Senior Account Executive, Merchant Acquisition (Flexity)

Questrade Financial Group•Toronto, ON

2d•Hybrid

About The Position

Questrade Financial Group (QFG) is a diverse financial services organization that leverages cutting-edge technology and AI-driven innovation to help Canadians achieve financial success. They offer a hybrid work environment that fosters creativity and curiosity. This specific role is for an existing vacancy within Flexiti, Canada's leading point-of-sale financing provider. The Senior Account Executive, Merchant Acquisition will be responsible for driving new merchant acquisition by identifying, engaging, and closing deals with prospective retail partners. This is a high-visibility role with significant income potential, reporting 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: you listen well, diagnose the real opportunity, and frame a compelling case around it.
Disciplined Salesforce CRM habits.
Excellent communication and negotiation skills — written, verbal, and in the room.
Self-starter mentality: you 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.