Head of Information Technology

<p>We’re seeking an experienced, strategic <strong>Head of IT</strong> to lead the company’s technology vision, infrastructure, and operations. This executive role is responsible for ensuring technology enables business growth, operational efficiency, data security, and an exceptional employee and client experience across the organization.</p><p><br></p><p>The<strong> Head of IT </strong>will bring extensive experience within insurance brokerage environments, with a deep understanding of industry-specific systems, workflows, and operational demands. This individual will possess strong expertise in platforms such as Applied Epic, along with a proven ability to support scalable growth, optimize system performance, and align technology infrastructure with the evolving needs of a multi-state insurance organization.</p><p><br></p><p><strong>Key Responsibilities</strong></p><ul><li>Serve as the <strong>enterprise owner of Applied Epic</strong>, ensuring optimal configuration, performance, and adoption across all business units</li><li>Lead system enhancements, integrations, and workflow standardization to improve productivity and data accuracy</li><li>Partner with Sales, Service, and Operations leadership to align Epic workflows with business objectives</li><li>Establish and maintain <strong>enterprise-wide IT asset management practices</strong>, including: Hardware lifecycle management (procurement, deployment, replacement), Software licensing compliance and optimization</li><li>Implement tracking systems to ensure visibility across all IT assets and reduce operational risk</li><li>Partner with Finance, Sales, and Operations teams to deliver <strong>accurate and timely reporting</strong></li><li>Oversee data integration and reporting tools tied to: Production metrics, Revenue tracking, Pipeline and performance KPIs</li><li>Ensure data integrity across systems, particularly between Applied Epic and reporting platforms</li><li>Lead enterprise cybersecurity strategy, including prevention, detection, and response protocols</li><li>Ensure compliance with all applicable regulations, including: Data privacy standards, Carrier and client data protection requirements</li><li>Oversee security tools, policies, and training programs to mitigate risk across the organization</li></ul><p><br></p><p><strong>Required Qualifications</strong></p><ul><li>10+ years of progressive IT leadership experience, ideally within an insurance brokerage or similar environment</li><li>Deep, hands-on expertise with Applied Epic (required)</li><li>Proven experience managing multi-site / multi-state IT operations</li><li>Strong background in: IT infrastructure and cloud environments, Systems integration and data management, Cybersecurity frameworks and risk management</li><li>Experience supporting high-growth or PE-backed organizations preferred</li><li>Demonstrated ability to align IT strategy with business outcomes</li></ul><p><br></p><p><strong>Preferred Qualifications</strong></p><ul><li>Experience within the insurance, financial services, or professional services industries</li><li>Familiarity with agency management systems, cloud‑based infrastructure, and modern collaboration tools</li><li>Experience supporting high‑growth or private‑equity‑backed organizations</li><li>Background in data analytics, system integrations, or technology‑enabled process improvement</li></ul><p><br></p><p><strong>Why Our Team</strong></p><ul><li>Executive leadership role with direct impact on enterprise strategy and scalability</li><li>Opportunity to modernize and shape IT capabilities in a rapidly growing organization</li><li>Collaborative executive team and strong organizational support</li><li>Competitive compensation and comprehensive benefits</li></ul><p></p>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

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The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

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Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

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This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...