Senior Account Executive, Merchant Acquisition (Flexity)

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.

What’s in it for you as an employee of 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

This job posting is for an existing vacancy.

We’re looking for our next Senior Account Executive, Merchant Acquisition. Could It Be You?

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.

Need more details? Keep reading…

In this role, responsibilities include but are not limited to:

New Business Development

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

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

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

So are YOU our next Senior Account Executive, Merchant Acquisition? You are if you…

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

Possess excellent communication and negotiation skills — written, verbal, and in the room

Embody a self-starter mentality: you thrive with autonomy, take ownership of outcomes, and find creative ways to win

Additional kudos if you…

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

Compensation Information:

Base salary: $120,000 + Commission

The final compensation package will be commensurate with the successful candidate's experience, skills, and geographic location (Canada). It includes a comprehensive benefits plan and a competitive incentive (bonus) program for Full-Time Permanent roles.

Sounds like you? Click below to apply!

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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. This is an environment where individuals are treated with dignity and respect. Here, the unique skills and experience you bring will be valued. 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. The AI system operates on predetermined criteria, with final decisions subject to human review.

Candidates selected for an interview will be contacted directly. If you require accommodation during the recruitment/selection process, please let us know and we will work with you to meet your needs.