Remote Senior Project Manager Jobs in Chicago, IL

POSITION OVERVIEW:

As a Senior Project Manager, you will lead delivery across multiple workstreams for large, complex enterprise clients. You will oversee sprint execution in Azure DevOps, guide planning and project working sessions, and ensure alignment across business stakeholders and Endeavor4’s functional and technical teams. The role includes managing enhancements, integrations, reporting, and day-to-day issue resolution within a complex Dynamics 365 CE and F&SC ecosystems.

This role works closely with Business Analysts, Developers, QA Analysts, Architects, and client leadership to ensure requirements are well defined, timelines are achievable, risks are addressed proactively, and deliverables remain on track. The Project Manager must be comfortable operating in an Agile environment and coordinating day-to-day work across teams to support enterprise-scale delivery.

A strong candidate will be able to lead discussions with business and IT leadership, communicate clearly across teams, and manage competing priorities across parallel workstreams.This is a primarily remote position; however, preference will be given to those located near or within reasonable proximity to the Lisle office.

ESSENTIAL DUTIES AND RESPONSIBILITIES:  

The Senior Project Manager (PM) is responsible for planning and coordinating enhancements, integrations, application changes, and operational improvements across clients’ D365 platform, including all supporting applications, data solutions, and reports. This includes sprint execution, release management, stakeholder communication, risk management, and enforcing Endeavor4’s delivery standards across all project workstreams.

Responsibilities include:

Azure DevOps & Delivery Management

• Maintaining all project work items in Azure DevOps, including Epics, Features, User Stories, Tasks, Bugs, and sprint backlogs, to ensure accurate tracking and alignment with client delivery standards.
• Leading all Agile ceremonies including backlog refinement, sprint planning, daily stand-ups, sprint reviews/demos, and retrospectives.
• Ensuring user stories, acceptance criteria, and tasks are clearly defined, properly documented, and fully traceable throughout delivery.
• Monitoring project progress against planned scope and milestones.
• Maintaining visibility into dependencies across functional, technical, and QA workstreams, while coordinating issue resolution as needed.
• Tracking issues, risks, and blockers in Azure DevOps and driving timely resolution or escalation as needed.

Stakeholder Management & Communication

• Leading work sessions with business and technical stakeholders to review progress, align on priorities, resolve blockers, and ensure cross-team clarity on scope and next steps.
• Preparing and leading monthly executive-level updates (e.g., steering committee meetings), including roadmap reviews, delivery summaries, risk escalations, and recommendations for business and IT leadership.
• Communicating status, scope changes, risks, and key decisions to client executives, SMEs, and project sponsors in a proactive and timely manner.
• Facilitating decision-making discussions across client teams and ensuring alignment on priorities and expectations.

Project Planning & Governance

• Creating project plans, timelines, communication plans, and resource forecasts to support delivery.
• Managing scope and enforcing change control processes to ensure alignment with agreed-upon objectives.
• Coordinating cross-system integration and dependency work across Azure services, on-premise applications, reporting systems, and financial applications.
• Ensuring that requirements, design, development, testing, and deployment follow a consistent documentation and delivery process.
• Supporting QA and UAT planning, including test script creation, defect management, and remediation cycles.
• Leading release planning, deployment coordination, and post-deployment reviews to ensure successful production delivery.

Operational and Continuous Improvement

• Identifying process gaps and recommending actionable improvements to enhance overall project execution.
• Ensuring all documentation, backlogs, and project artifacts are accurately maintained and aligned with Endeavor4’s delivery standards.

EDUCATION

• Bachelor’s degree in Information Systems, Computer Science, Business Administration, Finance or related field preferred.

MUST HAVE SKILLS

• 7+ years of project management experience for enterprise application or integration projects.
• Hands-on experience managing projects in Azure DevOps, including sprint planning, backlog management, boards, pipelines, and reporting.
• Experience leading Agile ceremonies such as backlog refinement, sprint planning, daily stand-ups, sprint reviews/demos, and retrospectives.
• Demonstrated experience running executive-level meetings (monthly status updates, quarterly reviews, roadmap discussions, etc.)
• Strong written and verbal communication skills, with the ability to present clearly to business leaders and technical teams.
• Experience coordinating work across functional analysts, developers, QA testers, SMEs, and system architects to keep tasks aligned and moving forward.
• Ability to manage dependencies across multiple systems.
• High attention to detail and consistent follow-through.
• Strong problem-solving and organizational skills, with the ability to bring clarity to complex or evolving situations.
• Ability to manage day-to-day project activities independently, while coordinating with project leadership on priorities and direction.

DESIRED SKILLS AND EXPERIENCE

• 7+ years of implementing or supporting business systems and applications, preferably Microsoft Dynamics 365.
• Experience working with finance/accounting systems.

REQUIRED TRAVEL

Occasional travel to local and non-local clients.

SALARY AND BENEFITS

The compensation range for this position is $140,000 to $160,000 depending on years of comparable experience, skill set, and the unique value you bring. This role is eligible for a competitive benefits package, which includes medical, dental, and vision insurance; paid vacation, sick time, and paid holidays; a 401(k) retirement savings plan; performance‑based bonus opportunities; maternity and paternity leave; short‑ and long‑term disability coverage; and access to a fitness center for employees based near the Lisle office.

Endeavor4 is a consulting firm that designs, develops, and manages technology solutions and transformative business applications to help clients meet today’s business challenges. Our services ­– which include IT infrastructure, ERP implementations, cloud migration, cybersecurity, and analytics – help medium and large enterprises operate and grow their businesses securely, efficiently, and intelligently. Endeavor4’s customized solutions and data analytics increase revenue, improve customer relationships, and optimize productivity for clients across industries. As a Microsoft Gold Partner, Endeavor4\'s onshore professionals have extensive experience with Microsoft technologies, including Dynamics 365, Azure, and Office/Microsoft 365. Our deep partnerships formed with clients, coupled with our reputation for outstanding service, give clients freedom to focus on meaningful work that drives their companies’ success. 

EQUAL OPPORTUNITY EMPLOYER

Endeavor4 will provide equal opportunity to all employees and applicants for employment regardless of race, color, religion, age, sex, pregnancy, national origin, ancestry, disability (mental or physical), genetic information, military status, marital status, order of protection status, gender identity, or sexual orientation all in accordance with applicable law.  Such action shall include, but is not limited to: initial consideration for employment; job placement and assignment of responsibilities; performance evaluation; promotion and advancement; compensation and fringe benefits; training and professional development opportunities; formulation and application of human resource policies and rules; facility and service accessibility; and discipline and termination.

Endeavor4 is an equal employment opportunity employer and will not discriminate against any employee or applicant for employment in a manner that violates applicable state and local laws governing nondiscrimination in employment in every location in which the Company has employees.