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.

Pharmacy Technician

Company: CVS Health

Location: Springfield, IL

Posted Jan 23, 2025

CVS Health emphasizes its commitment to human-centric health care, guided by a single purpose: 'Bringing our heart to every moment of your health.' The company aims to deliver enhanced, personalized, convenient, and affordable health care solutions. Pharmacy Technicians play a crucial role in this mission, supporting pharmacy teams to ensure smooth operations, accurate prescription fulfillment, and exceptional patient service. Technicians are expected to demonstrate empathy, genuine care, and a growth mindset, contributing to a safe, inclusive, and engaging team dynamic. They must complete a rigorous training program and satisfy all registration, licensing, and certification requirements.

Software Quality Engineer

Company: Vivid Seats

Location: Chicago, IL

Posted Jan 23, 2025

Vivid Seats, a leading online ticket marketplace founded in 2001, is seeking a Software Quality Engineer to join their Vegascom team. The role involves championing quality for the platform and products, testing new software applications, and applying test methodology engineering and product knowledge. The ideal candidate should have experience in software quality principles, understanding of Object-Oriented languages, and familiarity with automation frameworks. The role offers a competitive salary range of $80,000 - $100,000 USD, along with benefits such as FLEX PTO, mental health days, medical, dental, and vision insurance, 401K matching, and discounts for attending live events. The company values diversity and offers a hybrid working model.

Site Director at Butterfield School

Company: KinderCare Learning Companies

Location: Mundelein, IL

Posted Jan 23, 2025

KinderCare Learning Companies, a recognized early childhood education provider, is seeking a Site Director. The role involves leading a team of teachers to create engaging classroom experiences, ensuring operational standards, partnering with families, and cultivating positive relationships. The ideal candidate should have at least one year of teaching experience, a passion for children, strong organizational skills, and the ability to build relationships. KinderCare offers comprehensive benefits, including discounted child care, medical coverage, mental health support, and more. The company operates in over 2,000 sites across 40 states, committed to providing high-quality child care for all families.

Adoption Change Management

Company: Reply

Location: Chicago, IL

Posted Jan 23, 2025

Valorem Reply is an award-winning digital transformation firm specializing in Microsoft technologies. Their Modern Work practice focuses on creating exceptional employee experiences through digital workspaces, intranets, and collaboration platforms. As an Adoption Change Management consultant, you'll lead change management activities, plan communications campaigns, develop training plans, and contribute to business development. The role requires a Bachelor's degree, 2 years of experience in change management, and fluency in Microsoft 365 applications. Preferred qualifications include PROSCI certification, M365 adoption experience, and delivery focus.

Clinical Science Liaison

Company: iRhythm Technologies

Location: Deerfield, IL

Posted Jan 23, 2025

iRhythm Technologies is a leading digital healthcare company dedicated to creating trusted solutions for detecting, predicting, and preventing diseases, particularly focusing on cardiac care. The company is seeking a Clinical Science Liaison to serve as the primary clinical and scientific contact for healthcare providers, ensuring appropriate use of ambulatory cardiac monitoring services. The role involves providing customer education, emphasizing regulatory compliance, and scientific exchange. The ideal candidate should have a clinical or scientific degree in health sciences, preferably with a specialization in cardiology, electrophysiology, or diagnostic sciences. They should have 3-5 years of experience in a similar role, particularly in a regulated environment. The position requires strong relationship-building and communication skills, as well as familiarity with guidelines on off-label use and other SIUU frameworks.

Product Manager - Pangea (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 23, 2025

The job posting is for a Product Manager role at Enova International, a leading financial technology company. The role involves owning the success of key product initiatives, working closely with cross-functional teams to deliver customer-centric solutions, and driving business outcomes. The ideal candidate should have 4+ years of experience as a Product Manager or Product Owner in an agile environment, strong organizational and project management skills, and excellent communication skills. The role offers a competitive salary range of $87,000 - $126,000, along with comprehensive benefits including health, dental, and vision insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Enova International is committed to providing equal employment opportunities and fostering an inclusive culture.

