iPipeline Executive and Leadership Team

June, 2026

Leadership Overview

iPipeline has 7 executives leading key functions including strategy, finance, operations, technology, human resources, and people management.

Driven by innovation, iPipeline provides cloud-based software solutions for the life insurance and financial services industry, focusing on enhancing digital engagement and streamlining critical business processes.

Leadership Roles at iPipeline

  • Chief Executive Officer - Cary Toner
  • Chief Financial Officer - Adam Boone
  • President - Andrea Evans
  • Chief of Staff - Daphne Thomas
  • Chief Technology Officer - Steven Cover
  • Chief Human Resources Officer - Holly McGiboney
  • Chief People Officer - Diane Rowell
  • Cary Toner - Chief Executive Officer

    Cary Toner, the Chief Executive Officer at iPipeline, directs the company's overall strategic vision and operational execution. Toner guides the organization's expansion within the life insurance and financial services sectors, ensuring alignment with market demands and technological advancements. This leadership role involves fostering innovation across all departments, from product development to client relations, to maintain iPipeline's competitive edge. The Chief Executive Officer oversees the executive team, driving performance and accountability to achieve ambitious growth targets. By focusing on scalable solutions and client success, Toner ensures the company delivers significant value to its partners and stakeholders. The strategic direction set by Cary Toner underpins the company's mission to transform digital engagement within the industry.

    Adam Boone - Chief Financial Officer

    Adam Boone, the Chief Financial Officer at iPipeline, manages all financial aspects of the organization, including financial planning, risk management, and record-keeping. Boone oversees budgeting, forecasting, and capital allocation, ensuring fiscal responsibility and sustainable growth. This critical role involves analyzing financial data to provide strategic insights that support executive decision-making and drive profitability. The Chief Financial Officer also manages investor relations and secures funding necessary for expansion initiatives. By optimizing financial operations and identifying cost-saving opportunities, Adam Boone strengthens the company's financial health and operational efficiency. Boone's expertise ensures robust financial controls and compliance with regulatory standards, supporting iPipeline's long-term stability and market position.

    Andrea Evans - President

    Andrea Evans, the President at iPipeline, holds significant responsibility for driving operational excellence and strategic growth across key business units. Evans oversees the day-to-day operations, ensuring that all departments function cohesively to meet company objectives and client expectations. This leadership position involves managing critical business functions, fostering strong client relationships, and identifying new market opportunities. The President plays a crucial role in translating the company's strategic vision into actionable plans and ensuring their effective implementation. By focusing on operational efficiency and market penetration, Andrea Evans contributes directly to iPipeline's sustained success and expansion within the financial services technology sector. Evans's leadership ensures the seamless execution of iPipeline's mission.

    Daphne Thomas - Chief of Staff

    Daphne Thomas, the Chief of Staff at iPipeline, acts as a strategic partner to the executive leadership, facilitating the execution of key initiatives and operational improvements. Thomas manages cross-functional projects, ensuring seamless collaboration between departments and driving progress on critical business objectives. This role involves streamlining communication channels and optimizing workflows to enhance organizational efficiency. The Chief of Staff supports the Chief Executive Officer by preparing strategic analyses, coordinating executive meetings, and overseeing special projects. By bridging operational gaps and driving strategic alignment, Daphne Thomas ensures that iPipeline's resources are effectively deployed to meet its goals. Thomas's efforts contribute directly to the company's agility and its capacity to respond to evolving market dynamics.

    Steven Cover - Chief Technology Officer

    Steven Cover, the Chief Technology Officer at iPipeline, leads the company's technology strategy, product development, and infrastructure management. Cover oversees the engineering teams responsible for building and maintaining iPipeline's cloud-based software solutions for the life insurance and financial services industry. This pivotal role involves driving innovation in technology, ensuring the scalability and security of the platform, and aligning technological roadmaps with business objectives. The Chief Technology Officer champions the adoption of new technologies to enhance product offerings and improve operational efficiency. By directing the technological evolution of iPipeline's services, Steven Cover ensures the company remains at the forefront of digital transformation. Cover's leadership guarantees robust, cutting-edge solutions that meet the complex needs of clients.
    Steven Cover

    Holly McGiboney - Chief Human Resources Officer

    Holly McGiboney, the Chief Human Resources Officer at iPipeline, directs the company's human capital strategy, focusing on talent acquisition, development, and retention. McGiboney oversees the implementation of HR policies and programs designed to foster a positive and productive work environment. This leadership position involves managing employee relations, compensation and benefits, and organizational design to support iPipeline's growth objectives. The Chief Human Resources Officer ensures that the company attracts and retains top talent, aligning workforce capabilities with strategic business needs. By cultivating a strong organizational culture and promoting employee engagement, Holly McGiboney enhances the overall effectiveness of the workforce. McGiboney's strategic approach to HR is vital for supporting iPipeline's mission and operational success.
    Holly McGiboney

    Diane Rowell - Chief People Officer

    Diane Rowell, the Chief People Officer at iPipeline, spearheads initiatives focused on employee experience, organizational development, and culture transformation. Rowell collaborates with HR leadership to design and implement programs that enhance employee engagement, well-being, and professional growth across the organization. This executive role involves shaping iPipeline's people strategy to align with its business goals and foster a high-performance culture. The Chief People Officer oversees the development of leadership capabilities and ensures that the company's values are embedded in all people-related practices. By championing employee success and fostering a supportive environment, Diane Rowell contributes significantly to iPipeline's ability to attract and retain talent. Rowell's focus on people ensures a cohesive and motivated workforce driving company objectives.
    Diane Rowell

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    Frequently Asked Questions Regarding iPipeline Top Executives and Leadership Team

    Who leads iPipeline?
    iPipeline is led by Cary Toner (Chief Executive Officer), along with executives such as Adam Boone (Chief Financial Officer) and Andrea Evans (President).
    Who is part of iPipeline’s executive team?
    The executive team of iPipeline includes leaders such as Cary Toner (Chief Executive Officer), Adam Boone (Chief Financial Officer), Andrea Evans (President) and other senior executives.
    How many executives does iPipeline have?
    iPipeline has 7 executives leading key business areas.
    What roles are included in iPipeline’s leadership team?
    The leadership team of iPipeline includes roles such as Chief Executive Officer, Chief Financial Officer, President, Chief of Staff, Chief Technology Officer.