Deputy Chief Technology Officer | Remote

King’s Insurance Staffing is partnering with an established Property & Casualty insurance carrier to identify a technology leader who will join as Deputy Chief Technology Officer, work alongside the current CTO, and prepare to assume the CTO position through a structured succession plan. This opportunity is especially well suited to someone whose foundation is application development, insurance core systems, and enterprise technology implementations, with the leadership skills to connect technology decisions to business results.

This is a fully remote position with limited travel requirements (quarterly or semi-annually for board meetings and leadership events). You’ll initially focus on applications, legacy system migrations, and modernization initiatives while working directly with business leaders to prioritize projects, improve efficiency, and make effective use of internal teams and vendor partners. Over time, your responsibilities will expand across the technology organization, including infrastructure, cybersecurity, financial management, governance, and board-level communication.

With a 35+ person IT organization (and growing), including approximately 22 employees focused on applications, this role offers meaningful influence over technology direction, resource allocation, and business outcomes.

What We’re Looking For

• 10+ years of progressive technology leadership experience, with substantial responsibility for application development and enterprise systems.
• 5+ years of P&C insurance experience with a strong understanding of how applications and data connect underwriting, claims, rating, and other business functions.
• Experience leading legacy migrations and core application implementations, such as policy administration, rating, underwriting, or claims platforms.
• Experience with Guidewire, Duck Creek, or comparable insurance platforms. Guidewire experience is a plus, rather than a requirement.
• A track record of owning technology delivery within an organization and partnering directly with internal business teams.
• Strong experience managing vendors, negotiating contracts, reviewing agreements, and overseeing technology budgets.
• An approachable, collaborative leadership style, with the ability to explain complex issues, navigate differing priorities, and provide sound guidance to executives.
• A development background and experience with AI integrations, automation, or other efficiency initiatives would be valuable.
• Candidates should bring fresh ideas while taking time to understand the business, its people, and its existing strengths.

Salary & Benefits

• Base salary: $190,000–$210,000+, plus comprehensive benefits and Lucrative Short-term and Long-term incentive plans
• Flexible schedule and ability to work remote
• Comprehensive medical, dental, and vision insurance.
• Paid time off and company-paid holidays.
• Retirement programs, including a 401(k), pension, and profit-sharing.
• Additional company-sponsored benefits and programs.