Senior Product Manager, Small Business
Chexy
Product
Toronto, ON, Canada · Delhi, India
Posted on Dec 19, 2025
About Chexy
At Chexy, we’re reshaping the way money moves - making payments smarter, faster, and more rewarding.
We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money - helping you get more value from every dollar you spend.
As a high-growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.
About the role
This role sits at the heart of Chexy’s vision to become the default way Canadians and small businesses spend and manage money. You’ll build products that automate payments, improve cash flow, and unlock rewards on business spend that would otherwise go unrewarded.
What you'll do
- Own the roadmap for Chexy’s small business accounts payable and spend products
- Build intuitive workflows for paying vendors, managing bills, scheduling payments, and moving money
- Enable businesses to pay how they want while earning meaningful rewards on core business spend
- Design features that give businesses flexibility over when and how money leaves their account
- Provide clear, real-time visibility into upcoming payments, liabilities, and available spend
- Help small business owners make better cash flow decisions without requiring financial expertise
- Expand Chexy’s coverage across key small business spend categories and verticals
- Identify opportunities to capture a greater share of a business’s total spend within Chexy
- Partner cross-functionally with Engineering, Design, Partnerships, Marketing, and Operations to ship scalable, reliable payment products
- Define success metrics tied to spend capture, adoption, retention, and product performance
- Use data to prioritize work, evaluate impact, and iterate
What we’re looking for
- Experience building products for small businesses, or a strong interest in SMB financial workflows
- Familiarity with accounts payable, invoicing, payments, or cash flow management (direct or adjacent experience)
- Strong product judgment, with the ability to balance user needs, business impact, and technical constraints
- ‘Builder’ type experience at a prior startup, or 0-1 product experience
- Comfort operating in ambiguity and owning problems end-to-end
- Excellent analytical skills, with the ability to pull data yourself using SQL, interpret it, and make data-driven decisions
- Scrappy (execution and outcome-focused), curious, and teachable
What success looks like
- Chexy captures 100% of spend in key small business verticals
- Small businesses choose Chexy as their default platform to spend money and accept payments
- Chexy becomes embedded in day-to-day operations for paying vendors and managing cash flow
Why this role is special
- Small businesses drive a large part of Chexy’s impact and growth, and this role directly shapes how they use Chexy every day
- The impact is massive: small business owners spend countless hours managing payments and cash flow. Your work directly gives that time back.
- You’ll have real ownership over a critical pillar of Chexy’s long-term vision to power how businesses spend