Chief Information Officer

GUARANTEE TRUST LIFE INS CO•Glenview, IL

3d•Hybrid

About The Position

Guarantee Trust Life Insurance Company (GTL) is currently seeking a Chief Information Officer to join our team! Since 1936, GTL has offered cutting-edge insurance solutions and personalized service for our policyholders and distributors, while supporting personal growth and civic involvement from our employees. We’re seeking candidates who are looking for meaningful work, who want to invest in their growth, and contribute to a company built on timeless virtues and best business practices. This position is required to work on-site in our Chicagoland (Glenview, IL) office most days. Everyone receives 3 flexible remote days per month and 6 additional Friday PTO days each year! And, we offer half-day Fridays – every Friday! The Chief Information Officer (CIO) serves as GTL’s senior technology executive and a member of the Executive Committee, responsible for shaping enterprise technology strategy and ensuring technology capabilities enable business growth, operational excellence, innovation, client service, and effective risk management. GTL’s CIO leads GTL’s Information Technology department with enterprise-wide responsibility for applications, infrastructure, cybersecurity, software development, artificial intelligence, architecture, service delivery, vendor strategy, and technology transformation. Partnering closely with business and functional leaders, the CIO modernizes GTL’s technology environment, strengthens resilience and governance, and delivers a roadmap that supports the company’s strategic priorities while contributing to enterprise performance, culture, and long-range planning.

Requirements

Executive presence with the ability to influence senior leaders and build trust across the organization.
Strong strategic thinking, operational discipline, and a bias for execution.
Excellent communication skills with the ability to translate complex technology topics for non-technical audiences.
Proven ability to lead change, align stakeholders, and develop high-performing teams.
Sound judgment in balancing innovation, risk, speed, cost, and long-term enterprise value.
Deep knowledge of enterprise applications, infrastructure, cybersecurity, analytics, architecture, and IT service management.
Strong insurance and/or financial services acumen, with deep understanding of industry operations, regulatory environments, and the role of technology in driving growth, efficiency, and risk management.
Experience across Microsoft enterprise platforms, including Windows Server, Active Directory/Azure AD, Azure cloud services, and web infrastructure.
Strong command of modern development and DevOps tooling, including Azure Pipelines, GitHub, Docker containerization, and mobile application development.
Experience leading large-scale transformation, modernization, and implementation efforts.
Strong understanding of governance, risk management, resiliency, disaster recovery, vendor strategy, and technology investment oversight.
Working knowledge of cloud platforms, integration, automation, AI enablement, and emerging technologies.
Bachelor’s degree in Information Technology, Computer Science, Engineering, or a related field required; advanced degree such as an MBA is a plus.
15+ years of progressive technology leadership experience, including significant responsibility for enterprise IT strategy, operations, transformation, and organizational leadership in the insurance or financial services industries.

Nice To Haves

advanced degree such as an MBA is a plus

Responsibilities

Set and lead GTL’s enterprise technology strategy, operating model, multi-year roadmap in alignment with the company’s strategic priorities and Executive Committee alignment.
Serve as a member of the Executive Committee, contributing to enterprise planning, operating performance, organizational effectiveness, and strategic decision-making.
Lead the IT department (team of approximately 65 professionals) across enterprise applications development and support, infrastructure, cybersecurity, architecture, service delivery, and end-user support.
Drive modernization of GTL’s technology landscape, including core systems, cloud capabilities, integration, automation, and digital enablement.
Establish governance, standards, and performance metrics that improve reliability, scalability, security, service quality, and cost discipline.
Partner with business leaders to translate strategic priorities into technology investments, delivery plans, and measurable business outcomes.
Oversee enterprise cybersecurity, resilience, business continuity, vendor strategy, and the IT budget.
Build a high-performing technology organization and communicate technology strategy, priorities, risks, and transformation progress to executive stakeholders.