Senior Account Executive, Merchant Acquisition; Flexity

North American Centre, 5700 Yonge St #210B, North York, ON M2M 4G3, Canada

Posted Tuesday, July 21, 2026 at 4:00 AM

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.

At QFG, we combine human‑centric collaboration with AI‑driven innovation to redefine financial services. 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.

Join our diverse, inclusive, and hybrid workplace to unleash your creativity and nurture your curiosity without limits. If you share this sense of infinite possibility, come shape your future at QFG.

• Health & wellbeing resources and programs
• Paid vacation, personal, and sick days for work‑life balance
• Competitive compensation and benefits packages
• Work‑life balance in a hybrid environment with at least 3 days in office
• Career growth and development opportunities
• Opportunities to contribute to community causes
• Work with diverse team members in an inclusive and collaborative environment

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. We’re looking for someone who brings both the instincts of a seasoned hunter and the curiosity to use modern tools to find, engage, and close faster.

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.

• Build and execute a disciplined outbound prospecting strategy across both established verticals and new categories.
• 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.
• 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.
• Stay sharp on Flexiti’s product capabilities and roadmap so you can sell with confidence and credibility.
• 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.

• 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…