Delivery Manager

Role: Delivery Manager

Location: Canada, Remote

Contract

Release Management & Delivery Leadership

• Forward plan and manage release windows and deployment cycles across a portfolio of business-critical applications, including IICES and its integrated ecosystem.
• Manage release scope, schedules, dependencies, risks, and quality to ensure successful delivery of business and technology initiatives.
• Coordinate release content and deployment activities based on project demand, service request backlogs, infrastructure changes, vendor releases, security patches, and operating system upgrades.
• Lead Release Readiness Reviews, Milestone Reviews, Operational Readiness Assessments, and Business Go/No-Go decision meetings.
• Produce and maintain deployment plans, implementation procedures, rollback strategies, runbooks, and support transition documentation.
• Coordinate with development, QA, infrastructure, cybersecurity, application support, vendors, and business stakeholders to ensure seamless release execution.
• Lead and coordinate Go-Live and Hypercare activities, ensuring successful transition to production and operational support teams.
• Maintain release repositories, deployment procedures, release calendars, technical dependencies, and stakeholder notification lists.
• Monitor release performance metrics and identify opportunities to improve release management processes, automation, efficiency, and delivery quality.
• Participate in Change Advisory Board (LCAB) meetings to assess release readiness, risks, and deployment impacts.

RUN Operations & Application Portfolio Management

• Provide operational leadership and oversight for RUN activities across multiple applications supporting core insurance, policy administration, claims, billing, customer service, finance, and enterprise platforms.
• Manage production support processes including incident management, problem management, service requests, defect triage, and operational escalations.
• Partner with business and technical teams to prioritize support initiatives, production enhancements, and application maintenance activities.
• Ensure compliance with service-level agreements (SLAs), operational KPIs, regulatory requirements, and organizational standards.
• Lead root cause analysis efforts and drive corrective and preventive actions to improve overall system stability and performance.
• Oversee vendor support engagement, application maintenance contracts, and third-party service providers.
• Drive continuous improvement initiatives focused on operational excellence, automation, monitoring, and support optimization.
• Coordinate annual application reviews, technology health assessments, and lifecycle management activities.

Cyber Risk & Security Governance

• Lead and coordinate Cyber Risk Assessments (CRA), Threat Risk Assessments (TRA), Security Reviews, Vulnerability Assessments, and Privacy Impact Assessments across multiple client initiatives.
• Act as the primary liaison between Cyber Security, Enterprise Architecture, Infrastructure, Compliance, Privacy, and Project Delivery teams.
• Facilitate risk identification, mitigation planning, and remediation tracking to ensure security compliance and project approval milestones are achieved.
• Support internal and external audits by providing architecture documentation, control evidence, and compliance artefacts.
• Ensure application and solution designs align with enterprise security standards, regulatory requirements, and industry best practices.
• Track and manage cybersecurity risks, exceptions, dependencies, and remediation activities throughout project and operational lifecycles.

Guidewire Strategy, Blueprinting & Business Architecture

• Lead business and solution blueprinting workshops with business stakeholders, product owners, architects, and technology teams to define future-state capabilities, objectives, and transformation roadmaps.
• Facilitate requirements discovery sessions to identify business goals, operational challenges, process improvements, and system integration opportunities.
• Translate business needs into Guidewire solution strategies, target operating models, and capability roadmaps.
• Collaborate with Guidewire product teams and implementation partners to align business priorities with platform capabilities and strategic objectives.
• Support architecture review activities and provide recommendations for solution design, integration approaches, and modernization initiatives.
• Develop business capability maps, process models, solution blueprints, value streams, and transformation strategies.
• Ensure alignment between business objectives, enterprise architecture standards, and technology delivery roadmaps.

Architecture & Legacy Application Stewardship

• Maintain ownership of legacy application architecture, technical landscapes, integration patterns, and operational dependencies.
• Develop and maintain current-state and future-state architecture documentation for both strategic and legacy systems.
• Document application roadmaps, technical debt, modernization opportunities, and platform lifecycle recommendations.
• Provide architectural guidance and decision support for enhancement initiatives, support activities, and strategic projects.
• Assess the impact of business and technology changes across the application ecosystem and recommend appropriate solution approaches.
• Collaborate with Enterprise Architecture teams to ensure consistency with organizational standards and technology strategies.
• Maintain application inventories, system interaction diagrams, data flows, and dependency mapping across the enterprise landscape.

Governance, Stakeholder & Portfolio Management

• Participate in weekly, monthly, quarterly, and executive governance forums supporting both project delivery and RUN operations.
• Prepare and present status updates, risks, issues, dependencies, operational metrics, and strategic recommendations to senior leadership and executive stakeholders.
• Facilitate governance reviews, steering committee meetings, architecture review boards, and operational review sessions.
• Manage stakeholder relationships across business units, technology teams, vendors, client organizations, and executive leadership.
• Drive decision-making by providing clear visibility into project health, operational performance, risk exposure, and delivery progress.
• Coordinate portfolio-level planning activities to ensure alignment between strategic initiatives, operational priorities, resource constraints, and technology roadmaps.
• Support budget planning, forecasting, vendor management, and resource allocation activities across delivery and operational initiatives.

