Guild Executive and Leadership Team

September, 2026

Leadership Overview

Guild has 5 executives leading key functions including marketing, financial operations, organizational culture, human resources, and commercial strategy.

Driven by a commitment to equitable opportunity, Guild empowers individuals and organizations to thrive amidst the rapid evolution of work through innovative education and training solutions.

Leadership Roles at Guild

  • Executive Business Partner To Chief Financial Officer and Head of Legal - Dani Wilkins
  • President & Chief Commercial Officer - Natalie McCullough
  • Chief Marketing Officer - Rebecca Biestman
  • Chief of Staff & Chief Operations Officer, Culture To The - Casey Boyles
  • Chief People Officer - Alana Brandes
  • Dani Wilkins, the Executive Business Partner To Chief Financial Officer and Head of Legal at Guild, manages the intersection of financial planning and corporate governance. Overseeing complex regulatory compliance and fiscal reporting, the Executive Business Partner To Chief Financial Officer and Head of Legal ensures that all operational activities align with long-term financial stability. This role involves coordinating with the Board to maintain transparency while supporting the legal framework necessary for rapid organizational scaling. By optimizing internal processes, Dani Wilkins facilitates seamless communication between the finance and legal departments. The Executive Business Partner To Chief Financial Officer and Head of Legal mitigates risk while enabling the company to pursue aggressive growth targets. Wilkins provides the structural support required for the executive team to make informed, data-backed decisions. This function remains critical to maintaining the integrity of the business model as the company expands its footprint across the United States.

    Natalie McCullough - President & Chief Commercial Officer

    Natalie McCullough, the President & Chief Commercial Officer at Guild, directs all revenue-generating activities and commercial partnerships. Overseeing the expansion of the client base, the President & Chief Commercial Officer ensures that the company effectively delivers its educational solutions to large-scale enterprise partners. This leadership role involves identifying new market opportunities and refining the sales strategy to meet the demands of a changing economy. By managing key relationships with major employers, Natalie McCullough drives the growth of the business model. The President & Chief Commercial Officer collaborates with the executive team to align commercial goals with the overarching mission of distributing opportunity. McCullough executes strategies that increase market share and solidify the company reputation as a premier provider of workforce training. Through rigorous analysis of market trends, the President & Chief Commercial Officer ensures that the company remains at the forefront of the education industry, consistently delivering value to both partners and their employees.

    Rebecca Biestman - Chief Marketing Officer

    Rebecca Biestman, the Chief Marketing Officer at Guild, directs all brand positioning and market engagement strategies. Overseeing the development of high-impact campaigns, the Chief Marketing Officer ensures that the Guild mission reaches diverse talent pools across North American markets. This leadership role involves translating complex educational benefits into clear value propositions for enterprise partners. By aligning marketing initiatives with the evolving needs of the modern workforce, Rebecca Biestman drives significant growth in user acquisition and brand awareness. The Chief Marketing Officer collaborates closely with product teams to refine messaging that resonates with both employers and employees. Through data-driven storytelling, Biestman elevates the company profile, ensuring that the core belief in evenly distributed opportunity remains central to all external communications. This strategic focus supports the broader goal of scaling educational access in an increasingly automated economy.

    Casey Boyles - Chief of Staff & Chief Operations Officer, Culture To The

    Casey Boyles, the Chief of Staff & Chief Operations Officer, Culture To The at Guild, architects the internal operational frameworks that sustain company culture. Overseeing the integration of cross-functional workflows, the Chief of Staff & Chief Operations Officer, Culture To The ensures that organizational values remain embedded in daily business practices. This leadership role involves streamlining communication channels to enhance efficiency across all departments. By fostering a cohesive environment, Casey Boyles supports the company mission of talent development during periods of rapid technological change. The Chief of Staff & Chief Operations Officer, Culture To The manages high-level projects that require alignment between executive vision and operational execution. Boyles drives initiatives that improve employee engagement and organizational agility. Through meticulous oversight of internal systems, the Chief of Staff & Chief Operations Officer, Culture To The secures the operational foundation necessary for the company to thrive in a competitive education landscape.
    Casey Boyles

    Alana Brandes - Chief People Officer

    Alana Brandes, the Chief People Officer at Guild, directs all human capital strategies and talent development programs. Overseeing the recruitment, retention, and professional growth of the workforce, the Chief People Officer ensures that the internal team reflects the same commitment to opportunity that the company provides to its clients. This leadership role involves designing inclusive policies that support a diverse and high-performing organization. By aligning talent management with the broader business objectives, Alana Brandes fosters a culture of continuous learning and innovation. The Chief People Officer collaborates with other C-suite leaders to ensure that organizational structure supports the company mission of empowering talent. Brandes drives initiatives that enhance employee well-being and productivity across all regional operations. Through strategic workforce planning, the Chief People Officer secures the human resources necessary for the company to maintain its market position as a leader in the education and training sector.

    Explore Leadership Teams in Education

    Frequently Asked Questions Regarding Guild Top Executives and Leadership Team

    Who leads Guild?
    Guild is led by Dani Wilkins (Executive Business Partner To Chief Financial Officer and Head of Legal), along with executives such as Natalie McCullough (President & Chief Commercial Officer) and Rebecca Biestman (Chief Marketing Officer).
    Who is part of Guild’s executive team?
    The executive team of Guild includes leaders such as Dani Wilkins (Executive Business Partner To Chief Financial Officer and Head of Legal), Natalie McCullough (President & Chief Commercial Officer), Rebecca Biestman (Chief Marketing Officer) and other senior executives.
    How many executives does Guild have?
    Guild has 5 executives leading key business areas.
    What roles are included in Guild’s leadership team?
    The leadership team of Guild includes roles such as Executive Business Partner To Chief Financial Officer and Head of Legal, President & Chief Commercial Officer, Chief Marketing Officer, Chief of Staff & Chief Operations Officer, Culture To The, Chief People Officer.