🤝Originations Associate - Paperstack (Hybrid, Toronto)
Posted on Aug 5, 2026
Join a fast-growing fintech company that's scaled significantly in the past year. You'll build relationships with e-commerce brands and help guide them toward the working capital they need to grow.
Hybrid role in Toronto with travel.
This role is ideal for someone with sales experience who is ambitious, ownership-minded, and excited to grow into a full-cycle relationship role in a fast-moving fintech environment.
At Paperstack, we provide working capital financing to e-commerce brands, purpose-built for how modern commerce scales. We're backed by Google for Startups and Techstars, and our team has doubled in the past 12 months. We move fast, and we're looking for someone who wants to move fast with us.
Why Paperstack
We're a US-based fintech backed by top-tier investors and programs including Google for Startups and Techstars. Over the past 12 months, we've more than doubled our team and we're continuing to grow.
You'll be working with e-commerce brands, building real relationships, and helping business owners access the capital they need to scale.
This isn't a support role at a slow-moving company. You'll have real ownership from day one, and your speed is determined by your results, not by how long you've been here.
Our team comes together once a year for an offsite. Past trips have taken us to Morocco and Europe.
The Role
As an Originations Associate, you'll identify and reach out to e-commerce brands, build relationships with prospects, understand their businesses, work with underwriting to structure offers, and close deals as clients grow with us.
Hybrid role in Toronto — This role involves in-person relationship building in Toronto and the ability to travel.
Application deadline: Applications will be reviewed on a rolling basis.
To apply: Email your resume to hiring@paperstack.ai.
Email subject line: Please use Originations Associate Application.
How This Role Works
This is a single sales career path, not two separate jobs. You'll run the full relationship from day one, building rapport with e-commerce brands, understanding their business, and guiding them toward a deal.
In the beginning, you'll do this alongside a senior closer for your first several deals. Once you've shown you can run it independently, you take over the full cycle on your own.
There's no fixed timeline. Some people will make that jump in a few months. Others will take longer. Your speed is determined by your results, not by how long you've been here.
What You'll Be Doing
Identify and reach out to e-commerce brands that need working capital
Build relationships with prospects, including meeting them in person
Understand each business's needs and guide them toward the right fit
Work with underwriting to structure and present offers
Close deals and manage the relationship as they grow with us
Who This Is For
You have experience in sales
You're motivated by ownership, not by tenure
You are a problem solver
"No" doesn't stop you. It just means "not yet"
You are ambitious
You believe you create your own luck
What You'll Get
Direct coaching and fast, real feedback
A clear, KPI-based path to full independence, not a fixed tenure ladder
Real ownership as we scale
Annual team offsites — Morocco and Europe so far
Qualifications
Sales experience preferred
Excellent written and verbal communication
Self-directed, able to manage your own pipeline and time
Ability to travel and work in a hybrid environment in Toronto
Compensation
Base plus uncapped commission
Ready to apply? Send your resume to hiring@paperstack.ai.
Please use the subject line Originations Associate Application.