Flexible Schedules Jobs in Chicago, IL

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

Data Solutions Account Executive

Company: G2

Location: Chicago, IL

Posted Jan 16, 2025

G2 is a global company that values its diverse workforce and offers a range of benefits. The company is currently seeking an ambitious consultative seller for its Investor AE team. The role involves sales, collaboration with internal resources, and driving executive engagement. The ideal candidate should have experience in B2B sales, particularly in the financial services industry, and a proven track record of high performance.

Senior Interconnection Engineer

Company: Nexamp

Location: Chicago, IL

Posted Jan 16, 2025

Nexamp is seeking a Senior Solar Grid Integration Engineer with expertise in PV system design and interconnection. The role involves managing a portfolio of utility interconnection applications, providing technical advice, and collaborating with internal teams. The ideal candidate should have 2+ years of relevant experience, strong knowledge of industry standards, and a Bachelor's degree in Mechanical or Electrical Engineering. Nexamp offers a competitive compensation package, flexible work environment, and opportunities for professional growth.

Product Manager

Company: Screencastify

Location: Chicago, IL

Posted Jan 15, 2025

Screencastify, a leading educational technology company, is seeking a dynamic and results-oriented Product Manager. The company is dedicated to improving communication and learning outcomes with video, primarily focusing on the K12 education sector in the US. Screencastify is used by over 15M people and is committed to accountability, commitment, and speed. The role involves gathering insights about customer needs, collaborating with cross-functional teams, driving product adoption, and leading cross-departmental feature release teams. The ideal candidate should have 4+ years of hands-on experience in product management, specifically with SaaS products, and a deep hands-on approach. The role is based in Chicago with a hybrid work model, offering competitive compensation, flexible time off, parental leave, and comprehensive health benefits.

Talent Acquisition Administrative Assistant

Company: Zeno Group

Location: Chicago, IL

Posted Jan 17, 2025

Zeno Group is seeking a dynamic Talent Acquisition Administrative Assistant with at least 2 years of experience in an administrative role. The ideal candidate will have strong organizational skills, attention to detail, and the ability to manage multiple calendars and projects. They should be a people person, comfortable with learning new technology, and have experience with Talent Acquisition tracking systems. The role involves guiding employees through the interview process, maintaining a positive culture, and ensuring efficiency. Zeno Group offers competitive benefits, including health insurance, mental health support, and a focus on work-life balance.

Shift Supervisor Trainee

Company: CVS Health

Location: Joliet, IL

Posted Jan 13, 2025

CVS Health emphasizes a heart-centric approach to healthcare, aiming to deliver personal, convenient, and affordable services. The Shift Supervisor Trainee role prepares employees for higher-level supervisory roles, focusing on management, customer service, and key business aspects. Successful trainees can be promoted to Operations Supervisor or Shift Supervisor, crucial for store execution, performance, and customer loyalty. The role requires deductive reasoning, communication skills, and flexibility, offering a pay range of $16.00 - $26.00. CVS Health provides comprehensive benefits and well-being programs.

Commercial Legal Counsel

Company: Coates Group

Location: Chicago, IL

Posted Jan 15, 2025

Coates Group, a global technology company, is seeking a Commercial Legal Counsel to join their team. With over 60 years of experience, they specialize in creating dynamic, personalized, and engaging customer experiences. They have worked with major brands like McDonalds and have offices in 9 global markets. The role involves contract management, legal advisory, and process improvement. The ideal candidate should have a Juris Doctor degree, 3-5 years of relevant experience, and expertise in commercial and intellectual property laws. Key competencies include strong communication skills, independent problem-solving, attention to detail, and a collaborative mindset.

Assistant General Manager - Gurnee Town Center

Company: Gap Inc.

Location: Gurnee, IL

Posted Jan 13, 2025

Old Navy is seeking an Assistant General Manager with 2-4 years of retail management experience. The role involves creating and executing the store business plan, driving profitable sales growth, and leading a team of managers and employees. The candidate should be a good communicator, determined to inspire others, and driven by metrics to deliver results. Old Navy offers competitive benefits including a merchandise discount, extensive Paid Time Off, a 401(k) plan, and health insurance. The company is committed to diversity and inclusion, having been recognized by Forbes as one of the World's Best Employers and one of the Best Employers for Diversity.

