Vice President, IT Enterprise Systems

Navigatr Group is a privately held company that invests in travel companies that elevate the customer experience and drive innovation. Our expansive and growing group of brands empowers seamless access to a comprehensive range of luxury travel options and services globally with over $1 billion transactions annually.

Navigatr Group’s goal is to create a more purposeful travel industry through its strategic investment, best-in-class services and philanthropy.

Navigatr Group is seeking a high-impact, execution-driven Vice President, IT Enterprise Systems to lead the enterprise-wide evaluation, optimization, and integration of critical business systems across our portfolio of brands, including Kensington Tours, Ensemble, Travel Edge, and TripArc. 

This newly created, head-office-level role focuses on solving complex enterprise-wide technology problems and identifying scalable, best-in-class solutions. It requires a unique blend of strategic thinking, consultative problem-solving, and hands-on execution. The VP, IT Enterprise Systems will assess current-state platforms (including CRM, ERP, ETL/data integration, and service automation), benchmark them against leading market options, and drive the implementation of systems and integrations that unlock operational efficiency and business value. 

We have a strong preference for candidates with a consulting background—someone who brings a structured, analytical mindset and has worked with complex client environments. But this is not a strategy-only role. Success requires someone equally comfortable building roadmaps and leading cross-functional teams through hands-on delivery, execution, and change management. 

Key Responsibilities 

Enterprise Systems Evaluation & Execution 

• Evaluate the organization’s current enterprise platforms—including CRM, ERP, ETL/integration tools, and service automation—for fitness, scalability, and market competitiveness. 

• Compare systems against best-in-class technologies and provide clear recommendations backed by cost-benefit analysis and business impact. 

• Drive forward the implementation of new systems or enhancements across the portfolio; this includes leading integration efforts and ensuring on-time, on-budget execution. 

Strategic Planning & Roadmap Development 

• Develop and maintain an enterprise systems roadmap that is practical, value-driven, and closely aligned with business priorities. 

• Translate strategic direction into clear, actionable initiatives with measurable outcomes. 

Cross-Portfolio Technology Alignment 

• Align enterprise technology investments across brands to maximize synergies and eliminate duplication or inefficiencies. 

• Ensure smooth integration between proprietary platforms and third-party enterprise systems to support business operations and customer experiences. 

Governance, Risk & Data Security 

• Implement strong governance frameworks and controls, especially around cybersecurity, data protection (e.g., PIPEDA, GDPR), and risk mitigation. 

• Partner with compliance, legal, and security stakeholders to ensure that all enterprise systems meet internal and regulatory requirements. 

Stakeholder Engagement & Influence 

• Engage and influence executive leadership, business stakeholders, and decentralized IT teams to ensure enterprise-wide alignment. 

• Build trust and credibility through structured analysis, transparent communication, and consistent delivery of results. 

Vendor & Program Management 

• Lead selection, negotiation, and management of enterprise technology vendors, including system integrators and platform providers. 

• Establish performance metrics and ensure accountability for delivery, quality, and ROI. 

Hands-On Leadership & Change Delivery 

• Provide hands-on leadership to advance key initiatives—supporting system migration, implementation, and operational rollout. 

• Champion change management to ensure successful adoption of new processes and technologies across business units. 

Team Leadership & Culture 

• Build and lead a lean, high-performing team responsible for enterprise systems strategy and execution. 

• Foster a culture of collaboration, agility, accountability, and innovation consistent with Navigatr’s values. 

Qualifications 

• 10+ years of progressive IT leadership experience, ideally across consulting and in-house roles focused on enterprise systems. 

• Strong preference for candidates with management consulting experience (Big Four or equivalent) working with large, complex organizations. 

• Proven ability to assess enterprise-wide technology environments and drive both strategic plans and tactical delivery. 

• Deep knowledge of enterprise systems including CRM (e.g., Salesforce, HubSpot), ERP (e.g., NetSuite, Dynamics), ETL/integration platforms, and service automation tools (e.g., ServiceNow, Zendesk). 

• Expertise in system architecture, vendor evaluation, integration planning, and program delivery. 

• Hands-on approach with strong execution discipline and the ability to manage multiple cross-functional initiatives simultaneously. 

• Proven ability to influence across decentralized, matrixed organizations and drive consensus among diverse stakeholders. 

• Strong project management, change management, and communication skills. 

• Familiarity with Microsoft technologies (e.g., Microsoft 365, Azure, .NET) is an asset. 

We are committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act. If you require accommodation due to a disability at any stage of our hiring process, please advise us when completing your application.

We thank all candidates for their interest however only those selected for an interview will be contacted.