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Chexy is building modern financial tools for Canadians and Canadian businesses, starting with major payments. The company helps consumers pay rent, tuition, insurance, taxes, and mortgages in smarter ways, and helps businesses pay suppliers, taxes, payroll, and rent using flexible payment methods. With ~$2B in annual payment volume and backing from Khosla Ventures, Crossbeam Venture Partners, Venrex, Antler, and Air Canada, Chexy is scaling its B2B sales operation.
As an Account Executive, you will own the full sales cycle from prospecting through close. This is a full-cycle role requiring both pipeline generation and closing capability. You will cold call, cold email, and prospect into high-potential businesses to open new conversations and build your own pipeline. You'll run focused discovery calls, understand how prospects pay major expenses, and identify where Chexy creates value. You will manage a high volume of active opportunities with strong follow-up, handle objections, negotiate deals, and move them forward with urgency.
You'll work closely with BDRs to improve targeting, qualification, and conversion. You'll test new industries, personas, messaging, and outbound approaches, tracking patterns across objections, deal velocity, win/loss reasons, and customer needs. Market feedback will be brought back to Growth and Product teams to improve sales processes and product development.
The role is based in Toronto with 5 days per week in-office work. You'll have the freedom to create your own pipeline, test approaches without bureaucracy, and access equity in a high-growth fintech.
REQUIREMENTS:
- 2–4 years of B2B sales experience, ideally in an AE or full-cycle sales role
- Strong outbound experience; 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 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
- Track record of consistently exceeding quota