Senior Digital Support Specialist (Self-Help Tools)

Company: Caterpillar

Location: Peoria, IL

Posted Jan 17, 2025

Caterpillar Inc. is seeking a selfhelp support specialist for their Digital and Data Technology sector. The role involves developing expertise in selfhelp content, monitoring and evaluating its effectiveness, assisting clients with new features, and responding to inquiries. The candidate will also collaborate on establishing customer support policies, maintain technical knowledge of software products, and measure selfhelp effectiveness. Top candidates should have experience with UAT, Salesforce, and BI tools like PowerBI or Tableau. The position is based in Peoria, IL with a flexible hybrid work environment. Caterpillar offers competitive compensation, benefits, and opportunities for career development.

Account Manager

Company: Coates Group

Location: Chicago, IL

Posted Jan 15, 2025

Coates Group, a global technology company, is seeking an Account Manager for a key US-based QSR account. The role involves managing and developing account management for various projects, ensuring brand performance and financial objectives are met, and building strong client relationships. The company is known for its innovative spirit, industry leadership, and commitment to creating dynamic, personalized customer experiences. Coates Group values diversity, creativity, and continuous growth, offering competitive benefits and a positive work environment.

Special Education Teacher SY25-26

Company: Noble Schools

Location: Chicago, IL

Posted Jan 16, 2025

Illinois Teaching License (PEL or ELS) with Learning Behavior Specialist I endorsement (LBSI) or out-of-state equivalent of a Special Education teaching license…

General Manager

Company: Athenaeum Center for Thought & Culture

Location: Chicago, IL

Posted Jan 14, 2025

The Athenaeum Center for Thought & Culture is seeking a General Manager to oversee operations of its performing arts and event spaces. The GM will ensure effective utilization of all spaces, alignment with revenue goals, and operational excellence. Key responsibilities include mission-driven leadership, team leadership, sales collaboration, and financial management. The ideal candidate will have a Bachelor's degree in arts administration, business management, or a related field, and 5+ years of experience in venue management, arts administration, or a similar field.

Customer Service Representative

Company: Kinder Morgan

Location: Chicago, IL

Posted Jan 14, 2025

Creating plant operating orders, taking phone calls, interfacing with truck drivers, communicating via radio, contacting customers to and resolving conflicts.

Frequently Asked Questions

What are typical salary ranges for flexible‑schedule tech roles by seniority?
Junior developers in flexible settings earn $60k–$90k, mid‑level engineers $90k–$140k, senior engineers $140k–$200k, and tech leads or product managers $160k–$250k, with variations based on location, stack, and remote cost adjustments.
Which skills and certifications are most valuable for flexible‑schedule positions?
Proficiency in Git, CI/CD pipelines, and cloud platforms (AWS, Azure, GCP) is essential. Remote collaboration tools like Slack, Zoom, and Jira are standard. Certifications such as AWS Certified Solutions Architect, Certified Scrum Master, or Google Cloud Professional Data Engineer boost credibility.
How common is remote work availability in flexible‑schedule roles?
Over 80% of the 1501 listings allow full remote work, with 15% offering hybrid models that require 1–2 on‑site days per month. Companies set core hours (e.g., 10 am–3 pm UTC+2) to synchronize cross‑time‑zone teams.
What career progression paths exist within flexible‑schedule tech teams?
Typical paths move from Junior Engineer to Senior Engineer, then to Technical Lead or Engineering Manager, and ultimately to VP of Engineering or CTO. Roles such as Product Owner, UX Lead, or Data Engineering Lead also offer vertical growth while maintaining schedule flexibility.
What industry trends are shaping the future of flexible schedules?
The industry is moving toward AI‑driven scheduling tools that auto‑align meetings with optimal personal productivity windows. Companies are adopting outcome‑based performance metrics instead of fixed hours, and the demand for mental‑health‑friendly work hours is rising across all tech sectors.

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