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.

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.

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.

Sr. Director, Cyber Business Office

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 31, 2025

McDonald's is seeking a Sr Director Cyber Business Office to lead and oversee the execution of their Securing the Arches Strategy. The role involves implementing a comprehensive cybersecurity program, developing metrics and reporting frameworks, and collaborating with various teams. The ideal candidate should have experience leading sophisticated programs, influencing high-performing teams, and managing risks with a focus on security and compliance.

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 Consultant Terminal Planner

Company: Ricondo & Associates, Inc.

Location: Chicago, IL

Posted Jan 31, 2025

Ricondo, a reputable aviation consulting firm, is seeking a Senior Consultant Terminal Planner for their Chicago office. The role involves advanced planning duties, research, and implementation of aviation programs, with opportunities for diverse experience in various practice areas. The ideal candidate should have a degree in a relevant field, 35 years of experience in airport planning, excellent analytical and communication skills, and the ability to work onsite at client locations. The company offers a competitive benefits package, including an ESOP, 401k, health insurance, paid time off, and professional development opportunities.

Consultant

Company: Ricondo & Associates, Inc.

Location: Chicago, IL

Posted Jan 31, 2025

Ricondo, a reputable aviation consulting firm, is seeking a Consultant to join their team. The ideal candidate will have a background in aviation or a strong desire to learn. The role involves conducting field surveys, data collection, report preparation, and providing technical assistance. The firm offers a competitive benefits package, including an ESOP, 401k, health insurance, and generous time-off. Ricondo emphasizes quality, accountability, and a collaborative environment.

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.

Sales Brand Manager – Illinois

Company: Wana Brands

Location: Chicago, IL

Posted Jan 31, 2025

Canopy USA LLC, a leading multistate operator in the US cannabis industry, is consolidating operations across its three business units - Wana Brands, Jetty, and Acreage. The company aims to realize synergies, cost savings, and support growth in state-legal markets, particularly in the Midwestern and Northeastern US. Canopy USA LLC values its employees, encouraging continuous learning and growth, and is seeking a passionate and experienced individual to promote Wana Brands in Illinois. The role involves designing sales strategies, managing KPIs, and building relationships with key retailers. The company offers competitive compensation and benefits, including health insurance, life insurance, and a 401k plan.

Fraud Operations Analyst

Company: Avant

Location: Chicago, IL

Posted Jan 31, 2025

Avant is seeking a Fraud Analyst for its Fraud Operations team in Chicago. The ideal candidate should have a knack for spotting patterns, excellent attention to detail, and a passion for solving complex fraud cases. The role involves investigating suspicious activities, examining data, reporting findings, collaborating with various teams, applying creative problem-solving skills, ensuring regulatory compliance, maintaining accurate records, conducting deep-dive analysis, continuously improving skills, and staying updated on fraud trends. The position requires a bachelor's degree in a relevant field, strong working memory, high accuracy, a genuine passion for fraud investigation, proficiency in data analysis tools, effective communication skills, and the ability to work in a fast-paced environment. The compensation range is $60,000 - $90,000 per year, with additional incentives. Avant values diversity, collaboration, and offers a flexible work environment with numerous benefits.

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.

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.

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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