Description

Reporting to the Chief Financial Officer, the Director of Information Technology (IT) serves as the senior technology leader for the organization. This role is accountable for shaping, executing, and continuously improving the organization’s technology vision, strategy, and operational delivery.

The Director, IT is responsible for the full lifecycle of technology leadership, including technology strategy, cybersecurity, data and reporting enablement, systems architecture, vendor management, and delivery of technology initiatives that directly support business objectives. This role is both strategic and highly hands-on requiring a leader who is willing and able to engage directly in day-to-day technical work, problem solving, and project execution when necessary.

This position operates in a regulated insurance environment and plays a critical role in protecting sensitive client and financial data, ensuring system reliability, and maintaining audit and compliance readiness. The Director is expected to demonstrate strong process discipline, rigorous project management, and a high degree of personal accountability for outcomes. This role partners closely with executive leadership and business stakeholders to translate business needs into practical, secure, and scalable technology solutions.

Requirements

Essential job duties include but are not limited to:

Develop, own, and execute the organization’s overall technology strategy and roadmap, ensuring alignment with business objectives, financial priorities, and operational needs.
Serve as the primary technology advisor to executive leadership, providing insight on technology trends, digital transformation opportunities, emerging risks, and trade-offs.
Own governance frameworks for technology risk management, cybersecurity, data integrity, and compliance in a regulated insurance environment.
Lead, manage, and develop the internal IT team, setting clear priorities, expectations, and accountability for execution and outcomes.
Act as a working manager, remaining hands-on in infrastructure, systems, security, and project delivery as needed to support business continuity and success.
Establish and maintain strong operational hygiene, including documentation, standard operating procedures, change management, and incident response processes.
Own and govern the organization’s technology stack, including evaluation, selection, implementation, integration, and retirement of systems and tools.
Evaluate, vet, and approve new software, platforms, and vendors to ensure alignment with the technology roadmap, security standards, scalability, and cost discipline.
Assess emerging technologies, including automation and artificial intelligence, and determine practical, value-driven use cases for the organization.
Lead and rigorously manage technology projects and initiatives, ensuring delivery within defined scope, timeline, and budget.
Establish and enforce disciplined project management practices, including prioritization, resource allocation, risk management, and status reporting.
Oversee enterprise data initiatives, including system migrations, platform integrations, and data quality standards to ensure accuracy, integrity, and usability.
Own the organization’s cybersecurity posture, including security policies, access management, incident response, security awareness, and ongoing risk mitigation.
Serve as executive sponsor and escalation point for security incidents, outages, and high-impact technology issues.
Ensure compliance with applicable regulatory requirements, industry best practices, and audit expectations.
Provide executive-level oversight and support for core business systems, including the Applied Epic agency management system, ensuring effective use, stability, and alignment with business processes.
Partner with business leaders to improve data reporting, analytics, and technology-enabled decision making.
Manage IT budgeting, forecasting, vendor contracts, and cost controls in partnership with Finance.
Collaborate with managed service providers (MSP), managed security service providers (MSSP), and other partners to enhance delivery and security outcomes as applicable.
Drive continuous improvement in IT service delivery, system reliability, and operational effectiveness.

Qualifications

Note that these requirements are representative, but not all-inclusive, of the knowledge, skill, and ability required to perform this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

Required Knowledge/Skills

Strong understanding of enterprise infrastructure, cloud and hybrid environments, identity and access management, and cybersecurity principles.
Proven experience developing and executing technology strategy and governance frameworks.
Strong project management discipline with the ability to manage scope, cost, and timelines rigorously.
Experience overseeing cybersecurity programs, risk management, and incident response.
Ability to evaluate and govern technology stack decisions with a focus on integration, security, scalability, and ROI.
Strong business partnering skills, including the ability to translate technical concepts into business impact and recommendations.
Excellent organizational, process design, and documentation skills.
Experience working in agile or iterative delivery environments.
Strong leadership, communication, and vendor management skills.
Willingness to remain hands-on and directly involved in operations and delivery as required.
Evening, weekend, and on-call work may be required as job duties demand.

Experience

Minimum of 10+ years of progressive experience in IT operations, infrastructure, systems, or technology leadership roles.
Demonstrated experience leading IT teams and managing complex technology environments.
Proven track record of strategic IT planning, governance, and risk management.
Experience delivering enterprise technology initiatives, system migrations, or integrations.
Experience working in insurance, financial services, or other regulated professional services environments preferred.

Education/Certifications

Bachelor’s degree in Information Technology, Computer Science, or a related field required; equivalent experience considered.
Preferred Certifications/Experience (not required):
CISSP, CISM, or other cybersecurity certifications
Microsoft Azure Administrator or Architect
Microsoft Identity and Access Administrator
ITIL, PMP, or Agile/Scrum certifications
Experience with Power BI, including partnering with business stakeholders on data visualization, reporting requirements, and dashboard enablement.

Gregory & Appel

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