Kyler Professional Search · 13 hours ago
IT and Security Leader Fractional
Pittsburgh, PA
Contract
Onsite
Senior Level, Lead/Staff, Director/ExecutiveKyler Professional Search is seeking a Fractional Head of Information Technology & Security for a rapidly growing insurance services organization. This hands-on role involves developing IT strategy, overseeing cybersecurity, and ensuring systems integration across partner agencies, with the potential to transition to a permanent position.
Human Resources
Hiring Manager
Amylyn Kyler
Responsibilities
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
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
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
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
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
Qualification
Required
MUST BE CURRENTLY BASED IN THE PITTSBURGH AREA
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
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
Preferred
Experience supporting multiple business units or locations is strongly preferred
Background in insurance, financial services, or other regulated environments is helpful but not required
Company
Kyler Professional Search
In today’s ever changing workforce many organizations find themselves… • Paying the high price of executive and/or contingent Recruiters to source for niche requirements.
Founded in 2015
2-10 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase