Skyward Executive and Leadership Team

October, 2026

Leadership Overview

Skyward has 8 executives leading key functions including strategy, marketing, operations, finance, and organizational management.

Committed to educational excellence, Skyward delivers robust software solutions for K-12 school districts, streamlining administrative tasks and enhancing student outcomes through innovative technology.

Leadership Roles at Skyward

  • Chief Executive Officer - Ben Jamison
  • Chief Financial Officer - Mary Tomazin
  • Chief Operating Officer - Karen Hrubiak
  • President & Co-Founder - Jason Wu
  • President - Ray Ackerlund
  • Chief Marketing Officer - Tom King
  • Chief of Staff - Ksenia Kapoor
  • Chief Operations Officer - Kevin Duda
  • Ben Jamison - Chief Executive Officer

    Ben Jamison, the Chief Executive Officer at Skyward, directs the overarching strategic vision for the organization. Overseeing the development of software solutions for K-12 school districts, the Chief Executive Officer ensures alignment between product innovation and the evolving needs of educational institutions. This leadership role involves managing high-level partnerships and driving growth across domestic and international markets. By prioritizing the integration of student information systems and human resources administration, Ben Jamison maintains the company's competitive edge in the ERP software sector. The Chief Executive Officer fosters a culture of continuous improvement, ensuring that all departments remain focused on delivering value to public and private school districts. Through rigorous oversight of corporate objectives, Jamison secures long-term stability and operational excellence for the entire enterprise.

    Mary Tomazin - Chief Financial Officer

    Mary Tomazin, the Chief Financial Officer at Skyward, manages the fiscal health and long-term financial planning for the organization. Overseeing capital allocation and revenue management, the Chief Financial Officer ensures that the company maintains the resources necessary to innovate within the ERP software space. This leadership role involves analyzing financial performance across financing and consulting divisions to drive sustainable growth. By implementing rigorous fiscal controls, Mary Tomazin supports the company's ability to serve K-12 school districts effectively. The Chief Financial Officer works closely with the executive team to evaluate investment opportunities and mitigate financial risks. Through strategic financial oversight, Tomazin secures the capital required to expand the company's reach and maintain its position as a leader in educational software solutions.

    Karen Hrubiak - Chief Operating Officer

    Karen Hrubiak, the Chief Operating Officer at Skyward, directs internal scaling and infrastructure development to support the company's software delivery. Overseeing the efficiency of administrative systems, the Chief Operating Officer ensures that internal processes remain robust enough to handle the demands of international school districts. This leadership role involves optimizing the delivery of IT consulting and HR administration services. By refining operational workflows, Karen Hrubiak improves the speed and reliability of software deployment for K-12 clients. The Chief Operating Officer collaborates with technical teams to ensure that internal systems support the company's growth objectives. Through constant monitoring of operational metrics, Hrubiak maintains high service standards and ensures that the organization remains agile in a rapidly evolving educational technology market.

    Jason Wu - President & Co-Founder

    Jason Wu, the President & Co-Founder at Skyward, provides foundational leadership and long-term strategic guidance for the company. Overseeing the evolution of the core software platform, the President & Co-Founder ensures that the organization remains true to its mission of supporting K-12 education. This leadership role involves fostering innovation in student information systems and financing tools. By leveraging deep industry knowledge, Jason Wu guides the company through market shifts and technological advancements. The President & Co-Founder collaborates with the executive team to define the future trajectory of the business and maintain its competitive advantage. Through consistent focus on quality and service, Wu ensures that the company continues to provide essential solutions to school districts worldwide.

    Ray Ackerlund - President

    Ray Ackerlund, the President at Skyward, directs the day-to-day execution of corporate strategy and business development. Overseeing the expansion of software services into new markets, the President ensures that the company effectively addresses the needs of both public and private school districts. This leadership role involves managing key client relationships and driving the adoption of HR administration and IT consulting tools. By aligning departmental goals with the company's overarching mission, Ray Ackerlund fosters a high-performance environment. The President works closely with other executives to ensure that product development and market outreach remain synchronized. Through strategic leadership and a focus on customer success, Ackerlund drives growth and strengthens the company's reputation as a premier provider of educational software solutions.

    Tom King - Chief Marketing Officer

    Tom King, the Chief Marketing Officer at Skyward, architects the global brand strategy and market positioning for the company's suite of educational software. Overseeing demand generation and customer acquisition, the Chief Marketing Officer drives engagement with K-12 school districts across diverse geographic regions. This leadership role involves analyzing market trends to refine messaging for financing, IT consulting, and HR administration tools. By optimizing digital outreach and industry presence, Tom King directly impacts the company's ability to scale its footprint in the competitive ERP landscape. The Chief Marketing Officer collaborates with product teams to ensure marketing initiatives accurately reflect the technical capabilities of the software. Ultimately, King secures brand loyalty and expands the reach of the organization within the global education technology sector.

    Ksenia Kapoor - Chief of Staff

    Ksenia Kapoor, the Chief of Staff at Skyward, coordinates cross-functional initiatives to ensure seamless execution of corporate priorities. Overseeing internal communications and executive workflows, the Chief of Staff facilitates alignment between the leadership team and various departments. This leadership role involves managing complex projects related to human resources administration and IT consulting services. By streamlining decision-making processes, Ksenia Kapoor enhances organizational efficiency and supports the company's mission to serve K-12 school districts. The Chief of Staff acts as a primary liaison for strategic planning, ensuring that all operational goals remain synchronized with the broader vision. Through meticulous attention to detail and resource allocation, Kapoor drives productivity and maintains high standards of performance across the entire organization.

    Kevin Duda - Chief Operations Officer

    Kevin Duda, the Chief Operations Officer at Skyward, focuses on supply chain logistics and the technical implementation of software solutions for school districts. Overseeing the deployment of IT consulting services, the Chief Operations Officer ensures that technical infrastructure meets the specific needs of K-12 environments. This leadership role involves managing the logistical aspects of software rollouts and ensuring that client support systems function at peak capacity. By streamlining the technical delivery process, Kevin Duda enhances the overall user experience for educational institutions. The Chief Operations Officer coordinates with product development teams to ensure that operational capabilities align with new software features. Through proactive management of technical resources, Duda drives operational excellence and supports the company's commitment to reliable service delivery.
    Kevin Duda

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    Frequently Asked Questions Regarding Skyward Top Executives and Leadership Team

    Who leads Skyward?
    Skyward is led by Ben Jamison (Chief Executive Officer), along with executives such as Mary Tomazin (Chief Financial Officer) and Karen Hrubiak (Chief Operating Officer).
    Who is part of Skyward’s executive team?
    The executive team of Skyward includes leaders such as Ben Jamison (Chief Executive Officer), Mary Tomazin (Chief Financial Officer), Karen Hrubiak (Chief Operating Officer) and other senior executives.
    How many executives does Skyward have?
    Skyward has 8 executives leading key business areas.
    What roles are included in Skyward’s leadership team?
    The leadership team of Skyward includes roles such as Chief Executive Officer, Chief Financial Officer, Chief Operating Officer, President & Co-Founder, President.