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Fun Project Management Jobs in Chicago, IL (NOW HIRING)

Senior IT Project Manager

Rosemont, IL · On-site

$132K - $132K/yr

Wintrust provides community and commercial banking, specialty finance and wealth management ... We hold ourselves accountable to high standards, share wins, operate ethically, and have fun * This ...

Senior IT Project Manager

Rosemont, IL · On-site

$132K - $132K/yr

Wintrust provides community and commercial banking, specialty finance and wealth management ... We hold ourselves accountable to high standards, share wins, operate ethically, and have fun * This ...

Enjoy the people you work with, have fun, and do great work. These principles define our consulting ... Who You Are: * 7+ years of Project Management experience leading technology or business ...

Enjoy the people you work with, have fun, and do great work. These principles define our consulting ... Who You Are: * 7+ years of Project Management experience leading technology or business ...

Impact Advisors, LLC is a nationally recognized healthcare management consulting firm delivering ... Our People and Culture At Impact Advisors, we cultivate a caring, fun, honest, and autonomous work ...

Workday Senior Project Manager

Chicago, IL · On-site +1

$154K - $230K/yr

Impact Advisors, LLC is a nationally recognized healthcare management consulting firm delivering ... Our People and Culture At Impact Advisors, we cultivate a caring, fun, honest, and autonomous work ...

... fun, and grow with us by offering unparalleled opportunities for career development. Senior Project ... Bachelor's degree in Construction Management, Civil/Structural Engineering, or a related field will ...

Showing results 41-60

Fun Project Management information

See Chicago, IL salary details

$39.7K

$105.8K

$166.9K

How much do fun project management jobs pay per year?

As of Aug 6, 2026, the average yearly pay for fun project management in Chicago, IL is $105,777.00, according to ZipRecruiter salary data. Most workers in this role earn between $80,900.00 and $126,700.00 per year, depending on experience, location, and employer.

What is fun project management?

A Fun Project Management job focuses on organizing and overseeing projects that are designed to be engaging, creative, and enjoyable. This role often involves managing events, entertainment initiatives, team-building activities, or interactive experiences. It requires strong organizational skills, creativity, and the ability to coordinate various stakeholders to ensure successful execution. The goal is to deliver projects that not only meet objectives but also create a positive and memorable experience for participants.

What are the typical challenges faced in fun project management?

A key challenge in Fun Project Management is balancing creativity and innovation with practical considerations like budgets, deadlines, and stakeholder expectations. Since these projects often involve coordinating diverse teams and managing logistics for events or activities, project managers must be quick thinkers and adept at handling last-minute changes. You'll frequently collaborate with creative staff, vendors, and clients, making strong interpersonal and negotiation skills essential. Embracing flexibility and maintaining a positive attitude are important for overcoming obstacles and ensuring each project delivers an engaging experience.

What are the key skills and qualifications needed to thrive in fun project management?

To thrive in a Fun Project Management role, you need strong organizational and leadership skills, experience managing events or creative projects, and often a background in project management or related certifications. Familiarity with project management tools such as Asana, Trello, or Microsoft Project is advantageous, as is knowledge of event planning software. Creative problem-solving, adaptability, and excellent communication are vital soft skills for engaging teams and stakeholders effectively. These abilities help ensure the successful execution of enjoyable, memorable projects while maintaining timelines and budgets.

What are the most commonly searched types of Fun Project Management jobs in Chicago, IL? The most popular types of Fun Project Management jobs in Chicago, IL are:
What are popular job titles related to Fun Project Management jobs in Chicago, IL? For Fun Project Management jobs in Chicago, IL, the most frequently searched job titles are:
Infographic showing various Fun Project Management job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 90% In-person, and 10% Remote job distribution, with an average salary of $105,777 per year, or $50.9 per hour.

Senior IT Project Manager

Wintrust

Rosemont, IL • On-site

$132K - $132K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 9 days ago


Wintrust rating

8.0

Company rating: 8.0 out of 10

Based on 20 frontline employees who took The Breakroom Quiz

73rd of 170 rated banks


Job description

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol "WTFC."

Why join us?

  • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 8 years) and Employee Recommended award by Globe & Mail (past 6 years)

  • Competitive pay and discretionary bonus eligible

  • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few

  • Promote from within culture

Why join this team?

