Dandy Executive and Leadership Team

August, 2026

Leadership Overview

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

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

  • Head of Legal Automation Chief of Staff - Carrie Cessna
  • Operations Chief of Staff - Olamide Anyanwu
  • Biz Systems & IT Chief of Staff - Sara Myers
  • Biz Systems & IT Chief of Staff - Sara Self
  • Carrie Cessna, the Head of Legal Automation Chief of Staff at Dandy, directs the integration of automated compliance frameworks within the digital health platform. By streamlining regulatory workflows, Cessna ensures the company maintains rigorous standards during the national US rollout. The Head of Legal Automation Chief of Staff manages cross-functional partnerships to mitigate risk while scaling virtual care services. Carrie Cessna architects sophisticated legal technology solutions that support rapid organizational growth. This leadership role involves constant collaboration with executive leadership to align legal operations with the broader mission of improving dental experiences. Through the implementation of advanced software, the Head of Legal Automation Chief of Staff optimizes internal processes, allowing the company to focus on patient outcomes. Cessna drives efficiency across the legal department, ensuring that all digital health initiatives remain compliant with evolving healthcare regulations while supporting the expansion of the business model.

    Olamide Anyanwu - Operations Chief of Staff

    Olamide Anyanwu, the Operations Chief of Staff at Dandy, manages the logistical infrastructure required to bridge in-person dental treatment with virtual care delivery. Overseeing the national US rollout, Anyanwu coordinates supply chain efficiency and clinical resource allocation to ensure seamless patient experiences. The Operations Chief of Staff drives operational excellence by refining the workflows that connect doctors with advanced diagnostic tools. Olamide Anyanwu architects scalable systems that support the company's rapid growth in the health services sector. This leadership role requires constant synchronization with the executive team to maintain high standards of care quality. By optimizing daily operational throughput, the Operations Chief of Staff directly impacts the company's ability to scale across diverse markets. Anyanwu secures long-term stability by implementing data-driven improvements to the core service delivery model, ensuring that every patient receives consistent, high-quality dental care regardless of the specific treatment location.

    Sara Myers - Biz Systems & IT Chief of Staff

    Sara Myers, the Biz Systems & IT Chief of Staff at Dandy, directs the development of internal software architectures that power the digital health platform. By managing the enterprise technology stack, Myers ensures that all business systems support the seamless integration of virtual care and in-person dental services. The Biz Systems & IT Chief of Staff architects robust data security protocols to protect patient information during the national US rollout. Sara Myers oversees the deployment of cloud-based tools that enhance communication between doctors and patients. This leadership role involves aligning IT strategy with the company's mission to modernize the dental experience. Through the optimization of internal digital infrastructure, the Biz Systems & IT Chief of Staff drives productivity across all departments. Myers secures the technological foundation of the company, enabling rapid innovation and ensuring that all digital health services remain reliable, scalable, and highly effective for the entire user base.

    Sara Self - Biz Systems & IT Chief of Staff

    Sara Self, the Biz Systems & IT Chief of Staff at Dandy, manages the implementation of advanced diagnostic software and hardware integration for the dental network. By focusing on the technical interface between virtual care platforms and physical clinics, Self ensures that practitioners possess the tools necessary for optimal patient outcomes. The Biz Systems & IT Chief of Staff drives the adoption of new digital health technologies to maintain a competitive edge in the market. Sara Self architects the connectivity solutions that allow for real-time data sharing across the national US footprint. This leadership role involves coordinating with the engineering team to refine the user experience for both doctors and patients. Through the continuous improvement of business systems, the Biz Systems & IT Chief of Staff enhances operational agility. Self secures the company's position as a leader in health services by ensuring that all IT initiatives directly support the core mission of dental innovation.

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    Frequently Asked Questions Regarding Dandy Top Executives and Leadership Team

    Who leads Dandy?
    Dandy is led by Carrie Cessna (Head of Legal Automation Chief of Staff), along with executives such as Olamide Anyanwu (Operations Chief of Staff) and Sara Myers (Biz Systems & IT Chief of Staff).
    Who is part of Dandy’s executive team?
    The executive team of Dandy includes leaders such as Carrie Cessna (Head of Legal Automation Chief of Staff), Olamide Anyanwu (Operations Chief of Staff), Sara Myers (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 Head of Legal Automation Chief of Staff, Operations Chief of Staff, Biz Systems & IT Chief of Staff, Biz Systems & IT Chief of Staff.