- 12 Month Contract with opportunity for extensions

4 days a week on site - Downtown Toronto

Hourly Rate: $70-80/hr T4A

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 workplace.

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.

Required Skills & Experience: 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 workstreams.

Ability to influence without authority and drive change across teams.

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)

Confluence

Preferred Industry Experience

Commercial Banking

*We may use artificial intelligence tools to assist with the screening, assessment, or selection of potential applicants for this position.

Vacancy: This posting is for a currently vacant role, and the successful candidate will be hired into an existing open position.

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