Technology Strategy Lead - AI Transformation (Remote)

Ramaker & Associates; Madison (WI); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Health insurance with HRA

401(k) with company match

Employee Stock Ownership Plan

Compressed workweeks

Paid vacation and holidays

Job summary

Ramaker & Associates, Inc. is seeking a Technology Leader to guide strategy and execution across a diverse technology environment, helping modernize systems, advance AI capabilities, and balance strategic vision with hands‑on execution.

This role will help align technology investments with business priorities and deliver measurable improvements in productivity and operational performance. Most employees work remotely; the position is eligible for remote work with regular travel to the

Qualifications

• Bachelor’s degree in Information Technology, Computer Science, Information Systems, or related field (or equivalent professional experience).
• 8+ years of progressively responsible experience leading enterprise technology, infrastructure, and software delivery teams.
• Proven experience driving digital transformation and multi‑faced systems modernization.
• Experience incorporating AI solutions into technology roadmaps aligned with operational business goals.
• Track record of collaborating effectively with executive leadership, operational leaders, department heads, and cross‑functional technology teams.
• Experience with Azure Cloud Services is preferred.
• Eligible to work in the United States without company sponsorship, both now and in the future.
• Able to work 1‑2 days per week on‑site.

Responsibilities

• Develop and execute the overall technology strategy, performance, and continuous improvement roadmap aligned with business and operational goals.
• Ensure the technology environment supports efficient, secure, and effective operations while identifying and implementing new technologies that improve business outcomes.
• Implement solutions that enhance employee efficiency and the overall technology experience.
• Oversee software development, infrastructure, and cybersecurity across multiple teams.
• Drive digital transformation initiatives and improve efficiency, scalability, and reliability.
• Collaborate with leadership to prioritize technology investments and roadmaps.
• Support and mentor cross‑functional teams to deliver scalable digital solutions.
• Contribute hands‑on technical work as needed within a three‑person team supporting a 90‑employee company.

Skills

Strategic leadership

Digital transformation

AI roadmap

Cloud computing

Cross-functional collaboration

Cybersecurity

Education

Bachelor’s degree (Information Technology/CS/IS)

Tools

Azure Cloud Services

Job description

Ramaker & Associates, Inc. is seeking a Technology Leader to guide strategy and execution across a diverse technology environment, helping modernize systems, advance AI capabilities, and balance strategic vision with hands‑on execution.

This role will help align technology investments with business priorities and deliver measurable improvements in productivity and operational performance. Most employees work remotely; the position is eligible for remote work with regular travel to the