Project Manager - Guidewire Implementation

Annex Consulting Group; Toronto; Hybrid; CAD 90,000 - 120,000; Full time

Job summary

A prominent consulting firm in Ontario is seeking a Technical Project Manager to lead technology workstreams, manage platform migrations from legacy to cloud, and ensure alignment across technical teams. The ideal candidate will have strong insurance platform knowledge and expertise in project planning and Agile methodologies. This position requires excellent communication and stakeholder management skills, offering a hybrid work model with in-office collaboration.

Qualifications

• Strong understanding of core insurance platforms.
• Experience with data migration and reporting.
• Familiarity with system architecture and APIs.

Responsibilities

• Lead technical workstreams for integration.
• Manage platform migration from legacy to cloud.
• Coordinate across multiple technical teams.

Skills

Understanding of core insurance platforms (Guidewire)

Data migration and mapping experience

System architecture familiarity

Understanding of cloud platforms (GCP, AWS, Azure)

Network, security, and access controls knowledge

Project planning and scheduling expertise

Managing technical dependencies

Agile, Scrum, Kanban experience

Proficient with Jira and Confluence

Effective communication skills

Strong stakeholder management skills

Tools

Jira

Confluence

MS Project

Job description

Overview

Offices: Toronto, Mississauga or Waterloo

Duration: 1 year contract

Work Model: 3 Days / Week in Office

Hours: 40HRS / Week

Summary

The Technical Project Manager leads technology workstreams to support integration, including managing the migration and consolidation of core platforms (from legacy to cloud). This role coordinates across technical teams - architecture, development, infrastructure, applications, QE, and data - to track dependencies, manage risks, support testing and cutover planning, and align deliverables with business timelines. Acts as the key liaison between business units and technology services, ensuring regulatory, operational, and scalability requirements are met.

Key Responsibilities

• Lead technical workstreams for integration
• Manage platform migration (legacy to cloud)
• Coordinate across architecture, development, QA, data, and infrastructure teams
• Track dependencies, manage risks, and plan cutovers
• Ensure alignment with business timelines and regulatory requirements
• Act as primary liaison between business and technology teams

Must-Have Skills

• Strong understanding of core insurance platforms (Guidewire Policy, Billing, Claims Center)
• Experience with data migration, data mapping, and reporting
• Familiarity with system architecture, APIs, and release planning
• Understanding of cloud platforms (GCP, AWS, Azure, Oracle)
• Understanding of network, security, and access controls
• Expertise in project planning, scheduling, and resource management
• Skilled in managing technical dependencies, risks, and change control
• Ability to manage multiple concurrent workstreams
• Experienced with Agile, Scrum, Kanban, SAFe, Waterfall, and hybrid delivery
• Proficient with Jira, Confluence, and MS Project
• Clear, concise technical and executive-level communication
• Strong stakeholder management and issue resolution skills
• Comfortable presenting status updates and risk assessments to executives