Software Engineer

Job Overview

Developer IV leads technical modernization efforts across Wheels' application landscape, with a mandate to evolve legacy systems toward a modern, AI-enabled architecture. This role owns the technical roadmap that connects day-to-day support of mission-critical legacy applications with the organization's broader goal of becoming AI-first, identifying where AI tooling, modern integration patterns, and cloud-ready design can reduce technical debt, accelerate delivery, and improve system resilience. The role blends hands-on technical leadership of the legacy systems programming team with a forward-looking architecture mandate: evaluating, piloting, and scaling AI-assisted development practices, and building the case for, and executing against, a modernized technology stack.

Key Responsibilities

Essential Functions

Serve as technical lead for the legacy systems programming team, guiding, reviewing, and directing technical work to ensure business needs and modernization goals are met. Act as technical team leader on projects, coordinating development and modernization efforts from architecture design through implementation. Instruct, coach, and mentor team members, including on AI-assisted development tools and modern engineering practices, to raise the team's overall technical capability. Participate in scrum activities with Web Development and broader Engineering teams to align legacy and modern workstreams.

Architecture Evolution & AI-First Modernization

Own and evolve the technical roadmap for migrating legacy systems functionality toward modern, API-first, cloud-ready architecture. Partner with Enterprise Architecture and Engineering leadership to define target-state architecture and sequence modernization work into deliverable, low-risk increments. Evaluate, pilot, and scale AI-enabled development tooling (e.g., AI coding assistants, automated code comprehension and refactoring, AI-assisted testing and documentation) to accelerate legacy modernization and improve day-to-day delivery. Identify opportunities to apply AI/ML within business applications themselves, not just the development process, such as intelligent automation, anomaly detection, and decision support. Champion replacement of point-to-point integrations with standardized, event-driven, and API-based integration patterns. Define, track, and report modernization KPIs (e.g., deployment frequency, change failure rate, legacy footprint reduction, technical debt trend) to demonstrate measurable progress. Ensure all AI tooling and automation adopted by the team complies with Wheels' data governance, security, and compliance standards.

Application Development & Support Work

Work with business users to understand requirements, issues, and business processes, translating them into sound technical designs. Develop, test, maintain, and support business application programs, adhering to departmental standards while identifying opportunities to modernize as work is touched. Perform quality assurance testing for all created or modified programs, plus any other applications affected. Analyze production applications to isolate problems, determine more efficient methods, and surface modernization candidates. Research and implement problem resolutions in a timely and effective manner. Maintain current knowledge of standard languages, coding methods, and emerging AI-assisted development practices; recommend enhancements to departmental standards as needed.

Other Duties

Document technical requirements and create technical designs for self and others based on business requirements, including target-state architecture diagrams. Ensure the quality of software implemented by the team meets Wheels' quality standards. Provide project and system documentation per department standards. Present modernization progress, risks, and recommendations to technical and business stakeholders. Respond to on-call emergencies pertaining to recent application/module enhancements as needed. Other duties and responsibilities as assigned.

Leadership Responsibilities

This position carries technical leadership responsibility for the legacy systems programming team, guiding, reviewing, and directing technical work, along with architecture-level influence over Wheels' legacy-to-modern application roadmap. This role is expected to shape how AI-assisted development is adopted across the broader Engineering organization, not only within its own team.

Competencies: Skills

Remain customer focused by creating useful internal and external collaborative relationships. Demonstrate problem-solving and resourcefulness by obtaining results through decisive action. Work independently in an organized and structured manner, consistently achieving thoroughness and accuracy while successfully juggling competing priorities. Think architecturally, balancing near-term delivery against long-term technical debt and modernization goals. Demonstrate fluency with AI-assisted development tools and a practical, evidence-based approach to evaluating new technology. Communicate technical strategy and trade-offs clearly to both technical teams and business stakeholders. Establish cross-cultural capability through a responsive commitment to global perspective and organizational goals and objectives. Effectively manage time for self and team.

Education and Experience

BS/BA in Computer Science, Business Information Systems, or Business Administration with a computer-related minor, or commensurate professional experience. Minimum 10 years' experience in a professional environment with significant emphasis on application development and data management. Strong programming skills in legacy systems languages, with proven ability to support and modernize mission-critical legacy systems. Demonstrated experience with, or strong aptitude for, modern architecture patterns (APIs, microservices, event-driven integration) and AI-assisted development tooling. Excellent communication (verbal, written) and project management skills, with a strong analytical thought process and an aptitude to learn quickly.

Core Values

At Wheels, we believe in fostering a culture that is built on our Core Values and Guiding Principles. We cultivate a culture of excellence and innovation by upholding these values, driving our collective success and growth. Integrity - Always act with integrity and honesty. One Team - Treat others with dignity and respect; act as a cohesive, inclusive and accountable team that is making a difference. Innovation - Drive continuous improvement, spark creativity and embrace next generation thinking. Customer Success - Ensure that customer and driver success is at the heart of everything we do.

