Sales Development Representative

Upgrade•Toronto, ON

40d•Remote

About The Position

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.

Requirements

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)

Nice To Haves

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

Responsibilities

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 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.