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 quotas in a self-directed, hunter-oriented role
  • Experience selling to executives and building lasting business relationships
  • Strong consultative selling skills with the ability to diagnose needs and present compelling cases
  • Disciplined use of Salesforce CRM as a business asset
  • Excellent communication and negotiation skills across various formats
  • Self-starter mentality, thriving in autonomous environments

Responsibilities

  • Build and execute an outbound prospecting strategy targeting existing and new categories
  • Leverage AI tools for research, engagement, and pipeline acceleration
  • Manage and convert inbound leads alongside self-generated opportunities
  • Develop executive relationships with prospective partners using a consultative approach
  • Own the complete sales cycle from outreach to contract close
  • Create tailored business cases that demonstrate Flexiti's revenue impact for prospects
  • Maintain a high-quality pipeline in Salesforce, accurately tracking progress and forecasts

Benefits

  • Comprehensive benefits plan
  • Competitive bonus program for performance
  • Hybrid work model offering flexibility
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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