Associate Director of Technology (Software Engineering, Infrastructure & AI)

TalentFish; Chicago (IL); On-site; USD 220,000 - 250,000; Full time

Benefits offered by this job

Health insurance

401(k)

Paid time off

Job summary

A leading technology recruitment firm is seeking an Associate Director of Technology in Chicago. In this pivotal role, you will provide technical leadership and guide teams in software engineering and AI implementation. The ideal candidate has over 10 years of experience, a proven record in building engineering cultures, and exceptional communication skills. The position is 100% onsite with a salary range of $220,000 – $250,000 annually, offering a comprehensive benefits package.

Responsibilities

• Provide technical leadership across modern development practices.
• Guide teams through the full SDLC ensuring quality and reliability.
• Define long-term technology roadmap aligned with business growth.
• Translate operational challenges into scalable technical solutions.

Skills

10+ years of progressive experience in software engineering and technical leadership

Proven success building strong engineering cultures and developing technical leaders

Practical knowledge of IT infrastructure and cloud operations

Strong background implementing AI-driven solutions

Exceptional communication skills

Ability to mentor and coach high-performing teams

Job description

Job Title: Associate Director of Technology (Software Engineering, Infrastructure & AI)

Location: 100% Onsite – Pilsen Area (Local Candidates Only)

Position Type: Full-Time

Overview

TalentFish is casting a line for a senior-level Associate Director of Technology to join a high-performing IT organization. This is a fully onsite leadership role (5 days per week) and requires candidates to be local to the Pilsen area.

This leader will be responsible for building and sustaining a healthy, high-performing technology organization while driving excellence across software engineering, AI implementation, infrastructure reliability, and cross-functional business alignment.

The mission of this role is clear: lead the next evolution of custom software, AI development, data and analytics, and infrastructure operations—while cultivating a strong engineering culture that delivers measurable business results.

This opportunity is ideal for a high-caliber, high-energy technology executive who can bridge distributed software applications with stable infrastructure and operations, translating business strategy into clear, actionable technical outcomes.

What You Bring

• 10+ years of progressive experience in software engineering and technical leadership
• Proven success building strong engineering cultures and developing technical leaders
• Practical, working knowledge of IT infrastructure and cloud operations
• Experience modernizing custom applications using emerging and current technologies
• Strong background implementing AI-driven solutions and applied innovation
• Exceptional communication skills with the ability to align executive stakeholders and engineering teams
• Demonstrated ability to mentor, coach, and scale high-performing teams

Key Responsibilities

Software Engineering Leadership

• Provide hands-on technical leadership across modern development practices
• Guide teams through the full SDLC while ensuring quality, scalability, and reliability
• Design and oversee scalable, resilient architectures integrating custom software and enterprise infrastructure
• Ensure long-term performance, maintainability, and operational stability

Strategic Technology Direction

• Define and execute a long-term technology roadmap aligned with business growth
• Drive innovation across AI, software engineering, data, and infrastructure

Business Partnership

• Serve as the primary bridge between technology and business stakeholders
• Translate operational challenges into scalable technical solutions
• Foster trust, accountability, and cross-functional collaboration
• Coach, mentor, and elevate future technical leaders
• Build an environment where teams can perform at their highest level

What Success Looks Like

First 90 Days

• Establish strong relationships across IT and business teams
• Gain deep understanding of systems, applications, data, and infrastructure

6 Months

• Own delivery of systems and applications
• Launch initial AI-driven capabilities and modernization efforts

12 Months

• Demonstrable maturation of engineering culture
• Strong executive trust and business partnership
• Measurable impact from AI adoption and software modernization initiatives

Compensation

Expected salary range: $220,000 – $250,000 annually, based on experience and qualifications.

Comprehensive benefits package included (health insurance, 401(k), paid time off).

This position requires authorization to work in the U.S. without current or future sponsorship. All offers are contingent upon completion of standard background and verification processes.

If you are a strategic, hands-on technology leader ready to drive meaningful innovation in a fully onsite environment, I would welcome the opportunity to connect.

Contact Lorie for immediate review:

Local candidates only. 100% onsite commitment required.