This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Principal, Strategic Planning & Integration based in Canada.

This senior leadership role will serve as a strategic integration point across a complex technology and product ecosystem.

You will connect enterprise priorities with execution realities across distributed engineering and product teams.

The role combines strategic planning, operational execution, workforce planning, stakeholder influence, and executive communication.

You will help sequence major initiatives, reduce duplication, manage dependencies, and accelerate delivery of critical outcomes.

You will also strengthen customer signal collection and strategic vendor alignment across multiple technology domains.

A key part of the role is translating complex progress and impact into compelling narratives for senior executives and governance forums.

This is an chance to shape how a large technology organization plans, collaborates, and delivers strategic value at scale.

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Accountabilities:

- Lead strategic planning and integration across a large network of distributed product and engineering teams, ensuring priorities, dependencies, and backlogs are appropriately sequenced to support enterprise outcomes.
- Coordinate complex, cross-domain initiatives such as infrastructure modernization, Infrastructure as Code transformation, and major vendor transitions requiring alignment across infrastructure, platforms, and product teams.
- Partner with Digital Product Managers to capture, structure, and incorporate customer needs and signals into technology priorities.
- Streamline stakeholder engagement and reduce duplicated requests, fragmented input, and unnecessary friction across initiatives.

- Lead workforce planning and future-readiness initiatives by aligning anticipated skill requirements and organizational capacity with business and technology demand.
- Support capability-building initiatives, including specialized onboarding programs, bootcamps, learning environments, and internal talent development for infrastructure teams.
- Strengthen strategic vendor relationships by aligning external partners with enterprise technology priorities, expectations, responsibilities, and value-delivery objectives.

- Develop and maintain clear strategic narratives that connect technology strategy, execution progress, business outcomes, and enterprise value.
- Prepare and curate executive-level materials for OKR reviews, operational risk and return governance, technology execution reviews, Board-level discussions,



and other senior leadership forums.
- Establish effective decision rights, governance mechanisms, accountability structures, and operating cadences across complex initiatives.

- Identify opportunities to improve processes, execution speed, organizational scalability, and cross-functional collaboration.
- Lead and develop teams while fostering accountability, continuous improvement, innovation, and strong succession pipelines.
- Influence senior leaders and stakeholders across functions and organizational levels, driving alignment and outcomes without relying solely on formal authority.

- Lead organizational change associated with large-scale transformations, technology implementations, integrations, and evolving operating models.

Requirements:

- Bachelor's degree preferred, or an equivalent combination of education and professional experience.
- 10+ years of progressive experience leading strategic initiatives within complex, technology-driven organizations.
- Experience in environments undergoing significant digital transformation, such as financial services, insurance, technology, consulting, or other highly regulated industries.
- Proven expertise in enterprise strategic planning and execution, with the ability to translate complex business and technology objectives into actionable plans and measurable outcomes.

- Strong understanding of technology and product operating models, with experience partnering across engineering, product, and business organizations.
- Demonstrated ability to prioritize initiatives, manage dependencies, coordinate distributed teams, and connect strategic priorities to delivery.
- Proven executive presence and ability to influence senior leaders and cross-functional stakeholders without direct authority.

- Exceptional strategic storytelling and communication skills, including the ability to synthesize complex information into clear, compelling executive narratives.
- Strong people leadership and talent development experience, including building high-performing organizations, establishing accountability, and developing future leaders.
- Advanced business acumen and analytical capabilities, with the ability to use data, insights, and technology fluency to support strategic decisions.





- Strong operational expertise and a demonstrated ability to optimize processes and consistently deliver against strategic outcomes.
- Strategic thinker with strong problem-solving skills, innovation mindset, and a commitment to continuous improvement.
- Experience leading significant organizational change, systems implementations, business transformations, or organizational integrations.

- Strong negotiation, consensus-building, stakeholder management, and communication capabilities.
- High learning agility and ability to operate effectively in complex, evolving environments.
- Experience with strategic planning, digital transformation, product management leadership, executive influence, and technical product management is highly valuable.

Benefits:

- Expected annual compensation of CAD $159,594–$209,594, with the actual offer determined by skills, experience, and other relevant factors.
- Fully remote work arrangement within Canada, specifically supporting the Ontario/GTA remote organization.
- Opportunity to operate at a senior strategic level across a complex technology and product ecosystem.
- Significant influence over enterprise technology planning, integration, execution, and organizational transformation.
- Opportunity to work closely with senior executives and cross-functional leaders.

- Exposure to large-scale digital transformation and strategic technology initiatives.
- Leadership and talent-development opportunities.
- Environment focused on innovation, continuous improvement, collaboration, and meaningful business impact.

- Opportunity to contribute to initiatives that help protect customers, families, and communities.

nHow Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

📌 Principal, Strategic Planning & Integration (Canada)
🏢 Jobgether
📍 Canada