Senior Account Executive, Merchant Acquisition (Flexity)

Community Trust Company; Canada; On-site; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Health & wellbeing resources

Paid vacation, personal, and sick days

Competitive compensation

Hybrid environment (3 days in office)

Career growth opportunities

Community involvement

Diverse, inclusive team

Job summary

Flexiti, Canada’s leading BNPL/point‑of‑sale financer, seeks a Senior Account Executive, Merchant Acquisition to lead new merchant growth. You will own the full sales cycle from prospecting to close, build executive relationships, and use AI tools to accelerate outreach and win deals.

You’ll operate in a hybrid Canada-wide environment, collaborating with product, operations, and legal teams to remove roadblocks and drive revenue.

Qualifications

• 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 role.
• Experience selling at the executive level to secure deals.
• Strong consultative selling, diagnostic approach, and compelling business cases.
• Disciplined Salesforce CRM usage and pipeline management.
• Excellent communication and negotiation skills; autonomous and self-starting.

Responsibilities

• Build and execute a disciplined outbound prospecting strategy across 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 alongside your self-generated pipeline.
• Build executive-level relationships with prospective merchant partners to create urgency.
• Own the full sales cycle from cold outreach to contract close with cross-functional coordination.
• Maintain a high-quality, high-velocity Salesforce pipeline and accurate forecasting.
• Consistently meet or exceed quarterly and annual targets for new merchant signings and revenue.

Skills

B2B sales

Fintech/Payments/SaaS

Hunter mentality

Salesforce CRM

Executive-level selling

AI-assisted prospecting

Tools

Salesforce CRM

Job description

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

Job Description

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.

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

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.

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.
• 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.

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.
• 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

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!

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.

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