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About ChexyAt Chexy, we?re reshaping the way money moves?making payments smarter, faster, and more rewarding.We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we?re on a much bigger mission: to build a super app that acts as your co-pilot for all your money?helping you get more value from every dollar you spend.As a high-growth fintech startup, we?re at the forefront of payments innovation, and we?re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we?d love to work with you.If you want real ownership, autonomy, and the chance to shape how sales are done at Chexy from day one, this is that role.About the RoleThis is Chexy?s first Account Executive and the beginning of our outbound sales motion.You will be the person who defines how Chexy is sold to SMBs at scale ? which businesses convert best, what messaging breaks through, how objections are handled, and what actually gets deals closed. The work you do here will directly shape how Chexy signs thousands of businesses over the next year. This is a hands-on, outbound-heavy role. You?ll spend most of your time prospecting, cold calling, cold emailing, running demos, and closing. You?ll own the full sales cycle end-to-end and turn real customer conversations into a repeatable outbound engine.You?ll work closely with leadership to sharpen the pitch and turn what?s working into playbooks. If you?re successful, your fingerprints won?t just be on deals ? they?ll be on Chexy?s entire B2B engine.What You?ll DoOwn full-cycle outbound sales, from cold prospecting to closeSell Chexy to SMBs across multiple verticalsRun tight, high-quality demos that clearly explain Chexy?s valueWrite and iterate outbound messaging (email, phone, LinkedIn)Build and manage your own pipelineTrack learnings: objections, ICP patterns, deal velocity, win/loss reasonsWork to shape:Outbound strategySales collateralTarget industries and personasEarly sales process and toolingAct as the feedback loop between customers and productThis Role Is a Fit If YouThrive in outbound and don?t need warm leads to be effectiveLike ambiguity and enjoy building before things are ?figured out.?Can switch from high-volume cold outreach to thoughtful, consultative sellingWant ownership and upsideAre motivated by resultsThis Role Is Not a Fit If YouPrefer inbound-only or heavily scripted sales motionsNeed a fully built playbook to succeedWant a low-intensity roleAre uncomfortable being the first sales hireRequirements3+ years of experience in B2B sales (SDR or AE)Strong hunter mentality with outbound-first experienceExcellent written and verbal communication skillsComfortable selling without a set playbookStrong intuition for customer pain points and value-based sellingExperience using CRM and sales tools (Salesforce, HubSpot, etc.)Nice to haveExperience selling to SMBsBackground in fintech, payments, or hospitalityPrevious founding sales team or early sales team experienceWhy Join Chexy? Location Toronto , ON Work location On site Salary $ 29.00 to $ 88.00 HOUR hourly Terms of employment Permanent employment Full time Starts as soon as possible Source CareerBeacon #2611010 Various locations Toronto, ON
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