Principal Program Manager Workday Implementation & Transformation

Principal Program Manager - HCM Implementation & Transformation, DEPARTMENT The Principal Program Manager - HCM Implementation & Transformation serves as the primary execution and delivery leader supporting the Senior Director of HCM Implementation and Transformation. This role acts as an extension of senior leadership, translating strategy into execution across enterprise-scale HCM and HR technology initiatives. The role carries accountability for driving complex, multi-workstream programs, establishing disciplined governance, proactively managing risk, and ensuring stakeholder alignment across HR, IT, Finance, Operations, and external partners. This position requires deep experience leading large-scale transformations, executive-level communication skills, and the ability to operate with autonomy in a highly matrixed environment. Heartland Dental is the nation's largest dental support organization, providing non-clinical administrative support services to more than 3,000 supported doctors across 39 states and the District of Columbia in 1,900+ dental offices. Each Heartland Dental supported office is unique to the community and the patients they serve. Supported doctors are the clinical leaders of their practice, retain full clinical autonomy, and establish their own care philosophies. All Heartland Dental supported doctors are united by a common goal: delivering the highest quality dental care and patient experiences. To give you an idea of the team structure, you will report to the Sr. Director - HCM Implementation & Transformation and you will work closely with cross-functional leaders in Human Resources, Operations, Finance, IT, and external partners. Below is an overview of the duties and responsibilities you would take on in this role: Serve as the Senior Director's right-hand leader for day-to-day execution of enterprise HCM implementation and transformation initiatives. Own delivery management for complex, multi-workstream programs including planning, sequencing, dependency management, and execution oversight. Establish and maintain integrated master project plans across HR, IT, Finance, Operations, vendors, and system integrators. Lead program governance including steering committee facilitation, executive reporting, risk and issue escalation, and decision tracking. Proactively identify, assess, and mitigate delivery risks; recommend trade-offs and solutions to maintain program momentum. Drive accountability across cross-functional leaders and project teams to ensure commitments, milestones, and outcomes are met. Develop and maintain executive-ready dashboards, status reporting, and presentations for senior leadership audiences. Partner with change management, testing, data, security, and deployment leads to ensure readiness and successful adoption. Support post-go-live stabilization, optimization, and long-term roadmap execution for HCM platforms. Apply disciplined project, program, and portfolio management best practices across the HCM transformation portfolio. Mentor and guide project managers or workstream leads as applicable. Perform other related duties as assigned. Minimum Requirements Bachelor's degree in Business, Human Resources, Information Systems, or a related field required 8+ years of experience leading or managing enterprise-scale programs or transformations. Demonstrated experience delivering complex, cross-functional technology or operational initiatives. Strong expertise in project, program, and portfolio management methodologies and governance models. Proven ability to communicate effectively with executive leadership and influence without direct authority. Exceptional organizational skills with strong attention to detail and follow-through. Ability to manage ambiguity, competing priorities, and high-visibility initiatives in a fast-paced environment. Advanced proficiency with Microsoft Office and enterprise project management tools (e.g., Smartsheet, MS Project). Minimum Requirements Bachelor's degree in Business, Human Resources, Information Systems, or a related field required 8+ years of experience leading or managing enterprise-scale programs or transformations. Demonstrated experience delivering complex, cross-functional technology or operational initiatives. Strong expertise in project, program, and portfolio management methodologies and governance models. Proven ability to communicate effectively with executive leadership and influence without direct authority. Exceptional organizational skills with strong attention to detail and follow-through. Ability to manage ambiguity, competing priorities, and high-visibility initiatives in a fast-paced environment. Advanced proficiency with Microsoft Office and enterprise project management tools (e.g., Smartsheet, MS Project). Desired Qualifications Experience leading or supporting enterprise HCM platform implementations (e.g., Workday, SAP SuccessFactors, Oracle HCM). Project Management Professional (PMP) certification strongly preferred. Experience establishing or operating within an Enterprise PMO or Transformation Office. Healthcare, multi-site, or highly regulated environment experience preferred. Prior experience leading large portfolios, mentoring project managers, or serving in a transformation leadership role. Physical Requirements Ability to perform essential duties satisfactorily with or without reasonable accommodation. Prolonged periods sitting at a desk and working on a computer. Must be able to lift up to 15 pounds at times. We put our people first at Heartland Dental, and that shows in our generous benefits package. Company retains the sole discretion to change the duties of the position at any time. We provide all employees and applicants for employment the protections of federal, state, and local laws affording equal opportunity in employment.