Are you a visionary tech leader who thrives in fast-moving, entrepreneurial environments? Do you know how to translate complexity into clarity, break down silos, and lead high-impact transformation across people, platforms, and performance? A privately held, financially strong commercial insurance and benefits brokerage is conducting a search for a Chief Technology Officer to be based at their Midwest headquarters. This is not your typical CTO role. It’s hands-on, collaborative, and impact-driven—focused on AI integration, data structuring, and software enablement to unlock smarter, faster, and more connected decision-making across the enterprise. You’ll partner directly with business leaders to understand operational pain points, design scalable solutions, and champion a culture of continuous improvement and shared knowledge.

Help structure high-volume internal data to drive smarter analytics and better client interfacing. Identify opportunities to bring automation, AI, and RPA into key workflows and support adoption. Guide internal and external dev teams, define product specs, and support scalable systems architecture. Lead digitization initiatives and modernization of legacy systems across multiple business units. Build trust with practice leaders, align priorities across departments, and drive progress without bureaucracy.

You’re curious by nature, strategic by instinct, and practical by experience. You’ve likely served as a CTO or senior IT/product leader in a mid-sized insurance, brokerage, or B2B services organization, where you helped teams adopt AI, migrate from legacy systems, and rethink how tech supports business. Deep experience with data management, modeling, and analytics platforms. Hands-on leadership in software development and product delivery. Proven ability to lead AI, automation, or digitization initiatives. Strong understanding of how to prioritize across diverse business units. Excellent communicator with both technical and non-technical stakeholders. Collaborative and passionate about solving business problems.

Competitive salary, benefits, eligible for equity stake