Skyward Executive and Leadership Team

August, 2026

Leadership Overview

Skyward has 9 executives leading key functions including strategy, technology, marketing, operations, finance, staff, and president roles.

Driven by innovation, Skyward delivers comprehensive software solutions for K-12 education, finance, IT consulting, and human resources administration, impacting public and private school districts across the United States and internationally.

Leadership Roles at Skyward

  • Chief Executive Officer - Milton Dmello
  • Chief Financial Officer - Mary Tomazin
  • Chief Operating Officer - Karen Hrubiak
  • President - Raymond Ackerlund
  • President & Co-Founder - Jason Wu
  • Chief Technology Officer - Vitaliy Baklikov
  • Chief Marketing Officer - Thomas King
  • Chief of Staff - Ksenia Kapoor
  • Chief Operations Officer - Kevin Duda
  • Milton Dmello - Chief Executive Officer

    Milton Dmello, the Chief Executive Officer at Skyward, directs the company's overall strategic vision and operational execution. Dmello guides the enterprise in delivering robust software solutions for K-12 education, finance, IT consulting, and human resources administration. Overseeing all major business units, the Chief Executive Officer ensures alignment with market demands and company growth objectives. This leadership role involves fostering innovation and maintaining Skyward's commitment to serving public and private school districts. Milton Dmello drives the company's expansion and reinforces its position as a key provider in the software solutions sector. The Chief Executive Officer's purview encompasses long-term planning and resource allocation to support ongoing development and client success.

    Mary Tomazin - Chief Financial Officer

    Mary Tomazin, the Chief Financial Officer at Skyward, directs the company's financial planning, reporting, and investment strategies. Tomazin manages all fiscal operations, including budgeting, forecasting, and financial analysis for software solutions in K-12 education, finance, IT consulting, and human resources administration. The Chief Financial Officer ensures financial health and compliance with regulatory requirements. This position is key to supporting Skyward's growth and operational stability. Mary Tomazin's financial expertise guides strategic decision-making and resource management. The Chief Financial Officer's oversight extends to managing capital, mitigating financial risks, and optimizing profitability for the organization.

    Karen Hrubiak - Chief Operating Officer

    Karen Hrubiak, the Chief Operating Officer at Skyward, manages the day-to-day operational functions and service delivery. Hrubiak oversees the implementation and support of software solutions for students, financing, IT consulting, and human resources administration, ensuring client satisfaction. The Chief Operating Officer directs process improvements and operational efficiency across all departments. This role is crucial for maintaining the high standards of service Skyward provides to K-12 school districts. Karen Hrubiak's operational acumen drives seamless execution of company strategies. The Chief Operating Officer's responsibilities include optimizing resource allocation and ensuring the smooth functioning of all business processes to support client needs.

    Raymond Ackerlund - President

    Raymond Ackerlund, the President at Skyward, drives strategic growth and market expansion initiatives. Ackerlund focuses on developing and implementing business strategies that enhance Skyward's software solutions for K-12 education, finance, IT consulting, and human resources administration. The President oversees key business development efforts and fosters strategic partnerships. This role is instrumental in guiding the company's trajectory and market positioning. Raymond Ackerlund's leadership is crucial for achieving sustained growth and market leadership. The President's responsibilities include identifying new opportunities and ensuring the company's offerings meet evolving client needs.

    Jason Wu - President & Co-Founder

    Jason Wu, the President & Co-Founder at Skyward, provides foundational leadership and strategic direction for the company. Wu contributes to the vision and execution of Skyward's software solutions for students, financing, IT consulting, and human resources administration, leveraging deep industry insight. The President & Co-Founder plays a key role in shaping the company culture and long-term strategic planning. This position is vital for maintaining the innovative spirit and core mission of Skyward. Jason Wu's ongoing involvement ensures continuity and strategic foresight. The President & Co-Founder's focus includes driving innovation and upholding the company's commitment to its clients.

    Vitaliy Baklikov - Chief Technology Officer

    Vitaliy Baklikov, the Chief Technology Officer at Skyward, architects the company's technological infrastructure and product development roadmap. Baklikov leads the engineering teams responsible for creating and enhancing software solutions for students, financing, IT consulting, and human resources administration. The Chief Technology Officer ensures that Skyward's platforms are scalable, secure, and meet the evolving needs of K-12 school districts. This critical role involves evaluating emerging technologies and driving innovation in software design. Vitaliy Baklikov's expertise is essential for maintaining Skyward's competitive edge in the software industry. The Chief Technology Officer's responsibilities include overseeing all aspects of technology strategy and implementation, ensuring seamless integration and optimal performance for clients.

    Thomas King - Chief Marketing Officer

    Thomas King, the Chief Marketing Officer at Skyward, spearheads all marketing initiatives and brand strategy. King directs the development and execution of campaigns to promote Skyward's software solutions for K-12 education, finance, IT consulting, and human resources administration. The Chief Marketing Officer oversees market research, lead generation, and digital marketing efforts to expand the company's reach. This position is vital for communicating Skyward's value proposition to public and private school districts. Thomas King's leadership ensures effective market penetration and brand recognition. The Chief Marketing Officer's focus includes driving customer acquisition and fostering strong relationships within the education and administrative software sectors.

    Ksenia Kapoor - Chief of Staff

    Ksenia Kapoor, the Chief of Staff at Skyward, acts as a strategic advisor and facilitator across executive functions. Kapoor supports the Chief Executive Officer in driving key initiatives and ensuring cross-departmental alignment for software solutions in K-12 education, finance, IT consulting, and human resources administration. The Chief of Staff manages special projects and enhances organizational effectiveness. This role is pivotal in streamlining communication and operational workflows. Ksenia Kapoor's contributions are essential for executing strategic priorities and fostering a cohesive work environment. The Chief of Staff's responsibilities include coordinating executive communications and driving operational excellence throughout the company.

    Kevin Duda - Chief Operations Officer

    Kevin Duda, the Chief Operations Officer at Skyward, oversees the strategic execution of operational initiatives and service delivery excellence. Duda leads teams focused on enhancing the efficiency and effectiveness of software solutions for students, financing, IT consulting, and human resources administration. The Chief Operations Officer drives process optimization and ensures seamless integration of services for K-12 school districts. This leadership position is critical for maintaining Skyward's operational integrity and client support. Kevin Duda's focus is on scalable operations and continuous improvement. The Chief Operations Officer's responsibilities include managing operational budgets and implementing best practices to achieve organizational goals.
    Kevin Duda

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    Frequently Asked Questions Regarding Skyward Top Executives and Leadership Team

    Who leads Skyward?
    Skyward is led by Milton Dmello (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 Milton Dmello (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.