Questrade Financial Group (QFG), through its companies - Questrade, Questbank, Questrade Wealth Management, Community Trust Company, Zolo, and Flexiti, provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. We use cutting-edge technology to help Canadians become much more financially successful and secure. The ideal candidate will be a catalyst for change, using AI to transform and deliver unparalleled customer experiences and shaping a future where AI empowers our teams to do their best work.

Paid vacation, personal, and sick days for work-life balance Work-life balance in a hybrid workplace with at least 3 days in office Opportunities to contribute to community causes This job posting is for an existing vacancy. We’re looking for our next Senior Account Executive, Merchant Acquisition. Flexiti is Canada's leading point-of-sale financing provider, empowering retailers across the country to grow their businesses through flexible payment solutions.

As we scale, we're looking for a driven, entrepreneurial Senior Account Executive, Merchant Acquisition, to take the lead on new merchant acquisition. You’ll own the full sales cycle across Flexiti's existing verticals and play a key role in breaking into high-potential new categories. This is a high-visibility role with real income upside, reporting directly to the Managing Director of Sales & Account Management.

Leverage AI-powered tools to research targets, identify decision-makers, personalize outreach,



and accelerate pipeline velocity Manage inbound leads and convert them efficiently alongside your self-generated pipeline Build executive-level relationships with prospective merchant partners, using your network and consultative approach to earn trust and create urgency Sales Execution & Closing Own the full sales cycle from cold outreach through contract close, coordinating with internal teams (product, operations, legal) to remove roadblocks Build tailored, insight-led business cases that quantify the impact of Flexiti for each prospect — demonstrating how we drive incremental revenue, basket size, and customer conversion Maintain a high-quality, high-velocity pipeline in Salesforce CRM with accurate stage tracking, activity logging, and forecasting Consistently meet or exceed quarterly and annual targets for new merchant signings, net-new loan volume, and revenue contribution Market Intelligence & Positioning Monitor the BNPL, point-of-sale financing, and vertical-specific competitive landscape to sharpen positioning and objection handling Share field intelligence with leadership and product teams to influence strategy and roadmap priorities So are YOU our next Senior Account Executive, Merchant Acquisition? Have 5+ years of B2B sales experience, ideally in fintech, payments, SaaS, or retail tech Hold a proven track record of exceeding quota in a hunter-oriented,



self-directed sales role Bring experience selling at the executive level — you know how to get in front of the right people and build deals that stick Demonstrate strong consultative selling skills: you listen well, diagnose the real opportunity, and frame a compelling case around it Maintain disciplined Salesforce CRM habits — you treat your pipeline as a business asset, not a reporting burden Embody a self-starter mentality: you thrive with autonomy, take ownership of outcomes, and find creative ways to win Have experience in BNPL or point-of-sale retail/home improvement/healthcare/veterinary financing Possess an existing network in Canadian retail, home improvement, health, medical aesthetics, or specialty verticals Are comfortable using AI tools to accelerate prospecting, outreach, personalization, and meeting preparation It includes a comprehensive benefits plan and a competitive incentive (bonus) program for Full-Time Permanent roles.

At Questrade Financial

Group of Companies, with multiple office locations around the world, we are committed to fostering a diverse, inclusive and accessible work environment. You will be supported and motivated, so that you can harness your unlimited potential. Our team reflects the diversity of the communities we serve and operate in.

Having a collaborative and diverse team helps us push boundaries to bring the future of fintech into existence—not only for the benefit of our customers, but for those who build their career with us.

Questrade Financial

Group of companies Applicant Tracking System utilizes artificial intelligence (AI) for application screening.

📌 Senior Account Executive, Merchant Acquisition (Flexiti) (Winnipeg)
🏢 Questrade Financial Group
📍 Winnipeg