Senior Account Executive, Merchant Acquisition

Flexiti; Toronto; Hybrid; CAD 108,000 - 132,000; Full time

Benefits offered by this job

Health & wellbeing resources

Paid vacation & sick days

Competitive compensation

Hybrid work environment

Career growth opportunities

Community involvement

Diverse collaborative culture

Job summary

Questrade Financial Group is seeking a Senior Account Executive, Merchant Acquisition, in a hybrid Canada-wide capacity. You will own the full sales cycle—from prospecting to contract close—driving new merchant partnerships and revenue growth for Flexiti within existing verticals and new categories.

You'll leverage AI-assisted research, build executive-level business cases, and collaborate with product, operations, and legal teams to accelerate deals. Strong Salesforce discipline is essential.

Qualifications

• 5+ years of B2B sales experience, ideally in fintech, payments, SaaS, or retail tech.
• Proven track record of exceeding quota in hunter-oriented roles.
• Experience selling at the executive level and building deals that stick.
• Strong consultative selling skills and pipeline management.

Responsibilities

• Build and execute a disciplined outbound prospecting strategy across established verticals and new categories.
• Own the full sales cycle from outreach to close, coordinating with product/ops/legal to remove blockers.
• Develop tailored, insight-led business cases to demonstrate incremental revenue impact.
• Maintain a high-velocity Salesforce CRM pipeline with accurate forecasting.

Skills

B2B sales

Fintech experience

SaaS sales

Hunter mentality

Executive-level outreach

CRM discipline

Tools

Salesforce CRM

Job description

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 Flexiti?

• 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.

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.

At Questrade Financial Group of companies 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.