Waystar Executive and Leadership Team

July, 2026

Leadership Overview

Waystar has 4 executives leading key functions including finance, operations, legal, and human resources.

Driven by innovation, Waystar simplifies and unifies the revenue cycle, enabling healthcare organizations to collect more and reduce the cost of managing payer reimbursement and patient billing, ultimately improving client financial health.

Leadership Roles at Waystar

  • Chief Financial Officer - Steven Oreskovich
  • Chief of Staff & Vice President, Special Projects - Sandy Draper
  • Chief Legal Officer - Gregory Packer
  • Chief People Officer, Waystar (Nasdaq Way) - Kimberly Wittman
  • Steven Oreskovich - Chief Financial Officer

    Steven Oreskovich, the Chief Financial Officer at Waystar, directs all financial strategy and operations. Oreskovich oversees fiscal planning, budgeting, and financial reporting, ensuring robust financial health for the organization. This leadership role involves managing capital allocation and investment strategies to support Waystar's growth objectives within the healthcare technology sector. By optimizing financial processes, Steven Oreskovich directly contributes to the company's ability to deliver innovative revenue cycle solutions. The Chief Financial Officer ensures compliance with all financial regulations and drives initiatives to enhance profitability and shareholder value. Oreskovich's expertise is critical in navigating the complex financial landscape of healthcare technology, enabling Waystar to provide essential services to providers, hospitals, and health systems.
    Steven Oreskovich

    Sandy Draper - Chief of Staff & Vice President, Special Projects

    Sandy Draper, the Chief of Staff & Vice President, Special Projects at Waystar, spearheads critical strategic initiatives and operational enhancements. Draper manages cross-functional projects that drive innovation and efficiency across the organization, aligning with Waystar's mission to simplify the healthcare revenue cycle. This role involves close collaboration with executive leadership to identify and execute on key business opportunities, ensuring seamless project implementation. By overseeing special projects, Sandy Draper directly supports the company's efforts to improve payer reimbursement and patient billing processes for healthcare clients. The Chief of Staff & Vice President, Special Projects ensures that strategic objectives are translated into actionable plans, fostering a culture of continuous improvement and operational excellence. Draper's work is vital in advancing Waystar's technological solutions and market position.
    Gregory Packer, the Chief Legal Officer at Waystar, directs all legal affairs and ensures regulatory compliance. Packer oversees corporate governance, contract negotiations, and risk management, safeguarding the company's interests within the healthcare technology industry. This critical role involves advising executive leadership on legal implications of business strategies and operational decisions. By managing legal frameworks, Gregory Packer directly supports Waystar's commitment to simplifying the revenue cycle for providers and health systems. The Chief Legal Officer ensures adherence to all applicable laws and industry standards, protecting the company's reputation and assets. Packer's expertise is fundamental to Waystar's ability to operate ethically and effectively, enabling clients to focus on patient care.
    Gregory Packer

    Kimberly Wittman - Chief People Officer, Waystar (Nasdaq Way)

    Kimberly Wittman, the Chief People Officer, Waystar (Nasdaq Way), leads all human capital strategies and organizational development. Wittman oversees talent acquisition, employee engagement, and culture initiatives, fostering a high-performance environment that supports Waystar's mission. This executive function involves developing programs to attract, retain, and develop top talent essential for driving innovation in revenue cycle management technology. By championing people-centric policies, Kimberly Wittman directly contributes to the company's operational capacity and client service excellence. The Chief People Officer ensures that Waystar's workforce is equipped to meet the evolving needs of healthcare organizations, enhancing the company's ability to deliver unified revenue cycle solutions. Wittman's leadership is key to building a robust and motivated team.

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    Frequently Asked Questions Regarding Waystar Top Executives and Leadership Team

    Who leads Waystar?
    Waystar is led by Steven Oreskovich (Chief Financial Officer), along with executives such as Sandy Draper (Chief of Staff & Vice President, Special Projects) and Gregory Packer (Chief Legal Officer).
    Who is part of Waystar’s executive team?
    The executive team of Waystar includes leaders such as Steven Oreskovich (Chief Financial Officer), Sandy Draper (Chief of Staff & Vice President, Special Projects), Gregory Packer (Chief Legal Officer) and other senior executives.
    How many executives does Waystar have?
    Waystar has 4 executives leading key business areas.
    What roles are included in Waystar’s leadership team?
    The leadership team of Waystar includes roles such as Chief Financial Officer, Chief of Staff & Vice President, Special Projects, Chief Legal Officer, Chief People Officer, Waystar (Nasdaq Way).