Senior Account Executive, Merchant Acquisition

Questrade Financial Group•Toronto, ON

2d•Hybrid

About The Position

Questrade Financial Group (QFG) is a diversified financial services provider that uses cutting-edge technology to help Canadians become more financially successful and secure. QFG combines 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. This role is within Flexiti, Canada's leading point-of-sale financing provider, empowering retailers across the country to grow their businesses through flexible payment solutions. The Senior Account Executive, Merchant Acquisition will be responsible for new merchant acquisition, taking the lead on finding, engaging, and closing deals. This is a high-visibility role with significant income potential, reporting directly to the Managing Director of Sales & Account Management.

Requirements

5+ years of B2B sales experience, ideally in fintech, payments, SaaS, or retail tech.
Proven track record of exceeding quota in a hunter-oriented, self-directed sales role.
Experience selling at the executive level.
Strong consultative selling skills.
Disciplined Salesforce CRM habits.
Excellent communication and negotiation skills — written, verbal, and in the room.
Self-starter mentality: thrive with autonomy, take ownership of outcomes, and find creative ways to win.

Nice To Haves

Experience in BNPL or point-of-sale retail/home improvement/healthcare/veterinary financing.
Existing network in Canadian retail, home improvement, health, medical aesthetics, or specialty verticals.
Comfortable using AI tools to accelerate prospecting, outreach, personalization, and meeting preparation.

Responsibilities

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.