Back to jobs
New

Sr. Director of Program Management

Remote

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.

Position Overview

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.

Primary Job Duties:

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.

Minimum Qualifications:

  • 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.

Preferred Qualifications:

  • 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 Profile:

  • 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% 

About Us:

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.

View our CCPA disclosure notice here

Create a Job Alert

Interested in building your career at Rectangle Health? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Rectangle Health’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.