Director, Project Management Office

Location: Shawnee Mission

The Director, Project Management Office is responsible for leading the project management office within Well Sky’s professional services organization. The scope of this job includes partnering with professional services leaders to develop and maintain best practices while tailoring execution strategies based on client and business needs.

Key Responsibilities:

Ensure all projects are delivered on time, within scope, budget, and with adequate resources by establishing and enforcing compliance, best practices, and standardized methodologies.

Establish a center of excellence by developing, implementing, and maintaining project management guidelines, tools, and quality standards aligned with Project Management Institute (PMI) requirements and Well Sky’s internal priorities.

Optimize project execution efficiency to meet or exceed financial expectations within the statement of work to mitigate budgetary risks through proactive review of financial and resource metrics.

Serve as the primary liaison to executive leaders within sales, solution management, engineering, and support teams to facilitate seamless project coordination and delivery.

Continuously elevate the PMO team performance through mentorship, knowledge sharing, and goal setting to develop skills and foster a culture of accountability.

Participate in client contract management and compliance activities, including negotiating contract amendments and addendums, and ensure Well Sky can deliver on contractual obligations.

Perform other job duties as assigned.

Required Qualifications:

Bachelor’s Degree or equivalent work experience

At least 4 – 5 years relevant management work experience

At least 8 – 10 years relevant work experience

Experience leading large, cross-functional project management or professional services organizations.

Experience managing managers and developing high-performing leadership teams.

Demonstrated success establishing PMO governance, project delivery standards, and operational processes.

Experience partnering with executive leadership and presenting project portfolio health, risks, and strategic initiatives to senior stakeholders.

Experience overseeing project portfolio planning, forecasting, resource management, and budget governance.

Preferred Qualifications:

PMP certified

Experience leading a Project Management Office (PMO) across multiple business units, product lines, or service organizations.

Experience driving organizational change, process improvement, and operational excellence initiatives.

Experience evaluating and implementing project management, PSA, or workflow automation tools.

Healthcare technology, software, consulting, or professional services industry experience.

Experience leveraging AI-enabled tools and technologies to improve team productivity, project delivery, or operational efficiency.

Job Expectations:

Willing to travel up to 20% based on business needs

Willing to work additional or irregular hours as needed

Must work in accordance with applicable security policies and procedures to safeguard company and client information

Must be able to sit and view a computer screen for extended periods of time#LI-Onsite Well Sky  is where independent thinking and collaboration come together to create an authentic culture. We thrive on innovation, inclusiveness, and cohesive perspectives. At Well Sky you can make a difference.

Here are some of the exciting benefits full-time teammates are eligible to receive at Well Sky:

Excellent medical with Rx, dental, and vision benefits

Mental Health support through EAPGenerous paid time off, plus 13 paid holidays
100% vested 401(K) retirement plans

Educational assistance up to $2500 per year

WellSky provides equal employment opportunities to all people without regard to race, color, national…