Head Of Enterprise PMO
At Gifthealth, we're revolutionizing the way people experience healthcare by simplifying the process of managing prescriptions and health services. Our mission is to provide a seamless, personalized, and efficient healthcare experience for all our customers. We're a dynamic, innovative, and customer-centric company dedicated to making a positive impact on people's lives.
Position Summary
The Head of Enterprise PMO will build, lead, and scale Gifthealth's enterprise-wide Project Management Office (PMO), embedding agile discipline, operational excellence, and strategic alignment across all business units. This role is responsible for establishing PMO governance, frameworks, and performance metrics that drive visibility, accountability, and success for all initiatives enterprise-wide, including technology, operations, pharmacy, digital health, and patient experience.
This leader will collaborate cross-functionally with executives, engineering, finance, and operational teams to ensure that every project aligns with corporate strategy, delivers measurable business outcomes, and operates within budget. The ideal candidate is a transformational, data-driven, and agile leader who thrives on building disciplined, high-performing teams and driving change at scale.
Key Responsibilities
PMO Leadership & Strategy
- Establish, scale, and continuously evolve the Enterprise PMO vision, structure, and operating model.
- Develop and enforce governance standards, agile methodologies, and project delivery frameworks across all programs.
- Translate strategic business goals into executable project portfolios, aligning resources and timelines to company OKRs.
- Partner with executive leadership to define and communicate enterprise-wide KPIs, OKRs, and SLAs to measure performance and impact.
- Serve as the primary advisor to the executive team on program performance, prioritization, and enterprise readiness.
Program Portfolio & Financial Management
Lead portfolio management across all functions (technology, operations, finance, HR, and pharmacy).Oversee the annual project budget, ensuring initiatives are financially justified, resourced properly, and executed within approved spend.Drive transparency in project investments through regular performance dashboards and executive reports.Ensure each program and project demonstrates measurable ROI, operational efficiency, and alignment with company objectives.Implement portfolio analytics and financial tracking to enable real-time performance and risk insights.Agile PMO Implementation
Champion the Agile-at-Scale mindset across the organization, promoting iterative delivery, transparency, and adaptability.Introduce and embed agile frameworks (Scrum, Kanban, SAFe, hybrid) across project teams and business units.Partner with Engineering, Product, and Operations to ensure alignment between agile delivery and business outcomes.Coach teams and leaders on agile principles, standups, sprint reviews, retrospectives, and adaptive planning.Change Management & Transformation
Lead enterprise-wide change management efforts, ensuring effective adoption of new systems, processes, and cultural shifts.Develop and implement standardized change management frameworks (Prosci or equivalent) to ensure project success and stakeholder alignment.Act as a cultural ambassador for disciplined execution and continuous improvement.Foster strong communication between business units, breaking down silos and driving cross-functional collaboration.Performance, KPIs & OKRs
Define and maintain enterprise-wide PMO metrics, including project delivery timelines, budget adherence, ROI, and strategic alignment.Develop and manage dashboards that visualize PMO performance against company OKRs and department SLAs.Partner with the COO, CFO, and department leaders to review outcomes and identify opportunities for acceleration or course correction.Ensure project performance reporting drives accountability and informs business decisions at the executive level.Technology, Innovation & Implementation
Lead the deployment of project management systems, tools, and dashboards to improve transparency and execution speed.Evaluate and integrate AI-driven analytics and automation to optimize project tracking, forecasting, and performance.Oversee enterprise-level implementations (ERP, CRM, automation, infrastructure) ensuring on-time and on-budget completion.Partner with IT and data teams to ensure technology initiatives align with strategic priorities and operational needs.Team Development & Organizational Leadership
Build, lead, and inspire a team of project managers, program leads, and portfolio analysts.Establish clear performance standards, coaching frameworks, and development paths.Promote a culture of agility, accountability, and excellence across the PMO organization.Serve as a mentor and change agent for cross-functional teams, strengthening enterprise project management capabilities.Qualifications
Education : Bachelor's degree in Business, Technology, or related field required; Master's degree preferred.Experience :
15+ years of progressive project, program, or portfolio management experience.7+ years in senior leadership within a high-growth or transformation-driven organization.Proven success in building or leading enterprise PMOs across multiple business units.Strong experience with Agile at scale, SAFe, and hybrid delivery models.Demonstrated ability to lead large-scale enterprise transformations, digital initiatives, and M&A integrations.Financial acumen with experience managing portfolios exceeding $50M+.Certifications :
PMP, PgMP, PfMP, or Agile certifications (SAFe, CSM, PMI-ACP).Prosci or equivalent certification in Change Management preferred.Skills :
Deep understanding of Agile enterprise delivery and PMO maturity models.Expertise in KPI / OKR implementation and performance tracking.Strong knowledge of portfolio and budget management best practices.Executive presence and ability to influence across all levels of the organization.Exceptional communication, analytical, and leadership skills.Proficient with modern PMO tools (Smartsheet, Jira, Asana, Monday.com, or similar).Desired Attributes :
Visionary leader who balances structure with agility.Quick learner with strong business acumen and curiosity.Passionate about transformation, operational excellence, and continuous improvement.Skilled in cross-functional collaboration and stakeholder management.Committed to embedding accountability, transparency, and delivery discipline organization-wide.Work Environment
Location : HybridSchedule : Full-time : occasional evening or weekend availability may be required to support enterprise rollouts.Meetings : Regular collaboration with executive leadership, Finance, Operations, IT, and Pharmacy divisions.Key Essential Functions
Must be able to operate in a fast-paced, changing environment.Must be comfortable presenting to C-suite and board-level executives.Must be able to manage multiple concurrent enterprise initiatives.Employment Classification
Status : Full-time FLSA : Exempt
Equal Employment Opportunity (EEO) Statement
Gifthealth is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. All employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity, transgender status, national origin, age, disability, veteran status, or any other legally protected status. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you do not meet every requirement but still feel you would be a great fit for this role, we encourage you to apply!
Disclaimer
This job description is intended to describe the general nature and