Sales Development Representative, Flex Pay

Upgrade is a company that helps customers access affordable and responsible financial products. They are seeking a driven Sales Development Representative to join their Flex Pay team and expand their footprint in the retail and non-travel sectors by generating qualified opportunities and building trusted relationships.

Responsibilities:

• 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
• 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
• Experience with payments, BNPL, or financial technology is a strong plus