Chief of Staff - Enterprise Systems Transformation

Chief of Staff
- Enterprise Systems Transformation Job#: 3052303

Job Description:

Chief of Staff
- Enterprise Systems Transformation

Location:

Chicago, Illinois (Partial Remote)

Role Overview An experienced Chief of Staff / Portfolio Advisor is sought to support a senior Application Development leader during a period of significant business and technology transformation. This individual will provide portfolio management, executive communications, governance, and operational support across several strategic initiatives. This role acts as a force multiplier for leadership, creating capacity to focus on key project delivery while maintaining oversight of a broader transformation portfolio.

Key Responsibilities Serve as a trusted advisor and extension of the Application Development leader.

Manage priorities, executive action items, decision tracking, and follow-up activities.

Prepare executive presentations, briefing materials, and status reports for leadership reviews with the VP of Application Development and Chief HRO.Provide coordination, visibility, and governance across a portfolio that includes Corporate Financial Transformation, Procurement Transformation, Everyday AI initiatives, MyEmployee Travel Management (MyETM) redesign, and Employee Time & Attendance (ETA) modernization.

Maintain awareness and executive-level reporting on the Workday Transformation and Service Now Employee Experience Portal deployment.

Assist tactically at the Change Request level, including review and potential proxy sign-off.

Facilitate leadership operating rhythms and cross-functional alignment meetings.

Drive accountability across business, product, technology, HR, finance, procurement, and PMO stakeholders.

Required Qualifications 8+ years of experience in Chief of Staff, Portfolio Management, Program Management, Consulting, PMO Leadership, or Enterprise Transformation roles.

Experience supporting Director, VP, or Executive-level leaders.

Proven ability to manage complex, cross-functional business and technology portfolios.

Strong executive communication, presentation development, and stakeholder management skills.

Experience building content for executive reviews, steering committees, and leadership communications.

Exceptional organizational, prioritization, and follow-through capabilities.

Preferred Qualifications

Experience with enterprise HR, Finance, Procurement, or Employee Experience transformations.

Familiarity with Workday or Service Now-related programs.

Experience with AI strategy and adoption initiatives.

Background in large-scale corporate environments.

Airline or transportation industry experience.

Everforth Apex is a world-class IT services company that serves thousands of clients across the globe. When you join Everforth Apex, you become part of a team that values innovation, collaboration, and continuous learning. We offer quality career resources, training, certifications, development opportunities, and a comprehensive benefits package.

Our commitment to excellence is reflected in many awards, including Clearly Rateds Best of Staffing in Talent Satisfaction in the United States and Great Place to Work in the United Kingdom and Mexico.

Everforth Apex uses a virtual recruiter as part of the application process.  for more details. By applying for this job, you agree to receive calls, AI-generated calls, text messages, or emails from Everforth Apex and its affiliates, and contracted partners. Frequency varies for text messages. Message and data rates may apply. Carriers are not liable for delayed or undelivered messages. You can reply STOP to cancel and HELP for help.

You can access our privacy policy at Everforth Apex Benefits Overview:
Everforth Apex offers a range of supplemental benefits, including medical, dental, vision, life, disability, and other insurance plans that offer an optional layer of financial protection. We offer an ESPP (employee stock purchase program) and a 401K program which allows you to contribute typically within 30 days of starting, with a company match after 12 months of tenure. Everforth Apex also offers a HSA (Health Savings Account on the HDHP plan), a Support Linc Employee Assistance Program (EAP) with up to 8 free counseling sessions, a corporate discount savings program and other discounts.

In terms of professional development, Everforth Apex hosts an on-demand training program, provides access to certification prep and a library of technical and leadership courses/books/seminars once you have 6+ months of…