Director, Office of the CEOReports to: Chief Executive OfficerPosition SummaryThe Director, Office of the CEO serves as a strategic advisor and execution partner to the CEO.This role exists to enhance executive effectiveness, strengthen alignment across the leadership team, and ensure that strategic priorities translate into measurable results.Working in close partnership with the CEO and alongside the COO and CAO, this position operates at the center of executive coordination without assuming operational ownership of functional areas.Core Purpose of the RoleIncrease the CEO’s strategic capacityImprove cross-functional alignmentsStrengthen execution disciplineSurface risk and opportunity earlyDrive clarity and accountability at the executive levelKey ResponsibilitiesStrategic Planning & CEO AdvisoryPartner with the CEO in annual and quarterly planning processesSupport development and tracking of corporate objectives and prioritiesTranslate strategic discussions into structured action plansConduct analysis to inform executive decision makingPrepare board materials and executive level presentationsExecutive Alignment & Governance SupportAttend executive leadership and cross-functional meetingsCapture decisions, risks, and accountability ownersMonitor progress on strategic initiativesIdentify execution gaps or misalignment across departmentsEnsure leadership cadence and review rhythms are maintainedBusiness Performance & InsightDevelop executive dashboards and summary reportingAnalyze financial and operational data to support CEO decisionsEvaluate business cases for major initiativesProvide structured insight into growth risks and performance trendsCross-Functional Strategic InitiativesLead or coordinate CEO-sponsored initiativesFacilitate collaboration across departments on priority projectsRemove barriers impacting execution of strategic goalsSupport high-impact corporate initiatives as requiredCEO Office ManagementManage CEO calendar aligned to strategic prioritiesFilter and synthesize incoming informationPrepare briefing materials in advance of key engagementsDraft executive communications as requiredRepresent the CEO in designated internal forumsDecision AuthorityThe Director, Office of the CEO may:Facilitate prioritization discussions across leadershipDrive execution of CEO-sponsored initiativesRepresent the CEO in internal meetings when delegatedMake recommendations regarding strategic trade-offsFinal authority remains with the CEO and respective functional executives.Qualifications7–12 years of experience in strategy, consulting, operations, or executive advisory rolesExperience supporting senior leadership in growth environmentsStrong financial and business acumenAdvanced analytical and problem-solving capabilityExceptional written and verbal communication skillsExecutive maturity, discretion, and sound judgmentAbility to influence without formal authorityPreferred:MBA or equivalent strategic trainingExperience preparing board-level materialsCompetenciesStructured thinkerPolitically astuteHighly accountableComfortable with ambiguityBias toward actionAble to challenge respectfullyResilient under pressureExcellent communication skills both written and verbalWhat's in it for you? (Salary, Commissions & Benefits)On-site position located in Brampton, ON, Canada — join a collaborative team in our local officeCompetitive base salary as the core of your compensation packageFull Health and Dental BenefitsPillway is an inclusive employer and provides accommodations for applicants with disabilities throughout the recruitment process. Please let us know if you require accommodation.