Flexible Schedules Jobs in Chicago, IL

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

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.

Client Partner - TMT

Company: Blend360

Location: Chicago, IL

Posted Jan 27, 2025

BLEND360 is a forward-thinking data, digital marketing, and AI solutions company seeking a Client Account Partner with at least 10 years of experience in client management or business development. The role involves leading account strategy, growth execution, and overarching P&L. The Client Account Partner will identify new business opportunities, negotiate pricing, manage the pipeline, ensure client satisfaction, and facilitate the right Blend360 talent to client decision-makers. The ideal candidate should have a proven track record, be proactive, passionate about impacting clients' results through data analytics and technology, and possess strong leadership, presentation, and organizational skills.

Partner Engagement Intern

Company: iManage

Location: Chicago, IL

Posted Jan 28, 2025

iManage offers a paid internship program for students to gain hands-on experience in a dynamic technology company. The program, based in Chicago, runs from June 2nd to August 8th and includes project-based activities, team building, and social events. Interns will support the iManage Cloud Customer Lifecycle, assist with tool rollouts, develop playbooks, test workflows, rebrand content, and support Salesforce CRM. iManage values diverse candidates with a growth mindset, prioritizing communication skills and flexibility. The company is dedicated to making knowledge work and innovating to solve complex professional challenges.

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.

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.

Product Manager (General Consideration) (Remote)

Company: Inspira Financial

Location: Chicago, IL

Posted Jan 28, 2025

Inspira Financial is seeking a Product Manager to join their innovative build team, designing a state-of-the-art greenfield platform for Health & Benefits customers. The role involves contributing to product strategy and delivery, managing a team of engineers, and defining a product roadmap. The ideal candidate should have a Bachelor's degree in business, marketing, computer science, or a related field, with 3+ years of experience in product management. They should possess strong understanding of software development processes, Agile methodologies, and cross-functional collaboration skills. Familiarity with product management tools and analytical mindset are also required. A background in Healthcare, HealthTech, Finance, FinTech, or start-ups is preferred, along with knowledge of UX/UI principles and customer-centric design.

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.

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.

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.

Client Experience Specialist

Company: Renata’s Organic Skincare

Location: Park Ridge, IL

Posted Jan 27, 2025

*Transactional Accuracy:* Process cash and credit transactions following established protocols. *Uphold Standards:* Ensure that all areas, including waiting and…

Frequently Asked Questions

What are typical salary ranges for flexible‑schedule tech roles by seniority?
Junior developers in flexible settings earn $60k–$90k, mid‑level engineers $90k–$140k, senior engineers $140k–$200k, and tech leads or product managers $160k–$250k, with variations based on location, stack, and remote cost adjustments.
Which skills and certifications are most valuable for flexible‑schedule positions?
Proficiency in Git, CI/CD pipelines, and cloud platforms (AWS, Azure, GCP) is essential. Remote collaboration tools like Slack, Zoom, and Jira are standard. Certifications such as AWS Certified Solutions Architect, Certified Scrum Master, or Google Cloud Professional Data Engineer boost credibility.
How common is remote work availability in flexible‑schedule roles?
Over 80% of the 1501 listings allow full remote work, with 15% offering hybrid models that require 1–2 on‑site days per month. Companies set core hours (e.g., 10 am–3 pm UTC+2) to synchronize cross‑time‑zone teams.
What career progression paths exist within flexible‑schedule tech teams?
Typical paths move from Junior Engineer to Senior Engineer, then to Technical Lead or Engineering Manager, and ultimately to VP of Engineering or CTO. Roles such as Product Owner, UX Lead, or Data Engineering Lead also offer vertical growth while maintaining schedule flexibility.
What industry trends are shaping the future of flexible schedules?
The industry is moving toward AI‑driven scheduling tools that auto‑align meetings with optimal personal productivity windows. Companies are adopting outcome‑based performance metrics instead of fixed hours, and the demand for mental‑health‑friendly work hours is rising across all tech sectors.

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