[Remote] Sr. Director of Program Management

Note: The job is a remote job and is open to candidates in USA. Rectangle Health is a leading financial technology company that empowers healthcare practices with innovative technology solutions. The Senior Director of Program Management is responsible for establishing and leading the Program Management Office (PMO) to ensure strategic initiatives are coordinated and executed effectively across the organization.ResponsibilitiesEstablish and lead the Program Management Office (PMO)Develop standards, governance, and reporting processes for enterprise initiativesBuild and maintain visibility into all significant cross-functional projects and programsEnsure initiatives are aligned to company priorities and business objectivesProvide executive leadership with portfolio-level reporting and insightsOwn the centralized intake process for strategic and cross-functional initiativesFacilitate initiative review, prioritization, and resource planningAssess organizational impact, dependencies, risks, and capacity requirementsEnsure initiatives have defined objectives, ownership, timelines, and expected outcomesIdentify competing priorities and recommend sequencing decisionsCoordinate initiatives spanning multiple departments and business functionsEnsure impacted stakeholders are identified and engaged throughout planning and executionMonitor progress against milestones, deliverables, and commitmentsEscalate risks, blockers, and dependency issues requiring executive interventionDrive accountability and follow-through across workstreamsMaintain enterprise initiative dashboards and reportingProvide regular updates to COO and other executive leadership on initiative progress, risks, and outcomesSupport Board reporting and strategic planning activitiesTrack initiative performance against expected business outcomesPartner with COO to drive enterprise-wide operational improvement, strategic initiatives, and transformation effortsTranslate executive priorities into executable programs, workstream, and implementation plansSupport organizational effectiveness, process redesign, automation, scalability, and operational maturity initiativesIdentify cross-functional risks, dependencies, and opportunities for improvementTrack initiative outcomes and ensure expected business benefits are realizedFacilitate alignment across business functions while maintaining focus on enterprise priorities established by the COODrive accountability, execution discipline, and visibility across major company initiativesManage Project Managers and future PMO resourcesDevelop program management capabilities and best practicesFoster a culture of accountability, transparency, and execution excellenceSkills8+ years of program management, PMO, business operations, transformation, or operational leadership experience8+ years of experience leading complex cross-functional initiativesExperience establishing or managing Project Management Office (PMO) functionsStrong executive communication and stakeholder management skillsDemonstrated ability to influence across functions without direct authorityExperience managing Project Managers and program resources across multiple initiativesExperience managing direct reportsStrong analytical, organizational, and problem-solving skillsExperience within SaaS, fintech, healthcare technology, payments, or PE-backed organizationsBachelor's degree in business or related fieldRelevant Program/Project Management CertificationsExperience operating in high-growth or scaling environmentsBenefitsCompetitive Medical Health Plans, Low, Mid, High.Employer Paid Low Medical Plan for Employee & Dependents (HSA Eligible)Employer Paid Dental & Vision for EmployeeEmployer Paid Life Insurance for EmployeeEmployer Paid Long-term Disability for EmployeeEmployer Paid Hospital Confinement for Employee ~ (If enrolled in Medical)Voluntary Supplemental Insurance Coverage Options15 days PTO & 7 Sick Days Annually10 Fixed Paid Holidays Off Annually401(k) Matching up to 3%Company OverviewRectangle Health is the leading healthcare payment and premium processing company. It was founded in 1992, and is headquartered in Valhalla, New York, USA, with a workforce of 201-500 employees. Its website is https://www.rectanglehealth.com.