Strategic CTO: AI-Driven Data & Security Transformation

Socket.dev

Wisconsin

On-site

USD 180,000 - 260,000

Full time

14 days+

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Job summary

Ansay & Associates is a growing, employee-focused insurance agency with strong community roots. The CTO will define and execute the enterprise technology, AI, data strategy, and cybersecurity initiatives in partnership with the executive leadership team and the CEO.

You will drive digital transformation, improve client experience, optimize operations, and deliver measurable ROI through scalable platforms, governance of AI, vendor management, and data-enabled decision making.

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.
Working knowledge of cybersecurity frameworks 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 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.
Collaborate with VP of Operations, CRO, CFO, CDO, and CHRO to improve customer experience.
Identify, evaluate, and recommend vendors, technologies, and tools that enhance productivity.
Lead the implementation process for approved solutions, including pilots, integration planning and ROI measurement.
Ensure scalable and integrated technology ecosystem across agency management systems, CRM, data analytics.
Establish an enterprise data strategy to support real-time decision-making.
Own vendor selection and performance management; build Insurtech partnerships.
Lead AI strategy, governance, and automation across operations and sales.
Establish AI governance framework for responsible use and auditability.
Own cybersecurity posture including threat detection, incident response planning, and risk management.
Report cyber risk at the executive and board level with defined thresholds.