Upgrade helps customers move in the right direction with affordable and responsible financial products. Since 2017, we’ve helped over 7.5 million customers access over $42 billion in consumer credit. With a relentless focus on improving our customers' financial well-being, we build products that put more money in their pocket and support their journey toward a better financial future. We’re backed by some of the most prominent technology investors and were most recently valued at $7.3B.

*We’re consistently recognized for our collaborative and inclusive culture. Most recently, we were named one of the World’s Top Fintech Companies by CNBC, Best Places to Work by Built In, Best Places to Work by the San Francisco Business Times, America’s Greatest Workplaces by Newsweek, Best Startup Employer by Forbes, and Healthiest Employers by Phoenix Business Journal. *

We’re looking for new team members who get excited about designing and delivering new and better products. Come join us and help build a better financial future for millions of people.

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 Flex Pay’s differentiated BNPL offering to enterprise and mid-market merchants.

What You’ll Do:

• Build and manage FFa 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 e Commerce, CFOs, and Heads of Payments).

• Translate Flex Pay’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.

What We Look For:

• Currently based in Canada, or remote with strong ties to the Canadian market

• Proven experience selling into Canadian customers or accounts

• Strong understanding of the Canadian business landscape, buying behavior, and market.

• Established network or relationships within key industries or regions in Canada

• Ability to navigate regional differences (e.g., provinces, regulations, or cultural considerations)

• Experience working with Canadian enterprise or mid-market organizations is a plus

What We Offer You:

• 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

*We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. *

Upgrade does not accept unsolicited resumes from staffing agencies, search firms, or any third parties. Any resume submitted to any employee of Upgrade without a prior written agreement in place will be considered the property of Upgrade, and Upgrade will not be obligated to pay any referral or placement fee. Agencies must obtain advance written approval from Upgrade's Talent Acquisition department to submit resumes and only in conjunction with a valid, fully executed agreement. English is required for all positions, as it involves interacting with staff at Upgrade's offices worldwide.