Job Title

About Chexy At Chexy, were reshaping the way money movesmaking 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, were on a much bigger mission: to build a super app that acts as your copilot for all your moneyhelping you get more value from every dollar you spend. As a highgrowth fintech startup, were at the forefront of payments innovation, and were looking for hungry, ambitious people to help us scale. If you thrive in a fastmoving, highenergy environment and want to be part of something big, wed 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 Role This role is about creating Chexys SMB sales motion from the ground up. You are Chexys first Account Executive. There is no inherited pipeline, no polished playbook, and no safety net. Together, we will figure out how Chexy wins in the SMB market who buys, why they buy, what stops them, and what finally gets deals signed. Your days will be spent in the work: outbound prospecting, cold calls, demos, and closing. Youll generate demand, build pipeline from scratch, and turn realworld selling into systems that scale. If you succeed, this role becomes careerdefining, and your work will directly shape Chexys revenue, product roadmap, and future sales team. What Youll Do Own fullcycle outbound sales, from cold prospecting to close Sell Chexy to SMBs across multiple verticals Run tight, highquality demos that clearly explain Chexys value Write and iterate outbound messaging (email, phone, LinkedIn) Build and manage your own pipeline Track learnings: objections, ICP patterns, deal velocity, win/loss reasons Work to shape: Outbound strategy Sales collateral Target industries and personas Early sales process and tooling Act as the feedback loop between customers and product This Role Is a Fit If You Thrive in cold outbound and dont need warm leads to be effective Like ambiguity and enjoy building before things are figured out. Can switch from highvolume cold outreach to thoughtful, consultative selling Want ownership and upside Are motivated by results This Role Is Not a Fit If You Prefer inboundonly or heavily scripted sales motions Need a fully built playbook to succeed Want a lowintensity or highly structured AE role Are uncomfortable being the first sales hire Requirements 3+ years of experience in B2B sales (SDR or AE) Strong hunter mentality with outboundfirst experience Excellent written and verbal communication skills Comfortable selling without a set playbook Strong intuition for customer pain points and valuebased selling Experience using CRM and sales tools (Salesforce, HubSpot, etc.) Nice to have Experience selling to SMBs Background in fintech, payments, or hospitality Previous founding sales team or early sales team experience #J-18808-Ljbffr