Senior Account Executive, Merchant Acquisition

Questrade Financial Group

$120K *
Finance & Insurance
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of B2B sales experience, preferably in fintech, payments, SaaS, or retail tech.
  • Proven track record of exceeding sales quota in a self-directed, hunter role.
  • Experience selling directly to executives and building lasting relationships.
  • Strong consultative selling skills to diagnose opportunities and create compelling cases.
  • Disciplined use of Salesforce CRM for pipeline management and reporting.
  • Excellent communication and negotiation skills in various settings.
  • Self-starter mentality who thrives with autonomy and creative problem-solving.

Responsibilities

  • Develop and implement an outbound prospecting strategy to target both established and new verticals.
  • Utilize AI-powered tools for researching targets and enhancing outreach effectiveness.
  • Manage and convert inbound leads while growing a self-generated pipeline.
  • Cultivate executive-level relationships with potential merchant partners through a consultative approach.
  • Oversee the entire sales cycle from initial contact to contract finalization, collaborating with internal teams as needed.
  • Create customized business cases that highlight Flexiti's value to each prospect.
  • Ensure a robust and accurate pipeline in Salesforce CRM, tracking all activities and forecasts.

Benefits

  • Work with a leading point-of-sale financing provider in Canada.
  • High visibility and direct reporting line to the Managing Director of Sales & Account Management.
  • Opportunity for significant income upside through performance-based compensation.
  • Access to advanced AI tools for prospecting and sales efficiency.
Full Job Description
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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