Executive Reporting & Strategic Communication

• Develop executive-level presentations, dashboards, architecture narratives, and portfolio reporting materials for senior management.
• Communicate strategic initiatives, operational performance, technology risks, and transformation progress to executive audiences.
• Provide concise summaries of complex technical and business issues, enabling effective decision-making by leadership teams.
• Maintain portfolio health reporting including release status, operational KPIs, cyber risk posture, architecture initiatives, and modernization efforts.
• Track and communicate key milestones, achievements, dependencies, and emerging risks across the application portfolio.
• Support annual planning, strategic roadmap development, and executive investment discussions through data-driven recommendations.

Continuous Improvement & Innovation

• Drive adoption of release automation, DevOps practices, CI/CD capabilities, and operational efficiency improvements.
• Evaluate emerging technologies, methodologies, and industry best practices to improve application delivery and RUN operations.
• Promote continuous improvement culture through process optimization, lessons learned reviews, and operational excellence initiatives.
• Collaborate with cross-functional teams to identify opportunities for modernization, simplification, cost optimization, and capability enhancement across the application portfolio.

Qualifications and Skills Required

Qualifications & Experience

• Bachelor's degree in Computer Science, Information Technology, Business Administration, Engineering, or a related discipline.
• 10+ years of progressive experience in Release Management, Application Delivery, IT Operations, Project Management, Business Architecture, or Technology Leadership roles.
• 8-10+ years of experience within large-scale enterprise information systems environments, preferably supporting Financial Services, Insurance, or highly regulated industries.
• Strong understanding of Policy Administration, Claims Management, Billing, and Insurance Core Platforms, with Guidewire experience considered a significant asset.
• Demonstrated experience managing complex application portfolios consisting of both strategic and legacy platforms across multiple business domains.
• Extensive knowledge of Software Development Life Cycle (SDLC), Agile, Waterfall, DevOps, CI/CD, Release Management, and ITIL operational practices.
• Formal training or certification in Project Management, Agile Delivery, ITIL, Business Analysis, Release Management, or Enterprise Architecture is preferred.
• Proven experience leading enterprise-wide release planning, deployment coordination, production support, and operational governance activities.
• Strong understanding of Cyber Risk Assessment (CRA), Security Governance, Compliance Frameworks, Audit Requirements, and Risk Management processes.

Leadership & Relationship Management

• Demonstrated ability to build trusted relationships with senior business leaders, technology teams, vendors, implementation partners, and executive stakeholders.
• Strong political acumen with the ability to navigate complex organizational structures, competing priorities, and stakeholder interests while maintaining alignment toward strategic objectives.
• Proven experience managing and influencing diverse stakeholder groups across North American organizations, with a strong understanding of regional business practices, communication styles, and cultural dynamics.
• Experience working with clients, partners, and delivery teams across Canada and the United States in both project and operational environments.
• Exceptional relationship management skills with the ability to establish credibility, gain consensus, resolve conflicts, and facilitate decision-making at all organizational levels.
• Demonstrated leadership in managing cross-functional, geographically distributed, and multi-vendor teams toward successful business outcomes.
• Ability to influence without direct authority and drive alignment across business, technology, security, architecture, and operations teams.

Business Architecture & Strategic Planning

• Experience leading business blueprinting, discovery workshops, strategic planning sessions, and requirements definition activities.
• Strong understanding of business capability modeling, process improvement, operating model design, and technology transformation initiatives.
• Ability to translate business objectives into technology strategies, roadmaps, solution architectures, and delivery plans.
• Experience developing executive presentations, business cases, strategic recommendations, and portfolio roadmaps for senior leadership audiences.

Technical Knowledge

• Advanced knowledge of enterprise application architecture, system integrations, cloud technologies, and technology modernization initiatives.
• Development experience with Java, SQL Server (MSSQL), API integration technologies, and enterprise application platforms is highly desirable.
• Knowledge of Guidewire PolicyCenter, ClaimCenter, BillingCenter, or similar insurance platforms is considered an asset.
• Experience supporting production environments, application monitoring, incident management, problem management, and service delivery processes.
• Familiarity with enterprise architecture frameworks, configuration management, release automation, and DevOps toolsets.

Communication & Executive Engagement

• Exceptional written, verbal, presentation, and facilitation skills with the ability to communicate effectively to technical, operational, business, and executive audiences.
• Demonstrated experience preparing and delivering executive-level updates, governance materials, risk assessments, architecture narratives, and portfolio status reporting.
• Strong negotiation, conflict resolution, and stakeholder management skills.
• Ability to simplify complex technical concepts into clear business-focused messaging and recommendations.

Analytical & Professional Skills

• Strong analytical, problem-solving, organizational, and decision-making capabilities.
• Proven ability to manage multiple priorities, competing deadlines, and complex dependencies in fast-paced environments.
• Demonstrated effectiveness in risk identification, mitigation planning, issue resolution, and continuous improvement initiatives.
• Ability to work independently while fostering collaboration across large, matrixed organizations.

Tools & Certifications

• Expert-level proficiency with Microsoft Office Suite, including Excel, PowerPoint, Word, Visio, and Teams.
• Working knowledge of Microsoft Access, SharePoint, Azure DevOps, JIRA, ServiceNow, and related enterprise collaboration tools.
• Experience with reporting, dashboarding, and portfolio management tools.
• PMP, PRINCE2, ITIL, SAFe, Guidewire, TOGAF, Business Architecture, or related certifications are considered strong assets.