Project Manager – Cybersecurity & Insurance Background (JOB-31511)

Start Date: ASAP
Contract Length: 6 Months
Location: Toronto, ON (Hybrid, 2 days per week in office)
Work Type: Staff Augmentation

About the Role

We are seeking an experienced Project Manager with strong Cybersecurity implementation expertise and a background in insurance to lead a 6-month initiative. The ideal candidate will be based in Calgary or Toronto and have proven success delivering complex projects involving cybersecurity tools, actuarial models, and vendor integrations.

This role will focus on leading the Proof-of-Concept / Discovery phase, managing multiple vendor assessments, coordinating stakeholders across IT, actuarial, and underwriting teams, and ensuring timely delivery of high-level recommendations and plans.

Key Responsibilities

• Lead and manage the end-to-end POC/Discovery phase of the Cyber Hub initiative.

• Collaborate with vendor partners to evaluate solutions against business and technical requirements.

• Oversee two primary workstreams:

  1. Security Scanning Tool Evaluation – Assess vendor tools capable of scanning URLs, identifying vulnerabilities, and presenting actionable insights for underwriting decisions.

  2. Actuarial Rater Development – Support the design and validation of a new algorithmic rating tool for cyber risk assessment.

• Deliver a vendor recommendation report for the scanning tool, with an associated high-level breakdown for configuration/customization.

• Define the framework and roadmap to integrate the selected vendor tool into a planned Cyber Hub.

• Provide leadership in risk management, timeline tracking, and cross-functional alignment.

• Serve as the primary liaison between internal stakeholders and external vendor teams.

Must-Have Qualifications

• Residency in Calgary or Toronto (only candidates currently residing in these locations will be considered).

• Proven experience as a Project Manager in Cybersecurity implementation projects.

• Strong insurance industry background, with deep familiarity in underwriting, actuarial models, and risk-rating methodologies.

• Hands-on experience managing vendor evaluations, proof-of-concepts, and discovery phases.

• Excellent communication and stakeholder management skills, with the ability to translate technical concepts into business language.

• Strong organizational, risk management, and reporting capabilities.

Nice-to-Have Skills

• Prior experience working with cybersecurity scanning tools or vulnerability management platforms.

• Knowledge of actuarial rating methodologies for cyber insurance.

• Familiarity with integration of SaaS tools into enterprise hubs.

• PMP or equivalent certification.

Deliverables

• Vendor recommendation report for the Security Scanning Tool.

• High-level work breakdown structure for customization and configuration.

• Conceptual plan for establishing the Cyber Hub to integrate with vendor solutions.

• Support for the development of a new cyber actuarial rater tool.