Our client, a prominent leader in the Canadian financial services and insurance sector, is undergoing a major modernization journey. We are seeking a high-caliber, strategically-minded Strategic Program Manager to steer large-scale digital and business transformation initiatives. Acting as the trusted right hand to the Vice President of Operations, the successful candidate will play a pivotal role in translating high-level corporate strategies into executable roadmaps, ensuring alignment across matrixed business and technology units, and driving complex operational evolution.
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Advantages
Flexible Work Model: 100% remote working environment (with occasional, planned travel as needed).
Long-Term Engagement: Initial 12-month contract with a strong likelihood of extension based on project milestones.
Executive Exposure: Direct collaboration and visibility with C-suite and VP-level leadership.
Impactful Work: Opportunity to pioneer a flagship digital transformation that shapes the future operating model of a major enterprise.
Professional Growth: Work within a highly dynamic, modern corporate culture driving large-scale industry innovation.
Responsibilities
Strategic Governance & Roadmap Design: Translate overarching corporate strategies into practical, phased transformation roadmaps with clearly defined outcomes, milestones, and success metrics.
Executive Advisory: Serve as the strategic advisor and right hand to the VP of Operations, facilitating high-level decision-making, executive steering committees, and status reporting.
End-to-End Program Delivery: Oversee the lifecycle of multi-stream transformation programs, managing intricate dependencies, program budgets, resource allocation, and risk mitigation.
Stakeholder Alignment: Foster collaboration across highly matrixed environments, bridging the gap between business operations, IT architecture, product delivery teams, and external vendors.
Operational Modernization: Spearhead shifts in processes, data structures, and technologies to achieve superior operational efficiency and enhance customer value.
Change Advocacy & Leadership: Mitigate delivery bottlenecks and lead cross-functional teams with clarity, championing organizational readiness and continuous improvement throughout the transformation.
Qualifications
Extensive Leadership Background: 10 to 15+ years of dedicated experience directing enterprise-wide program portfolios, specifically focusing on complex business and digital transformations within large, matrixed organizations.
Industry Expertise: Proven track record within the insurance, wealth management, or broader financial services sectors. Experience navigating dealer or distribution networks is highly valued.
Methodological Mastery: Strong command over hybrid delivery models (Agile, Scrum, Waterfall), vendor management, and structured change management practices.
Executive Presence: Superb communication and negotiation skills, with a demonstrated ability to influence executive leadership and resolve ambiguous, high-stakes delivery challenges.
Education & Credentials: Bachelor’s degree in Business, Engineering, Technology, or a related field (Master's preferred). Certifications such as PMP, PgMP, or Agile equivalents are strong assets.
Language Requirements: Complete professional fluency in English is mandatory. Proficiency in French is considered a significant asset.
Our client operates in Canada. The company takes all reasonable steps to limit the number of positions in Quebec that require knowledge of a language other than French, and only requires it when necessary and its existing bilingual employees are unable to perform these duties. Based on an assessment conducted by our client, it has been determined that this position requires candidates to be fluent in English (both spoken and written). In particular, this position will require the employee to interact with centralized internal departments (e.g., Operations / HR / Finance / Legal / Contracts / Sales) that support the organization in Canada and that do not speak French.
Summary
Location: Remote (Candidates based in Toronto or Montreal hubs preferred; occasional travel required).
Duration: 12-Month Contract (Initial).
Position Type: Contract / Independent Consultant.
Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.
Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.
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Our client, a prominent leader in the Canadian financial services and insurance sector, is undergoing a major modernization journey. We are seeking a high-caliber, strategically-minded Strategic Program Manager to steer large-scale digital and business transformation initiatives. Acting as the trusted right hand to the Vice President of Operations, the successful candidate will play a pivotal role in translating high-level corporate strategies into executable roadmaps, ensuring alignment across matrixed business and technology units, and driving complex operational evolution.
Advantages
Flexible Work Model: 100% remote working environment (with occasional, planned travel as needed).
Long-Term Engagement: Initial 12-month contract with a strong likelihood of extension based on project milestones.
Executive Exposure: Direct collaboration and visibility with C-suite and VP-level leadership.
Impactful Work: Opportunity to pioneer a flagship digital transformation that shapes the future operating model of a major enterprise.
Professional Growth: Work within a highly dynamic, modern corporate culture driving large-scale industry innovation.
...
Responsibilities
Strategic Governance & Roadmap Design: Translate overarching corporate strategies into practical, phased transformation roadmaps with clearly defined outcomes, milestones, and success metrics.
Executive Advisory: Serve as the strategic advisor and right hand to the VP of Operations, facilitating high-level decision-making, executive steering committees, and status reporting.
End-to-End Program Delivery: Oversee the lifecycle of multi-stream transformation programs, managing intricate dependencies, program budgets, resource allocation, and risk mitigation.
Stakeholder Alignment: Foster collaboration across highly matrixed environments, bridging the gap between business operations, IT architecture, product delivery teams, and external vendors.
Operational Modernization: Spearhead shifts in processes, data structures, and technologies to achieve superior operational efficiency and enhance customer value.
Change Advocacy & Leadership: Mitigate delivery bottlenecks and lead cross-functional teams with clarity, championing organizational readiness and continuous improvement throughout the transformation.
Qualifications
Extensive Leadership Background: 10 to 15+ years of dedicated experience directing enterprise-wide program portfolios, specifically focusing on complex business and digital transformations within large, matrixed organizations.
Industry Expertise: Proven track record within the insurance, wealth management, or broader financial services sectors. Experience navigating dealer or distribution networks is highly valued.
Methodological Mastery: Strong command over hybrid delivery models (Agile, Scrum, Waterfall), vendor management, and structured change management practices.
Executive Presence: Superb communication and negotiation skills, with a demonstrated ability to influence executive leadership and resolve ambiguous, high-stakes delivery challenges.
Education & Credentials: Bachelor’s degree in Business, Engineering, Technology, or a related field (Master's preferred). Certifications such as PMP, PgMP, or Agile equivalents are strong assets.
Language Requirements: Complete professional fluency in English is mandatory. Proficiency in French is considered a significant asset.
Our client operates in Canada. The company takes all reasonable steps to limit the number of positions in Quebec that require knowledge of a language other than French, and only requires it when necessary and its existing bilingual employees are unable to perform these duties. Based on an assessment conducted by our client, it has been determined that this position requires candidates to be fluent in English (both spoken and written). In particular, this position will require the employee to interact with centralized internal departments (e.g., Operations / HR / Finance / Legal / Contracts / Sales) that support the organization in Canada and that do not speak French.
Summary
Location: Remote (Candidates based in Toronto or Montreal hubs preferred; occasional travel required).
Duration: 12-Month Contract (Initial).
Position Type: Contract / Independent Consultant.
Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.
Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.
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