Head of Information Technology

Position Summary

Reporting to the Chief Underwriting Officer (CUO) The Head of Information Technology (IT) is responsible for shaping and executing Signal’s technology strategy in alignment with business goals. This leader will oversee the IT organization, drive the continued evolution of core insurance technologies, manage the partners across the technology ecosystem, and deliver innovative solutions that enhance customer experience while enabling operational efficiency.

The ideal candidate will have deep experience in core insurance systems, digital transformation, and technology leadership, with the ability to manage internal staff and multiple third-party technology partners. As a senior leader in the organization, it is expected that you will be versed in working with senior management teams and presenting to Board level officers.

This role needs to be someone who is a continuous learner, staying ahead of emerging technologies, trends, and evolving expectations across the technology space.

Key Responsibilities

Strategic Leadership

• Work through the continuing definition and execution of Signal’s IT strategy to support business growth, operational resilience, and enhanced effectiveness
• Partner with senior leadership to align technology initiatives with business objectives
• Serve as a key advisor to the senior leadership team and Board of Directors on technology trends, risks, and opportunities

Technology & Operations

• Oversee core insurance systems (claims, underwriting, portal) and enable an optimal integration strategy across the architecture
• Manage overall enterprise architecture, infrastructure, cloud adoption, and cyber / data security programs
• Drive modernization and evolution of the technology footprint toward scalable, cloud-based, and API-enabled solutions
• Champion the effective use of Microsoft Azure and other strategic platforms to optimize our effectiveness

Innovation & AI Adoption

• Lead the adoption of AI to drive business insights and efficiency across the organization, embedding capabilities into Signal’s technology solutions
• Foster a culture of innovation to identify emerging technologies that can differentiate the business

Team Leadership

• Build, mentor, and lead a high-performing IT team (hybrid in-sourced and out-sourced) with expertise in application management, service delivery, cloud / infrastructure, and security
• Champion change management and continuous improvement across the broader Signal organization
• Foster a culture of collaboration, accountability, and humility

Governance, Risk & Compliance

• Ensure IT systems meet all regulatory, compliance, and cybersecurity standards, working with the group CISO and other regulatory compliance officers
• Assist with the design and testing of business continuity, disaster recovery, and information security programs
• Maintain vendor governance and ensure performance accountability of third-party technology partners

Qualifications

• Bachelor’s degree in Computer Science, Information Systems, Engineering, or related field (Master’s preferred)
• 15 years of progressive IT leadership experience, including at least 10 years in the insurance industry or a top-tier consulting firm serving insurers
• Proven success in leading enterprise technology strategy, large-scale transformations, and vendor management
• Strong knowledge of core insurance technologies (policy administration, claims, billing, CRM, digital engagement)
• Deep expertise in Microsoft Azure and cloud computing
• Experience with data management, cybersecurity, and regulatory compliance
• Track record of successfully implementing AI, automation, or digital initiatives
• Exceptional communication skills with ability to present complex technology topics to business leaders and the Board
• Demonstrated financial acumen in managing multi-million-dollar technology budgets
• Experience with Salesforce, Workday, MuleSoft and Azure DevOps preferred

Competencies

• Strategic thinker with strong business and risk management acumen
• Strong decision-making, prioritization, and execution skills
• Collaborative, with ability to influence across executive and board levels
• Results-oriented and not afraid to dive into the project to get things done

Job Type: Full-time

Pay: $180,000.00 - $220,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Employee assistance program
• Flexible spending account
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Parental leave
• Vision insurance

Education:

• Bachelor's (Required)

Ability to Commute:

• South Norwalk, CT 06854 (Required)

Work Location: In person

Salary : $180,000 - $220,000