Contract | 1-Year Term At MSH, passion meets profession. We're a team of dedicated enthusiasts who find genuine fulfilment in what we do, and we're looking for someone who feels the same way. The Role The Director, PMO sits between the PMO Lead and the EVP, PMO, serving as the hands-on delivery leader and governance anchor for complex, enterprise-wide programs. This is not a purely administrative role. You'll be expected to understand system architecture, data flows, and delivery trade-offs well enough to challenge vendors, guide technical teams, and translate decisions into clear executive recommendations. You'll also personally lead the Finance System Replacement initiative, one of the organisation's highest-priority transformation programs. What You'll Be Doing PMO leadership and governance Provide day-to-day leadership of the PMO, ensuring consistent application of methodology, governance, and delivery standards Act as the primary escalation point for delivery risks, resourcing constraints, and cross-team dependencies Support the EVP in translating strategic priorities into executable programs and delivery roadmaps Oversee CAPEX delivery in line with executive priorities and financial governance Contribute to RFP processes, vendor selection, contract reviews, and delivery oversight Technical delivery oversight Provide technical oversight across complex implementations, including architecture, integrations, and data flows Challenge vendors and delivery partners on scope assumptions, estimates, and solution design Guide testing strategy, data migration, cutover planning, and post-implementation stabilisation Ensure non-functional requirements, including security, performance, scalability, and auditability, are defined and addressed Finance system replacement Serve as project lead with end-to-end accountability for delivery Define scope, roadmap, milestones, and success criteria with Finance leadership and implementation vendors Lead executive and steering committee governance, risk management, and decision facilitation Ensure effective change management, business readiness, and transition to operational ownership post-go-live Stakeholder management and collaboration Navigate complex, matrixed environments and influence without formal authority Facilitate steering committees and executive-level governance forums Drive alignment across Finance, Software Development, Operations, Compliance, and external partners What We're Looking For Required Bachelor's degree in Business, Finance, Technology, or a related field, or equivalent experience 7-10+ years of progressive program management experience, including leadership of enterprise-scale initiatives Proven experience leading complex system implementations or replacements in finance, ERP, or core operational platforms Strong understanding of system architecture, application models, data flows, and integrations Experience managing project financials, budgets, CAPEX governance, and vendor performance Exceptional communication and executive presentation skills Preferred PMP or equivalent certification SQL and development background Insurance/healthcare / TPA experience Agile, waterfall, and hybrid delivery, Automated testing exposure Financial reporting and reconciliation What's In It For You Salary Range: $120,000 - $140,000 CAD annually (Final compensation will reflect the candidate's experience, skills, and qualifications) Hybrid work environment Comprehensive health benefits + Employee Assistance Program Wellness spending account RRSP matching Minimum 3 weeks' vacation + generous sick and flex days Clear pathways for vertical and horizontal growth, pursue what excites you Inclusive, supportive leadership that genuinely invests in your success MSH is an equal opportunity employer committed to fostering an inclusive, barrier-free recruitment process. We welcome applications from all qualified individuals regardless of race, ancestry, colour, ethnic origin, citizenship, creed, sex, sexual orientation, gender identity or expression, age, record of offences, marital status, family status, or disability. If you require accommodation at any stage of the recruitment process, please reach out. We will work with you in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act (AODA). We thank all applicants for their interest. Only those selected for an interview will be contacted. In accordance with Ontario's Working for Workers Four Act, 2024, MSH confirms that artificial intelligence tools may be used in the recruitment and selection process for this position.