Chief Technology Officer

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

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 fordefining and executing the agency's enterprise technology, AI, digitaltransformationsand 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

• Define and execute a multi-year enterprise technology roadmap aligned with agency growth and scalabilityobjectives.
• 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 toidentify, 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.
• Establish an enterprise data strategy to support real-time decision-making.
• Identifyandleverageinternal and external data sources for growth, market expansion, and M&A.
• Own vendor selection, negotiation, and performance management.
• Ensure alignment of vendor investments with strategicobjectivesand 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.
• 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 recordof building and leading technology teams through periods ofsignificant change.
• Bachelor’s degreerequired; advanced degree preferred.
• 10+ years of technology or digital leadership experience.
• Experience in insurance or service-based industries preferred.
• Proventrack recordof 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’sthe Ansay Way! As such the following core values guide our behaviors:Respect–Compassionate and LoyalIntegrity–Honesty and Trustworthy,Accountability–Responsible for Actions & ResultsPassion–Unfailing Dedication & Pride In WorkPositive “I Can Do” Mentality–Constant, Never-Ending ImprovementExcellence / Professionalism–High Expectations & Pursuit of Opportunities to further our Capabilities

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Equal Opportunity Employer
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