Agile Coach, PMO

Odyssey Reinsurance Company (OdysseyRe) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), AsiaPacific and London.

OdysseyRe is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth.

OdysseyRe is rated A+ (Superior) by AM Best and A+ (Strong) by Standard and Poor’s. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH.

Position Overview 

We are seeking a dynamic and experienced Agile Coach with dual responsibility for overseeing the operations of our Project Management Office (PMO). This role is ideal for a professional with a strong background in Agile methodologies, who can not only guide teams through Agile transformations but also bring strategic leadership to our PMO operations, automation tools, and project portfolio management (PPM) dataThe Agile Coach will work collaboratively across departments to drive continuous improvement, enhance project delivery, and instill a culture of agility and innovation within the organization. 

Key Responsibilities 

Agile Coaching & Transformation 

• Agile Methodology Adoption: Lead the adoption and implementation of Agile practices across the organization, with a focus on Scrum, Scrumban, and Scaled Agile frameworks, ensuring alignment with company goals and objectives. 

• Team Coaching & Development: Provide hands-on coaching to Agile teams, scrum masters, and product owners to enhance their skills, improve team performance, and promote Agile best practices. 

• Agile Maturity Assessment: Conduct regular assessments of Agile maturity and Agile delivery performance improvement metrics  to identify and support recommended actions and investments for continuous improvement. 

• Facilitation & Training: Facilitate Agile workshops, training sessions, and group coaching to ensure all stakeholders have the necessary skills and knowledge to thrive in an Agile environment. 

• Change Management: Guide teams and leaders through the cultural and organizational shifts required to adopt Agile practices, helping to overcome resistance to change and fostering an Agile mindset. 

PMO Operations & Leadership 

• PMO Oversight: Lead and manage the Project Management Office, ensuring the efficient governance of all project portfolios, and that projects are delivered on time, within scope, and on budget. 

• Portfolio Management: Oversee the project portfolio and prioritize initiatives based on business value, capacity, and resources. Ensure alignment with strategic business goals. 

• Project Delivery: Provide support to Project Managers to ensure consistent project delivery methodology is followed, incorporating Agile practices where possible while ensuring overall project success. 

• Governance & Reporting: Establish and enforce best practices for project governance, risk management, and reporting. Create and present regular project status reports to senior leadership and stakeholders. 

• Resource Management: Collaborate with business leaders to assess resource capacity, project allocation, and identify potential project constraints or bottlenecks. 

• Process Improvement: Identify opportunities to streamline PMO operations, enhance processes, and integrate Agile practices for more effective project execution. 

• PMO technology product ownership: Provide product ownership of PMO technology and data resources required to support project portfolio governance, delivery performance and efficiency,  risk management, regulatory compliance, and Enterprise IT strategic planning 

Alignment to IT Finance and Architecture 

• Facilitate annual budgeting and roadmapping between IT Finance and Architecture 

• Drive integration with EA processes 

• Drive integration with IT Finance and Procurement processes 

• Drive integration with Information Security and Compliance Risk and Controls Processes 

Collaboration & Stakeholder Engagement 

• Cross-functional Collaboration: Act as a liaison between Agile teams and business stakeholders to ensure clear communication, shared understanding of project objectives, and alignment with business needs. 

• Leadership Engagement: Work closely with senior leadership to shape the vision and strategy for Agile adoption and PMO operations, aligning both to organizational objectives. 

• Conflict Resolution: Help facilitate conflict resolution and foster collaboration between teams, ensuring a harmonious, productive work environment. 

Qualifications & Requirements 

• Experience: 

• 5+ years of experience as an Agile Coach, Scrum Master, or in a similar Agile leadership role within a corporate environment (preferably within the insurance or financial services industry). 

• 3+ years of experience leading and managing a PMO, including overseeing project portfolios and managing project delivery. 

• Certifications (nice to have): 

• Certified ScrumMaster (CSM), Certified Agile Coach (ICP-ACC), or equivalent Agile certification is highly preferred. 

• PMP (Project Management Professional) or equivalent Project Management certification is a plus. 

• Skills: 

• Deep understanding of Agile frameworks (Scrum, Kanban, Lean, etc.) and how they can be applied to enhance project and product delivery. 

• Strong leadership, communication, and facilitation skills with the ability to coach and mentor individuals at all levels. 

• Experience in setting up and running PMO processes, including project governance, reporting, risk management, and resource planning. 

• Ability to manage multiple projects and priorities in a fast-paced, dynamic environment. 

• Strong interpersonal skills, with a collaborative and results-driven mindset. 

• Tools: 

• Azure DevOps, PowerBI, Microsoft Office Suite, Power Automate, and Co-Pilot 

• Preferred Experience: 

• Experience in Agile transformations within the insurance industry. 

• Familiarity with insurance industry-specific regulatory requirements and how they affect project management processes. 

Additional Attributes: 

• Change Agent: Demonstrates a passion for driving change and continuous improvement within an organization. 

• Problem-Solver: Strong analytical skills, with a pragmatic approach to resolving complex challenges. 

• Relationship Builder: Excellent at building strong, collaborative relationships with cross-functional teams, executives, and external stakeholders. 

Why Join Us? 

• Impact: Be part of a transformative journey, shaping the future of project management and Agile practices and technologies at a leading insurance company. 

• Growth Opportunities: Work in an environment that values personal and professional development, with ample opportunities for training, mentorship, and career advancement. 

• Collaborative Culture: Join a passionate and innovative team dedicated to improving processes and delivering value to our customers. 

If you are a strategic thinker with a passion for Agile methodologies and project management, and you thrive in a fast-paced, collaborative environment, we invite you to apply for this exciting role. Join us in driving success through Agile transformation and PMO excellence! 

We are an E-Verify employer - all hired positions require successfully passing an E-Verify Check.  

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