Executive Director, Applications

Position Title: Executive Director, Applications and Development

Reports to: Chief Technology Officer (CTO)

Location: Availability to be present in one of the five locations in a hybrid capacity

THE ORGANIZATION

Portage Mutual Insurance (“PMI”) is a proudly 100% Canadian-owned company, established in 1884 upon the principles of security, integrity, hard work, and personalized service. Over the years, PMI has continued to grow and has built a reputation as one of the most responsive property and casualty (P&C) insurers in Canada. And, the principles that guide the company, and the friendly, small town style of doing business, remain the same.

PMI offers a wide range of insurance products that, in many cases, have helped set the industry standards for residential, automobile, commercial, and agricultural business coverage. Serving over 167,000 policyholders and taking pride in giving thoughtful, personalized service on each each and every claim, earns PMI’s top ratings for claims service. The company’s products are marketed through over 295 independent insurance brokers and more than 700 points of distribution. This reflects a partnership approach which aims to deliver better service and value to policyholders.

The combination of PMI’s logo and tagline Facing the storm with you is an apt metaphor to describe a company whose purpose is to take on risk and protect people.

Values

• Integrity: Since 1884, we have held a principled dedication to honesty and the highest standard of ethics.
• Mutuality: We believe deeply in our moral obligation to value and support the well‑being of our policyholders, our team and our communities.
• Peace of Mind: We value the trust of our policyholders and partners. Portage Mutual is committed to protecting their financial security.
• Progressive: We are passionate about our business, seeking excellence today and preparing for a dynamic future.
• Reliability: Our financial strength ensures stability and is a commitment to being an insurer our policyholders and partners can rely on.

THE OPPORTUNITY

PMI is seeking an experienced Executive Director, Applications & Development to join their senior management team and is responsible for the strategic technology leadership, delivery effectiveness, and long‑term sustainability of the organization’s application portfolio. This newly created role includes accountability for core enterprise platforms (including Guidewire and Microsoft Dynamics), digital channels, broker and customer‑facing solutions, and the organization’s integration and API ecosystem.

With a strong mandate for transformation, this role balances enterprise‑level strategy with disciplined execution, ensuring that application delivery enables business priorities, supports regulatory and operational requirements, and positions the organization for future modernization. The Executive Director builds and sustains high‑performing teams, supports succession planning, and fosters a culture of collaboration, accountability, and continuous improvement. In addition, the Executive Director serves as the CTO’s principal delegate for application delivery and acts as second‑in‑command within the IT organization when required.

KEY ACCOUNTABILITIES

• Own the end‑to‑end application delivery portfolio, ensuring investments align with business strategy, customer and broker experience, and long‑term platform health.
• Translate enterprise and technology strategy into a cohesive, executable delivery roadmap, balancing speed, risk, cost, and capability development.
• Provide executive leadership on platform lifecycle decisions, including modernization, technical debt management, and vendor dependency reduction.
• Act as a senior decision‑maker for delivery execution, sequencing, and capacity trade‑offs once priorities are set.
• Serve as the CTO’s delegate, providing continuity of leadership, governance, and executive representation as required.
• Build strong partnerships with senior business leaders, enabling informed decisions through clear articulation of delivery implications, risks, and constraints.

Delivery Excellence & Predictability

• Establish and maintain a disciplined, predictable delivery model across internal teams and external partners.
• Ensure initiatives are delivery‑ready through rigorous intake, feasibility assessment, and dependency management.
• Drive measurable improvements in time‑to‑market, quality, and operational stability while operating within a regulated insurance environment.

Product Oriented Operating Model

• Champion a product‑oriented delivery mindset where appropriate, emphasizing platform ownership, long‑lived teams, and continuous improvement.
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