Flexible Work Environment Jobs in Chicago, IL

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

Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

All agents must be able to obtain licensing through the Illinois Department of Financial and Professional Regulation, are required to score a minimum of 95%…

Security Officer (Pt)

Company: City Colleges of Chicago

Location: Chicago, IL

Posted Aug 11, 2025

Must have a valid driver’s license, current CPR and/or first aid certification, and hazardous material training. Ability to lift and carry up to 50 pounds.

Construction Management, Project Manager -- Superintendent, Chicago

Company: Bushman Construction Management

Location: Chicago, IL

Posted Aug 10, 2025

0-5+years field experience in commercial construction. Chicago, IL 60630is a general contractor providing complete commercial construction and construction…

CDL-A Truck Driver - Temp-Controlled Freight - up to $1,650/week

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,365/week. *Home weekly* – typically for 48 hours.

School Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

Ensure the safety of staff and student. Ability to operate surveillance equipment. Report on daily activities and any security incidents.

CDL A Dry Van Truck Driver: Home Weekly

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

Master Plumber

Company: Leaf Home

Location: Chicago, IL

Posted Aug 10, 2025

Train, coach and develop installation employees and contractors both in the office and in the field. Must hold a valid driver's license.

Program Manager, Data Centers

Company: JLL

Location: Chicago, IL

Posted Aug 11, 2025

Working collaboratively with various stakeholders, you'll ensure successful program execution while proactively addressing risks and driving operational…

Strategy and Operations Associate, Retail, Product, Go-To-Market

Company: Google

Location: Chicago, IL

Posted Aug 11, 2025

Collaborate cross-functionally across business areas and regions to drive insights and recommendations to leadership and working teams, based on analysis,…

Security Associate

Company: Midwest Goods Inc.

Location: Bensenville, IL

Posted Aug 11, 2025

Have an active CPR and AED Certification valid for at least 2 years. You also manage entry permissions to ensure that only authorized individuals gain access to…

Midmarket Software Sales - Founding Team Member for AI Startup

Company: Nestbox AI

Location: Chicago, IL

Posted Aug 10, 2025

*Founder-Level Impact:* You’ll be the first sales hire, working directly with our technical founders to shape GTM strategy, refine our offering for midmarket…

Frequently Asked Questions

What are typical salary ranges by seniority in flexible work roles?
Entry‑level (0‑2 yrs) typically earns $70k–$90k. Mid‑level (3‑5 yrs) ranges $90k–$120k. Senior (6‑10 yrs) $120k–$160k. Staff/Principal engineers $160k–$200k. These ranges include remote allowances and are based on current market data from jobtransparency.com.
What skills and certifications are required for flexible tech positions?
Essential skills include JavaScript (React, Node.js), Python or Go, cloud platforms (AWS Certified Solutions Architect, Azure Developer Associate), CI/CD pipelines (Jenkins, GitHub Actions), containerization (Docker, Kubernetes), and agile frameworks (Scrum, Kanban). Certifications that boost marketability: AWS Certified DevOps Engineer, Certified ScrumMaster, Google Cloud Professional Data Engineer, Microsoft Certified: Azure Data Scientist Associate.
Is remote work available for most flexible roles?
Yes—over 90% of positions are fully remote with optional hybrid options. Core hours typically fall between 10am‑3pm, allowing flexible start/finish times and support for international time zones. Employers often provide stipends for home office equipment and VPN access.
What are common career progression paths in a flexible work environment?
Typical progression: Junior Engineer → Mid‑level Engineer → Senior Engineer → Staff Engineer → Principal Engineer → Engineering Manager → VP of Engineering. Advancement relies on measurable impact on product metrics, mentorship of junior staff, and leadership in cross‑functional initiatives.
What industry trends are shaping flexible work roles?
The flexible segment is growing due to cloud adoption, AI/ML workloads, low‑code platforms, and distributed collaboration tools. Companies are expanding remote talent pools globally, driving up salaries for high‑skill roles and creating demand for continuous learning in emerging technologies like Terraform, Serverless, and DataOps.

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