Senior Program Manager – Website Migration / CMS Transformation Location: Toronto, ON Duration: 12-Month Contract Hybrid: 1 day/week onsite (subject to change)

Required Qualifications 10+ years of Program and/or Project Management experience Proven success leading large-scale digital transformation initiatives Experience managing website migrations and/or CMS implementations Advanced proficiency with Microsoft Project and detailed project planning Strong vendor and third-party management experience Expertise managing cross-functional teams, dependencies, and competing priorities Experience delivering complex programs under tight timelines Strong governance, risk management, issue resolution, and executive reporting skills Exceptional stakeholder management and communication abilities Experience within financial services, wealth management, banking, or other regulated industries

Nice-to-Have Qualifications Private Wealth Management or Investment Advisory experience Experience supporting advisor-facing digital platforms Hands-on experience with CMS platforms such as: Adobe Experience Manager (AEM) Sitecore Contentful Broadridge Digital platform or marketing technology implementation experience Change Management, Communications, and Training program experience PMP Certification Experience working within large enterprise environments

Responsibilities Lead the end-to-end delivery of a large-scale website migration and CMS transformation program Develop and maintain program plans, schedules, milestones, and dependency tracking Coordinate activities across business, technology, marketing, operations, training, and change management teams Manage external vendors and ensure alignment across delivery teams Identify and mitigate program risks, issues, and dependencies Drive governance, executive reporting, stakeholder communications, and program reviews Facilitate working sessions, steering committees, and cross-functional meetings Support training, communications, and change management readiness activities Partner with business and technology leaders to resolve challenges and maintain delivery momentum Monitor program health, milestones, and key delivery metrics Support adoption and stakeholder engagement throughout the transformation

Overview Insight Global is seeking a Senior Program Manager to lead a large-scale digital transformation initiative involving the migration of approximately 1,000 advisor websites to a new CMS platform. This individual will oversee program planning, execution, and delivery while coordinating cross-functional teams across business, technology, marketing, training, change management, advisor enablement, and external vendors. The ideal candidate combines strong strategic leadership with hands-on program execution and has experience delivering complex digital transformation or website migration initiatives within highly regulated environments.

Pay range: $65-74/hr (depending on skillset and experience)