Senior Technical Project Manager – Enterprise Technology Transformation

Position: Senior Technical Project Manager
Industry: Insurance / Financial Services / Enterprise Technology
Employment Type: Contract
Location: TBD
Experience Level: Senior (8+ years preferred)

Position Overview

Our client, a leading Canadian enterprise organization, is seeking experienced Senior Technical Project Managers to support complex, large-scale technology transformation initiatives.

The ideal candidate brings a strong technical foundation and extensive experience delivering enterprise application, cloud, integration, and modernization projects within complex technology environments.

This is not a traditional project management role focused solely on schedules, budgets, and reporting. We are looking for technically proficient Project Managers who can confidently engage with Solution Architects, Engineering Leads, Developers, and technology vendors to understand technical challenges, manage complex dependencies, and drive successful project delivery.

Candidates do not need to be hands-on developers but must possess sufficient technical depth to understand architectural discussions, challenge assumptions, identify risks, and translate technical issues into meaningful business impacts for senior stakeholders.

Key Responsibilities

• Lead end-to-end delivery of complex enterprise technology projects involving multiple applications, platforms, business units, and technical teams.

• Partner closely with Solution Architects, Technical Leads, Developers, Infrastructure Teams, and external systems integrators to coordinate technical delivery.

• Manage complex cross-functional and cross-application dependencies, identifying downstream impacts of technical changes and ensuring alignment across workstreams.

• Oversee projects involving application modernization, system integration, cloud migration, data migration, and enterprise platform transformation.

• Facilitate technical discussions and working sessions, ensuring architectural decisions, integration challenges, and technical risks are clearly understood and addressed.

• Identify and proactively manage technical risks, dependencies, integration challenges, and delivery blockers.

• Translate complex technical issues into clear business impacts, recommendations, and updates for senior leadership and executive stakeholders.

• Coordinate delivery activities across internal engineering teams, third-party vendors, and systems integrators.

• Ensure project milestones, technical deliverables, testing activities, migration plans, and deployment dependencies are appropriately managed.

• Support enterprise transformation initiatives involving legacy system modernization, platform consolidation, and technology integration.

• Drive accountability across multiple technical workstreams while maintaining alignment with broader program objectives.

Required Qualifications

• 8+ years of project management experience, with significant experience delivering complex technical or enterprise technology initiatives.

• Demonstrated success managing projects involving enterprise applications, application architecture, systems integration, cloud transformation, or application modernization.

• Strong technical understanding of:

  • Enterprise application architecture and interconnected systems

  • APIs, middleware, and system integrations

  • Cloud platforms and cloud migration initiatives

  • Data migration, conversion, and integration

  • Application modernization and legacy system transformation

  • Software development lifecycles (SDLC), testing, and deployment processes

• Exceptional dependency management skills, particularly across multiple applications, technology teams, vendors, and business workstreams.

• Proven ability to engage confidently with Solution Architects, Developers, Engineering Leads, and other technical stakeholders.

• Experience identifying and communicating the downstream impacts of architectural changes, integration challenges, and technical delivery decisions.

• Strong stakeholder management skills, including experience communicating with Directors, VPs, and executive leadership.

• Experience coordinating external vendors, technology partners, and systems integrators.

• Excellent communication, analytical thinking, problem-solving, and organizational skills.

• Ability to work effectively in complex enterprise environments with competing priorities and interconnected initiatives.

Preferred Qualifications

• Experience delivering technology transformation projects within the property and casualty (P&C) insurance industry.

• Exposure to Guidewire InsuranceSuite, including PolicyCenter, BillingCenter, or ClaimCenter.

• Experience with Guidewire Cloud migrations, implementations, or modernization initiatives is highly desirable.

• Experience supporting post-acquisition technology integrations, application rationalization, or enterprise platform consolidation.

• Experience with enterprise applications such as Oracle or Salesforce.

• Exposure to cloud environments such as Google Cloud Platform (GCP), AWS, or Microsoft Azure.

• Experience working on large-scale enterprise data transformation or system conversion programs.

• PMP, PMI-ACP, or other relevant project management certifications are considered assets.