Winstead Executive and Leadership Team

May, 2026

Leadership Overview

Winstead has 4 executives leading key functions including strategy, operations, technology, and finance.

Driven by a commitment to comprehensive legal solutions, Winstead provides a full range of business legal services, impacting market dynamics through expert counsel and strategic advisory across its national footprint.

Leadership Roles at Winstead

  • Chairman & Chief Executive Officer - David Dawson
  • Co-Founder & Chief Executive Officer - Jody Ambrose
  • Chief Financial Officer - Katherine Hall
  • Chief Information Officer - Christopher Di Masi
  • David Dawson - Chairman & Chief Executive Officer

    David Dawson, the Chairman & Chief Executive Officer at Winstead, directs the firm's overall strategic vision and operational execution. Dawson guides the firm's expansion and market positioning, ensuring alignment with the evolving needs of national business clients. This leadership role involves fostering a culture of legal excellence and client-centric service across all firm operations. Overseeing the firm's growth initiatives, David Dawson drives the development of new service lines and geographic expansions, solidifying Winstead's presence in key markets like Texas and North Carolina. The Chairman & Chief Executive Officer ensures robust governance and strategic planning, directly impacting the firm's long-term sustainability and market leadership in providing comprehensive business legal services.
    David Dawson

    Jody Ambrose - Co-Founder & Chief Executive Officer

    Jody Ambrose, the Co-Founder & Chief Executive Officer at Winstead, shapes the firm's foundational principles and ongoing strategic direction. Ambrose champions the firm's mission to deliver a full spectrum of business legal services, fostering innovation and client success. This executive function involves cultivating strong relationships with key stakeholders and driving the firm's commitment to legal expertise. Overseeing the firm's core values and operational framework, Jody Ambrose ensures that Winstead consistently meets the complex demands of its national clientele. The Co-Founder & Chief Executive Officer's leadership directly influences the firm's reputation for providing strategic legal counsel and achieving impactful business outcomes for clients across various industries.
    Jody Ambrose

    Katherine Hall - Chief Financial Officer

    Katherine Hall, the Chief Financial Officer at Winstead, directs the firm's financial planning, management, and reporting. Hall oversees all fiscal operations, ensuring financial stability and optimizing resource allocation across the firm's national network of offices. This executive responsibility includes managing budgets, analyzing financial performance, and developing strategies to support the firm's growth objectives. Overseeing the financial health of the organization, Katherine Hall ensures compliance with all financial regulations and drives initiatives for fiscal efficiency. The Chief Financial Officer's expertise is integral to sustaining Winstead's capacity to provide a full range of business legal services and maintain its strong market presence.

    Christopher Di Masi - Chief Information Officer

    Christopher Di Masi, the Chief Information Officer at Winstead, architects and manages the firm's technology infrastructure and digital strategy. Di Masi drives the implementation of advanced technological solutions to enhance legal service delivery and operational efficiency across all offices, including those in Texas and North Carolina. This critical role involves safeguarding sensitive client data and ensuring the seamless integration of information systems. Overseeing the firm's digital transformation, Christopher Di Masi ensures that Winstead leverages cutting-edge technology to provide superior legal services and maintain a competitive edge. The Chief Information Officer's strategic oversight directly supports the firm's ability to offer comprehensive business legal services with enhanced security and accessibility.

    Frequently Asked Questions Regarding Winstead Top Executives and Leadership Team

    Who leads Winstead?
    Winstead is led by David Dawson (Chairman & Chief Executive Officer), along with executives such as Jody Ambrose (Co-Founder & Chief Executive Officer) and Katherine Hall (Chief Financial Officer).
    Who is part of Winstead’s executive team?
    The executive team of Winstead includes leaders such as David Dawson (Chairman & Chief Executive Officer), Jody Ambrose (Co-Founder & Chief Executive Officer), Katherine Hall (Chief Financial Officer) and other senior executives.
    How many executives does Winstead have?
    Winstead has 4 executives leading key business areas.
    What roles are included in Winstead’s leadership team?
    The leadership team of Winstead includes roles such as Chairman & Chief Executive Officer, Co-Founder & Chief Executive Officer, Chief Financial Officer, Chief Information Officer.