The Opportunity

RIP Medical Debt’s search for the first Executive Director to follow its founders is an exceptional opportunity to take the reins of this flourishing nonprofit with a powerful mission and to lead the organization’s transformation from startup to mature growth and strategic expansion.

RIP Medical Debt has an impressive track record of success: abolishing $700 million in debt since its founding in 2014, shining a national spotlight on this critical issue, and positively affecting more than 250,000 individuals whose medical debt it has erased.

Reporting to the Board of Directors and overseeing a team of professionals, including the founders who currently serve as technical experts and department leads, the Executive Director will help write the next chapter of RIP Medical Debt’s story by leveraging the significant achievements of its first five years and leading the charge to build the organization’s capacity to exceed those achievements and meet anticipated growth in the years ahead.

The role is based in New York City where the organization’s founders and Board of Directors are located. The new Executive Director will actively engage the Board, which includes the founders, in the shaping of a shared vision, effective governance, while strategically deploying their strengths and interests in the highest support of the organization.

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About the Organization

Combining compassion and debt buying expertise, founders Jerry Ashton and Craig Antico started RIP Medical Debt in 2014 to empower donors to help those in need break out of the destructive bonds of medical debt. The organization accomplishes this by making it possible for donor contributions to buy and forgive millions in oppressive medical debt for pennies on the dollar; $100 forgives $10,000 in medical debt.

Medical debt devastates American families: nearly 40% of American households have outstanding medical debt or problems paying medical bills. In the last year alone, nearly 75 million people had to choose between medical bills and basics like food, heating, or housing. RIP Medical Debt’s simple program of abolishing medical debt for individuals in need has touched the lives of more than 250,000 individuals since 2014; this number does not include immediate and extended families who experience significant residual benefits of the primary debtor’s medical debt forgiveness.

By identifying, targeting and purchasing bulk debt portfolios, RIP Medical Debt’s abolishment program has the power to transform the lives of entire communities. Medical debt forgiveness gives struggling individuals a fresh start, allows them to seek the continued medical care they need, and helps along the path to financial stability. The economic impact of this work is currently the subject of research at MIT, UCLA, UC-Berkeley, and the University of Chicago.

RIP has been featured nationally on NBC Nightly News, in The New York Times and on HBO's Last Week Tonight, among many others. Founders Jerry Ashton and Craig Antico were recognized by Town & Country Magazine as Top Philanthropists of 2018.

Ideal Candidate

The Executive Director of RIP Medical Debt is a seasoned executive leader who derives as much satisfaction overseeing operational excellence as they do tackling complex strategic questions.

The ideal candidate is passionate about RIP Medical Debt’s mission to eliminate medical debt for those in need, and is excited by the opportunity to use their leadership to advance the organization by building on what’s working, scanning the horizon for what lies ahead, and managing the right level of risk. A calm demeanor and “no drama” approach to the excitement and commotion that can result from being in the media spotlight is a critical attribute.

A sharp strategist who possesses the administrative sophistication to lead an organization operating in a complex market, the successful candidate also brings deep familiarity with best practices in nonprofit management. RIP Medical Debt has an ambitious agenda to transform lives of entire communities through the abolishment of medical debt. Candidates must be able to assess strategic opportunities, manage competing priorities, make hard decisions and ensure the technology and services supporting the program maintain the highest standards.

Exceptional communication and interpersonal skills are required to be an effective and inspiring public advocate for the organization. A high level of emotional intelligence, diplomacy and impeccable relationship- building skills will allow the Executive Director to readily engage with diverse audiences, be they high net worth donors, community organizations, hospital boards or media personalities. An appreciation for the value of public relations and marketing to RIP Medical Debt’s growth, as well as fluency in the digital/social media world and comfort with maintaining a public profile on behalf of the organization, is essential.

RIP Medical Debt relies on complex technology and data analytics to conduct business and achieve scale. To be an effective manager, the Executive Director must demonstrate a comfort with technology and the role of data analytics to pinpoint the medical debt portfolios of those most in need of relief.

Key Priorities & Responsibilities

The new Executive Director will have overall strategic and operational responsibility for RIP Medical Debt’s staff, programs, finances, fundraising future strategy development and fulfillment of its mission. The following represent the key priorities in the Executive Director’s first year:


  • Provide strategic vision and leadership to fulfill RIP Medical Debt’s mission to remove the burden of medical debt for those most in need.

  • Operationalize growth by identifying and implementing optimal structures, systems and processes to support scaling while simultaneously ensuring consistent operational quality and compliance of all organizational functions, including finance and administration, resource development, marketing and communications, and program delivery.

  • Build organizational capacity by identifying, assessing and acting on critical strategic opportunities—partnerships, collaborations, business deals, grants/investments—that increase the platform’s reach and impact.

  • Harness the power of technology and data to scale the organization assuring compliance with privacy laws and regulations.


  • Actively engage in building and diversifying the organization’s funding base and lead the effort to grow revenue and donors, with the support of the resource development team, to ensure RIP Medical Debt has the funds required to meet its ambitious debt abolishment goals.

  • Serve as a public face and key spokesperson for RIP Medical Debt, representing the organization with credibility and enthusiasm, leveraging its strong brand, and clearly communicating its vision and value proposition.

  • Further build external presence to evangelize RIP Medical Debt as an innovator in debt abolishment; leverage status as the new Executive Director to build visibility for the brand with support of communications consultants.


  • Determine optimal staffing structure and create a shared understanding of the organization’s strategy to ensure all staff are clear on how their specific roles contribute to the wider strategic context.

  • Champion teamwork across the organization by providing effective internal leadership, coaching, performance management and professional development.

  • Build a cohesive culture and strong esprit de corps across a distributed team structure that prides itself on being a lean and flat organization.

  • Lead effective change management to support the organization’s evolution and growth.


Candidates should have at least ten to fifteen years of progressively responsible senior leadership roles in a dynamic and entrepreneurial social sector organization, preferably in a CEO or Executive Director role. Private sector or corporate leadership experience, when combined with significant nonprofit engagement (as demonstrated by noteworthy leadership roles on nonprofit boards, committees or task forces) will be considered.

A genuine passion for RIP Medical Debt’s mission is essential. Knowledge of the healthcare sector is preferred. Successful candidates must have experience working with boards of directors and knowledge of best practices related to nonprofit governance. Candidates must have a participatory and inclusive leadership style that fosters diverse points of view, respectful collaboration and accountability. They bring the financial acumen required to manage a $6.8 million annual budget and oversee annual debt elimination in the hundreds of millions of dollars.

RIP Medical Debt is a high-profile organization whose growth to date has been driven by extraordinary media attention. A demonstrated ability to operate under a spotlight and leverage that attention into significant contributed income is required.