Chief Technology Officer

Ansay & Associates•, WI

About The Position

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.

Requirements

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.
Proven track record of enterprise transformation.
Strong financial and analytical skills.
Excellent communication and leadership abilities.

Nice To Haves

Experience in insurance or service-based industries preferred.

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.
Execute key components of the Customer Experience Strategic Initiative, focusing on streamlining workflows, improving operational effectiveness, and enhancing the overall customer experience.
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).
Ensure a scalable and integrated technology ecosystem across agency management systems, CRM and client experience platforms, and data and analytics infrastructure.
Reduce duplication, friction points, and manual processes through system interoperability.
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.
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.
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.
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.