Account Executive

About Chexy

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.

We're also backed by world-class investors including Khosla Ventures, Crossbeam Venture Partners, Venrex, Antler, and Air Canada.

About the role

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 new conversations, and building your own pipeline when needed.

We are not looking for a traditional inbound-only AE.

We want someone who can cold call, cold email, run a sharp discovery, demo the product, handle objections, follow up with urgency, and close.

We want someone who likes hunting, selling, and winning and who takes ownership of the number rather than waiting for opportunities to appear.

What You'll Be Doing

• 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.
• Run focused discovery calls and product demos.
• 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 clear next steps.
• Handle objections, negotiate, and move deals forward with urgency.
• Work closely with BDRs to improve targeting, qualification, handoffs, and conversion.
• 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.

What We're Looking For

• 2–4 years of B2B sales experience, ideally in an AE or full-cycle sales role.
• Strong outbound experience — you're comfortable generating your own opportunities, not just working inbound leads.
• Proven experience running a full sales cycle from discovery through close.
• Comfortable cold calling, cold emailing, and prospecting into new accounts.
• Strong discovery, objection handling, and closing skills.
• Comfortable selling to founders, owners, operators, or finance teams.
• Strong written and verbal communication skills.
• Competitive, resilient, and motivated by hitting and exceeding targets.
• Strong CRM discipline and comfort working with modern sales tools.

Nice To Have

• Experience selling to SMBs.
• Experience in fintech, payments, financial services, or B2B SaaS.
• Experience in a high-velocity or transactional sales environment.
• Experience at an early-stage or high-growth startup.
• A track record of consistently exceeding quota.

This Probably Isn't the Role for You If

• You prefer inbound-only sales.
• You don't enjoy prospecting.
• 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.
• You aren't motivated by clear targets and closed revenue.

Why Join Chexy?

📈 Own a real number: Your performance directly impacts the growth of Chexy's overall and B2B business.

☎️ Build and close: 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.

🛠️ Move quickly: 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.

How We Hire

We keep our hiring process clear and human. You'll go through a mix of conversational interviews and practical discussions designed to show how you prospect, sell, handle objections, and move deals forward.

We use AI tools to help us organize and review applications; every decision about who we interview and who we hire is made by a person. This posting is for an existing vacancy.

Chexy is an equal opportunity employer. If you require any accommodations or support during the hiring process, let us know and we'll do our best to help.

Know someone who would be a perfect fit? Let them know!