Group Chief Information Officer

A highly regarded and financially strong property & casualty insurance organization is seeking a Segment CIO to lead technology strategy and execution for its Professional Liability business. This is a key member of the executive leadership team, with direct influence on growth, operational performance, and long-term modernization efforts across multiple operating companies.

This role offers the opportunity to step into a business that is both stable and expanding, where technology is viewed as a true enabler of underwriting and claims performance—not simply a support function. The organization has made consistent investments in its platforms, people, and long-term strategy, creating an environment where meaningful transformation can be executed with the right level of support and alignment.

What makes this different:

True seat at the table – You’ll partner directly with segment leadership, operating company presidents, underwriting, claims, and actuarial to shape strategy

Real transformation work – Modernizing core platforms across policy, billing, and claims while introducing scalable digital capabilities

Balanced environment – Financially strong, not driven by short-term cuts or layoffs

Complex, interesting business – Professional Liability is nuanced, specialized, and full of opportunity for someone who understands it

Employee Testimonials:

• No matter the role you're in, your voice matters.
• You are respected and valued.
• The amount of knowledgeable people you work with, they are always willing to lend you a helping hand.
• Innovative culture, great career growth opportunities, wonderful coworkers

Title: CIO Business Unit – Professional Liability P&C Insurance

Salary: $225,000 – $275,000 Bonus Equity

Location: Hartford, CT, Manhattan, NY or Chicago, Ill

This role offers the opportunity to step into a business that is both stable and expanding, where technology is viewed as a true enabler of underwriting and claims performance—not simply a support function. The organization has made consistent investments in its platforms, people, and long-term strategy, creating an environment where meaningful transformation can be executed with the right level of support and alignment.

Success in this role requires a strong understanding of the commercial insurance landscape, particularly within complex or specialty lines. The right individual will bring a track record of leading large-scale transformation initiatives within a matrixed environment, with the ability to balance long-term strategy and near-term execution. Equally important is the ability to build alignment across business and technology stakeholders, while developing and mentoring a high-performing team.

This position is well suited for a senior technology leader currently operating within an established insurance carrier who is looking for broader scope, greater visibility, and the ability to shape the direction of a growing business segment.

For those who have spent their careers in property & casualty insurance and are ready to take on a role with real influence and long-term impact, this represents a compelling next step.

The CIO will serve as a strategic partner to senior business leadership, working closely with underwriting, claims, actuarial, and product teams to ensure that technology initiatives are directly tied to business outcomes. This includes leading the continued evolution of core systems across policy, billing, and claims, while advancing digital capabilities, data and analytics, and the thoughtful adoption of emerging technologies such as AI and API-driven architectures.

What you’ll be leading:

• A multi-company technology organization supporting diverse lines of Professional Liability business
• Core system evolution (policy, billing, claims) — both build and buy strategies
• Data, analytics, and AI initiatives that actually tie back to underwriting performance and loss outcomes
• API-driven architecture, cloud adoption, and modern engineering practices
• Strategic vendor partnerships and ecosystem decisions
• A strong team that needs direction, alignment, and continued elevation

Ideal experience:

• Deep experience in commercial insurance, ideally within Professional Liability or complex specialty lines.
• You’ve led enterprise-scale transformation, not just incremental upgrades
• Strong understanding of policy, billing, and claims platforms — and the tradeoffs between custom vs. packaged solutions.
• Comfortable operating in a matrixed environment, influencing across business units.
• Able to translate between business strategy and technology execution without losing either side