At Chexy, we're building modern financial tools for Canadians and Canadian businesses, starting with the biggest payments they make. For consumers, that means helping people pay major expenses like rent, tuition, insurance, taxes, and mortgages in smarter, more rewarding ways. For businesses, Chexy helps companies pay suppliers, taxes, payroll, rent, and other major expenses using flexible payment methods while improving cash flow, rewards, and how money moves through the business.

With ~$2B in annual payment volume and a rapidly growing customer base, we're building financial infrastructure that makes large, recurring payments simpler, more flexible, and more valuable. Chexy is looking for an ambitious Account Executive to help scale our B2B business. This is a full cycle sales role for someone who is comfortable both creating pipeline and closing it .

You'll work qualified opportunities from discovery through close, while also prospecting into high-potential businesses, opening recent conversations, and building your own pipeline when needed. Own the full sales cycle from prospecting and first conversation through close. Build your own pipeline through cold calling, email, LinkedIn, referrals, and other outbound channels.

Understand how prospects pay suppliers, taxes, payroll, rent, and other major expenses and identify where Chexy creates value. Manage a high volume of active opportunities with strong follow-up and explicit next steps. Test new industries, personas, messaging, and outbound approaches.

Track patterns across objections,



deal velocity, win/loss reasons, and customer needs. Bring market feedback back to Growth and Product to help improve how we sell and what we build. 2–4 years of B2B sales experience, ideally in an AE or full-cycle sales role. ~ Proven experience running a full sales cycle from discovery through close. ~ Comfortable cold calling, cold emailing, and prospecting into new accounts. ~ Strong CRM discipline and comfort working with modern sales tools.

Experience in a high-velocity or transactional sales environment.

Experience at an early-stage or high-growth startup. You prefer inbound-only sales. You expect BDRs to fully own your pipeline. You need a highly scripted sales process to succeed. You aren't comfortable managing a high volume of opportunities. You want a low-intensity sales role. Your performance directly impacts the growth of Chexy's overall and B2B business. You'll own opportunities end to end and have the freedom to create pipeline yourself.

Help scale the sales engine: Join while the motion is still evolving and help make it stronger. Test messaging, industries, tools, and sales approaches without layers of bureaucracy.

Early equity: Access equity in a high-growth fintech.

Toronto office: We work in-office 5 days a week. We use AI tools to help us organize and review applications; This posting is for an existing vacancy. If you require any accommodations or support during the hiring process, let us know and we'll do our best to help.

📌 Remote: Account Executive (Sales) (Toronto)
🏢 Chexy
📍 Toronto