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The Chief Technology Officer (CTO) will serve as a strategic technology leader responsible for setting the vision, strategy, and execution of Core Specialty’s technology roadmap. Reporting to the Chief Information Officer (CIO), the CTO will ensure that our systems, infrastructure, and products align with business objectives, deliver measurable value, and meet the highest standards of security, reliability, and scalability.

This role requires a proven leader who can balance innovation with operational excellence, guiding multidisciplinary teams across engineering, architecture, and operations.

Key Accountabilities/Deliverables:

• Define and execute the enterprise technology strategy in alignment with business goals.

• Drive digital transformation initiatives to modernize platforms, streamline operations, and enhance customer experiences.

• Partner with executive leadership on long-term business planning and growth.

• Oversee enterprise architecture, software engineering, infrastructure, end-user computing, service management, and operations.

• Lead development and implementation of scalable platforms, including cloud adoption (Azure, AWS), insurance underwriting systems and DevOps automation.

• Ensure system resilience, uptime, and performance to support mission-critical insurance operations.

• Identify opportunities for AI, machine learning, and automation to improve underwriting, claims, and security.

• Evaluate and integrate new technologies that drive efficiency and competitive advantage.

• Build strong relationships with vendors (Microsoft, AWS, Zscaler, Palo Alto, Duck Creek) and technology consulting partners.

• Lead and develop a diverse team of engineers, architects, SREs and operations staff.

• Foster a culture of collaboration, innovation, accountability, and continuous improvement, embracing ownership across all technology teams.

• Scale the technology organization to support ongoing mergers & acquisitions and rapid business growth.

Technical Knowledge and Understanding:

• Exceptional communication, influencing, and executive presence skills.

• Familiarity with and expertise in insurance policy administration systems, especially Duck Creek systems, and integration and development around policy administration system.

• Strong financial acumen with experience in IT budgeting, capitalizable expenses, and fixed-asset accounting.

Experience:

• 15+ years of progressive IT leadership experience, with 7+ years in senior executive roles.

• Deep experience in insurance, financial services, or highly regulated industries preferred.

• Proven track record in cloud transformation, platform engineering, cybersecurity, and enterprise systems.

• Demonstrated success in leading through M& A integrations and scaling technology teams in growth environments.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa for this position.



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At Core Specialty, you will receive a competitive salary and opportunities for professional development and advancement. We offer medical, dental, vision, and life insurances; short and long-term disability; a Company-match of 100% of a 6% contribution 401(k) plan; an Employee Assistance Plan; Health Savings Account, Flexible Spending Account, Health Reimbursement Account, and a wellness program