Fractional Head of Information Technology & Security

MUST BE CURRENTLY BASED IN THE PITTSBURGH AREA

(Opportunity to Transition to Permanent Role)

Our client is a rapidly growing insurance services organization formed in 2023 by a seasoned leadership team with a shared vision for modernizing how independent agencies operate. With multiple partner agencies already in place and an active growth strategy underway, the organization is seeking a Fractional Head of Information Technology & Security to help build, connect, and secure the technology foundation that will support long-term scale.

This is a hands-on, high-impact role ideal for a technology leader who enjoys working in an entrepreneurial environment and wants the opportunity to help shape both near-term execution and long-term strategy. As the organization grows, this role is expected to evolve into a full-time, permanent leadership position.

Position Overview

The Fractional Head of IT & Security will serve as the central technology leader across all partner agencies, owning IT strategy, cybersecurity, systems integration, and day-to-day technology enablement. This individual will balance strategic planning with practical execution—from desk-side support and vendor coordination to future-state architecture and data security.

You will work closely with executive leadership and external technology partners to streamline systems, connect data across agencies, and ensure secure, compliant operations as the organization scales.

Key Responsibilities

Technology Strategy & Leadership

• Develop and execute a technology roadmap aligned with business growth and acquisition strategy

• Act as a trusted advisor to leadership on current and future technology needs

• Evaluate emerging technologies to improve efficiency, security, and scalability across agencies

• Help define what “good” technology looks like for a modern, multi-agency insurance platform

Systems Integration & Enablement

• Oversee IT operations and technology standards across all owned agencies

• Connect systems, data, and workflows to improve visibility, reporting, and efficiency

• Support agency leadership with technology adoption, training, and best practices

• Partner with third-party providers supporting hardware, infrastructure, and implementation

Cybersecurity & Risk Management

• Establish and maintain security standards to protect agency and client data

• Ensure appropriate controls, access management, and data protection practices are in place

• Lead vendor risk assessments and oversee third-party security posture

• Develop incident response, disaster recovery, and business continuity plans

Hands-On Support & Execution

• Provide pragmatic, solutions-oriented support ranging from troubleshooting to process improvement

• Serve as the escalation point for technology issues across the organization

• Translate business needs into practical, secure technology solutions

Vendor & Partner Collaboration

• Act as the primary liaison with external technology partners supporting development and infrastructure

• Manage vendor relationships, contracts, and service levels

• Ensure technology investments align with business priorities and ROI expectations

Ideal Background

• Experience leading IT in a small, high-growth, or startup-style environment

• Proven ability to operate comfortably at both the strategic and tactical levels

• Strong understanding of systems integration, data flows, and security fundamentals

• Experience supporting multiple business units or locations is strongly preferred

• Background in insurance, financial services, or other regulated environments is helpful but not required

Technical & Professional Skills

• Broad IT leadership experience covering infrastructure, applications, security, and vendors

• Strong working knowledge of Microsoft-based environments (Microsoft 365, SharePoint, etc.)

• Experience with cloud or hybrid environments

• Practical cybersecurity and data protection experience

• Ability to communicate complex technical concepts to non-technical stakeholders

Why This Role Stands Out

• Fractional flexibility with a clear path to a permanent leadership role

• Opportunity to build from the ground up rather than inherit legacy systems

• Direct access to executive leadership and influence over company direction

• A true “player/coach” role with visibility, autonomy, and long-term upside

• While this is a VP title role you must be willing to work at all levels