Guild Executive and Leadership Team

May, 2026

Leadership Overview

Guild has 5 executives leading key functions including strategy, finance, operations, people, and commercial.

Driven by the belief that opportunity should be as evenly distributed as talent, Guild empowers individuals and fuels company growth through accessible education, adapting to the evolving future of work.

Leadership Roles at Guild

  • Chief Executive Officer & Co-Founder - Rachel Romer
  • Executive Business Partner To Chief Financial Officer - Dani Wilkins
  • President & Chief Commercial Officer - Natalie McCullough
  • Chief of Staff & Chief Operations Officer, Culture To The - Casey Boyles
  • Chief People Officer - Alana Brandes
  • Rachel Romer - Chief Executive Officer & Co-Founder

    Rachel Romer, the Chief Executive Officer & Co-Founder at Guild, directs the company's overarching strategy and vision. Romer architects the long-term growth initiatives, ensuring Guild remains at the forefront of educational technology and workforce development. Overseeing all major strategic partnerships and investor relations, Romer drives the company's mission to distribute opportunity evenly. This leadership role involves navigating the complexities of the evolving work landscape, particularly as AI and new technologies reshape industries. By fostering a culture of innovation, Rachel Romer ensures the company's offerings continuously adapt to meet the accelerating need for accessible education and career advancement. Romer's strategic direction solidifies Guild's market position and its commitment to economic thriving through talent development.

    Dani Wilkins - Executive Business Partner To Chief Financial Officer

    Dani Wilkins, the Executive Business Partner To Chief Financial Officer at Guild, provides critical operational support to the finance function. Wilkins manages key projects and initiatives that enhance financial efficiency and strategic planning. This role involves coordinating cross-departmental efforts to ensure seamless execution of financial objectives. By streamlining communication and workflow between the CFO and other executive leaders, Dani Wilkins facilitates informed decision-making. The position demands meticulous attention to detail in managing schedules, preparing reports, and supporting the financial team's operational needs. Wilkins's contributions are vital for maintaining the financial health and strategic alignment of Guild's operations, ensuring resources are effectively allocated to support company growth and mission.

    Natalie McCullough - President & Chief Commercial Officer

    Natalie McCullough, the President & Chief Commercial Officer at Guild, drives the company's commercial strategy and revenue growth. McCullough directs all sales, marketing, and business development efforts, forging key partnerships that expand Guild's reach and impact. This executive position is pivotal in translating the company's mission into tangible market success, ensuring that educational opportunities are accessible to a broad audience. By overseeing the commercial functions, Natalie McCullough ensures alignment with market needs and company objectives, particularly in response to technological disruptions in the workforce. McCullough's leadership focuses on expanding market share and solidifying Guild's position as a leader in the education technology sector. The commercial acumen brought to this role is essential for achieving sustained growth and fulfilling the company's promise of opportunity.

    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, spearheads operational excellence and cultivates a robust company culture. Boyles directs the implementation of strategic initiatives, ensuring alignment across all departments and optimizing internal processes for maximum efficiency. This leadership position involves overseeing day-to-day operations, driving productivity, and fostering an environment where employees can thrive. By managing key operational projects and ensuring the company's cultural values are embedded throughout the organization, Casey Boyles supports sustainable growth. Boyles's responsibilities extend to enhancing organizational effectiveness and ensuring that Guild's operational framework supports its mission of distributing opportunity. The focus on culture ensures a cohesive and motivated workforce, critical for navigating the dynamic future of work.
    Casey Boyles

    Alana Brandes - Chief People Officer

    Alana Brandes, the Chief People Officer at Guild, leads all human capital strategies and talent management initiatives. Brandes architects programs designed to attract, develop, and retain top talent, ensuring Guild's workforce is equipped for the evolving demands of the future of work. This role is central to fostering an inclusive and high-performing culture that reflects the company's core belief in distributed opportunity. By overseeing employee engagement, organizational development, and compensation and benefits, Alana Brandes ensures a supportive and dynamic work environment. Brandes's strategic oversight of people operations is critical for scaling the organization effectively and maintaining a strong connection to Guild's mission. The focus on talent development and employee well-being directly contributes to the company's ability to innovate and grow.

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    Frequently Asked Questions Regarding Guild Top Executives and Leadership Team

    Who leads Guild?
    Guild is led by Rachel Romer (Chief Executive Officer & Co-Founder), along with executives such as Dani Wilkins (Executive Business Partner To Chief Financial Officer) and Natalie McCullough (President & Chief Commercial Officer).
    Who is part of Guild’s executive team?
    The executive team of Guild includes leaders such as Rachel Romer (Chief Executive Officer & Co-Founder), Dani Wilkins (Executive Business Partner To Chief Financial Officer), Natalie McCullough (President & Chief Commercial 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 Chief Executive Officer & Co-Founder, Executive Business Partner To Chief Financial Officer, President & Chief Commercial Officer, Chief of Staff & Chief Operations Officer, Culture To The, Chief People Officer.