Organization: Confidential

Position Title: Chief Technology Officer (CTO)

Reports to: President & Chief Executive Officer

Location: Hybrid/Remote, Canada THE ORGANIZATION

Our client is a well-established, property and casualty insurance organization with a long history of success in Canada. Guided by strong values the organization has earned a strong reputation for responsiveness and personalized service while maintaining a collaborative and relationship-driven culture. Its success has been built on long-standing broker relationships, a commitment to service excellence, and a business model that balances innovation with the values and responsiveness often associated with community-focused organizations.

Today, the company continues to pursue sustainable growth while maintaining a culture that emphasizes partnership, accountability, and exceptional client outcomes.

Operating through an extensive network of independent distribution partners, the organization has established a broad national presence and a strong market position. The organization provides a comprehensive portfolio of insurance solutions across personal, commercial, and specialty lines, serving a large and diverse policyholder base across the country. It is recognized for its customer-centric approach, particularly in claims service, and has consistently focused on delivering tailored solutions that meet the evolving needs of individuals, businesses, and agricultural clients.

THE OPPORTUNITY

Our client is seeking an accomplished Chief Technology Officer (CTO) to join its executive team. At a pivotal stage in its evolution, the organization requires a transformational leader to advance its ambitious growth strategy across a multi-provincial platform.

Reporting directly to the President & CEO, the CTO is a member of the Senior Leadership Team responsible for the organization’s enterprise technology strategy, governance, cybersecurity, digital transformation, data, and artificial intelligence agenda. The CTO ensures technology investments align with business priorities, regulatory requirements, and risk appetite while enabling innovation, operational excellence, and sustainable growth. The role provides leadership for enterprise architecture, applications, infrastructure, cybersecurity, data and analytics, AI, system integrations, development operations, and strategic technology partnerships.

The CTO serves as a trusted advisor to the Executive Team and Board, balancing operational stability with future-focused technology innovation.

Within the first 12-18 months, the successful CTO will position the organization for its next phase of growth by:

- Executing the organization’s technology, digital transformation, and AI strategies.
- Ensuring reliable, secure, and resilient technology operations.
- Delivering priority technology investments with measurable business value.
- Strengthening cybersecurity, governance, and risk management.
- Improving vendor performance and optimizing technology spending.
- Advancing digital maturity, innovation, and responsible AI adoption.
- Enhancing employee, broker, and member experiences through technology and data-driven solutions.
- Building future-ready technology capabilities and leadership bench strength.

KEY RESPONSIBILITIES

Strategic Leadership & Business Partnership





- Develop and execute the organization's enterprise technology, data, and AI strategy in alignment with corporate objectives.
- Advise the CEO, Senior Leadership Team, and Board on technology trends, opportunities, risks, and investments.
- Lead enterprise technology governance, portfolio prioritization, investment planning, and performance measurement.
- Foster a culture of innovation, continuous improvement, and business partnership across the organization.

Technology, Architecture & Delivery

- Define and maintain the organization’s technology vision, enterprise architecture, standards, and technology roadmap.
- Oversee application development, Guidewire strategy, digital platforms, cloud services, integrations, and DevOps capabilities.
- Ensure technology solutions are secure, scalable, resilient, and aligned with business needs.
- Lead the successful delivery of technology initiatives and realization of business value.

Data, AI & Innovation

- Develop and oversee the organization’s enterprise data and AI strategy, governance framework, and roadmap.
- Leverage AI, automation, advanced analytics, and emerging technologies to improve operational performance, decision-making, staff & broker experience, and business outcomes.
- Ensure the ethical, secure, transparent, and compliant use of AI technologies.
- Promote innovation through experimentation, technology partnerships, and continuous advancement of the organization’s digital capabilities.

Vendor & Technology Partner Management

- Develop and execute enterprise sourcing and vendor strategies.
- Lead strategic technology partnerships, contract negotiations, vendor performance management, and value realization.
- Optimize technology investments while ensuring service quality, security, and business alignment.

People Leadership & Culture

- Build and lead a high-performing technology organization focused on accountability, innovation, customer service, and continuous learning.
- Develop leadership capabilities, succession plans, and talent pipelines within the technology function.
- Foster a culture that encourages collaboration, knowledge sharing, and professional growth.
- Promote engagement and ensure technology teams are aligned with the organization’s values and strategic objectives.

Board & Committee Liaison

- Prepare and present Executive reports/presentations to the Board at regular and adhoc meetings.
- Serve as key liaison to the Technology Committee including preparations, presentations and recommendations.
- Foster an open, honest and authentic relationship with the board and committee members.

IDEAL SKILLS & EXPERIENCE The ideal candidate will possess the following experience, qualifications, knowledge, skills and attributes:

- Experience leading technology functions within mid-sized or growth-oriented organizations, combining strategic leadership with a pragmatic,



hands-on approach and a willingness to engage directly with teams to advance key initiatives and deliver business outcomes.
- Insurance or financial services experience would be considered a strong asset.
- Significant experience leading enterprise technology strategy, governance, cybersecurity, and large-scale business transformation including digital transformation initiatives and enterprise technology modernization.
- Proven experience overseeing application development, enterprise architecture, cloud technologies, DevOps, and systems integration.
- Demonstrated success managing complex vendor ecosystems and strategic technology partnerships.
- Experience presenting to executive leadership teams and Boards of Directors.
- Experience evaluating, implementing, or governing AI, machine learning, advanced analytics, automation, or emerging technology solutions.
- Strong understanding of AI governance, ethical AI principles, data privacy, cybersecurity, and regulatory considerations.
- Experience developing technology roadmaps that balance innovation with operational excellence and risk management.
- Demonstrated knowledge of how AI can be applied within financial services or insurance environments is considered a strong asset.
- Exceptional leadership, influence, and stakeholder management skills.
- University degree in Computer Science, Information Technology, Engineering, Business, or a related discipline.
- Master's degree in Business Administration, Information Systems, or a related field is considered an asset.
- Minimum 10-15 years of progressive leadership experience in information technology, digital transformation, or technology operations.

If you require accommodation to participate as a candidate in the hiring process, please communicate your needs to the LHH Knightsbridge project team.

This is a job posting for an existing role/vacancy. LHH Knightsbridge does not use artificial intelligence (AI) to screen, assess, or select applicants for a position.

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 recent 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.

📌 Chief Technology Officer (Greater Toronto Area)
🏢 LHH Knightsbridge
📍 Greater Toronto Area