Flexible Work Schedule Jobs in Chicago, IL

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

Manager of Cybersecurity Governance & Compliance

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 23, 2025

McDonald's is seeking a Manager of Cybersecurity Governance & Compliance to support their cybersecurity team. The role involves collaborating with global experts to develop, deploy, and maintain policies and standards, ensuring regulatory compliance, and governing foundational programs. The ideal candidate should have a Bachelor's degree in Engineering, Computer Science, or related fields, with 5+ years of experience in IT Security governance, compliance, or IT audit. Desired skills include experience with key compliance and IT frameworks, familiarity with complex multinational companies, and professional certifications such as CISA, CISM, CRISC, CPA, CA, CIA, CISSP, CIPP, CIPT, and PMP.

Nurse Manager-$10,000 Sign On Bonus

Company:

Location: Belleville, IL

Posted Jan 23, 2025

Retail Sales Merchandiser

Company:

Location: Chicago, IL

Posted Jan 23, 2025

Senior Manager - Aircraft Cybersecurity

Company:

Location: Northbrook, IL

Posted Jan 23, 2025

United Airlines is inviting applications for a Senior Manager - Aircraft Cybersecurity Operations role. This position involves leading a team of cybersecurity engineers to ensure end-to-end security architecture of United's aircraft-related products. The role requires aviation experience, strong technical communication skills, and experience in risk management. United offers a competitive benefits package and values diverse experiences. The ideal candidate will have a STEM or Engineering degree, 9+ years of related experience, and knowledge of aviation cybersecurity and IT security best practices.

Manager-Technical Product Management

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 23, 2025

McDonald's is accelerating its growth strategy, 'Accelerating the Arches', focusing on Delivery, Digital, and Drive-Thru. The company is investing in technology innovation, including AI and robotics, to enhance customer experience. The Product Manager Restaurant Development role involves leading the technical product management team, managing external vendor squads, and ensuring high-quality product delivery. The role requires a strong background in software development, Agile methodologies, and excellent communication skills.

Senior Manager - Aircraft Cybersecurity

Company:

Location: Chicago, IL

Posted Jan 23, 2025

United Airlines is inviting applications for a Senior Manager - Aircraft Cybersecurity Operations role. This position involves leading a team of cybersecurity engineers to ensure end-to-end security architecture of United's aircraft-related products. The role requires aviation experience, strong technical communication skills, and experience in risk management. United offers a competitive benefits package and values diverse experiences. The ideal candidate will have a STEM or Engineering degree, 9+ years of related experience, and knowledge of aviation cybersecurity and IT security best practices.

Senior Manager, Technology Deployment

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 23, 2025

McDonald's is seeking a collaborative and proactive individual to lead and manage deployment and change control activities, enhancing operational efficiency and consumer satisfaction. The role involves overseeing the change control process, planning and executing projects, engaging with stakeholders, and monitoring performance. The ideal candidate should have a strong background in change control, project management, and strategic planning, with a proven track record of driving organizational success.

Principal Architect - Application Cybersecurity (Remote)

Company:

Location: Chicago, IL

Posted Jan 23, 2025

United Airlines is inviting applications for a Principal Architect - Application Cybersecurity position. The role involves ensuring services, applications, and websites adhere to United's secure development standards. The successful candidate will work closely with various teams to integrate security into the product lifecycle, from design to deployment. Key responsibilities include validating secure development standards, performing application security assessments, and providing remediation guidance. United offers a competitive benefits package, including parental leave, 401k, and travel privileges. The ideal candidate should have a Bachelor's degree in STEM or Computer Science, at least 9 years of experience in the field, and a deep understanding of OWASP Top 10 and CWE 25.

Frequently Asked Questions

What are typical salary ranges for flexible work schedule roles at different seniority levels?
Entry‑level (0‑2 years) $60k–$80k; Mid‑level (2‑5 years) $80k–$120k; Senior (5‑10 years) $120k–$180k; Lead/Principal (10+ years) $180k–$250k. International remote roles may have adjusted ranges such as $40k–$60k in emerging markets, reflecting local cost of living while maintaining equity.
What key skills and certifications are required for flexible work schedule positions?
Technical: Proficiency in Git, Docker, Kubernetes, and cloud platforms (AWS Certified Solutions Architect, Google Cloud Professional Data Engineer, or Azure Solutions Architect). Agile and project tools: Jira, Confluence, and automated testing frameworks. Soft skills: asynchronous communication, cultural competence, self‑management, and time‑zone coordination. Certifications like Certified Scrum Master (CSM), ITIL Foundation, and PMP are highly regarded for product and project roles.
Is remote work always an option for flexible schedule roles?
Most flexible schedule positions offer 100% remote or hybrid arrangements, with occasional on‑site requirements for quarterly collaboration or training. Companies often specify the percentage of remote work (e.g., 80% remote, 20% on‑site) and provide stipends for home‑office equipment. Applicants can verify the remote policy in the job description or during the interview.
What career progression paths exist within flexible work schedule roles?
Typical paths include: Junior Engineer → Senior Engineer → Tech Lead → Principal Engineer → Engineering Manager; or Product Manager → Senior Product Manager → Director of Product → VP of Product. Lateral moves into architecture, security, or data science are common for professionals seeking broader impact while maintaining flexible arrangements.
What are the current industry trends affecting flexible work schedule jobs?
Key trends: growth of asynchronous communication tools (e.g., Loom, Notion), AI‑driven workflow automation (e.g., GitHub Copilot, ChatGPT for code review), distributed version control at scale, micro‑tasking platforms, flexible sprint lengths, well‑being metrics integration, and digital nomad visas supporting cross‑border talent. Companies are also investing in continuous learning portals and remote‑first hiring practices.

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