Business Development Representative in Toronto

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

• What You'll Be Doing
• Generate new business opportunities through cold calling, email, Linked In, and other outbound channels.
• Research and identify high-potential businesses and decision makers.
• Qualify prospects and understand whether Chexy is a strong fit for their business.
• Test and improve outbound messaging, sequences, targeting, and tactics.
• Work closely with Account Executives to create strong handoffs and move qualified opportunities forward.
• Track what you're learning from prospects, including objections, customer needs, industries, and messaging that resonates.
• Help improve the tools, processes, and playbooks that make our outbound motion more effective.
• Bring new ideas for how we can find and engage more businesses.

What We're Looking For

• 1–3 years of experience in a BDR, SDR, sales, or other customer-facing role.
• Comfortable cold calling and reaching out to people who aren't expecting to hear from you.
• Strong written and verbal communication skills.
• Curious about businesses and good at understanding what actually matters to the person you're speaking with.
• Competitive, resilient, and motivated by targets.
• Comfortable testing new approaches and learning quickly.
• Organized and able to manage a high volume of prospects and follow-ups.
• Excited to learn quickly and become exceptional at sales.
• Nice To Have
• Experience selling to SMBs or finance teams.
• Experience in fintech, payments, financial services, or B2B Saa S.
• Experience at an early stage or high growth startup.
• Experience using Hubspot CRM, sequencing, and outbound sales tools.
• This Probably Isn't the Role for You If
• You want to work mostly inbound leads.
• You don't enjoy cold calling.
• You need a fully built script to be effective.
• You get discouraged easily by rejection.
• You want a slow moving or highly structured sales environment.
• You're uncomfortable being measured against clear activity and pipeline goals.

Why Join Chexy?

Learn real outbound

Build the skill of finding, engaging, and qualifying customers from scratch.

See your impact

The pipeline you create directly contributes to the growth of Chexy's B2B business.

Build with us

Help shape how outbound works as the sales team scales.

Move quickly

Test messaging, industries, tools, and approaches without layers of bureaucracy.

Work closely with the team

Partner directly with Account Executives, Growth, and leadership.

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 think, communicate, and approach outbound sales.

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!

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