Director Ai Developer Jobs in Chicago, IL (NOW HIRING)

Who We Are

Everlake is a leading life insurance company headquartered in Northbrook, IL, with offices in Chicago, IL, and Lincoln, NE. If you have a passion for the insurance business, value working in a dynamic team environment, and are ready to roll up your sleeves to help us achieve best-in-class results, this may be the role for you. At Everlake, you will find the dynamics of a small entrepreneurial organization and the strength of a larger corporation rolled into one. We think big and evolve quickly, backed by a collaborative mindset and a solid financial foundation.

Position Summary

The Director, AI Engineering & Adoption will lead the development, implementation, and adoption of artificial intelligence capabilities across Everlake. Reporting directly to the Chief Technology Officer, this role serves as a peer to Data Engineering leadership and is responsible for both building enterprise AI solutions and driving meaningful adoption across business functions. Unlike traditional technology roles that separate platform development from organizational change management, this position is accountable for both the design and implementation of AI solutions and the realization of measurable business value through enterprise adoption. The position combines hands-on technical execution with organizational change leadership to ensure AI capabilities deliver measurable business value.

The successful candidate will personally contribute to the design and implementation of AI-enabled solutions, including large language model (LLM) applications, retrieval augmented generation (RAG) capabilities, and agentic workflow solutions. Working closely with Data Engineering, Information Security, and business stakeholders, the role will establish scalable AI platforms that support innovation while maintaining appropriate governance, security, and regulatory standards. 

This position requires a highly skilled technology leader who can translate business challenges into practical AI solutions while driving organizational adoption and behavioral change. The individual must be equally comfortable engaging with executive leadership on strategic priorities and working directly with business users to improve day-to-day workflows and realize measurable productivity and operational improvements.

The Director, AI Engineering & Adoption must be an approachable and influential leader who thrives in an environment of ambiguity, displays a strong bias for execution, and consistently balances technical excellence with practical business outcomes. Success in this role will be measured not only by the quality of the solutions delivered, but by the degree to which they are adopted and create meaningful value across the organization.

Key Responsibilities

•    Lead the development and execution of Everlake's AI engineering and adoption strategy in alignment with the Company's technology and business objectives.

•    Design, build, and implement enterprise AI solutions, including LLM applications, retrieval-augmented generation (RAG) architectures, intelligent workflow automation, and emerging AI capabilities.

•    Personally contribute to the design, development, and deployment of enterprise AI solutions while providing technical leadership across the AI function.

•    Partner with business leaders to identify, prioritize, and deliver AI use cases that drive measurable business value and operational improvement.

•    Collaborate closely with Data Engineering to leverage enterprise data assets and establish scalable AI platforms and solutions.

•    Work with Information Security, Risk, Legal, and Compliance teams to ensure appropriate governance, security, model oversight, and regulatory compliance for AI-enabled solutions.

•    Establish standards, practices, and technical frameworks supporting responsible AI development and deployment across the organization.

•    Serve as the primary advocate and change agent for AI adoption, helping business teams integrate AI capabilities into their daily workflows and decision-making processes.

•    Develop training, awareness, and enablement programs that increase AI literacy and accelerate adoption across business functions.

•    Monitor solution usage, adoption trends, and business outcomes to assess effectiveness and identify opportunities for improvement.

•    Define success metrics and regularly report progress, risks, adoption indicators, and realized business value to technology and business leadership.

•    Evaluate emerging AI technologies, vendor capabilities, and industry trends to identify opportunities that support Everlake's strategic objectives.

•    Foster relationships across Technology and business functions to encourage collaboration, innovation, and practical application of AI capabilities.

•    Provide technical leadership, mentoring, and guidance as the AI function grows and organizational capabilities mature.

•    Support enterprise technology initiatives and strategic programs requiring AI expertise and advanced automation capabilities.

Qualifications

•    Bachelor's degree in Computer Science, Information Technology, Engineering, Data Science, or a related field; advanced degree preferred.

•    Typically 8 or more years of progressive experience in software engineering, data platforms, machine learning, artificial intelligence, or related technology disciplines.

•    Demonstrated experience designing, developing, and deploying production AI solutions utilizing large language models, retrieval-augmented generation architectures, intelligent automation, or related technologies.

•    Strong hands-on technical expertise with modern AI development frameworks, vector databases, cloud platforms, and application development practices.

•    Experience driving organizational adoption of new technology capabilities through structured change management, stakeholder engagement, and user enablement programs.

•    Proven ability to translate complex business requirements into practical, scalable technology solutions.

•    Experience partnering with Information Security, Risk, Compliance, or governance functions to implement enterprise technology solutions in regulated environments.

•    Strong understanding of AI governance principles, model risk management concepts, and responsible AI practices.

•    Excellent communication, influence, presentation, and relationship-building skills with both technical and non-technical stakeholders.

•    Demonstrated ability to operate independently, manage competing priorities, and deliver results in a dynamic and evolving environment.

•    Experience within insurance, financial services, healthcare, or other regulated industries is preferred but not required.

•    Familiarity with life insurance, annuities, reinsurance, or financial services operations is beneficial but not required.

Benefits

•    Medical, dental and vision benefits

•    401-k plan

•    Incentive Programs (Annual & Long Term)

•    Flexible paid time off plan

•    Hybrid work environment

•    Paid holidays

•    Tuition assistance