutions to accelerate growth, create new revenue streams, and gain competitive advantage.

We are looking for a senior sales leader with a background in leading highly effective teams and deep experience in the Canadian Financial Services & Insurance ecosystem. You will lead the AWS FSI business across Canada, overseeing account teams responsible for banking, capital markets, insurance, payments, and wealth management customers. You will actively own the strategy and operations of the AWS FSI segment in Canada as part of Amazon Global Sales (AGS).

You will collaborate with and lead across multiple functions as part of the broader AGS Canada team, which includes Account Management, Business Development, Solution Architecture, Customer Solutions Management, Partners, and Marketing. This includes the ability to influence and lead teams without direct reporting lines to drive outcomes for your customers.

You should be a self-starter with an entrepreneurial spirit who is motivated by helping financial services organizations rapidly develop the capability to drive digital transformation, optimize their use of AWS technologies, and collaborate with services and ISV Partners. You thrive in a fast-paced environment, execute against ambitious goals, and have a passion for technology.

As the FSI Sales Leader, you will report to the Managing Director, AWS Canada. You will lead a team of sales leaders and their account managers to drive growth and shape the future of cloud adoption across Canada's financial services and insurance sector. Your responsibilities will include building and managing a high-performing team focused on driving adoption and market penetration across Canadian FSI enterprises.

As a member of the Canadian Senior Leadership Team, you will be expected to contribute to the overall success of AWS in Canada beyond your segment responsibilities. This includes actively participating in cross-functional strategic planning, mentoring leaders across the organization, representing AWS Canada externally, and modeling the leadership behaviours that drive our culture and business outcomes.

Requirements

• Experience negotiating complex deals with customers and partners or equivalent
• 15+ years of experience in enterprise technology sales, with at least 5 years in a leadership role managing sales teams
• Proven track record of consistently meeting or exceeding revenue targets in enterprise accounts, preferably within financial services
• Deep experience selling and managing software products or technology services, including the development of Enterprise Agreements
• Experience selling cloud-based technology solutions (IaaS, PaaS, SaaS)
• Experience driving AI/ML or cloud-based AI solution adoption with enterprise customers
• Experience leading teams working with large financial services and insurance customers
• Track record of building rapport with senior customer executives (CEO, CIO, CTO, CDO) and closing large revenue engagements
• Excellent interpersonal, verbal, and written communication, analytical, and presentation skills

Nice To Haves

• Experience in engineering, computer science, or MIS
• Experience in a heavily matrixed sales environment, including developing, implementing, and executing cross-functional solutions-led go-to-market growth initiatives
• Proven ability to effectively lead a scaled sales organization and work across a variety of organizations, management levels, cultures, and personalities
• Deep understanding of cloud technologies, including public and hybrid cloud platforms
• Knowledge of FSI regulatory frameworks and compliance requirements (e.g., OSFI, privacy regulations)
• Experience leading sales teams through technology transitions, particularly in AI and machine learning, with demonstrated ability to position AI capabilities (including agentic AI) as business transformation enablers
• Experience leading teams across multiple geographies within Canada
• Recognized industry expertise within financial services with proven public speaking and thought leadership
• Demonstrated decision-making, problem-solving, and negotiating skills
• Experience operating in the Canadian FSI market with an established network of executive relationships

Responsibilities

• Own and drive the overall revenue and market share growth for the AWS FSI business across Canada, spanning banking, capital markets, insurance, payments, and wealth management
• Lead, develop, and inspire a team of account managers focused on FSI customers
• Ensure customer satisfaction and long-term retention across the FSI portfolio
• Increase share of wallet with key strategic FSI customers by winning large and complex deals in alignment with AGS/AWS leadership
• Meet or exceed quarterly revenue targets across all FSI sub-verticals
• Support FSI customers in migrating to the cloud, innovating at scale, driving digital transformation, and adopting modern DevOps practices
• Develop and execute a comprehensive FSI business plan for the Canadian market, with customer-specific strategies for key accounts
• Actively coach your team to articulate compelling value propositions around AWS and Amazon, tailored to FSI regulatory requirements and industry needs
• Build, own, and facilitate long-term C-level relationships with key FSI accounts
• Scale the business by working with internal and external stakeholders, including Partners, Solution Architects, and Customer Solutions Managers
• Collaborate cross-functionally with AGS Canada leadership to align on go-to-market strategy and resource allocation

Benefits

• health insurance (medical, dental, vision, prescription, basic life & AD&D insurance)
• Registered Retirement Savings Plan (RRSP)
• Deferred Profit Sharing Plan (DPSP)
• paid time off
• other resources to improve health and well-being
• sign-on payments
• restricted stock units (RSUs)
• sales incentives (where applicable)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed