OTT Pay is part of the OTT Financial Group, which is a fully funded, established fintech leader delivering streamlined financial payment solutions. We are a results-driven organization aggressively scaling our mobile-first platform, which spans acquiring, card issuing, cross-border payments, loyalty solutions, and our rapidly evolving SuperApp ecosystem.We are seeking an experienced Key Account Manager to drive enterprise-level growth within Canada’s restaurant, retail, and multi-location service sectors. This is not a high-volume transactional sales role. You will focus on winning and expanding large enterprise accounts, each representing significant annual transaction volume and long-term strategic value.The ideal candidate thrives in complex sales environments, manages multi-stakeholder buying processes, and builds trusted advisor relationships with senior executives.BenefitsBase Salary $90K + CommissionsExtended Health, Dental, and Vision BenefitsLife and Disability InsurancePerformance BonusVacation LeaveLearning and Professional Development SupportA chance to work in a agile, collaborative, progressive and high performing teamCommunity involvement through the annual Terry Fox RunTremendous opportunities for Growth and DevelopmentKey ResponsibilitiesEnterprise Account AcquisitionIdentify, target, and win multi-location and enterprise-level clientsConduct strategic account research and develop executive outreach plansManage long, complex sales cycles (3–12+ months)Achieve 12-20 new enterprise wins annuallyComplex Sales ManagementNavigating multi-stakeholder environments (Finance, IT, Operations, Procurement)Lead RFP responses, proposal development,



and contract negotiationsCoordinate internal technical, legal, and product teams to advance dealsSolution & Value PositioningDesign tailored payment solutions aligned with client business modelsBuild and present ROI-driven business cases to senior leadershipAddress technical integration requirements in partnership with engineeringAccount Growth & RetentionServe as a long-term strategic advisor post-saleConduct regular business reviews and identify expansion opportunitiesDrive upsell, cross-sell, and footprint growth while maintaining solid retentionStrategic ContributionGather competitive and market insights from enterprise clientsProvide structured feedback to leadership and product teamsSupport development of vertical and enterprise growth strategiesSkills & CompetenciesStrong executive-level communication and presentation skillsHigh commercial acumen and financial literacy (ROI, TCO, EBITDA understanding)Strategic thinker with consultative selling approachStrong stakeholder mapping and influence managementExcellent organizational and pipeline management skillsStrong negotiation and commercial acumenExcellent relationship-building and communication skillsAbility to engage executive and technical stakeholdersSelf-starter with an entrepreneurial mindsetPreferred QualificationsExisting network within Canadian POS or ISV ecosystemsExperience building a partner program from early stageBackground in restaurant, retail, or SaaS verticalsOTT Financial Group is committed to fostering an inclusive and accessible environment where all employees feel valued and respected. We are committed to providing reasonable accommodation, if required, and will work with you to meet your need.#J-18808-Ljbffr

📌 Key Account Manager - $90,000 A Year (Winnipeg)
🏢 OTT Pay
📍 Winnipeg