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.

Director, Product Management - Search

Company: Grainger

Location: Chicago, IL / Remote

Posted Jan 23, 2025

Channel Manager, CDW

Company: Yubico

Location: Chicago, IL

Posted Jan 23, 2025

Senior Security Engineer, GCP IAM

Company: CVS Health

Location: Buffalo Grove, IL

Posted Jan 23, 2025

Injection Mold Design Engineer

Company: Flex

Location: Buffalo Grove, IL

Posted Jan 23, 2025

Flex, a diversified manufacturing partner, is seeking an Injection Molding Design Engineer for a role in Buffalo Grove, IL. The successful candidate will design and engineer tooling protocols for molds, participate in design reviews, and collaborate with team members. Required skills include Auto CAD, plastic injection molding experience, and proficiency in Excel and MS Office. Flex offers a comprehensive benefits package and a respectful, inclusive work environment.

Senior Architect - Data Engineering and Analytics

Company: West Monroe

Location: Chicago, IL

Posted Jan 23, 2025

West Monroe, a digital services firm, is seeking a Senior Architect for their Technology and Experience Practice. The role involves providing guidance on DataBricks, designing data flow pipelines, and offering data management expertise. The ideal candidate should have 10+ years of professional experience, 5+ years with DataBricks, and strong technical knowledge. The position offers a competitive rewards package, including medical benefits, 401k, and unlimited flexible time off. West Monroe values diversity, inclusion, and growth, fostering a collaborative culture to deliver beyond expectations.

Energy Sales Retail Associate

Company: Sunrun

Location: Schaumburg, IL

Posted Jan 23, 2025

Sunrun, a leading U.S. solar, storage, and energy services company, is hiring for a retail position. The role involves acting as the face of Sunrun in a designated partner retail store, building relationships, and educating potential customers on renewable energy and storage solutions. The successful candidate will have strong communication skills, technology skills, resilience, self-motivation, and a passion for Sunrun's mission. The company offers a full benefits package, competitive sales commissions, and opportunities for career advancement. Top performers can earn up to $160,000/year.

Personal Banker

Company: PNC

Location: St. Charles, IL

Posted Jan 23, 2025

PNC is seeking a Spanish bilingual candidate for a Personal Banker position in St. Charles, IL. The role involves strengthening customer relationships through a defined sales process, identifying appropriate financial solutions, and driving proactive sales conversations. The ideal candidate should possess skills in accountability, banking, client loyalty, customer experience, customer service, identifying opportunities, leveraging technology, and proactive sales. PNC offers a comprehensive benefits package including medical/prescription drug coverage, dental and vision options, life insurance, disability protection, 401(k) with PNC match, and more. The base salary ranges from $46,800.00 to $57,500.00.

Prisma Cloud Sales Specialist, Strategics

Company: Palo Alto Networks

Location: Chicago, IL

Posted Jan 23, 2025

Palo Alto Networks is seeking a Major Accounts Manager with 7+ years of experience in exceeding sales quotas. The role involves managing a territory, driving sales for Prisma Cloud security solutions, and achieving ACV sales quotas. The candidate should have a deep understanding of Public Cloud, DevOps, and cloud native technologies. They will be responsible for winning new logos, renewing existing customers, and expanding business within their territory. The company offers comprehensive benefits, including FLEXBenefits wellbeing spending account, mental and financial health resources, and personalized learning opportunities.

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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