Chief Technology & AI Transformation Leader

Ansay & Associates; Wisconsin; On-site; USD 180,000 - 320,000; Full time

Benefits offered by this job

Career development opportunities

Job summary

Ansay & Associates seeks a visionary Chief Technology Officer to define and execute enterprise technology, AI, and data strategy from Wisconsin. You will align tech investments with business outcomes, strengthen cybersecurity, and drive measurable improvements in operations and client experience.

The role leads AI initiatives, vendor governance, and cross-functional collaboration with executive leadership to accelerate growth and efficiency across the agency.

Qualifications

• Demonstrated experience leading AI or ML initiatives with vendor selection.
• Familiarity with agentic AI frameworks and workflow automation platforms.
• Working knowledge of cybersecurity frameworks like SOC 2, NIST, ISO 27001.
• Experience with regulatory compliance in financial services or insurance.
• Proven track record of building and leading technology teams through change.
• Bachelor’s degree required; advanced degree preferred.
• 10+ years of technology or digital leadership experience.
• Experience in insurance or service-based industries preferred.
• Strong financial and analytical skills.
• Excellent communication and leadership abilities.

Responsibilities

• Define and execute a multi-year enterprise technology roadmap aligned with agency growth.
• Serve as strategic advisor to the CEO on technology investments and priorities.
• Establish technology as a measurable business driver with ROI and performance outcomes.
• Collaborate with VP of Operations, CRO, CFO, CDO, and CHRO to streamline workflows and improve customer experience.
• Identify, evaluate, and implement vendors and tools to boost productivity and ROI.
• Lead AI strategy deployment across operations, client experience, sales and support.
• Develop an AI governance framework for responsible use and auditability.
• Own vendor selection and performance management to ensure ROI and scalability.
• Ensure scalable, integrated tech ecosystem among management systems, CRM, data analytics.
• Drive data strategy for real-time decision-making and growth.

Skills

AI Leadership

Enterprise Technology

Strategy Development

Data Analytics

Cybersecurity Governance

Cross-functional Leadership

Communication Skills

Financial Acumen

Vendor Management

Digital Transformation

Education

Bachelor’s degree

Advanced degree preferred

Tools

n8n

Make

LangChain

Job description

Ansay & Associates seeks a visionary Chief Technology Officer to define and execute enterprise technology, AI, and data strategy from Wisconsin. You will align tech investments with business outcomes, strengthen cybersecurity, and drive measurable improvements in operations and client experience.

The role leads AI initiatives, vendor governance, and cross-functional collaboration with executive leadership to accelerate growth and efficiency across the agency.