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Chexy is building modern financial tools for Canadians and Canadian businesses, focusing on major payments like rent, tuition, insurance, taxes, and mortgages for consumers, and supplier payments, payroll, and taxes for businesses. The company processes ~$2B in annual payment volume and is backed by investors including Khosla Ventures, Crossbeam Venture Partners, Venrex, Antler, and Air Canada.
As a Business Development Representative, you will generate new business opportunities through outbound channels including cold calling, email, LinkedIn, and other prospecting methods. You'll research and identify high-potential businesses and decision makers, qualify prospects to determine fit, and test and refine outbound messaging, sequences, and targeting tactics. You'll work closely with Account Executives to create smooth handoffs and move qualified opportunities through the pipeline. A key part of the role involves tracking prospect feedback—objections, needs, industries, and messaging that resonates—and using those insights to improve tools, processes, and playbooks. You'll also contribute ideas for finding and engaging more businesses.
The role offers exposure to real outbound sales fundamentals, direct visibility into pipeline impact, and the opportunity to shape how outbound scales as the sales team grows. You'll work in a fast-moving environment without bureaucratic layers, partner closely with Account Executives and leadership, and gain early equity in a high-growth fintech. The position is based in the Toronto office with a 5-day-per-week in-office expectation.
REQUIREMENTS:
- 1–3 years of experience in a BDR, SDR, sales, or other customer-facing role
- Comfortable with cold calling and outbound prospecting to unexpected contacts
- Strong written and verbal communication skills
- Curiosity about businesses and ability to understand what matters to prospects
- Competitive, resilient mindset with motivation toward targets
- Comfort testing new approaches and learning quickly
- Organizational skills to manage high volume of prospects and follow-ups
- Eagerness to learn and become exceptional at sales
NICE TO HAVE:
- Experience selling to SMBs or finance teams
- Background in fintech, payments, financial services, or B2B SaaS
- Experience at early-stage or high-growth startups
- Familiarity with HubSpot CRM, sequencing tools, and outbound sales platforms
