[Hiring] Sales Development Representative @Upgrade

Role Description

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.

What You’ll Do:

• 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.

Qualifications

• 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.

Nice to Have:

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

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

Compensation

The compensation range of this position is a base salary of USD $95,000 - $115,000 annually, plus uncapped variable compensation (OTE ~$150,000), equity and benefits. Within this range, an individual's base pay will be dependent on a variety of factors, including without limitation, job-related knowledge, skills, education, and experience.