Lead IT Scrum Master – Insurance Technology
Role Overview
This position leads agile execution within a high-velocity technology environment, focusing on data and digital initiatives. The successful candidate will guide multiple teams through complex delivery cycles, ensuring alignment with enterprise Agile frameworks and strategic objectives.
Key Responsibilities
- Lead and refine Agile practices across teams, ensuring consistent application of SAFe principles and effective management of scope, stakeholders, and interdependencies.
- Facilitate Program Increment planning cycles, configure and maintain JIRA boards, and coordinate Scrum of Scrums to sustain flow across teams.
- Drive sprint-level execution by leading planning, reviews, and retrospectives, removing blockers, and maintaining team focus on deliverables.
- Establish strong project governance through clear communication, financial oversight, and tracking of business outcomes and benefits realization.
- Coach teams in Agile mindset and Scrum theory, adapting facilitation approaches to team maturity and dynamics.
- Identify, document, and manage risks and issues with clear mitigation strategies to ensure delivery continuity.
Qualifications
Candidates must bring:
- Minimum of five years as a Scrum Master in a SAFe Agile environment.
- Undergraduate degree and Certified Scrum Master (CSM) or equivalent credential.
- Proven experience in Agile delivery, SDLC, and team coaching within complex technical landscapes.
- Advanced understanding of project management disciplines: planning, scheduling, metrics, risk analysis, budgeting, and financial tracking.
- Strong interpersonal skills in negotiation, communication, and team development.
- Proficiency with JIRA and Confluence for Agile tracking and collaboration.
Preferred Background
- Advanced Scrum Master or SAFe Practitioner certification.
- Experience in large, matrixed organizations, particularly in regulated industries.
- Familiarity with insurance or financial services operations.
Technical Environment
Agile Estimation, Agile Frameworks, Kanban, JIRA, Confluence, SDLC, SCRUM, SAFe
Work Environment
This is an onsite role based at 6880 Financial Drive, Mississauga, within the Meadowvale Business Park. The organization supports flexible work-life balance, enabling sustainable performance and personal well-being.
Compensation & Benefits
Competitive salary, performance bonuses, commissions where applicable, and stock participation. Comprehensive flexible benefits package supports health, wellness, and financial security. Career development is prioritized through coaching and progressive responsibility.
Company Values
The workplace emphasizes client focus, integrity, collaboration, and excellence. Teams operate with a shared purpose, valuing diverse perspectives and inclusive practices. Employees are encouraged to innovate, grow, and contribute meaningfully. Equal opportunity and respect are foundational to culture and daily operations.
