Upland Executive and Leadership Team

September, 2026

Leadership Overview

Upland has 5 executives leading key functions including corporate strategy, financial oversight, operational management, and global sales productivity.

Focused on delivering cloud-based enterprise applications, Upland drives operational efficiency and digital engagement through a specialized portfolio of software products designed to optimize knowledge management and information governance across diverse global industries.

Leadership Roles at Upland

  • Chief Executive Officer & President (NASDAQ: UPLD) - Sean Nathaniel
  • Chairman & Chief Executive Officer - Jack McDonald
  • Interim Chief Financial Officer - David Tamez
  • President & Chief Operating Officer - Karen Cummings
  • Chief Sales Officer - Oliver Yates
  • Sean Nathaniel - Chief Executive Officer & President (NASDAQ: UPLD)

    Sean Nathaniel, the Chief Executive Officer & President (NASDAQ: UPLD) at Upland, directs the overarching corporate strategy and long-term vision for the enterprise software portfolio. Nathaniel manages the integration of specialized cloud-based applications, ensuring each product enhances customer experience and digital engagement for global clients. By aligning internal resources with market demands, the Chief Executive Officer & President (NASDAQ: UPLD) optimizes operational efficiency across the entire organization. Sean Nathaniel maintains rigorous standards for information governance, supporting the company mission to provide scalable solutions for complex business challenges. Through constant evaluation of acquisition targets and product performance, Nathaniel secures the competitive position of the firm within the software sector. This leadership role involves frequent collaboration with the Board to drive sustainable growth and shareholder value. By prioritizing innovation in project management and sales productivity tools, the executive ensures the company remains a leader in enterprise software delivery.
    Sean Nathaniel

    Jack McDonald - Chairman & Chief Executive Officer

    Jack McDonald, the Chairman & Chief Executive Officer at Upland, architects the high-level business strategy and capital allocation framework for the organization. McDonald oversees the acquisition and integration of specialized enterprise software products, ensuring these assets contribute to the broader goal of improving organizational efficiency. As the Chairman & Chief Executive Officer, McDonald guides the executive team in executing the company mission to deliver robust cloud-based applications. This role involves monitoring market trends to identify opportunities for expanding the footprint of the firm in knowledge management and customer experience sectors. Jack McDonald maintains strong relationships with investors and stakeholders, communicating the strategic direction and financial health of the business. By fostering a culture of operational excellence, the Chairman & Chief Executive Officer drives the company toward long-term success. Through disciplined management of the product portfolio, McDonald ensures that every application meets the evolving needs of enterprise customers across various industries.
    Jack McDonald

    David Tamez - Interim Chief Financial Officer

    David Tamez, the Interim Chief Financial Officer at Upland, directs all financial planning, reporting, and fiscal strategy for the enterprise software company. Tamez manages the capital structure and ensures the financial health of the organization while supporting the acquisition-led growth model. As the Interim Chief Financial Officer, Tamez oversees the budgeting process and provides critical data analysis to the executive team to inform strategic decision-making. This role involves maintaining compliance with information governance standards and ensuring accurate financial disclosures. David Tamez collaborates with department heads to optimize resource allocation, directly impacting the efficiency of cloud-based application delivery. By monitoring revenue streams and operational costs, the Interim Chief Financial Officer secures the financial stability required for continued market expansion. Tamez provides the necessary fiscal oversight to ensure that the company meets its performance targets while delivering high-value software solutions to a diverse global customer base.

    Karen Cummings - President & Chief Operating Officer

    Karen Cummings, the President & Chief Operating Officer at Upland, executes the daily operational strategy and manages the internal processes that support the delivery of cloud-based applications. Cummings oversees the integration of acquired software products into the existing ecosystem, ensuring seamless functionality for customers focused on digital engagement and project management. As the President & Chief Operating Officer, Cummings drives initiatives to improve internal efficiency and streamline cross-departmental workflows. This leadership role involves coordinating with product teams to maintain high standards for knowledge management and information governance. Karen Cummings monitors operational performance metrics to ensure that the company meets its service level agreements and customer experience goals. By optimizing the internal infrastructure, the President & Chief Operating Officer supports the broader mission of providing scalable enterprise solutions. Cummings ensures that the organization remains agile and responsive to the needs of clients across various industries, maintaining a focus on operational excellence.
    Karen Cummings

    Oliver Yates - Chief Sales Officer

    Oliver Yates, the Chief Sales Officer at Upland, directs the global sales strategy and manages the revenue-generating activities for the enterprise software portfolio. Yates oversees the sales productivity initiatives, ensuring that the team effectively communicates the value of cloud-based applications to prospective clients. As the Chief Sales Officer, Yates drives market penetration and expands the customer base for products focused on digital engagement and customer experience. This role involves aligning sales efforts with the broader company mission to provide specialized software solutions that solve complex business problems. Oliver Yates collaborates with marketing and product teams to refine the go-to-market approach and capture new opportunities in the enterprise sector. By implementing data-driven sales processes, the Chief Sales Officer ensures consistent revenue growth and long-term client retention. Yates leads the sales organization in achieving performance targets, directly contributing to the overall success and market impact of the company.
    Oliver Yates

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    Frequently Asked Questions Regarding Upland Top Executives and Leadership Team

    Who leads Upland?
    Upland is led by Sean Nathaniel (Chief Executive Officer & President (NASDAQ: UPLD)), along with executives such as Jack McDonald (Chairman & Chief Executive Officer) and David Tamez (Interim Chief Financial Officer).
    Who is part of Upland’s executive team?
    The executive team of Upland includes leaders such as Sean Nathaniel (Chief Executive Officer & President (NASDAQ: UPLD)), Jack McDonald (Chairman & Chief Executive Officer), David Tamez (Interim Chief Financial Officer) and other senior executives.
    How many executives does Upland have?
    Upland has 5 executives leading key business areas.
    What roles are included in Upland’s leadership team?
    The leadership team of Upland includes roles such as Chief Executive Officer & President (NASDAQ: UPLD), Chairman & Chief Executive Officer, Interim Chief Financial Officer, President & Chief Operating Officer, Chief Sales Officer.