Flexible Work Arrangements Jobs in Chicago, IL

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

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.

Outside Sales Reps Hiring Immediately

Company:

Location: Oak Park, 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, offering them protection at reduced costs. The company stands out due to its fully staffed departments, enabling sales reps to focus on sales without administrative burdens. AmeriPro Roofing offers competitive compensation including 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. The role involves prospecting, qualifying, and closing new sales, managing a territory, conducting property inspections, 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: 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 by seniority for flexible work arrangement roles?
Junior remote developers earn $70k–$95k, mid‑level professionals earn $95k–$140k, and senior specialists or leads earn $140k–$200k. Remote‑specific allowances can add 5–10% on top of base pay for high‑cost‑of‑living locations.
What skills and certifications are required for flexible work roles?
Core technical skills include Git, Docker, Kubernetes, and proficiency in at least one cloud platform (AWS, Azure, GCP). Remote collaboration skills involve Slack, Zoom, Notion, and Asana. Certifications such as Certified Remote Work Manager, AWS Certified Solutions Architect, Azure Fundamentals, Google Cloud Professional, PMP, or CSM are highly valued.
How widely available are remote work opportunities in this category?
All 2964 positions support remote work, offering full‑time, part‑time, and contract options. Companies provide VPN, zero‑trust security, and remote onboarding tools, enabling employees to start from any location with a reliable internet connection.
What career progression paths exist for professionals in flexible work arrangements?
Typical paths move from Junior Remote Engineer → Senior Remote Engineer → Remote Technical Lead → Remote Engineering Manager or Remote Product Lead. Parallel tracks include Remote UX Lead, Remote Data Lead, or Remote Customer Success Manager, with opportunities to transition into remote operations or CTO roles.
What industry trends are shaping flexible work arrangements?
The remote‑first trend is accelerating, with 60% of tech firms adopting hybrid models by 2025. Adoption of AI‑driven collaboration tools, real‑time code review, and remote cybersecurity protocols is increasing. Companies increasingly offer remote benefits such as home‑office stipends and global health plans, driving higher demand for qualified remote professionals.

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