Associate Director of Technology; Software Engineering, Infrastructure & AI

Title:

Associate Director of Technology (Software Engineering, Infrastructure & AI)
Location:
Chicago, IL (onsite)
Position:
Full-Time Direct Hire

Join a Market Leader Known for Excellence!

Talent Fish is casting a line for a senior-level Technology Leader to join a high-performing Information Technology organization. The Associate Director of Technology will be accountable for creating and sustaining a healthy IT department while driving excellence across software engineering execution, AI implementation, infrastructure reliability, and cross-business alignment. You will lead the organization s next evolution of custom software, AI development, data and analytics, and infrastructure, while building a strong, high-trust engineering culture that delivers measurable business outcomes.

This role is based on site in Chicago, five days per week by design not by accident. Our client is a family-owned, multi-generation business with a deeply collaborative, people-first culture and exceptionally low turnover. Technology leadership is built on trust, proximity, and partnership with the business
. Leaders are present, visible, and engaged with both technical teams and operational stakeholders. This environment rewards hands‑on leadership, long‑term thinking, and accountability not politics or constant reorgs.
If you do your best work being embedded in the business, value stability, and want to build something meaningful, this is a rare opportunity!

This role is designed for a hands‑on, people‑centered technology leader who thrives in a stable, relationship‑driven environment. You ll bridge the gap between distributed software applications and stable infrastructure and operations, translating business needs into clear technical outcomes through hands‑on leadership and collaboration.

• Demonstrated success building healthy engineering cultures, developing leaders, and improving team execution.
• Experience leading technology teams in operational, business‑critical environments where reliability, trust, and execution matter daily.
• 10+ years of experience in software engineering development and technical leadership.
• Thorough understanding of full‑stack application development.
• Practical, working knowledge of IT infrastructure and cloud operations.
• Experience modernizing custom applications using current and emerging technologies.
• Strong background in AI implementation and applied software innovation.
• Excellent communication and business‑alignment skills with the ability to translate between executive stakeholders and engineering teams.
• Proven ability to mentor, coach, and grow high‑performing technical teams.

• Software Engineering Leadership
  • Lead by example through hands‑on technical leadership and deep proficiency in modern software development practices.
  • Guide teams through the full development lifecycle while maintaining high standards of quality and reliability.
• System Design & Architecture
  • Design and oversee scalable, resilient system architectures that integrate custom software with enterprise infrastructure.
  • Ensure long‑term reliability, performance, and maintainability.
• Strategic Technology Vision
  • Define and execute a long‑term technology roadmap aligned to business growth and future needs.
  • Drive innovation across software, AI, data, and infrastructure domains.
• Business & Technology Alignment
  • Serve as the primary bridge between technology and the business.
  • Identify operational pain points and solve real‑world problems through technical solutions.
• Collaborative Leadership
  • Foster strong working relationships through in‑person collaboration and day‑to‑day engagement across software engineering, infrastructure, and business teams.
  • Build a culture of trust, accountability, and open communication.
• People Leadership & Coaching
  • Coach, mentor, and challenge teams to perform at a high level.
  • Develop future technical leaders while cultivating an environment where people can do their best work.

• First 90 Days
  • Build strong, healthy relationships across technology teams and business partners.
  • Gain deep…