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!

TalentFish 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.

Why This Role Is Different

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!

Overview

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.

What You Bring to the Role (Ideal Experience)

• 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.

What You'll Do (Skills Used in This Position)

• 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.

What Success Looks Like

• First 90 Days
• Build strong, healthy relationships across technology teams and business partners.
• Gain deep understanding of existing processes, applications, systems, data, and infrastructure.
• 6 Months
• Own delivery of systems and applications.
• Ship initial AI-driven capabilities and modernization initiatives.
• 12 Months
• A visibly mature and healthy engineering culture.
• Strong trust from business stakeholders.
• Measurable business impact from AI adoption and application development.

Compensation and Employment

This role requires authorization to work in the U.S. without current or future visa sponsorship. The expected salary range for this position is $220,000 - $250,000 per year, depending on experience and qualifications. This role also qualifies for full comprehensive employee benefits.

TalentFish is committed to pay transparency and equal opportunity. The salary range provided is in compliance with applicable state and federal regulations. All offers are contingent upon the completion of a background check, which may include but is not limited to reference checks, education verification, employment verification, drug testing, criminal background checks, and any required certifications or compliance requirements based on end-client policies and applicable laws.

TalentFish is an employee-owned company pioneering a new realm in talent acquisition. We are redefining IT staffing through AI, video screening, and our proprietary platform focused on delivering the best possible experience for employees, consultants, and clients. TalentFish is an Equal Opportunity Employer. We embrace and encourage diversity.