Senior Account Executive, Merchant Acquisition

Flexiti is part of the Questrade Financial Group, and shares in Questrade’s mission to help Canadians become much more financially successful and secure.

For nearly 30 years, Questrade Financial Group has been delivering on that mission through investing, banking, mortgages, and real estate. Together, we tilt finance in favour of ambitious Canadians, creating new ways for them to seize the financial future they deserve.

Flexiti is a Canadian fintech, and the financing behind some of the biggest purchases Canadians make. Every one of those sales has two customers: a Canadian ready to buy, and the retail partner earning their trust. We help one buy what matters and the other close the sale. Today, that’s more than a million active customers and thousands of partners across 8,000+ locations.

We’re looking for people who are ready to enter their career inflection point. Mission-driven, exceptional folks that never settle. The work here is hard because the responsibility is real. If that’s the standard you’ve been looking for, keep reading.

Req # 4180

The return on your career investment

• Compensation and incentives built to reward the value you bring.
• RRSP matching of up to 6%.
• Health and wellness resources and programs, including $5,000 in mental health practitioner coverage.
• $5,000 in tuition subsidies for job-related courses, every year.
• 100% parental top-up, up to 26 weeks for birthing parents and 18 weeks for non-birthing parents.
• A hybrid environment, with at least three days in the office built for working together.
• Paid vacation, personal, and sick days.
• A community care day to give back to the causes you care about.

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. 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.

The mandate

In this role, you will:

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

You’re ready for this mandate if you have the following qualifications

• 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

Nice to have

• 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.

Enter your career inflection point. Apply now. 

#LI-NK1, #LI-Hybrid

Technology and AI

We mix human ingenuity with advanced technology. For ambitious builders like you, we provide the latest technology to enable your creativity. You'll have everything you need to build the best outcomes and products for our clients.

Diversity and Inclusion

At Questrade Financial Group of Companies, we’re committed to fostering a diverse, inclusive, and accessible work environment where individuals are treated with dignity and respect. Our global team reflects the diversity of the communities we serve and operate in.

Accessibility statement

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

AI in hiring

Questrade Financial Group of companies Applicant Tracking System uses artificial intelligence (AI) for application screening. The AI system operates on predetermined criteria, with final decisions subject to human review.