Upgrade, Inc.

Sales Development Representative

Upgrade, Inc.

full-time

Posted on:

Location Type: Remote

Location: Canada

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Job Level

Junior

About the role

  • 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.

Requirements

  • 1–3 years of B2B SDR/BDR experience in technology, fintech, or e-commerce SaaS.
  • Experience with payments, BNPL, or financial technology is a strong plus.
  • Proven track record of exceeding activity and meeting targets while generating qualified pipeline.
  • Fluent with modern sales tools (Salesforce, Slack, Builtwith Outreach/Salesloft, LinkedIn Sales Navigator, Zoominfo).
  • Strong written and verbal communicator — clear, confident, and persuasive.
  • Comfortable with cold calling, creative outbound, and tailoring messages to diverse audiences.
  • Self-motivated, goal-oriented, and comfortable with ambiguity in a high-growth environment. Curious, coachable, and energized by learning about fintech, retail, and emerging technologies.
Benefits
  • Competitive salary and stock option plan
  • 100% paid coverage of medical, dental and vision insurance
  • Flexible PTO
  • Opportunities for professional growth and development
  • Paid parental leave
  • Health & wellness initiatives
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
B2B salesSDRBDRpipeline managementoutbound prospectingqualifying leadsmessaging experimentationtarget account strategyCRM managementactivity tracking
Soft Skills
communicationpersuasivenessself-motivationgoal orientationadaptabilitycuriositycoachabilityrelationship buildingcollaborationproblem-solving