Sales Development Representative Jobs in Canada (Remote)
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Top Benefits
About the role
- We are seeking a driven, experienced Sales Development Representative (SDR) to join our Flex Pay team and help expand our footprint in the retail and non-travel sectors
- As one of our first SDR hires, you will play a pivotal role in driving revenue growth by creating qualified opportunities, building trusted relationships, and fueling pipeline through a consultative, value-driven outreach approach
- This role is ideal for a self-starter who thrives in a fast-paced, entrepreneurial environment and is energized by the challenge of bringing innovative fintech solutions to market
- Working closely with our sales team and leadership, you’ll help shape our prospecting motion and introduce FlexPay’s differentiated BNPL offering to enterprise and mid-market merchants
- Build and manage a high-velocity prospecting engine across outbound channels (email, phone, LinkedIn, social) to generate qualified meetings
- Identify, research, and prioritize high-potential accounts and buyer personas across e-commerce, payments, and retail decision-makers (e.g., VPs of eCommerce, CFOs, and Heads of Payments)
- Translate FlexPay’s BNPL value proposition into clear, compelling outreach that resonates with both technical and business stakeholders
- Qualify inbound interest to surface pain points, assess fit, and convert into high-quality pipeline
- Experiment with messaging, sequencing, and targeting to refine our early go-to-market motion
- Collaborate closely with Sales, Marketing, and Partnerships to align on ICP, narratives, and campaign execution
- Multi-thread into target accounts and nurture relationships with executives and key decision-makers
- Maintain CRM excellence — track activity, manage pipeline hygiene, and deliver accurate activity and meeting forecasts
Benefits
- Stock option plan
- 100% paid coverage of medical, dental and vision insurance
- Flexible PTO
- Opportunities for professional growth and development
- Health & wellness initiatives
- Paid parental leave- Proven experience selling into Canadian customers or accounts
- Ability to navigate regional differences (e.g., provinces, regulations, or cultural considerations)
- Strong understanding of the Canadian business landscape, buying behaviour, and market
- Experience working with Canadian enterprise or mid-market organizations is a plus
- Established network or relationships within key industries or regions in Canada
- Currently based in Canada, or remote with strong ties to the Canadian market
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About Upgrade, Inc.
Upgrade is a fintech unicorn founded in 2017. Since then we’ve helped customers access over $35 billion in consumer credit, with millions of families across America using a credit line, personal loan, or Rewards Checking or Premier Savings account through Upgrade.
We are looking for new team members who get excited about designing and delivering new and better products. Come join us if you like to tackle big problems and make a meaningful difference in people's lives! Our innovative Upgrade Card has been the fastest growing credit card in America (Nilson Report) for two years in a row. We’ve been named a “Best Place to Work in the Bay Area” for the last three years, as well as one of the “Top Companies to work for in Arizona” in 2021 and 2022. We’ve also been recognized as a best company for Diversity, Women, Veterans, Culture, Compensation, Engineering, and Overall Outlook by team members on Comparably.