Sr. Director of Program Management

At Rectangle Health, we believe that our team members are our most important asset. We grow our team by hiring best-in-class talent. We encourage all employees to contribute their individual talents and ideas to strengthen our team, our brand, and our services. We promote a culture that serves to empower and motivate employees beyond the standard corporate rhetoric one might see on motivational posters. Employees understand their individual roles in serving our customers, and this clarity of purpose encourages high job performance.

The Senior Director, Program Management is responsible for establishing and leading enterprise program governance across Rectangle Health. Reporting to the COO, this role provides visibility, coordination, prioritization, and execution oversight for strategic initiatives that span multiple functions and departments.

This leader will establish and manage the Program Management Office (PMO), ensuring enterprise initiatives are properly defined, prioritized, resourced, and executed. The role serves as the central point of coordination across business functions and enterprise initiatives.

The Senior Director, Program Management helps ensure Rectangle Health operates as one organization with aligned priorities, clear ownership, and disciplined execution. Serving as an extension of the COO, this role translates strategic priorities into coordinated cross-functional initiatives and measurable business outcomes.

Program Management Office (PMO) Leadership

• 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.

Initiative Intake & Prioritization

• 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.

Cross-Functional Execution

• 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.

Executive/COO Reporting & Governance

• 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.

Business Transformation & Operational Improvement

• 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.

Team Leadership

• Manage Project Managers and future PMO resources.
• Develop program management capabilities and best practices.
• Foster a culture of accountability, transparency, and execution excellence.

Success Measures

• Enterprise initiative visibility and governance established.
• On-time delivery of strategic initiatives.
• Reduction in cross-functional execution issues and delays.
• Improved prioritization and resource allocation decisions.
• Increased accountability across workstreams.
• Successful implementation of Operational Excellence initiatives.
• Executive confidence in initiative reporting and execution.

• 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.

• 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% 

Rectangle Health, a leading financial technology company, empowers medical, dental and specialty practices with seamless and secure technology to drive revenue by increasing patient payments and streamlining practice management and payment processing. Since 1992, the company’s innovative solutions have reduced administrative burden and rebalanced the ledger for its thousands of healthcare providers in the U.S., reliably processing billions of dollars in payments annually.