Executive Director, Applications and Development
Financial Services-Insurance
Organization: Portage Mutual Insurance
Position Title: Executive Director, Applications and Development
Reports to: Chief Technology Officer (CTO)
Location: Hybrid, Canada
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.
Vision: To be the most trusted mutual insurer in Canada
Our Vision is to achieve sustained, strategic growth enabled by our investments in people and an agile culture. Our trusted partnerships with brokers, pricing excellence, and customer-driven innovation will make us the insurer of choice in our markets. We will remain committed to brokers and committed to our communities.
Mission: To provide peace of mind
Portage Mutual Insurance provides quality insurance products and services with exceptional value, powered by passionate people. Our mission is protection and peace of mind for policyholders - promises we keep in partnership with brokers.
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
Enterprise Application Strategy & Portfolio Stewardship- 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.
- 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.
- Champion a product-oriented delivery mindset where appropriate, emphasizing platform ownership, long-lived teams, and continuous improvement.
- Balance product delivery with structured project governance for large, complex, or regulatory initiatives.
- Ensure delivery models evolve in support of cloud adoption, modernization, and future operating models.
- Ensure application delivery practices appropriately balance delivery velocity with controls, auditability, and risk management.
- Partner with infrastructure, security, and data governance leaders to protect system reliability, data integrity, and regulatory compliance.
- Ensure operational learnings from incidents and defects translate into sustained improvements in delivery practices.
- Lead and develop senior leaders and teams across application delivery, project management, QA, DevOps, release management, and functional disciplines, fostering high performance, professional growth, and technical excellence.
- Establish and sustain a high-performing, accountable culture grounded in transparency, collaboration, continuous improvement, and employee engagement.
- Define and execute workforce strategies that strengthen internal capability through training, mentorship, and succession development, while reducing over-reliance on external partners and building strong future leaders.
- Provide executive oversight of system integrators and strategic delivery partners.
- Ensure vendors operate within organizational standards and deliver against agreed outcomes.
- Influence vendor strategy, performance management, and knowledge transfer to support long-term sustainability.
IDEAL SKILLS & EXPERIENCE
The ideal candidate will possess the following experience, qualifications, knowledge, skills and attributes:
- A seasoned professional with 15+ years in technology delivery/application development with increasing scope and complexity including 3+ years in a senior leadership role leading manager.
- Extensive experience leading enterprise-scale application development and delivery organizations, including responsibility for multiple platforms, teams, and delivery models.
- Demonstrated accountability for delivery outcomes, prioritization trade-offs, and capacity alignment.
- Demonstrated success managing complex delivery portfolios involving internal teams, system integrators, and specialized vendors.
- Experience operating in regulated environments (insurance or financial services preferred), balancing delivery speed with stability, auditability, and compliance.
- Experience supporting or leading modernization initiatives, including platform transitions, cloud adoption, and evolving delivery operating models.
- Ability to translate enterprise and technology strategy into cohesive, executable delivery roadmaps.
- Strong executive judgment in sequencing work, managing trade-offs, and aligning capacity to priorities.
- Credibility and effectiveness as a trusted advisor to senior leaders and business partners.
- Deep understanding of modern software delivery practices, including Agile, product-oriented delivery, and traditional project governance where required.
- Strong working knowledge of enterprise platforms, integration patterns, DevOps, CI/CD, and quality assurance practices.
- Ability to use delivery metrics and tooling (e.g., Jira) to provide transparent, executive-level insight into progress, risk, and performance.
- Demonstrated capability to lead and develop senior leaders, managers, and technical professionals.
- Skill in building high-performing, accountable cultures grounded in transparency, collaboration, and continuous improvement.
- Experience defining and executing workforce and capability strategies that strengthen internal talent and reduce reliance on external partners.
- Exceptional communication skills, with the ability to articulate complex technical and delivery issues in clear, business-relevant terms.
- Strong stakeholder management skills, including the ability to align diverse groups through change and competing priorities.
- Ability to operate effectively in ambiguity and complexity, making sound decisions with incomplete information
- Ability to balance delivery velocity, operational stability, and long-term capability development.
- Ability to lead through influence as well as authority, particularly across matrixed teams and vendor environments.
- Ability to sustain executive confidence through consistent, accurate, and actionable reporting.
- Bachelor’s degree in computer science, Engineering, Information Systems, Business, or a related discipline, or an equivalent combination of education and progressively responsible experience.
- Professional certifications such as PMP, Agile/Scrum, SAFe, ITIL, or relevant platform and cloud certifications (e.g., Guidewire, Microsoft).
- Ongoing commitment to professional development and continuous learning is expected.
To better serve the diversity of its community, Portage Mutual Insurance is dedicated to creating an inclusive and equitable environment for both clients and staff, and to the representation and hiring of all ethnicities, races, sexual/gender identities, cultural backgrounds, abilities, and beliefs. Portage Mutual Insurance is committed to providing a barrier-free environment for everyone who enters its premises, accesses its information, or uses its services. Should you require accommodation to participate as a candidate in the hiring process, please communicate your needs to the LHH Knightsbridge project team.
CONTACT INFORMATION
If you are interested in being considered for this exciting and impactful senior leadership position, please forward your cover letter and resume to Lindsay Millard, Senior Consultant at lindsay.millard@lhhknightsbridge.com.
Should you have any questions regarding this opportunity, please contact a member of the project team:
Tara Veysey, Partner
tara.veysey@lhhknightsbridge.com
416.570.1409
Lindsay Millard, Senior Consultant
lindsay.millard@lhhknightsbridge.com
416.928.4558
About LHH Knightsbridge – www.lhhknightsbridge.com
LHH helps organizations simplify the complexity associated with transforming their leadership and workforce so they can accelerate results, with less risk.
As global leaders in Talent and Leadership Development, Career Solutions and Executive, Interim and Mid-Level Search, we assist organizations in finding new talent, and helping their employees navigate change, become better leaders, develop better careers, and transition into new jobs. We have the local expertise, global infrastructure, and industry leading technology and analytics required to simplify the complexity associated with executing critical talent and workforce initiatives, reducing brand and operational risk. Teams across Canada and around the world leverage our proven programs and global experience to deliver tailored solutions to clients that align talent with the needs of their business.
Established in 1967, we have been providing outplacement services for 52 years. LHH is a wholly owned subsidiary of Adecco, SA, a publicly held Fortune Global 500 firm and the world’s leading provider of HR solutions, with approximately 32,000 FTE employees and 5,100 branches in over 66 countries and territories around the world. LHH has more than 4,000 employees around the globe including 2,200+ certified Career Coaches.
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