Position Summary

The VP, 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

NOTE: This position is located in South Norwalk, CT and requires at least 3 days in office.

Salary Range: $180,000 - $220,000 (Depending on Experience)

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VP, Head of IT

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