Dayforce Executive and Leadership Team

October, 2026

Leadership Overview

Dayforce has 6 executives leading key functions including corporate strategy, human resources enablement, operational management, business development, financial trust services, and people operations.

Focused on delivering comprehensive workforce management solutions, Dayforce empowers global organizations to streamline HR administration, optimize labor scheduling, and enhance overall operational efficiency through advanced analytics and intuitive mobile-first software platforms.

Leadership Roles at Dayforce

  • Chief Executive Officer & Chairman of the Board - David Ossip
  • President & Chief Operating Officer - Stephen Holdridge
  • President, Dayforce National Trust Bank - Nicholas Cucci
  • Director, Human Resources Enablement & Chief of Staff - Kaitlin Burwick
  • Chief of Staff (Americas) New Business organization - Sherri Kolomayz
  • Executive Vice President & Chief People Officer - John Cardella
  • David Ossip - Chief Executive Officer & Chairman of the Board

    David Ossip, the Chief Executive Officer & Chairman of the Board at Dayforce, directs the overarching corporate vision and long-term strategic trajectory of the organization. By prioritizing the development of comprehensive HR software, the Chief Executive Officer & Chairman of the Board ensures the platform maintains a competitive edge in workforce management and labor scheduling. Ossip oversees the alignment of product innovation with global market demands, fostering a culture of high-performance software delivery. This leadership role involves constant engagement with the Board to drive shareholder value and sustainable growth. Through the integration of advanced analytics and user-friendly interfaces, David Ossip transforms how businesses manage complex human capital requirements. Ultimately, the Chief Executive Officer & Chairman of the Board secures the company's position as a leader in the global HR technology sector by championing faster application performance and superior business value for all enterprise clients.
    David Ossip

    Stephen Holdridge - President & Chief Operating Officer

    Stephen Holdridge, the President & Chief Operating Officer at Dayforce, executes the daily operational strategy and manages the delivery of workforce management solutions across global markets. Overseeing the deployment of labor scheduling and forecasting tools, the President & Chief Operating Officer ensures that client organizations achieve maximum operational efficiency. Holdridge directs the expansion of service offerings, focusing on the integration of mobile app capabilities to meet modern business needs. This leadership role involves close collaboration with the executive team to refine the company's B2B service delivery models. Through the optimization of task management and attendance tracking systems, Stephen Holdridge drives significant improvements in application performance. By scaling operations to support a diverse international client base, Holdridge maintains the company's reputation for reliability and innovation. The President & Chief Operating Officer consistently monitors performance metrics to ensure that all service delivery aligns with the core mission of simplifying complex workforce management processes.
    Stephen Holdridge

    Nicholas Cucci - President, Dayforce National Trust Bank

    Nicholas Cucci, the President, Dayforce National Trust Bank at Dayforce, manages the financial services division and ensures the secure handling of payroll and trust-related transactions. By overseeing the integration of banking services with the core HR software platform, the President, Dayforce National Trust Bank provides clients with a seamless experience for managing employee compensation and financial compliance. Cucci directs the regulatory and operational standards required to maintain the integrity of the trust bank's functions. This leadership role involves coordinating with the broader executive team to ensure that financial services support the company's overall workforce management mission. Through the implementation of secure, efficient payment processing, Nicholas Cucci enhances the value proposition of the platform for global organizations. By maintaining rigorous financial oversight, the President, Dayforce National Trust Bank mitigates risk and supports the company's commitment to accuracy and reliability. Cucci drives the strategic development of financial tools that complement the company's comprehensive suite of HR and labor management solutions.
    Nicholas Cucci

    Kaitlin Burwick - Director, Human Resources Enablement & Chief of Staff

    Kaitlin Burwick, the Director, Human Resources Enablement & Chief of Staff at Dayforce, manages the internal alignment of HR initiatives and executive operational workflows. By optimizing the internal HR software ecosystem, the Director, Human Resources Enablement & Chief of Staff ensures that organizational processes remain efficient and scalable. Burwick coordinates cross-functional projects that bridge the gap between administrative requirements and technical execution. This leadership role involves streamlining communication channels to support the broader mission of workforce management excellence. Through the implementation of robust HR administration tools, Kaitlin Burwick drives internal productivity and supports the company's commitment to superior employee self-service capabilities. By refining operational frameworks, Burwick enhances the overall effectiveness of the HR software platform. The Director, Human Resources Enablement & Chief of Staff maintains a focus on operational agility, ensuring that internal systems support the rapid growth and evolving needs of the global client base.

    Sherri Kolomayz - Chief of Staff (Americas) New Business organization

    Sherri Kolomayz, the Chief of Staff (Americas) New Business organization at Dayforce, drives the strategic expansion of new business initiatives throughout the North American market. By identifying emerging opportunities for workforce management software adoption, the Chief of Staff (Americas) New Business organization ensures that the company captures significant market share. Kolomayz coordinates the efforts of sales and business development teams to align with the broader corporate goal of delivering high-value HR solutions. This leadership role involves analyzing regional market trends to tailor the platform's B2B service offerings for diverse industry sectors. Through the application of data-driven insights, Sherri Kolomayz accelerates the acquisition of new enterprise clients. By fostering strong relationships with key stakeholders, the Chief of Staff (Americas) New Business organization strengthens the company's presence in the Americas. Kolomayz focuses on the seamless integration of new business processes, ensuring that the company's growth remains consistent with its commitment to operational excellence and technological innovation.

    John Cardella - Executive Vice President & Chief People Officer

    John Cardella, the Executive Vice President & Chief People Officer at Dayforce, architects the global human capital strategy and fosters a high-performance culture within the organization. By implementing advanced talent management and employee engagement programs, the Executive Vice President & Chief People Officer ensures that the company attracts and retains top-tier talent to support its software development goals. Cardella oversees the alignment of internal people operations with the company's mission to provide superior workforce management tools. This leadership role involves developing initiatives that promote diversity, equity, and inclusion across all global offices. Through the application of data-driven people analytics, John Cardella optimizes organizational structure and enhances employee productivity. By championing professional development and leadership training, the Executive Vice President & Chief People Officer strengthens the company's internal capabilities. Cardella consistently evaluates the effectiveness of people-centric policies to ensure they support the company's long-term growth and its commitment to delivering innovative HR technology solutions to the global market.

    Explore Leadership Teams in Human Resources Software

    Frequently Asked Questions Regarding Dayforce Top Executives and Leadership Team

    Who leads Dayforce?
    Dayforce is led by David Ossip (Chief Executive Officer & Chairman of the Board), along with executives such as Stephen Holdridge (President & Chief Operating Officer) and Nicholas Cucci (President, Dayforce National Trust Bank).
    Who is part of Dayforce’s executive team?
    The executive team of Dayforce includes leaders such as David Ossip (Chief Executive Officer & Chairman of the Board), Stephen Holdridge (President & Chief Operating Officer), Nicholas Cucci (President, Dayforce National Trust Bank) and other senior executives.
    How many executives does Dayforce have?
    Dayforce has 6 executives leading key business areas.
    What roles are included in Dayforce’s leadership team?
    The leadership team of Dayforce includes roles such as Chief Executive Officer & Chairman of the Board, President & Chief Operating Officer, President, Dayforce National Trust Bank, Director, Human Resources Enablement & Chief of Staff, Chief of Staff (Americas) New Business organization.