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Portfolio Scrum Master

Job in Toronto, Ontario, C6A, Canada
Listing for: Insight Global
Full Time position
Listed on 2026-10-19
Job specializations:
  • IT/Tech
    IT Project Manager, Scrum Master, Change Management, IT Consultant
Salary/Wage Range or Industry Benchmark: 110000 - 140000 CAD Yearly CAD 110000.00 140000.00 YEAR
Job Description & How to Apply Below
Job Description

We are seeking an experienced Scrum Master with strong Portfolio Agile delivery experience to support a large-scale Commercial Banking transformation initiative. This individual will lead and coach multiple Agile teams across a portfolio of work, driving delivery excellence while helping Product Owners, stakeholders, and delivery teams adopt and mature Agile practices.

The ideal candidate has experience working in large enterprise environments, possesses a strong understanding of Agile frameworks beyond basic Scrum ceremonies, and can respectfully challenge teams and leaders to improve outcomes. AI experience is highly desired, including exposure to AI-enabled products, implementations, and integrations.

Key Responsibilities
  • Lead and support multiple Agile teams within a portfolio environment.
  • Coach, mentor, and guide Product Owners, Scrum Teams, and stakeholders on Agile best practices.
  • Facilitate Agile ceremonies including sprint planning, retrospectives, backlog refinement, reviews, and daily stand-ups.
  • Help drive Agile transformation initiatives and support shifts in Agile maturity across teams.
  • Partner with Product Owners to prioritize work, manage dependencies, and align delivery to business objectives.
  • Remove roadblocks and proactively identify delivery risks.
  • Challenge assumptions and decision-making constructively to improve outcomes and team effectiveness.
  • Track portfolio-level progress, risks, dependencies, and delivery metrics.
  • Support cross-functional collaboration within a complex enterprise environment.
  • Foster a culture of continuous improvement and accountability.
Skills and Requirements
  • Required Qualifications:

    7+ years of experience as a Scrum Master in large enterprise organizations.
  • Strong experience managing Agile delivery across multiple teams or portfolios.
  • Deep understanding of Agile methodologies, frameworks, and scaling practices.
  • Proven ability to coach and mentor Agile teams and Product Owners.
  • Experience supporting large-scale transformation initiatives.
  • Strong stakeholder management and communication skills.
  • Experience navigating complex organizational structures and multiple work streams.
  • Ability to influence without authority and drive change across teams.
AI & Technology Experience
  • Must Have:
    Experience delivering or supporting AI-related initiatives.
  • Understanding of AI product development life cycles and implementation approaches.
  • Ability to discuss:
    How AI solutions were delivered.
  • Business use cases and outcomes.
  • AI integrations with existing platforms and systems.
  • Cross-functional collaboration required for AI adoption.
  • Nice to Have:
    Experience with Generative AI solutions.
  • Experience leveraging Microsoft Copilot, Jira Rovo, or similar AI productivity tools.
  • Passion for AI and technology with a demonstrated interest in applying AI to improve team efficiency and delivery outcomes.
Tools & Technologies
  • Jira (Advanced proficiency required)
  • Jira Roadmaps / Enterprise Roadmap Planning
  • Jira Rovo (preferred)
  • Confluence
  • Microsoft Copilot
  • Agile Portfolio Management tools
Preferred Industry Experience
  • Commercial Banking
  • Financial Services
  • Enterprise Digital Transformation
  • AI & Emerging Technology Programs

Required Qualifications 7+ years of experience as a Scrum Master in large enterprise organizations.

Strong experience managing Agile delivery across multiple teams or portfolios.

Deep understanding of Agile methodologies, frameworks, and scaling practices.

Proven ability to coach and mentor Agile teams and Product Owners.

Experience supporting large-scale transformation initiatives.

Strong stakeholder management and communication skills.

Experience navigating complex organizational structures and multiple work streams.

Ability to influence without authority and drive change across teams.

AI…

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