Flexible Schedule Jobs in Chicago, IL

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

Trade Desk Representative

Company: tastylive

Location: Chicago, IL

Posted Jan 15, 2025

tastytrade is seeking a Trade Desk Representative with FINRA Series 3, 7, and 63 certifications for an in-person role in Chicago, IL. The role involves providing customer service, assisting with complex option order execution, and analyzing customer positions. The company offers a competitive salary range of $90,000 to $110,000, along with performance bonuses, stock purchase options, and comprehensive benefits. The ideal candidate should have at least 2 years of experience in a similar role, strong interpersonal skills, and proficiency with technology. The office is located in Chicago's West Loop, known for its tech scene, cuisine, and high-end bars.

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.

Compliance Associate - Testing (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 18, 2025

Enova International is seeking a qualified candidate for a compliance testing and monitoring role. The position involves developing, implementing, and monitoring compliance testing to support the company's adherence to federal, state, and local laws, as well as company policies. The ideal candidate should have a Bachelor's degree, regulatory compliance experience in the consumer lending industry, and strong knowledge of business operations for compliance with laws and regulations. The role offers a competitive salary range of $55,000 to $70,000, along with comprehensive benefits including health, dental, and vision insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Enova International is a values-driven organization committed to creating accessible credit for millions through its AI and machine learning-powered Colossus™ platform.

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.

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.

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…

Oncology Data Analyst Specialist

Company: HCTec

Location: Chicago, IL

Posted Jan 16, 2025

*One (1) year (12 months)* of data management/analyst work experience in a clinical or healthcare related field. Salary Range: *$58,000.00 - 76,000.00.

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 roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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