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.

Senior Developer - Information Technology

Company:

Location: Chicago, IL

Posted Jan 23, 2025

United Airlines is currently offering an exciting opportunity for a Senior Software Developer in a hybrid role based in Chicago. The successful candidate will be responsible for developing critical applications, working with a team of developers, and focusing on delivering cloud-based solutions. The role involves managing the full development life cycle, serving as a technical expert, and collaborating with various teams. United Airlines values diversity and inclusion, and this role is part of the united.com payments team, supporting different forms of payments. The ideal candidate should have a Bachelor's degree in a relevant field, 5+ years of full-stack development experience, proficiency in React, Typescript, C#, Node.js, and AWS/cloud technologies, and a deep understanding of accessibility fundamentals.

Outside Sales Representative

Company:

Location: Bolingbrook, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Senior Manager - Aircraft Cybersecurity Operations

Company:

Location: North Riverside, IL

Posted Jan 23, 2025

Field Sales Representative - Hiring Now

Company:

Location: Naperville, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing sales reps more time for tasks. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with a 4% employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Project Manager-Residential Roofing

Company:

Location: Galesburg, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading company in storm restoration for home exterior improvements, is currently hiring a Project Manager for its Davenport, IA branch. The ideal candidate should have prior experience in the construction industry, particularly in roofing, siding, and gutter work. The role involves managing daily job builds, ensuring customer satisfaction, and acting as a liaison between the sales department and production crews. The company offers competitive compensation, including a vehicle allowance, full insurance benefits, a 401k plan, and more. AmeriPro Roofing is a rapidly expanding company with opportunities for sales management and leadership.

Roofing Sales Hiring Now Training Provided

Company:

Location: St. Charles, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Roofing Sales Hiring Now Training Provided

Company:

Location: Joliet, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling representatives to focus on sales. The company offers competitive compensation including draw advancement, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Responsibilities include prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Senior Manager - Aircraft Cybersecurity Operations

Company:

Location: Itasca, IL

Posted Jan 23, 2025

United Airlines is inviting applications for a Senior Manager - Aircraft Cybersecurity Operations. This role involves leading a team of cybersecurity engineers to ensure end-to-end security architecture of United's aircraft-related products. The successful candidate will be responsible for creating and implementing a strategy to maintain compliance with aircraft cybersecurity regulations and standards. Key responsibilities include managing aircraft cybersecurity processes, providing updates and education to staff, and leading the department to ensure the security of United's aircraft-related systems. The ideal candidate should have a STEM or Engineering degree, aviation experience, and strong communication skills. A master's degree and relevant certifications are preferred but not required.

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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