Chicago, Illinois, United States

Associate Director of Technology

 Job Description:

Job Title: Associate Director of Technology (Software Engineering, Infrastructure & AI)
Primary Location: On-Site (5 days per week, Pilsen area)
Position Type: Full-Time

Overview

TalentFish is casting a line for a senior-level Technology Leader to join a high-performing Information Technology organization. This role is accountable for creating and sustaining a healthy IT department while driving excellence across software engineering execution, AI implementation, infrastructure reliability, and cross-business alignment.

The reason this position exists is to lead the 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 designed for a high-caliber, high-energy technology leader who can 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

  • 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 collaboration 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 Information

The expected salary range for this position is $220,000-$250,000 per year, depending on experience and qualifications. This role also qualifies for comprehensive benefits, including health insurance, 401(k), and paid time off.

TalentFish is committed to pay transparency and equal opportunity. The salary range provided is in compliance with applicable state and federal regulations.

This role requires authorization to work in the U.S. without current or future visa sponsorship.

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.

About TalentFish

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.


  Required Skills:

Data Offers Adoption Talent Acquisition Development Driving Organization Authorization Transparency Operations Collaboration Compliance Video Checks Salary Accountability Screening Compensation Reason Reliability Architecture Software Development Coaching Insurance Infrastructure Analytics Information Technology Regulations Education Software Testing Design Engineering Business Leadership Communication