Director, Project Management Office

The Director, Project Management Office is responsible for leading the project management office within WellSky’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 WellSky’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 WellSky 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

WellSky is where independent thinking and collaboration come together to create an authentic culture. We thrive on innovation, inclusiveness, and cohesive perspectives. At WellSky you can make a difference.

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

• Excellent medical with Rx, dental, and vision benefits
• Mental Health support through EAP
• Generous 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 origin, ancestry, citizenship, age, religion, gender, sex, sexual orientation, gender identity, gender expression, marital status, pregnancy, physical or mental disability, protected medical condition, genetic information, military service, veteran status, or any other status or characteristic protected by law. WellSky is proud to be a drug-free workplace.

Applicants for U.S.-based positions with WellSky must be legally authorized to work in the United States. Verification of employment eligibility will be required at the time of hire. Certain client-facing positions may be required to comply with applicable requirements, such as immunizations and occupational health mandates.

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