CTO, AI Strategy & Digital Transformation

Ansay & Associates, LLC; Wisconsin; On-site; USD 180,000 - 260,000; Full time

Job summary

Ansay & Associates, LLC is seeking a Chief Technology Officer to define and execute enterprise technology, AI, and data strategies in partnership with the executive team. You will align technology investments with business outcomes, drive AI-driven capabilities, strengthen cybersecurity, and improve efficiency and revenue per FTE.

The role requires leading a multi-year tech roadmap, collaborating with senior leaders, and building a scalable tech ecosystem across CRM, data analytics, and

Qualifications

• Demonstrated experience leading AI or ML initiatives, including vendor selection and build-vs-buy.
• Familiarity with agentic AI frameworks and workflow automation platforms.
• Working knowledge of cybersecurity frameworks (SOC 2, NIST, ISO 27001).
• Experience with regulatory compliance in financial services or insurance.
• Track record of building and leading technology teams through 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.

Responsibilities

• 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.
• In close collaboration with the VP of Operations, CRO, CFO, CDO, and CHRO, execute key components of the Customer Experience Strategic Initiative.
• Partner with operations leaders to identify, evaluate, and recommend vendors, technologies, and tools that enhance productivity and efficiency; lead implementation including ROI measurement.
• Ensure a scalable and integrated technology ecosystem across agency management systems, CRM, and data analytics.
• Own vendor selection, negotiation, and performance management; align investments with objectives and benchmarks.
• Build and manage a high-performing ecosystem of Insurtech partners; drive ROI and scalability.
• Lead AI strategy, governance, deployment, and oversight across operations and client experience.
• Establish an AI governance framework with auditability and measurable outcomes; manage cybersecurity posture and vendor risk.

Skills

AI leadership

ROI focus

Data architecture

Cybersecurity governance

Vendor management

Team leadership

Communication skills

Education

Bachelor's degree

MBA or MS preferred

Tools

NIST

SOC 2

ISO 27001

Job description

Ansay & Associates, LLC is seeking a Chief Technology Officer to define and execute enterprise technology, AI, and data strategies in partnership with the executive team. You will align technology investments with business outcomes, drive AI-driven capabilities, strengthen cybersecurity, and improve efficiency and revenue per FTE.

The role requires leading a multi-year tech roadmap, collaborating with senior leaders, and building a scalable tech ecosystem across CRM, data analytics, and