Sales Development Representative, Upgrade
+ Stock Options
Offering responsible credit to mainstream consumers
Open for applications
Offering responsible credit to mainstream consumers
1001+ employees
Open for applications
+ Stock Options
1001+ employees
Company mission
To help our customers move in the right direction with responsible financial products that put more money in their pocket.
Role
Who you are
- 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 behaviour, 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 the job involves
- 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
- 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
Our take
Most credit cards don't encourage the owner to pay down their debt. The longer it takes to pay off the balance, the more money lenders are set to make. Upgrade is an online lender and card issuer doing things differently. The company offers personal loans and credit cards, but with a fixed instalment structure and a set number of equal payments. This ensures the balance reduces every month.
The company believes this model reduces default rates, as borrowers are forced to pay down rather than maintain their debt, and it encourages a greater commitment to repay the balance. Further, by combining the ease of a Visa card with the fixed payments and decreased rates of a personal loan, Upgrade sets itself apart from competitors.
In 2021, Upgrade launched its mobile banking and debit card to onboard new customers and increase loyalty. The fixed-rate nature of the company's cards is expected to be of use to customers in future years in an environment of rising rates. Off the back of impressive growth milestones in 2025, the company raised $165 million in Series G funding, raising its valuation to $7.3 billion, a comfortable position for a future IPO.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
18% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Oct 2025
$165m
SERIES G
Nov 2021
$280m
SERIES F
Total funding: $712m
Company benefits
- 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
Company HQ
Financial District, San Francisco, CA
Leadership
Renaud Laplanche
(Co-Founder & CEO)After an MBA at London Business School, Renaud spent 5 years as an Associate at Clearly Gottlieb Steen & Hamilton and co-founded MatchPoint. They then left Oracle after a year to co-found Lending Club in 2006 and co-founded Upgrade in August 2016.
Adelina Grozdanova
(Co-Founder & Head of Investor Group)Adelina started their career with 6 years at Morgan Stanley after a degree at Princeton. They left banking in 2012 to join Lending Club as VP, and after 3 years co-founded Upgrade, serving as Head of Investor Group since 2016.
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