Flexible Schedule Jobs in Chicago, IL

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Looking for Flexible Schedule jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Schedule position in the Chicago, IL area.

Training and Knowledge Specialist

Company: Caterpillar

Location: Peoria, IL

Posted Jan 29, 2025

Caterpillar Inc. is seeking a highly accountable individual with strong communication and organization skills for a role in their Digital and Data Technology area. The successful candidate will develop training materials, identify training needs, and lead training initiatives for the Cat Digital Support Center. They will also partner with third-party contact centers in launching new programs and ongoing operations. The role involves deploying various training methods, ensuring a seamless handoff of training and quality to third-party suppliers, and regularly reviewing curriculum materials. The position requires a college degree or equivalent experience in progressive training assignments, strong communication skills, and contact center experience. Caterpillar offers a flexible hybrid work environment, competitive compensation, and benefits, and is committed to a reduced-carbon future.

Technical Product Analyst

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 28, 2025

McDonald's is accelerating its growth strategy, focusing on Delivery, Digital, and Drive-Thru. The company aims to leverage AI, robotics, and emerging tech to digitize the Golden Arches and enhance customer experience. The Technical Product Analyst role is part of the Global Technology Infrastructure & Operations team, responsible for optimizing user experience, conducting user research, and translating insights into product strategy. The role requires a self-starter with strong project management skills, analytical capabilities, and excellent communication skills.

Lead Product Owner, Cat Foresight - Planned Maintenance (PM) (Remote)

Company: Caterpillar

Location: Peoria, IL

Posted Jan 28, 2025

Caterpillar Inc. is seeking a Lead Product Owner for the Cat Foresight Planned Maintenance product. The role involves close collaboration with various teams, understanding business needs, setting product direction, driving development, managing costs, and ensuring product quality. The ideal candidate should have a degree, experience in digital product ownership, practical domain expertise in Cat business processes, and strong skills in digital product strategy, user-centric design, data analysis, and technical fluency. The position offers a competitive salary, benefits, and opportunities for career growth and working with emerging technologies.

Associate Director, Time & Pay Technology​

Company: Kraft Heinz

Location: Chicago, IL

Posted Jan 28, 2025

The Associate Director of Time and Pay Technology at Kraft Heinz will lead the development and implementation of HR tech, ensuring alignment with engineering best practices. This role involves collaborating with cross-functional teams, optimizing HR systems, and managing a team of HR technology specialists. The ideal candidate will have significant experience in digital HR products, product strategy, and software engineering team leadership. The role is based in Chicago, IL, and offers a competitive salary range of $159,400 - $199,200, along with comprehensive benefits and wellbeing programs.

Senior Product Manager- Product strategy

Company: Ahold Delhaize USA

Location: Chicago, IL

Posted Jan 29, 2025

Ahold Delhaize USA is seeking a Product Strategy and Experimentation Manager for its Chicago office. The role involves driving strategic planning, managing the digital product roadmap, and leading a team of two product managers. The ideal candidate should have experience with agile development, cross-functional team leadership, and project management skills. The company offers a competitive salary range of $131,520 to $204,240 and values diversity, equity, inclusion, and wellness.

Manager Digital Project

Company: Caterpillar

Location: Peoria, IL

Posted Jan 28, 2025

Caterpillar Inc. is seeking a project manager for its Integrated Procurement (IP) platform, the largest ecommerce platform of the company. The role involves overseeing project activities, developing contingency plans, managing a global team, and ensuring adherence to quality standards. The ideal candidate should have strong Excel skills, experience with MS Project, multitasking abilities, technical aptitude, and excellent communication skills. Caterpillar offers a flexible hybrid work environment, competitive compensation, and benefits, including a 401k savings plan, health savings account, and tuition reimbursement. The job description is intended as a general guide and may be subject to change based on organizational needs.