Cultural Attributes

At Wheels, our culture guides us how we work every day, and we look for team members who show these behaviors: Discipline Drives Quality - Plan the Trip: Think proactively, hold a high bar, follow through by leveraging experience and systems. To produce quality outcomes, we must be intentional and deliberate in everything we do, from big bets to daily execution. Intellectually Curious - Fuel Your Minds: Be bold, challenge assumptions, think differently, look outside the box. Strive to unlock your own thinking and create new possibilities. Commit and Deliver - Own It: Take responsibility for your work, from start to finish, and be accountable for the results. Think and act like an owner of the business. Relationships Matter - Share the Ride: Trust is central, both with key internal and external stakeholders. Relationships are not a side effect of work but a driver of success.

Job Specifications, Physical Demands, and Work Environment

Work Environment: This position is in Georgia or Illinois and operates in a professional office environment.

Position Type/Standard Schedule: This is a full-time position, Monday through Friday.

Travel: Minimal (<10%) travel expected for this position.

Physical Demands: The level and duration of physical exertion generally required to perform critical tasks in support of critical job functions, for example: sitting, standing, walking, lifting, carrying, reaching, pushing, and pulling.

Disclaimer: Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.

Our Benefits

Wheels recognizes benefits are a significant part of your employee experience, and we've created a robust benefits package that is market-leading, competitive offerings so you and your family can receive outstanding care.

• 50+ health, wellness and engagement benefits
• 2,500+ online learning programs

Pay Range: $115,900-$162,200

The base salary range for this position is listed above. This position is eligible to participate in the annual incentive plan which is based on company performance and individual performance. Compensation ranges are based on several factors including job function, level, and geographic location. Final offer amounts are determined by multiple factors including candidate experience, education, certifications, skill level and expertise, and may vary from the amounts listed here.

EEO Statement

Wheels is a Drug-Free Workplace. All employment is contingent on successful completion of drug and background screening. Wheels is an equal opportunity affirmative action employer and administers all personnel practices without regard to race, color, religion, sex, age, national origin, sexual orientation, gender identity or expression, marital status or domestic partnership status, disability, protected veteran status or military status, genetic information, or any other category protected under applicable law. Wheels is committed to taking affirmative steps to promote the employment and advancement of minorities, women, persons with disabilities and protected veterans.

Wheels is Committed to Making Our Organization One of the Best Places to Work

As one of the largest fleet management companies in North America, Wheels features a portfolio of 900,000+ vehicles under management across the continent, a global alliance in 61 countries, and a client base that consists of some of the best-known businesses in the world. No matter the industry type or business size, we’re proud to work across sales and service fleets, trucks and equipment, and last mile delivery to ensure we power your potential. The culture at Wheels is the secret to our 80+ years of success. And the reason people choose to join — and stay with — our team. When you join the team, you'll work with professionals who are passionate, friendly and smart. We foster a welcoming and inclusive environment for all, combined with the encouragement to continuously learn and grow. From day one, we invest in your long-term development through annual performance goals and reviews, educational and wellness programs, awards and celebrations, and more.

Ready to experience the Wheels culture for yourself? 10 years average employee tenure 10 times recognized as one of Chicago's Best and Brightest Companies to Work For 50+ health, wellness and engagement benefits 2,500+ online learning programs Wheels is Invested in the Well-being of the Community and the World We Inhabit Diversity: Wheels deeply values the strength of diversity both in the communities we serve and our own employee base. This includes treating everyone as equal, respecting and valuing diversity, providing equal opportunity and fostering a safe space to work. Community: We are heavily involved in the communities where we operate. We offer opportunities for employees to make a positive impact through mentorship and tutoring elementary school students, participating in blood drives, donating to United Way and other charitable organizations in the greater Chicagoland and Toronto areas. Sustainability: Wheels is actively committed to becoming a cleaner fleet management company through recycling programs, public transportation support and more. We Are Dedicated to the Safety and Health of our Employees Our employees are critical to delivering on our commitment to client success, which is why we offer a variety of programs focused on the health and wellness of our people. Wheels Fosters More Than Just Work Relationships We hire people who have a customer-focused mindset and a strong collaborative nature. Because at Wheels, customer service and teamwork don't just happen in the office. It is during the informal moments when employee trust is strengthened and friendships are made. We value these moments, which is why we host departmental contests, summer gatherings, family events, holiday celebrations and more. At Wheels, your well-being is our priority. As part of our commitment to your health and well-being, we’re proud to offer access to the Advocate Health Care Wellness Portal—a personalized platform designed to help you take charge of your health journey. The 2026 Wellness Program is designed to support you in achieving your personal health goals. Best of all, it’s flexible and fits into your busy lifestyle. This program is designed to support your overall well-being—physically, emotionally, and financially—by providing tools and incentives that encourage healthy living.