Imagine Learning Executive and Leadership Team

September, 2026

Leadership Overview

Imagine Learning has 5 executives leading key functions including operations, revenue, finance, technology, and strategic coordination.

Focused on transforming the education landscape, Imagine Learning delivers digital curriculum solutions that empower students and educators. This organization prioritizes scalable learning outcomes through innovative technology and pedagogical excellence across diverse global markets.

Leadership Roles at Imagine Learning

  • Executive Vice President & Chief Financial Officer - David Alderslade
  • President & Chief Operating Officer - Joe Swenson
  • Chief of Staff - James Werner
  • Chief Revenue Officer - Andy Caulo
  • Senior VP & Chief Technology Officer - Anjeneya Dubey
  • David Alderslade - Executive Vice President & Chief Financial Officer

    David Alderslade, the Executive Vice President & Chief Financial Officer at Imagine Learning, manages the financial health and fiscal strategy of the organization. Alderslade oversees budgeting, financial reporting, and capital allocation to support the company's mission. By directing investment in educational technology, the Executive Vice President & Chief Financial Officer ensures that resources align with long-term growth targets. David Alderslade monitors cash flow and profitability to maintain a strong market position. This role involves collaborating with the Board to provide transparency regarding financial performance and risk management. Through rigorous analysis of market conditions, the Executive Vice President & Chief Financial Officer guides the company toward sustainable revenue models. Alderslade implements financial controls that foster operational efficiency across all departments. This leadership function remains essential for securing the capital necessary to advance the company's digital curriculum offerings and expand its reach within the education sector.

    Joe Swenson - President & Chief Operating Officer

    Joe Swenson, the President & Chief Operating Officer at Imagine Learning, manages the daily business operations and long-term strategic execution. Swenson oversees the implementation of educational programs and ensures that internal processes support the company's growth objectives. By directing the operational infrastructure, the President & Chief Operating Officer maintains high standards of service delivery for schools and districts. Joe Swenson coordinates with other C-suite leaders to translate the company's vision into actionable business plans. This role involves optimizing supply chain logistics and service deployment to ensure seamless access to digital curriculum. Through careful management of organizational resources, the President & Chief Operating Officer drives efficiency and scalability. Swenson monitors performance metrics to identify areas for improvement and innovation. This leadership position remains central to the company's ability to deliver consistent value within the education industry while expanding its operational footprint.

    James Werner - Chief of Staff

    James Werner, the Chief of Staff at Imagine Learning, coordinates cross-functional initiatives to ensure alignment with corporate objectives. Werner manages internal communications and facilitates decision-making processes across the executive leadership team. By streamlining operational workflows, the Chief of Staff enables the organization to maintain focus on core educational goals. James Werner monitors project timelines and resource allocation to support the company's mission of delivering high-quality digital curriculum. This role involves bridging gaps between departments to foster a cohesive work environment. Through rigorous oversight of strategic priorities, the Chief of Staff drives efficiency and accountability within the Scottsdale-based headquarters. Werner maintains a clear view of organizational health, ensuring that every team member contributes effectively to the broader educational impact. This position remains vital for maintaining the operational rhythm necessary for sustained growth in the competitive education technology sector.

    Andy Caulo - Chief Revenue Officer

    Andy Caulo, the Chief Revenue Officer at Imagine Learning, directs all sales strategies and market expansion efforts. Caulo oversees the development of revenue streams by identifying new opportunities within the K-12 education sector. By optimizing the sales funnel, the Chief Revenue Officer ensures that digital learning solutions reach schools across North America effectively. Andy Caulo manages relationships with key stakeholders and partners to secure long-term market presence. This leadership role involves analyzing market trends to adjust pricing models and service offerings. Through data-driven decision-making, the Chief Revenue Officer maximizes profitability while maintaining a focus on student success. Caulo collaborates with the marketing and product teams to align sales messaging with the company's core value proposition. Ultimately, the Chief Revenue Officer secures the financial stability required for the company to continue innovating in the digital education space.

    Anjeneya Dubey - Senior VP & Chief Technology Officer

    Anjeneya Dubey, the Senior VP & Chief Technology Officer at Imagine Learning, architects the digital infrastructure that powers the company's educational platforms. Dubey oversees the engineering and development teams responsible for creating scalable, secure, and user-friendly learning tools. By directing the technical roadmap, the Senior VP & Chief Technology Officer ensures that the company remains at the forefront of educational innovation. Anjeneya Dubey manages the integration of new technologies to enhance student engagement and learning outcomes. This role involves collaborating with product managers to translate pedagogical requirements into robust software solutions. Through the implementation of advanced data analytics, the Senior VP & Chief Technology Officer optimizes platform performance and reliability. Dubey drives the adoption of modern development practices to maintain a competitive edge in the education technology market. This leadership position remains critical for building the digital foundation that supports the company's mission of transforming education.
    Anjeneya Dubey

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    Frequently Asked Questions Regarding Imagine Learning Top Executives and Leadership Team

    Who leads Imagine Learning?
    Imagine Learning is led by David Alderslade (Executive Vice President & Chief Financial Officer), along with executives such as Joe Swenson (President & Chief Operating Officer) and James Werner (Chief of Staff).
    Who is part of Imagine Learning’s executive team?
    The executive team of Imagine Learning includes leaders such as David Alderslade (Executive Vice President & Chief Financial Officer), Joe Swenson (President & Chief Operating Officer), James Werner (Chief of Staff) and other senior executives.
    How many executives does Imagine Learning have?
    Imagine Learning has 5 executives leading key business areas.
    What roles are included in Imagine Learning’s leadership team?
    The leadership team of Imagine Learning includes roles such as Executive Vice President & Chief Financial Officer, President & Chief Operating Officer, Chief of Staff, Chief Revenue Officer, Senior VP & Chief Technology Officer.