Senior Adoption Change Management Consultant

Company: Reply

Location: Chicago, IL

Posted Jan 23, 2025

Valorem Reply is an award-winning digital transformation firm specializing in Microsoft technologies. They focus on data-driven enterprise IT modernization, customer experience, product transformation, and modern workplace solutions. The company's Modern Work practice comprises digital workplace experts who create exceptional employee experiences using Microsoft 365. As a Senior Adoption Change Management consultant, you will lead impactful technology change management projects, provide strategic thought leadership, and contribute to business development. The role requires a Bachelor's degree, 4+ years of change management experience, and proficiency in Microsoft 365 tools. The base compensation range is between $110,000 and $125,000.

Engineering Technical Services Manager

Company: Eaton

Location: Edwardsville, IL

Posted Jan 23, 2025

Senior Data Scientist - Retail Pharmacy Personalization

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health is seeking a machine learning expert to build predictive models for enhancing patient engagement and experience. The role involves deploying large-scale models, conducting A/B testing, collaborating with technical teams, and working with healthcare data. Required qualifications include 3+ years of ML/DL experience, proficiency in Python, SQL, and cloud-based ML frameworks, and strong Github and MLOps skills. A Master's degree or PhD is preferred. The company offers competitive compensation, benefits, and a supportive work environment.

Assistant Store Manager

Company: Staples

Location: Northbrook, IL

Posted Jan 23, 2025

Site Reliability Engineer Team Lead (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 23, 2025

Enova International is seeking a qualified candidate for a leadership role in the SRE team. The role involves leading day-to-day operations, collaborating with TechOps leadership, and mentoring team members. Responsibilities include balancing team activities, overseeing on-call rotations, and promoting operational best practices. Requirements include a Bachelor's degree in Computer Science or Engineering, strong IT infrastructure knowledge, and proven project management experience. The company offers a competitive salary, comprehensive benefits, and a values-driven work environment.

Product Manager

Company: Pangea Money Transfer

Location: Chicago, IL

Posted Jan 23, 2025

The job posting is for a Product Manager role at Pangea, a financial technology company. The role involves owning the success of key product initiatives, working closely with cross-functional teams to deliver customer-centric solutions, and driving business outcomes. The ideal candidate should have 4+ years of experience as a Product Manager or Product Owner in an agile environment, strong organizational and project management skills, and excellent communication skills. The role offers a competitive salary range of $87,000 - $126,000, along with comprehensive benefits including flexible scheduling, health insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Pangea values introspection, accountability, empowerment, excellence, and kindness, and is committed to providing equal employment opportunities.

Frequently Asked Questions

What are typical salary ranges for flexible work schedule roles at different seniority levels?
Entry‑level (0‑2 years) $60k–$80k; Mid‑level (2‑5 years) $80k–$120k; Senior (5‑10 years) $120k–$180k; Lead/Principal (10+ years) $180k–$250k. International remote roles may have adjusted ranges such as $40k–$60k in emerging markets, reflecting local cost of living while maintaining equity.
What key skills and certifications are required for flexible work schedule positions?
Technical: Proficiency in Git, Docker, Kubernetes, and cloud platforms (AWS Certified Solutions Architect, Google Cloud Professional Data Engineer, or Azure Solutions Architect). Agile and project tools: Jira, Confluence, and automated testing frameworks. Soft skills: asynchronous communication, cultural competence, self‑management, and time‑zone coordination. Certifications like Certified Scrum Master (CSM), ITIL Foundation, and PMP are highly regarded for product and project roles.
Is remote work always an option for flexible schedule roles?
Most flexible schedule positions offer 100% remote or hybrid arrangements, with occasional on‑site requirements for quarterly collaboration or training. Companies often specify the percentage of remote work (e.g., 80% remote, 20% on‑site) and provide stipends for home‑office equipment. Applicants can verify the remote policy in the job description or during the interview.
What career progression paths exist within flexible work schedule roles?
Typical paths include: Junior Engineer → Senior Engineer → Tech Lead → Principal Engineer → Engineering Manager; or Product Manager → Senior Product Manager → Director of Product → VP of Product. Lateral moves into architecture, security, or data science are common for professionals seeking broader impact while maintaining flexible arrangements.
What are the current industry trends affecting flexible work schedule jobs?
Key trends: growth of asynchronous communication tools (e.g., Loom, Notion), AI‑driven workflow automation (e.g., GitHub Copilot, ChatGPT for code review), distributed version control at scale, micro‑tasking platforms, flexible sprint lengths, well‑being metrics integration, and digital nomad visas supporting cross‑border talent. Companies are also investing in continuous learning portals and remote‑first hiring practices.

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