Chief Technology Officer

**This position is located in Wisconsin 

Role, Function & Position Summary 
Under the direction of the CEO and in partnership with the executive leadership team, the Chief Technology Officer (CTO) is responsible for defining and executing the agency's enterprise technology, AI, digital transformations and data strategy. This role is accountable for aligning technology investments with business outcomes, with a specific focus on deploying AI-driven capabilities, strengthening the agency's cybersecurity posture, and driving measurable improvements in operational efficiency, client experience, and revenue per FTE. 

Major Accountabilities

Enterprise Technology Strategy & Leadership 

• Define and execute a multi-year enterprise technology roadmap aligned with agency growth and scalability objectives. 
• Serve as a strategic advisor to the CEO and executive leadership team on technology investments and priorities. 
• Establish technology as a measurable business driver with defined ROI and performance outcomes. 

Operational Efficiency & Revenue Optimization  

• In close collaboration with the VP of Operations, CRO, CFO, CDO, and CHRO, execute key components of the Customer Experience Strategic Initiative, focusing on streamlining workflows, improving operational effectiveness, and enhancing the overall customer experience. 
• Partner with operations leaders to identify, evaluate, and recommend vendors, technologies, and tools that enhance employee productivity and operational efficiency. Lead the implementation process for approved solutions, including pilot programs, integration planning, change management, adoption strategies, and measurement of return on investment (ROI). 

Systems Architecture & Platform Strategy  

• Ensure a scalable and integrated technology ecosystem across: 
• Agency management systems 
• CRM and client experience platforms 
• Data and analytics infrastructure 
• Reduce duplication, friction points, and manual processes through system interoperability. 

Data & Analytics Strategy 

• Establish an enterprise data strategy to support real-time decision-making. 
• Identify and leverage internal and external data sources for growth, market expansion, and M&A. 

Vendor & Insurtech Management  

• Own vendor selection, negotiation, and performance management. 
• Ensure alignment of vendor investments with strategic objectives and financial benchmarks. 
• Build and manage a high-performing ecosystem of Insurtech partners. 
• Drive accountability for vendor ROI, utilization, and scalability. 

Digital Transformation & Automation  

• Lead the agency's AI strategy, including the evaluation, deployment, and governance of AI, machine learning tools, and automations across operations, client experience, sales, and support functions. 
• Move beyond task-level automation into agentic workflows, LLM-assisted processes, and intelligent decision support. 
• Establish and implement an AI governance framework that ensures responsible use, auditability, and measurable outcomes. 

Cybersecurity, Risk & Governance 

• Own the agency's cybersecurity posture, including threat detection, incident response planning, vendor risk management, and compliance with state insurance regulatory requirements, such as NYDFS and the NAIC model law. 
• Establish a formal risk framework aligned with industry standards, such as SOC 2, ISO 27001, or equivalent. Ensure cyber risk is reported at the executive and board level with defined thresholds and escalation paths. 

Qualifications

• Demonstrated experience leading AI or ML initiatives, including vendor selection and build-vs-buy decisions. 
• Familiarity with agentic AI frameworks and workflow automation platforms, such as n8n, Make, LangChain, or equivalent.  
• Working knowledge of cybersecurity frameworks, including SOC 2, NIST, and ISO 27001.  
• Experience with regulatory compliance in a financial services or insurance context.  
• Track record of building and leading technology teams through periods of significant change. 
• Bachelor’s degree required; advanced degree preferred. 
• 10+ years of technology or digital leadership experience. 
• Experience in insurance or service-based industries preferred. 
• Proven track record of enterprise transformation. 
• Strong financial and analytical skills. 
• Excellent communication and leadership abilities.

Why Work for Ansay? 

Ansay is a growing, employee-focused insurance agency with strong community roots. We value collaboration, continuous improvement, and professional growth, and we invest in our people through training, technology, and career development opportunities. 

At Ansay & Associates we believe in building lasting relationships and bringing every customer a level of service that exceeds expectations - It’s the Ansay Way! As such the following core values guide our behaviors: Respect – Compassionate and Loyal Integrity – Honesty and Trustworthy, Accountability – Responsible for Actions & Results, Passion – Unfailing Dedication & Pride In Work, Positive “I Can Do” Mentality – Constant, Never-Ending Improvement, Excellence / Professionalism – High Expectations & Pursuit of Opportunities to further our Capabilities