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.

Senior Director Cybersecurity - IAM and Architecture

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 31, 2025

McDonald's is seeking a Senior Director of Identity and Access Management to lead the development and implementation of innovative IAM strategies and solutions. The role involves driving the creation of pioneering IAM strategies, developing a strategic vision for User Access Enforcement, leading large-scale IAM projects, and providing strong leadership to the IAM team. The ideal candidate should have 5+ years of experience leading IAM teams, proficiency in IAM technologies, and strong people leadership skills.

Application Architect

Company: Inspire11

Location: Chicago, IL

Posted Jan 30, 2025

Inspire11 is a full-service consulting firm that helps clients reach their full potential by leveraging innovative and strategic thought with technology. They are seeking a Senior Application Architect with strong development and architecture skills to work with clients on technology needs. The role involves working directly with multiple clients, interacting with key decision-makers, and leading a team of developers. The ideal candidate should have strong full-stack development experience, be skilled in modern JavaScript frameworks, and have experience with both relational and non-relational databases. Inspire11 offers opportunities for collaboration with experienced technologists, cutting-edge work, and competitive compensation.

Marketing Analytics Manager

Company: SpotHero

Location: Chicago, IL

Posted Jan 31, 2025

SpotHero, a rapidly growing parking industry technology company, is seeking a Marketing Analytics Manager. The role involves leading a team of analysts, developing a marketing analytics roadmap, and designing marketing models. The ideal candidate should have a minimum of 3 years of experience in marketing analytics leadership, strong SQL and Python skills, and a deep understanding of marketing attribution and ROI methodologies. SpotHero offers a competitive salary, excellent benefits, flexible PTO, and a supportive work environment.

Vehicle Sales & Lead Manager

Company: Berman Auto Group

Location: Chicago, IL

Posted Jan 30, 2025

The job posting is for a Vehicle Sales & Lead Manager position at Berman Infiniti of Chicago. The role involves driving sales, managing customer leads, overseeing the sales process, collaborating with the sales team, and providing guidance to less experienced team members. The ideal candidate should have proven experience in automotive sales or finance management, strong knowledge of CRM systems, exceptional communication skills, and a customer-focused mindset. Benefits include competitive PTO, multiple insurance options, 401K, and automotive discounts. The position requires flexible hours, including evenings and weekends.

Senior Manager, Compensation and Benefits

Company: Point B

Location: Chicago, IL

Posted Jan 30, 2025

Point B is a business innovation firm that specializes in transformation, combining advanced technologies and industry expertise to help businesses reimagine their processes and stay ahead. They offer a world-class NPS score, proving their commitment to client success. The firm is seeking a Senior Compensation and Benefits Manager to lead their compensation and benefits programs, ensuring alignment with Point B's vision and competitive practices. The ideal candidate will have a strong analytical skill set, excellent communication skills, and a thorough understanding of compensation practices. Point B offers a career path based on expertise, a flexible lifestyle, and a comprehensive Total Rewards program. The estimated salary range for this role is $94,500 - $210,000 USD per year.

Senior Customer Success Manager

Company: Jobba Trade Technologies, Inc.

Location: Chicago, IL

Posted Jan 30, 2025

Jobba Trade Technologies is seeking a Senior Customer Success Manager to lead the successful transition from sale to client implementation, recommend workflows, develop and facilitate training, build trusted advisor relationships, and elevate the overall client experience. The role involves managing complex, valuable, and at-risk customers, developing processes and training programs, and coaching junior team members. Required skills include 57 years of experience in consulting services or software implementation, demonstrated success in driving product adoption, tech savviness, proactive client engagement, and business acumen. Preferred skills include a Bachelor's degree, construction or service industry experience, CRM ERP and client management experience, and curriculum and learning content development experience.

Manager, Technology Deployment - US Restaurant Platform

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 30, 2025

McDonald's is embarking on a growth strategy called 'Accelerating the Arches', focusing on enhancing the customer experience through Delivery, Digital, and Drive-Thru initiatives. The company aims to modernize its technology, including POS, back office hardware, network infrastructure, and digital menu boards, across all US restaurants over the next three years. A Manager is sought to lead this deployment, ensuring successful implementation, integration, and adoption of the new platform. The role involves leadership, supplier partner engagement, collaborator engagement, risk management, change management, performance monitoring, and continuous improvement.

Sr. Technical Business Analyst

Company: NinjaHoldings

Location: Chicago, IL

Posted Jan 30, 2025

NinjaHoldings, founded in 2017, aims to revolutionize financial services for overlooked Americans through digital banking and lending products. The company's EDGE brand offers analytics services to businesses. The Sr Technical Business Analyst role involves leading strategic conversations, managing teams, and driving project planning. The ideal candidate should have extensive experience in business intelligence, a deep understanding of financial products, and strong leadership skills.

Manager-Technical Product Management

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 30, 2025

McDonald's is accelerating its growth strategy, focusing on Delivery, Digital, and Drive-Thru. The company is investing in technology innovation, including AI and robotics, to enhance customer experience. The Product Manager Restaurant Development role involves leading the technical product management team, managing external vendor squads, and ensuring high-quality software development. The role requires a strong background in software development, Agile methodologies, and excellent communication skills.

Total Rewards Global Process Owner

Company: Kraft Heinz

Location: Chicago, IL

Posted Jan 30, 2025

The job description outlines a role for a Total Rewards Global Process Owner at Kraft Heinz. The position involves overseeing and harmonizing global Total Rewards processes, including compensation, benefits, and recognition administration. The role requires designing and running global capabilities for Total Rewards processes, collaborating with internal and external partners, and establishing key performance indicators. The ideal candidate should have deep experience in Total Rewards administration, strong leadership and communication skills, and a process improvement mindset. The role is based in Chicago, IL, and offers a competitive salary range, performance-based bonus, and comprehensive benefits package.

Manager, Partnership Marketing

Company: Barstool Sports

Location: Chicago, IL

Posted Jan 30, 2025

Barstool Sports is seeking a highly motivated, detail-oriented individual to join their partnerships team in Chicago. The role involves developing, managing, and executing large partnerships across various franchises and categories. Key responsibilities include overseeing team members in strategy development, serving as a daily contact for internal and external teams, building and renewing brand partnerships, and creating solutions for clients. The ideal candidate should have 4+ years of marketing, media, or sponsorship experience, a problem-solving attitude, strong organizational skills, and familiarity with Microsoft Office Suite. Barstool Sports offers competitive benefits, including medical, dental, vision insurance, a 401k match, unlimited vacation, and a monthly stipend for UberEats. The company values creativity, collaboration, and supporting one another.

Content Production Strategist (Hybrid or Remote)

Company: Simantel

Location: Peoria, IL

Posted Jan 30, 2025

The Content Production Strategist is a crucial role in the content production department, responsible for creating customer-focused content across various channels. The strategist must have strong communication skills, be able to work with different teams, and have decision-making authority over communication strategies, job development, and process improvements. The role involves partnering with various teams, directing writers, and creating editorial calendars. The ideal candidate should have a bachelor's degree, superior writing skills, and a willingness to learn. Success is measured by client outcomes, strong relationships, quality content, and growth in the content production service line.

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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