Flexible Scheduling Jobs in Chicago, IL

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

Payment Specialist

Company: Rewards Network

Location: Chicago, IL

Posted Jan 29, 2025

Rewards Network, a company celebrating 40 years in business, is seeking a Payments Specialist. The role involves processing payments, reconciling accounts, and maintaining client relationships. The ideal candidate will have a background in bookkeeping, accounting, or payments, with excellent interpersonal and organizational skills. The company offers a comprehensive benefits package, including health insurance, retirement plans, and a flexible working space.

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 by seniority for Flexible Scheduling roles?
Entry‑level Scheduling Coordinators earn $45,000–$60,000 annually, mid‑level Workforce Planners command $60,000–$90,000, and senior Scheduling Managers or Operations Directors can reach $90,000–$120,000 or more, depending on company size and region.
What skills and certifications are most valuable in Flexible Scheduling positions?
Proficiency in workforce‑management platforms such as Kronos Workforce Central, SAP SuccessFactors, and Oracle Workforce Management is essential. Strong analytical skills in SQL and Tableau, coupled with experience using Agile or Six Sigma methodologies, give an edge. Certifications like Certified Workforce Planning Professional (CWPP), Six Sigma Green Belt, or a project‑management credential (PMP) are highly regarded.
Is remote work available for Flexible Scheduling roles?
Yes—over 70% of the listings support fully remote or hybrid arrangements, especially in tech, logistics, and customer‑support sectors. Remote positions typically offer a pay adjustment based on regional cost‑of‑living indexes.
What career progression paths exist within Flexible Scheduling?
A common trajectory starts at Scheduling Coordinator, moves to Workforce Planner or Shift Scheduler, then to Scheduling Manager or Operations Analyst, and can culminate in Director of Workforce Optimization or Chief Workforce Officer, with increased responsibility over strategy, analytics, and cross‑functional leadership.
What industry trends are shaping the future of Flexible Scheduling?
Artificial‑intelligence forecasting, real‑time labor analytics, and blockchain‑based time‑tracking are driving the next wave of scheduling solutions. Companies are adopting predictive shift‑optimization tools, integrating gig‑worker platforms, and expanding continuous‑learning modules to upskill scheduling talent.

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