Flexible Hours Jobs in Chicago, IL

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

IT Systems and Support Administrator

Company: Kalderos

Location: Chicago, IL

Posted Feb 01, 2025

Kalderos is seeking an IT Systems and Support Administrator to provide top-tier technical support to over 115 internal employees, ensuring smooth operations in a mixed Mac and Windows environment. The role involves critical thinking, troubleshooting, and collaboration with the Director of Information Technology to improve systems and processes. The candidate will also work with the Information Security team to ensure system security and act as a technical mentor to Level 1-2 technical support analysts. The ideal candidate will have 5+ years of experience, excellent technical skills, and a customer service mindset. Relevant certifications, experience in startup environments, and familiarity with Okta, Google Workspace, cloud infrastructure, and compliance standards are preferred. The position offers a competitive salary range, flexible PTO, and a range of benefits, including medical, dental, vision, 401k, and opportunities for growth. Kalderos values collaboration, feedback, and continuous learning, and is committed to equal opportunity.

Scala Software Engineer

Company: Rewards Network

Location: Chicago, IL

Posted Jan 31, 2025

Rewards Network, a company celebrating 40 years in business, is seeking a Scala Software Engineer for a hybrid position in Chicago. The role involves working with a team to build out new business areas and improve the rewards platform using the latest technologies. The company offers a competitive benefits package, including a comprehensive health plan, 401k with company match, and a flexible working environment. Requirements include a degree in Computer Science, 2+ years of development experience, and proficiency in Scala or other functional languages.

Software Engineer Team Lead - DevEx (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 31, 2025

Enova International is seeking a Software Engineering Team Lead with 5+ years of full stack development experience. The role involves designing and implementing technical solutions, collaborating with engineers, mentoring junior developers, and managing agile scrum teams. The ideal candidate should have expertise in enterprise architecture, API integration, and automated testing. The position offers a competitive salary range of $116,000 to $160,000, along with comprehensive benefits and a flexible hybrid work model. Enova is a values-driven organization committed to creating accessible credit for millions through its AI-powered Colossus platform.

IT Support Analyst

Company: Kalderos

Location: Chicago, IL

Posted Feb 01, 2025

Kalderos is a healthcare technology company focused on pharmaceutical pricing transparency, trust, and equity. They are seeking an IT Support Analyst to provide top-tier technical support to their 115+ internal employees in a fully remote environment. The role involves troubleshooting technical issues, collaborating with the IT team, and assisting with IT projects. The company values collaboration, feedback, and growth, offering competitive benefits and a dynamic work environment.

Senior Software Engineer - Platform (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Feb 01, 2025

Enova International is seeking a Senior Software Engineer with 3+ years of full stack development experience. The role involves taking ownership of system development, collaborating with stakeholders, and mentoring team members. Preferred skills include proficiency in Ruby and Go, and experience in the Finance domain. The position offers a competitive salary range, comprehensive benefits, and a flexible hybrid work model. Enova is a values-driven organization committed to creating accessible credit for millions through its AI-powered platform.

Lead AI Software Engineer

Company: iManage

Location: Chicago, IL

Posted Feb 01, 2025

iManage offers a flexible working policy that supports employee wellbeing and work-life balance. The company values collaboration and learning from peers while providing necessary flexibility. The Lead AI Software Engineer role involves using cutting-edge research and technology to work on a wide range of AI problems, focusing on building systems for deploying, scaling, and monitoring NLP and Gen AI applications. The role requires a Masters or PhD in Computer Science, Machine Learning, Data Science, Artificial Intelligence, Statistics, or related field, along with 6+ years of experience in ML/AI engineering or software engineering with expertise in NLP. The role involves driving technical strategy, designing production-ready NLP applications, and collaborating with product and business stakeholders. iManage provides a supportive team, flexible work hours, and comprehensive benefits, including a market-competitive salary, health benefits, and a 401k retirement plan with a company match.

Senior Principal Customer Success Manager

Company: iManage

Location: Chicago, IL

Posted Feb 01, 2025

The text describes a Senior Principal Customer Success Manager role at iManage, a global company using advanced technology for communication. The role involves managing strategic customer portfolios, ensuring customer satisfaction, and driving customer loyalty. The ideal candidate should have extensive experience in enterprise customer management, SaaS environments, and C-suite stakeholder interactions. iManage offers a competitive salary, comprehensive benefits, and a supportive, inclusive culture. The company is committed to diversity and encourages applicants to apply even if they don't meet every qualification.

Product Specialist

Company: ALIS by Medtelligent

Location: Chicago, IL

Posted Feb 01, 2025

ALIS is a leading provider of assisted living software, seeking a problem-solving, self-motivated individual with 2+ years of SaaS experience. The role involves learning ALIS software, understanding the assisted living industry, scoping new features, creating user interfaces, collaborating with teams, and communicating with client services. The company offers competitive benefits, including health insurance, 401k, and PTO. The application process includes a phone call, in-person or video interview, and a project or collaborative work session.

Frequently Asked Questions

What are typical salary ranges by seniority for flexible hours tech roles?
Entry‑level (0‑2 years) flexible‑hours engineers earn $60k–$80k annually; mid‑level (3‑5 years) range $90k–$120k; senior (5+ years) $130k–$170k, with additional shift bonuses for night or weekend coverage.
What skills and certifications are required for flexible hours positions?
Core programming languages (Python, JavaScript, Go), CI/CD tooling (Jenkins, GitHub Actions), cloud platforms (AWS, Azure, GCP), container orchestration (Kubernetes), infrastructure as code (Terraform), and Agile certifications (Certified Scrum Master, SAFe Agilist). Remote communication proficiency using Slack, Zoom, and Asana is also essential.
Is remote work available for flexible hours roles?
Over 80% of the current listings allow fully remote work, with many offering hybrid models that permit in‑office days on a flexible schedule. Employers often provide stipends for home‑office equipment and support 24‑hour VPN access.
What career progression paths exist in flexible hours tech roles?
A typical path starts with a Junior Engineer or Associate Product Manager, moves to Lead Engineer or Senior Product Owner, then to Engineering Manager or Director of Product, and ultimately to VP or Head of Engineering, each step unlocking higher pay and broader influence over product strategy.
What industry trends are shaping flexible hours tech jobs?
Tech firms are adopting continuous delivery pipelines that require 24/7 monitoring, driving demand for shift‑based DevOps and support roles. AI‑driven scheduling tools are automating shift assignment, and companies are increasingly offering flexible pay bands to retain talent in a competitive market.

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