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.

Platform DevSecOps Engineer Intern (Summer 2025)

Company: Vail Systems, Inc.

Location: Chicago, IL

Posted Jan 28, 2025

The job posting is for a Platform DevSecOps Engineer Intern position at Vail, a company specializing in voice interactions. The role involves designing and implementing security solutions for Kubernetes and containerized environments, using tools like Kubernetes, Docker, Jenkins, GitLab, and security frameworks. The intern will develop automation scripts, collaborate with team members, create security metrics dashboards, test and implement Kubernetes security policies, and develop documentation for secure practices. The ideal candidate is a junior or senior-level student pursuing a degree in Computer Science, Cybersecurity, Software Engineering, or a related field, with foundational understanding of Secure Software Development Lifecycle, secure coding principles, and DevOps principles. Proficiency in scripting languages like Python or Bash is required, with experience in compiled languages like Go being a plus. Excellent communication skills and curiosity about modern security practices are also desired.

Client Partner - TMT

Company: Blend360

Location: Chicago, IL

Posted Jan 27, 2025

BLEND360 is a forward-thinking data, digital marketing, and AI solutions company seeking a Client Account Partner with at least 10 years of experience in client management or business development. The role involves leading account strategy, growth execution, and overarching P&L. The Client Account Partner will identify new business opportunities, negotiate pricing, manage the pipeline, ensure client satisfaction, and facilitate the right Blend360 talent to client decision-makers. The ideal candidate should have a proven track record, be proactive, passionate about impacting clients' results through data analytics and technology, and possess strong leadership, presentation, and organizational skills.

Partner Engagement Intern

Company: iManage

Location: Chicago, IL

Posted Jan 28, 2025

iManage offers a paid internship program for students to gain hands-on experience in a dynamic technology company. The program, based in Chicago, runs from June 2nd to August 8th and includes project-based activities, team building, and social events. Interns will support the iManage Cloud Customer Lifecycle, assist with tool rollouts, develop playbooks, test workflows, rebrand content, and support Salesforce CRM. iManage values diverse candidates with a growth mindset, prioritizing communication skills and flexibility. The company is dedicated to making knowledge work and innovating to solve complex professional challenges.

DevOps Engineer - Contractor

Company: Wavicle Data Solutions

Location: Chicago, IL

Posted Jan 27, 2025

Wavicle Data Solutions is a Minority Business Enterprise with a diverse workforce, offering complex business and digital transformation solutions. They are seeking a Data Engineer with DevOps experience for client projects. The role involves collaborating with development teams, writing and maintaining scripts, managing cloud infrastructure, ensuring security, and creating documentation. Wavicle is an Equal Opportunity Employer, committed to creating an inclusive environment.

Content Marketing Intern

Company: iManage

Location: Chicago, IL

Posted Jan 28, 2025

iManage offers a paid internship program for students to gain hands-on experience in a dynamic technology company. The program, based in Chicago, runs from June 2nd to August 8th and includes project-based activities, team building, and fun experiences. Interns will work on the Content Marketing team, creating engaging marketing content, building website pages, and reporting on content performance. The ideal candidate has a degree in Marketing, Business Administration, Communications, Journalism, English, or a related field, with strong writing and communication skills, knowledge of marketing strategy, and the ability to work independently and in a team. iManage is committed to diversity and encourages applications from all qualified candidates.

Information Technology Intern

Company: iManage

Location: Chicago, IL

Posted Jan 28, 2025

iManage offers a paid internship program in Information Technology, starting June 2nd and ending August 8th. The program includes project-based activities, team building, and learning opportunities. Interns will serve as the first point of contact for technical assistance, supporting in-office staff and resolving hardware/software issues. The ideal candidate has a degree in Computer Science or Information Technology, knowledge of ticketing systems, strong communication skills, and experience with Microsoft Windows, Mac OS X, Zoom, and Microsoft 365 administration.

Staff Systems Engineer

Company: Sibel Health

Location: Chicago, IL

Posted Jan 27, 2025

Sibel Health, a digital health startup with headquarters in Chicago and an office in Seoul, is seeking a Staff Systems Engineer. The role involves leading product development activities, system design, requirements management, integration, verification, and validation. The ideal candidate should have a Bachelor's degree in engineering or a related field, 8+ years of systems engineering experience, and knowledge of medical device regulations. The company offers competitive benefits, including medical, dental, vision, life, and disability insurance, a simple IRA plan with employer matching, and opportunities for professional development.

Network Engineer - Chicago

Company: Wolverine Trading

Location: Chicago, IL

Posted Jan 28, 2025

Wolverine Trading is seeking a network engineer with extensive experience in low-latency network design and implementation for their proprietary real-time trading systems. The candidate must have a strong background in network operating systems, firewalling, and VPN technologies. They will work closely with software engineers and traders to ensure high availability of the electronic trading infrastructure. The role involves designing and implementing low-latency network solutions, managing strategic projects, and troubleshooting network issues. The candidate should have excellent communication skills and be eligible to work in the US without sponsorship. Wolverine Trading offers a competitive salary, comprehensive benefits, and a positive work culture with opportunities for professional development.

Data Engineer Intern

Company: iManage

Location: Chicago, IL

Posted Jan 28, 2025

iManage U offers a paid internship program for students to gain hands-on experience in a dynamic technology company. The program, based in Chicago, runs from June 2nd to August 8th and includes project-based activities, team building, and social events. As a Data Engineer Intern, interns will work with enterprise data assets, implement solutions for business units, and develop ETL solutions. The role requires proficiency in Python, PySpark, and system-specific APIs, as well as a creative mindset for innovative solutions. iManage values diversity and encourages applications from those who may not meet every qualification.

Social Media Manager – Economics & Investments

Company: Interactive Brokers

Location: Chicago, IL

Posted Jan 27, 2025

Interactive Brokers Group Inc, a global financial services company, is seeking a Social Media Manager for a novel financial literacy initiative. The role involves crafting and executing a social media strategy, creating compelling content, and managing paid and organic campaigns. The ideal candidate should have a strong understanding of economics, investments, and financial markets, with 3+ years of social media experience. The company offers competitive benefits including a performance-based bonus, retirement plan, health benefits, and a generous parental leave policy.

Client Experience Specialist

Company: Renata’s Organic Skincare

Location: Park Ridge, IL

Posted Jan 27, 2025

*Transactional Accuracy:* Process cash and credit transactions following established protocols. *Uphold Standards:* Ensure that all areas, including waiting and…

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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