Database Administrator

Company: Belvedere Trading

Location: Chicago, IL

Posted Jan 28, 2025

Belvedere Trading, a leading proprietary trading firm based in Chicago, is seeking a skilled Database Administrator. The role involves supporting SQL Server, Google BigQuery, and Google Cloud SQL databases, optimizing performance, collaborating with developers, and maintaining monitoring systems. The ideal candidate should have proven experience in SQL Server infrastructure, query optimization, and performance tuning. Familiarity with cloud data warehouses and modern tools is beneficial. Excellent communication and problem-solving skills are required. Belvedere values diversity and inclusion, and encourages applications from all backgrounds.

Network Engineer - Chicago

Company: Wolverine Trading

Location: Chicago, IL

Posted Jan 28, 2025

Wolverine Trading is seeking a network engineer with extensive experience in low-latency network design and implementation for their proprietary real-time trading systems. The candidate must have a strong background in network operating systems, firewalling, and VPN technologies. They will work closely with software engineers and traders to ensure high availability of the electronic trading infrastructure. The role involves designing and implementing low-latency network solutions, managing strategic projects, and troubleshooting network issues. The candidate should have excellent communication skills and be eligible to work in the US without sponsorship. Wolverine Trading offers a competitive salary, comprehensive benefits, and a positive work culture with opportunities for professional development.

IT Analyst - Applications

Company: Caterpillar

Location: Peoria, IL

Posted Jan 28, 2025

Caterpillar Inc. is seeking a professional with expertise in agile development, data analytics, and ETL processes. The role involves analyzing customer requirements, discerning data accuracies, researching and documenting data specifications, and understanding software development and web technologies. The successful candidate will work with systems integration, database design, and cloud computing. Caterpillar offers a comprehensive total rewards package, including medical, dental, vision coverage, 401k, and potential annual bonuses. The primary locations for this position are East Peoria, IL, Nashville, TN, and Dallas, TX.

Software Engineer (Chicago)

Company: Nextpoint

Location: Chicago, IL

Posted Jan 29, 2025

Nextpoint, an award-winning team, offers transformative software and services for law firms. They value innovation, creativity, diversity, and initiative, fostering a happy workplace. The Level 2 Support Engineer role involves creating and maintaining a high-performing, reliable environment for clients, collaborating with engineering and product teams, and continuously improving system performance. The ideal candidate has a Bachelor's degree in computer science, 2+ years of support engineering experience, and strong problem-solving skills.

Senior Tax Accountant - Partnerships

Company: Wipfli

Location: Chicago, IL

Posted Jan 28, 2025

Wipfli is a company that values its employees and offers a career-defining opportunity for a Senior Manager in Partnership Tax. The role involves conducting primary and secondary reviews of complex tax returns, providing tax consulting services, and collaborating with the Partnership Tax team to make recommendations on return preparation and tax savings opportunities. The responsibilities also include managing staff, adhering to budgets and deadlines, and developing expertise in Subchapter K Partnership taxation. The company offers high-quality tools and resources, and emphasizes accuracy, quality, and client service. The estimated base pay range for this role is $75,000 to $116,000, and the company provides a variety of benefits to support employee wellbeing.

Revenue Integrity Analyst

Company: Keystone Advisors LLC

Location: Chicago, IL

Posted Jan 28, 2025

Keystone Advisors is seeking a Revenue Integrity Analyst to support a healthcare client in Chicago, IL. The role involves managing large data-driven projects across the Cook County Health Physician Revenue Services and Hospitals System. The analyst will ensure the charge description master file adheres to system policy, reflects clinical practice, and aligns with reporting requirements. Key responsibilities include managing Siemens and Cerner Patient Accounting tables, creating utilization management reports, automating manual processes, analyzing Revenue Cycle data, and responding to enhancement requests. Preferred qualifications include a Bachelor's degree in Business, Finance, Health Administration, or related field, 3+ years of Revenue Cycle experience, proficiency in Excel, Access, SQL, and Visual Basic, and strong analytical and communication skills.

Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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