Skyward Executive and Leadership Team

August, 2026

Leadership Overview

Skyward has 9 executives leading key functions including strategy, administration, marketing, operations, technology, finance, and organizational leadership.

Focused on delivering robust software solutions for K-12 education, Skyward empowers school districts globally through integrated platforms for student management, financial administration, and human resources.

Leadership Roles at Skyward

  • Chief Executive Officer - Ben Jamison
  • Chief Financial Officer - Mary Tomazin
  • Chief Operating Officer - Karen Hrubiak
  • President - Ray Ackerlund
  • President & Co-Founder - Jason Wu
  • Chief of Staff - Ksenia Kapoor
  • Chief Marketing Officer - Tom King
  • Chief Technology Officer - Vitaliy Baklikov
  • 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. Jamison architects long-term growth initiatives that expand the reach of software solutions across international K-12 school districts. By aligning internal resources with the evolving needs of educational institutions, the Chief Executive Officer ensures the company maintains a competitive edge in the ERP software market. This leadership role involves constant collaboration with the Board to refine product roadmaps and operational priorities. Ben Jamison monitors market trends to anticipate shifts in public and private sector requirements, ensuring the firm remains a leader in administrative technology. Through rigorous oversight of corporate performance, the Chief Executive Officer drives sustainable value for stakeholders while maintaining a commitment to the core mission of supporting student success through advanced digital infrastructure and reliable administrative tools.

    Mary Tomazin - Chief Financial Officer

    Mary Tomazin, the Chief Financial Officer at Skyward, manages the financial health and fiscal strategy of the organization. Tomazin directs all accounting, budgeting, and financial planning activities to support the company's long-term growth objectives. By providing accurate financial analysis, the Chief Financial Officer enables the leadership team to make informed decisions regarding investments in software development and market expansion. Mary Tomazin oversees the financial reporting processes that ensure compliance and transparency for the firm's stakeholders. This role involves managing capital allocation to maximize the impact of the company's resources on the K-12 education market. Through the implementation of robust financial controls, the Chief Financial Officer mitigates risk and ensures the sustainability of the business model. Tomazin drives fiscal discipline across all departments, ensuring that the company maintains the necessary resources to continue delivering high-quality administrative solutions to school districts.

    Karen Hrubiak - Chief Operating Officer

    Karen Hrubiak, the Chief Operating Officer at Skyward, oversees the internal scaling and administrative infrastructure required to support the company's software delivery. Hrubiak directs the daily operations of the firm, ensuring that human resources and internal business processes function with maximum efficiency. By optimizing the organizational framework, the Chief Operating Officer enables the company to meet the complex demands of K-12 school districts effectively. Karen Hrubiak manages the integration of new administrative tools that streamline internal workflows and improve service delivery. This role involves close coordination with other C-suite leaders to ensure that operational capacity matches the strategic growth targets of the business. Through the implementation of rigorous performance metrics, the Chief Operating Officer maintains high standards of service quality. Hrubiak drives operational stability, allowing the firm to focus on its core mission of providing essential software solutions to the education sector.

    Ray Ackerlund - President

    Ray Ackerlund, the President at Skyward, leads the execution of the company's business strategy and oversees the day-to-day management of the firm's core divisions. Ackerlund directs the alignment of product development with the specific needs of the K-12 education market. By fostering strong relationships with school district leaders, the President ensures that the company's software solutions remain relevant and impactful. Ray Ackerlund manages the cross-functional teams that deliver student management and financial administration tools to clients. This role involves driving the company's growth initiatives and ensuring that all departments work in harmony to achieve corporate goals. Through the oversight of key business units, the President maintains the firm's position as a leader in the educational software industry. Ackerlund drives organizational success by promoting a culture of service and innovation, ensuring that the company continues to provide essential support to educators and administrators.

    Jason Wu - President & Co-Founder

    Jason Wu, the President & Co-Founder at Skyward, provides the foundational vision and strategic guidance that define the company's long-term trajectory. Wu directs the development of the firm's core philosophy, emphasizing the importance of reliable software in the K-12 education sector. By leveraging decades of industry experience, the President & Co-Founder ensures that the company remains committed to its mission of supporting school districts through innovative technology. Jason Wu oversees the strategic partnerships that expand the firm's reach and influence in the global market. This role involves mentoring the leadership team and ensuring that the company's values are integrated into every aspect of the business. Through the continuous pursuit of excellence, the President & Co-Founder drives the firm's growth and maintains its reputation for quality. Wu secures the company's future by fostering a culture of dedication to the educational community and the students served by the software.

    Ksenia Kapoor - Chief of Staff

    Ksenia Kapoor, the Chief of Staff at Skyward, manages the execution of high-priority strategic projects across the organization. Kapoor coordinates cross-departmental workflows to ensure alignment with the primary mission of providing comprehensive software for K-12 education. By facilitating communication between the executive team and various business units, the Chief of Staff optimizes internal processes and accelerates decision-making cycles. Ksenia Kapoor oversees the implementation of corporate initiatives that enhance efficiency in human resources and financial administration modules. This role requires deep integration with the leadership team to translate high-level goals into actionable tasks for technical and administrative staff. Through meticulous planning and resource allocation, the Chief of Staff maintains organizational focus on delivering high-quality software solutions. Kapoor drives operational excellence by removing bottlenecks and fostering a culture of accountability throughout the company's diverse departments.

    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. King drives demand generation initiatives that highlight the value of integrated student management and financial systems to school districts across the United States and international markets. By analyzing market data and customer feedback, the Chief Marketing Officer crafts targeted campaigns that emphasize the reliability and scalability of the firm's technology. Tom King collaborates with product teams to ensure messaging accurately reflects the technical capabilities of the software. This leadership role involves managing the company's public image and expanding market share through strategic partnerships and industry engagement. Through the development of comprehensive marketing programs, the Chief Marketing Officer secures the firm's reputation as a premier provider of administrative solutions for K-12 institutions, ultimately supporting long-term revenue growth and brand loyalty.

    Vitaliy Baklikov - Chief Technology Officer

    Vitaliy Baklikov, the Chief Technology Officer at Skyward, architects the scalable cloud infrastructure and software architecture that power the company's educational platforms. Baklikov directs the engineering teams responsible for developing and maintaining the student management and financial software used by K-12 districts. By prioritizing security, performance, and user experience, the Chief Technology Officer ensures the firm's technology remains at the forefront of the industry. Vitaliy Baklikov oversees the research and development of new features that address the evolving needs of school administrators and IT staff. This role involves constant collaboration with the product and operations teams to ensure seamless deployment of software updates. Through the strategic application of modern development methodologies, the Chief Technology Officer drives innovation and maintains the integrity of the company's digital ecosystem. Baklikov secures the firm's technical advantage by fostering a culture of continuous improvement and engineering excellence.

    Kevin Duda - Chief Operations Officer

    Kevin Duda, the Chief Operations Officer at Skyward, focuses on the logistics and supply chain aspects of the company's software deployment and IT consulting services. Duda directs the teams responsible for the physical and digital implementation of software solutions within school districts. By optimizing the deployment process, the Chief Operations Officer ensures that clients receive timely support and effective integration of the firm's products. Kevin Duda manages the operational logistics required to scale services across diverse geographic regions, including international markets. This role involves coordinating with technical teams to ensure that the infrastructure supporting the software is robust and reliable. Through the management of service delivery protocols, the Chief Operations Officer drives customer satisfaction and operational efficiency. Duda maintains a focus on the practical application of the company's technology, ensuring that school districts have the tools necessary to manage their administrative functions effectively.
    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 9 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, President & Co-Founder.