Skyward Executive and Leadership Team

September, 2026

Leadership Overview

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

Committed to educational excellence, Skyward delivers robust software solutions for K-12 districts, financing, and human resources administration to empower schools across the United States and international markets.

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. Jamison architects long-term growth initiatives while overseeing the development of software solutions for K-12 school districts. By aligning internal resources with the evolving needs of public and private education, the Chief Executive Officer ensures the company maintains a competitive edge in the ERP software market. Jamison fosters collaboration across all departments to drive operational efficiency and product innovation. This leadership role involves constant engagement with the Board to secure sustainable financial performance and market expansion. Through the implementation of advanced technology frameworks, Ben Jamison strengthens the company's position as a leader in student information and human resources administration. The Chief Executive Officer prioritizes the delivery of high-quality tools that simplify complex administrative tasks for educators and staff globally.

    Mary Tomazin - Chief Financial Officer

    Mary Tomazin, the Chief Financial Officer at Skyward, manages the fiscal health and capital allocation strategies for the organization. Tomazin oversees financial planning, reporting, and risk management to support the delivery of software solutions for K-12 districts. By optimizing budgetary processes, the Chief Financial Officer ensures the company maintains the resources necessary for continuous innovation in student information and HR administration. Mary Tomazin collaborates with executive leadership to evaluate investment opportunities and drive revenue growth across North American and international markets. This role involves rigorous oversight of financial compliance and the development of long-term fiscal models that align with corporate objectives. Through precise analysis of market trends, the Chief Financial Officer secures the stability required for sustained operational success. Tomazin maintains a focus on maximizing shareholder value while supporting the core mission of providing essential tools to educational institutions.

    Karen Hrubiak - Chief Operating Officer

    Karen Hrubiak, the Chief Operating Officer at Skyward, manages internal processes and organizational scaling to support the delivery of software solutions. Hrubiak oversees the integration of human resources administration tools and student information systems across the enterprise. By streamlining workflows and enhancing cross-departmental communication, the Chief Operating Officer ensures the company maintains high standards of service for K-12 school districts. Karen Hrubiak drives initiatives focused on operational excellence and the optimization of internal infrastructure to support rapid growth. This leadership role involves coordinating with other C-suite members to align daily activities with the broader corporate strategy. Through the implementation of efficient management practices, the Chief Operating Officer improves productivity and service delivery speed. Hrubiak focuses on creating a scalable environment that allows the company to meet the complex needs of educational clients in both domestic and international markets.

    Jason Wu - President & Co-Founder

    Jason Wu, the President & Co-Founder at Skyward, directs the long-term vision and foundational growth of the organization. Wu architects the strategic direction for software solutions that support K-12 school districts and human resources administration. By leveraging deep industry knowledge, the President & Co-Founder ensures the company remains at the forefront of educational technology innovation. Jason Wu oversees the development of key partnerships and market expansion efforts that drive the company's success in the United States and abroad. This leadership role involves mentoring executive teams and maintaining the core values that define the company's mission. Through the pursuit of excellence in software design and service, the President & Co-Founder secures the company's legacy as a trusted partner for schools. Wu focuses on identifying emerging trends in the education sector to guide future product development and business strategy.

    Ray Ackerlund - President

    Ray Ackerlund, the President at Skyward, directs the day-to-day business operations and market execution for the organization. Ackerlund architects strategies to increase the adoption of software solutions for K-12 districts and financing services. By overseeing sales and customer success teams, the President ensures the company delivers exceptional value to educational institutions. Ray Ackerlund manages the alignment of product offerings with the specific needs of school districts to drive revenue and market share. This leadership role involves collaborating with the executive team to refine business models and improve service delivery. Through the implementation of customer-centric initiatives, the President strengthens the company's reputation as a leader in the ERP software space. Ackerlund maintains a focus on achieving operational targets and fostering long-term relationships with clients to ensure the continued success of the company's mission in the education sector.

    Tom King - Chief Marketing Officer

    Tom King, the Chief Marketing Officer at Skyward, directs all brand strategy and market positioning efforts. King architects comprehensive campaigns that highlight the value of software solutions for K-12 school districts and human resources administration. By analyzing customer feedback and market demand, the Chief Marketing Officer ensures the company effectively communicates the benefits of its ERP platforms to public and private school leaders. Tom King oversees lead generation and digital outreach to expand the company's footprint across diverse geographic regions. This leadership role involves close coordination with product teams to align messaging with new feature releases and service updates. Through the execution of data-driven marketing initiatives, the Chief Marketing Officer drives brand awareness and customer acquisition. Tom King maintains a focus on building strong relationships with educational stakeholders to ensure the company remains the preferred choice for school management technology.

    Ksenia Kapoor - Chief of Staff

    Ksenia Kapoor, the Chief of Staff at Skyward, directs the execution of strategic priorities and facilitates communication across the executive leadership team. Kapoor architects internal processes that enable the company to deliver software solutions for K-12 districts and financing more effectively. By managing high-level projects and coordinating cross-functional initiatives, the Chief of Staff ensures alignment with the company's mission of supporting educational institutions. Ksenia Kapoor oversees the flow of information between departments to maintain operational transparency and efficiency. This leadership role involves supporting the CEO in decision-making processes and ensuring that organizational goals are met within established timelines. Through the management of key corporate initiatives, the Chief of Staff drives progress on critical business objectives. Kapoor maintains a focus on fostering a collaborative culture that empowers teams to deliver high-quality software and consulting services to school districts globally.

    Kevin Duda - Chief Operations Officer

    Kevin Duda, the Chief Operations Officer at Skyward, directs the technical delivery and infrastructure support for the company's software solutions. Duda architects scalable cloud environments and IT consulting frameworks that serve K-12 school districts. By overseeing the technical operations team, the Chief Operations Officer ensures the reliability and security of student information and financing platforms. Kevin Duda manages the deployment of software updates and system enhancements to meet the evolving needs of educational clients. This leadership role involves coordinating with product development to ensure that technical capabilities align with market requirements. Through the optimization of IT service delivery, the Chief Operations Officer supports the company's commitment to providing robust and accessible technology. Duda maintains a focus on operational stability and the continuous improvement of technical processes to ensure seamless experiences for school administrators and staff.
    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.