Dandy Executive and Leadership Team

September, 2026

Leadership Overview

Dandy has 4 executives leading key functions including operations, legal automation, and business systems.

Focused on transforming dental care through digital innovation, Dandy delivers superior patient outcomes by integrating virtual care with in-person treatment across the United States.

Leadership Roles at Dandy

  • Operations Chief of Staff - Olamide Anyanwu
  • Head of Legal Automation Chief of Staff - Carrie Cessna
  • Biz Systems & IT Chief of Staff - Sara Self
  • Biz Systems & IT Chief of Staff - Sara Myers
  • Olamide Anyanwu - Operations Chief of Staff

    Olamide Anyanwu, the Operations Chief of Staff at Dandy, directs the internal workflows necessary for scaling national dental health services. Managing cross-functional teams, Anyanwu optimizes the intersection of virtual care platforms and physical clinical diagnostics. This leadership role requires constant coordination with the executive board to ensure operational efficiency during the rapid US market expansion. By streamlining logistical processes, Olamide Anyanwu improves the overall dental experience for both patients and practitioners. The Operations Chief of Staff monitors key performance indicators to maintain high standards of care delivery. Through rigorous oversight of daily operations, Anyanwu guarantees that the company maintains a competitive edge in the digital health sector. This position demands precise execution of strategic initiatives to support long-term growth objectives. Ultimately, Anyanwu secures the operational foundation required for the company to achieve its mission of modernizing dental health diagnostics and treatment protocols across the country.
    Carrie Cessna, the Head of Legal Automation Chief of Staff at Dandy, architects the digital frameworks governing regulatory compliance and contractual integrity. Overseeing the integration of automated legal systems, Cessna ensures that all virtual care protocols align with national health standards. This leadership role involves mitigating risk while facilitating the rapid deployment of dental diagnostic tools. By digitizing complex legal workflows, Carrie Cessna accelerates the pace of business operations. The Head of Legal Automation Chief of Staff collaborates with technical teams to build robust, automated safeguards for patient data and clinical documentation. Through the implementation of advanced software solutions, Cessna drives efficiency within the legal department. This position requires deep analytical focus to navigate the evolving landscape of digital health regulations. Ultimately, Cessna protects the company from liability while enabling the seamless expansion of services across the United States, ensuring that every digital interaction remains fully compliant and secure.

    Sara Self - Biz Systems & IT Chief of Staff

    Sara Self, the Biz Systems & IT Chief of Staff at Dandy, manages the core infrastructure supporting digital health diagnostics and virtual patient care. Directing the deployment of enterprise-wide IT systems, Self ensures that all technological platforms remain scalable for national operations. This leadership role involves aligning technical capabilities with the broader business strategy to enhance patient outcomes. By optimizing internal data systems, Sara Self improves the speed and accuracy of dental treatment planning. The Biz Systems & IT Chief of Staff coordinates with engineering teams to maintain high uptime for critical diagnostic software. Through the continuous improvement of IT architecture, Self supports the company's mission to modernize the dental experience. This position requires constant vigilance regarding cybersecurity and system performance. Ultimately, Self provides the technical backbone necessary for the company to thrive in the competitive health services market, ensuring that all digital tools function reliably for doctors and patients alike.

    Sara Myers - Biz Systems & IT Chief of Staff

    Sara Myers, the Biz Systems & IT Chief of Staff at Dandy, oversees the integration of business intelligence tools to refine clinical diagnostic workflows. Managing the data analytics pipeline, Myers ensures that the company leverages actionable insights to improve patient care delivery. This leadership role involves bridging the gap between technical IT requirements and business growth objectives. By implementing advanced reporting systems, Sara Myers enables data-driven decision-making across the organization. The Biz Systems & IT Chief of Staff collaborates with department heads to identify opportunities for technological optimization. Through the refinement of internal business systems, Myers enhances the efficiency of virtual care consultations. This position requires a focus on long-term system sustainability and the seamless adoption of new digital tools. Ultimately, Myers drives the technological evolution of the company, ensuring that all business systems support the overarching goal of providing high-quality, accessible dental care to patients throughout the United States.

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    Frequently Asked Questions Regarding Dandy Top Executives and Leadership Team

    Who leads Dandy?
    Dandy is led by Olamide Anyanwu (Operations Chief of Staff), along with executives such as Carrie Cessna (Head of Legal Automation Chief of Staff) and Sara Self (Biz Systems & IT Chief of Staff).
    Who is part of Dandy’s executive team?
    The executive team of Dandy includes leaders such as Olamide Anyanwu (Operations Chief of Staff), Carrie Cessna (Head of Legal Automation Chief of Staff), Sara Self (Biz Systems & IT Chief of Staff) and other senior executives.
    How many executives does Dandy have?
    Dandy has 4 executives leading key business areas.
    What roles are included in Dandy’s leadership team?
    The leadership team of Dandy includes roles such as Operations Chief of Staff, Head of Legal Automation Chief of Staff, Biz Systems & IT Chief of Staff, Biz Systems & IT Chief of Staff.