[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.

Responsibilities

• Establish and lead the Program Management Office (PMO)
• Develop standards, governance, and reporting processes for enterprise initiatives
• Build and maintain visibility into all significant cross-functional projects and programs
• Ensure initiatives are aligned to company priorities and business objectives
• Provide executive leadership with portfolio-level reporting and insights
• Own the centralized intake process for strategic and cross-functional initiatives
• Facilitate initiative review, prioritization, and resource planning
• Assess organizational impact, dependencies, risks, and capacity requirements
• Ensure initiatives have defined objectives, ownership, timelines, and expected outcomes
• Identify competing priorities and recommend sequencing decisions
• Coordinate initiatives spanning multiple departments and business functions
• Ensure impacted stakeholders are identified and engaged throughout planning and execution
• Monitor progress against milestones, deliverables, and commitments
• Escalate risks, blockers, and dependency issues requiring executive intervention
• Drive accountability and follow-through across workstreams
• Maintain enterprise initiative dashboards and reporting
• Provide regular updates to COO and other executive leadership on initiative progress, risks, and outcomes
• Support Board reporting and strategic planning activities
• Track initiative performance against expected business outcomes
• Partner with COO to drive enterprise-wide operational improvement, strategic initiatives, and transformation efforts
• Translate executive priorities into executable programs, workstream, and implementation plans
• Support organizational effectiveness, process redesign, automation, scalability, and operational maturity initiatives
• Identify cross-functional risks, dependencies, and opportunities for improvement
• Track initiative outcomes and ensure expected business benefits are realized
• Facilitate alignment across business functions while maintaining focus on enterprise priorities established by the COO
• Drive accountability, execution discipline, and visibility across major company initiatives
• Manage Project Managers and future PMO resources
• Develop program management capabilities and best practices
• Foster a culture of accountability, transparency, and execution excellence

Skills

• 8+ years of program management, PMO, business operations, transformation, or operational leadership experience
• 8+ years of experience leading complex cross-functional initiatives
• Experience establishing or managing Project Management Office (PMO) functions
• Strong executive communication and stakeholder management skills
• Demonstrated ability to influence across functions without direct authority
• Experience managing Project Managers and program resources across multiple initiatives
• Experience managing direct reports
• Strong analytical, organizational, and problem-solving skills
• Experience within SaaS, fintech, healthcare technology, payments, or PE-backed organizations
• Bachelor's degree in business or related field
• Relevant Program/Project Management Certifications
• Experience operating in high-growth or scaling environments

Benefits

• Competitive Medical Health Plans, Low, Mid, High.
• Employer Paid Low Medical Plan for Employee & Dependents (HSA Eligible)
• Employer Paid Dental & Vision for Employee
• Employer Paid Life Insurance for Employee
• Employer Paid Long-term Disability for Employee
• Employer Paid Hospital Confinement for Employee ~ (If enrolled in Medical)
• Voluntary Supplemental Insurance Coverage Options
• 15 days PTO & 7 Sick Days Annually
• 10 Fixed Paid Holidays Off Annually
• 401(k) Matching up to 3%

Company Overview