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.

Senior Analyst, Liquidity and Funding Risk

Company: BMO US

Location: Chicago, IL

Posted Jan 30, 2025

Typically between 4 - 6 years of relevant experience and post-secondary degree in related field of study or an equivalent combination of education and…

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.

Lead Due Diligence Specialist

Company: Discover

Location: Chicago, IL

Posted Jan 30, 2025

Discover offers a bright future with meaningful work from day one. The company values individuality and encourages growth. The role involves coordinating risk assessment and due diligence for new and existing business partners and new product initiatives. The position requires a Bachelor's degree in business administration, management, marketing, or a related field, and 4+ years of experience in financial services. The compensation ranges from $77,500 to $131,500, with additional incentives. Discover is committed to a diverse and inclusive workplace and complies with federal, state, and local laws regarding equal opportunity and reasonable accommodations.

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.

Product Manager (EMV Mobile Payments)

Company: Discover

Location: Chicago, IL

Posted Jan 30, 2025

Discover is offering a job opportunity for an EMV Mobile Payments Product Manager. The role involves developing and managing the Mobile DPAS product, which enables contactless payments using mobile devices. The successful candidate will be responsible for creating the product strategy, roadmap, and features based on client needs. They will also be accountable for achieving specific goals for each product, evaluating product performance, and identifying innovations to address customer needs. The ideal candidate should have a Bachelor's degree in a relevant field and at least 6 years of experience in Product Management. Bonus points for a Masters degree, experience in the payments industry, and knowledge of EMV specifications.

Senior Fundamental Research Analyst

Company: PEAK6

Location: Chicago, IL

Posted Jan 31, 2025

PEAK6 Capital Management, a 25-year-old proprietary options trading firm based in Chicago, is seeking a highly motivated Analyst for its growing trading team. The role involves conducting in-depth research, building financial models, performing valuation analysis, monitoring portfolio companies, generating investment ideas, and preparing presentations. The ideal candidate should have 5+ years of experience in a related field, excellent research and analytical skills, strong communication skills, and experience with financial modeling or valuation. PEAK6 offers a robust package of employee perks and benefits, including healthcare, competitive PTO, 401k match, and a paid subscription to the Calm app.

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.

Consultant, Comparative Analytics

Company: Strata Decision Technology

Location: Chicago, IL

Posted Jan 31, 2025

The job posting is for a Comparative Analytics Consultant role in healthcare. The successful candidate will work with healthcare organizations to implement, optimize, and provide advisory services for Strata's financial and operational benchmarking software solution. Key responsibilities include working with a team to implement the software, defining user requirements, configuring the system, leading customer training, communicating with team members, contributing to growth projects, collaborating with other solution consultants, and using SQL, Excel, and Strata tools. The ideal candidate should have a data-driven mindset, relevant experience, strong customer service skills, understanding of financial concepts, ability to adapt to new challenges, self-motivation, and willingness to travel. Additional points for professional or academic background in SQL, healthcare finance experience, setting productivity standards, and software implementation experience. The company values collaboration, continuous learning, and diversity, with a focus on inclusion and equity.

Director of Accounting

Company: R&R Human Resources Solutions

Location: Chicago, IL

Posted Jan 30, 2025

A downtown real estate development and investment firm is seeking a Director of Accounting with at least 8 years of progressive accounting experience, preferably in the real estate industry. The role involves overseeing general accounting functions, managing financial reporting, monitoring monthly operating results, and providing financial leadership. The ideal candidate will have excellent communication skills, strong leadership abilities, and advanced Microsoft Excel skills. Knowledge of employee relationship building and performance management techniques, as well as experience with computerized financial systems like Yardi, is also required.

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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