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.

Robust 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 workstreams.

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 lifecycles 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 Qualifications7+ 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 workstreams.Ability to influence without authority and drive change across teams.AI & Technology ExperienceMust HaveExperience delivering or supporting AI-related initiatives.Understanding of AI product development lifecycles 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 HaveExperience 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 & TechnologiesJira (Advanced proficiency required)Jira Roadmaps / Enterprise Roadmap PlanningJira Rovo (preferred)ConfluenceMicrosoft CopilotAgile Portfolio Management toolsPreferred Industry ExperienceCommercial BankingFinancial ServicesEnterprise Digital TransformationAI & Emerging Technology Programs

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal employment opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment without regard to race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please send a request to [email protected].

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📌 Portfolio Scrum Master (Ontario)
🏢 Insight Global
📍 Ontario