Enterprise Account Executive (Early-Stage Startup)You can be located in Toronto, Vancouver, Ottawa.We're partnering with a start-up looking for a builder—someone who thrives in early-stage environments and wants to help shape the sales engine from day one.This isn't a plug into a machine Account Executive role.You'll co-create the playbook, test what works, and driving revenue across Canada and the U.S.If you've sold in ambiguity, built pipeline from scratch, and enjoy building, this is the role for you.The RoleOwn the full sales cycle end-to-end—from first touch to close to expansion. You'll work closely with founders and cross-functional teams to win new business and turn early customers into long-term partners.What You'll DoBuild pipeline:Prospect, outbound, networkWork with the channel partner sales team to drive conversations and close deals togetherRun full-cycle deals:Discovery solution design, closing and also expansionSell value, not features:Tie solutions to real business outcomes and ROIShape the sales motion:Test messaging, refine ICP, and help define what good looks likeNavigate complex deals:Engage C-level stakeholders and manage 6+ month sales cyclesCollaborate internally:Work cross-functionally to deliver and expand accountsUse data to make decisions and run your sales pipeline:Use tools, CRM,



and insights to move rapid and improve constantlyWhat We're Looking For3–8 years in B2B sales (SaaS, IT consulting, or services)Early-stage/startup experience is a must —you've operated with limited structure and built your own pipelineProven track record of outbound success and hitting/exceeding quotaExperience selling to enterprise clients and C-level stakeholdersExperience selling into IT stakeholders is keyStrong command of sales frameworks (MEDDIC, Challenger, etc.)Comfortable with longer sales cycles and complex dealsHigh ownership mindset, you are a very autonomous person, and you are able to problem-solve and come up with new ideasBonus PointsExperience selling IT implementation or consulting servicesStrong use of AI tools (AI, prospecting, productivity)Active professional presence and personal brandWho You AreCurious, resourceful, and commercially sharpA true builder—you like creating systems more than maintaining systemsStructured in your thinking but flexible in executionRelentless about improving your craft, you have a growth mindsetIf you're excited by early-stage companies, high level of ownership, and the chance to build something meaningful, feel free to applyBase salaryCAD 90,000 to 120,000 + CommissionBenefitsBenefits package is extensive and will be shared during the recruitment process#J-18808-Ljbffr

📌 Enterprise Account Executive - C$90,000 - C$120,000 A Year (Winnipeg)
🏢 Optimyze1
📍 Winnipeg