  • We hold ourselves accountable to high standards, share wins, operate ethically, and have fun

  • This role offers the ability to make an impact and interface with IT and the various aspects of Wintrust's businesses

What you'll do:

The Senior IT Project Manager / Assistance Vice President (AVP) orchestrates the initiation, planning, execution, monitoring and closing of projects with a specific term that have a beginning, an end and specified technology deliverables. The IT Senior Project Manager is responsible for communicating and integrating IT activities into the broader plan held with the business unit/s. The Senior IT Project Manager acts as primary point of contact for project stakeholders across IT, IS, and IT vendors. The Senior IT Project Manager provides technology artifacts to support the movement of projects / programs through the Enterprise Project Management Office (ePMO) governance process including ePMO processes, templates and Project Portfolio Management (PPM) Clarity tool updates. The Senior IT Project Manager defines and maintains project plans, inclusive of scope, milestones, dependencies and technology deliverables. The Senior IT Project Manager is expected to have exposure to enterprise architecture, core banking systems, SaaS applications framework. The Senior IT Project Manager creates, manages and reports on projects / programs, technology, financials and budget. Projects may vary in number, size and complexity. Generally, manages moderate to high complexity, large to extra-large sized projects.

Key Accountabilities:

  • Project Ownership

  • Project Life Cycle:

    • Plan the Project

    • Execute the Project

    • Monitor and Control the Project

    • Close the Project

  • Technology Governance & Architecture Alignment

  • Efficiencies / Continuous Improvement

  • Other Duties, as assigned

  • People:

    • Participate in the recruiting and hiring of IT PMO staff, consultants and temp workers with appropriate skills

    • Take part to onboard new team members to the IT PMO team, Wintrust Technology and Wintrust Corporation

    • Mentor the team in the creation of all project artifacts, including project plans, statements of work, status reports, etc.

    • Build and maintain influential relationships across business, technology, compliance, legal, and external partner organizations.

Qualifications:

  • 5-10 years of related experience

  • Financial Services or Financial systems at mid-to-large organizations experience, preferred

  • Bachelor's degree or equivalent

  • Resolve non-routine problems

  • Exercise judgement within defined procedures and practices

  • Require minimum supervision

  • Track project actuals vs. budget. Validate receipt of goods/services before authorizing invoice payments. Prepare project budget submission and change requests, as needed

  • Accountable for project with broad scope

  • Project Management Professional (PMP) certification, Program Management Professional (PgMP), or PMI Agile Certified Practitioner (PMI-ACP), preferred

  • Certified ScrumMaster (CSM) or Professional Scrum Master (PSM II/III), preferred

  • Experience with one or more project management tools (Clarity preferred)

  • Good technology knowledge, understanding and experience leading technology projects / programs.

  • Ethical behavior and business practices

  • Communication: Speak, listen and write in a clear, thorough and timely manner. Comfortable talking with all levels of management

  • Strong interpersonal, organizational, attention to detail and follow-up skills

  • Identify and communicate issues early. Bring recommendations and options to resolve issues

  • Foster teamwork: Work cooperatively and effectively with others to set goals, resolve problems and make decisions

  • Leadership skills: Positively influence others to achieve results

  • Make decisions: Assess situations to determine importance, urgency and risks to produce clear decisions. Raise issues to Sr. management

  • Organizational skills: Set priorities, develop work schedule and monitor progress toward goals

  • Planning skills: Determine strategies to move projects forward; create and implement action plans and evaluate results

  • Problem-solving skills: Assess problem situations to identify causes, gather and process relevant information, develop possible solutions and make recommendations to resolve

  • Change orientation: Adapt to change effectively

  • Demonstrates leading by example and instills a calm, organized approach in all situations

Benefits:

Medical Insurance Dental Vision Life insurance Accidental death and dismemberment Short-term and long-term Disability Insurance Parental Leave Employee Assistance Program (EAP) Traditional and Roth 401(k) with company match Flexible Spending Account (FSA) Employee Stock Purchase Plan at 5% discount Critical Illness Insurance Accident Insurance Transportation and Commuting Benefits Banking Benefits Pet Insurance

Compensation:

The estimatedannual salary of $98,000 - $132,000.00 along with eligibility to earn an annual bonus. Actualpayrate may vary based on several factors, such as a candidate's qualifications, skills and experience

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From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.


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