Remote Senior Creative Project Manager Jobs in Chicago, IL

Team: Project Services
Salary Range: $100,000-$130,000 USD
Location: Remote - Chicago, Dallas, Atlanta, or Lincoln (Nebraska)

This role is aligned to our hub locations. While we’re especially interested in candidates in or near these areas, we welcome applications from outside of these locations as well.

Opportunity for Impact

Applied is where insurance technology gets reinvented, and we build it fast. Our cloud software and AI-powered solutions reach thousands of agencies and brokers worldwide, setting the pace for what modern insurance can do.

We’re looking for a Sr. Project Manager to join our Project Services andlead the delivery of complex, customer-facing implementation projects for some of Applied’s most strategic clients. In this role, you’ll serve as a trusted advisor, orchestrating cross-functional teams, driving exceptional customer experiences, and leveraging AI-enabled tools and innovative delivery practices to ensure predictable, high-quality project outcomes.

What You’ll Do

• Lead complex software implementation projects from initiation through completion, ensuring delivery against scope, timeline, budget, quality, and customer success objectives.
• Serve as a trusted advisor to customers, building strong relationships, driving executive-level communication, and proactively managing risks, expectations, and escalations.
• Partner with cross-functional teams including Consulting, Data Conversion, Product, Development, Support, Sales, and Customer Success to deliver seamless implementation experiences.
• Leverage AI-powered tools, data insights, and process improvements to enhance project delivery efficiency, customer outcomes, and operational effectiveness.

What We’re Looking For

• 5+ years of project management experience within software implementations, professional services, insurance technology, consulting, or a related customer-facing environment, including experience leading large-scale projects.
• Strong communication, stakeholder management, and problem-solving skills with the ability to translate technical concepts into clear business language for customers and executives.
• Proven ability to manage multiple priorities in a fast-paced environment while driving successful outcomes through collaboration, organization, and strategic thinking.

Bonus points if you also have:

• Experience with software implementations involving data migration, system integrations, or customer onboarding and activation projects.
• Project Management, Agile, Scrum, PMP, or related certifications and a demonstrated commitment to continuous professional development.
• Experience leveraging AI, automation, analytics, or modern project delivery tools to improve productivity, project visibility, and customer satisfaction.

Talent shows up in a lot of different ways, and we mean that. We welcome candidates from all backgrounds and experience levels, including military members and their spouses and those without a traditional degree or tech background. If this role speaks to you, apply.

Why You’ll Like Working on Team Applied
The best work happens when smart people move fast, together. For over 40+ years, Applied has built technology that solves real problems for insurance professionals - and we’re still pushing what’s possible.

You’ll be part of our people-first culture built on trust, inclusion, and growth - where you’re supported to deliver, collaborate with teammates who care, and grow with leaders invested in your success.

How We’ll Support You

We invest in the whole person, not just the role. Our benefits and resources are built to support your health, your time, and your life outside of work:

• Medical, Dental, and Vision Coverage
• Holiday and Vacation Time 
• Health & Wellness Days 
• A Bonus Day for Your Birthday 

Compensation Transparency

Our targeted starting base salary in the United States for this position considers a variety of factors, including depth and breadth of experience, skills and role scope. Depending on the role, team members may also be eligible for additional compensation plans (bonus and commission).

Your Security Matters: 
 Our candidates’ personal information and online safety are top of mind. Applied communicates with candidates only via a secure @appliedsystems.com email address or through our official careers portal. Recruiters will never request payments or ask for financial account or sensitive personal information like Social Security numbers.

AI Utilization

We leverage AI tools to streamline parts of our recruitment workflow (such as resume parsing and interview scheduling). However, final decisions are always conducted by real humans.

EEO Statement   

Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don’t discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.  

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