Square Executive and Leadership Team

August, 2026

Leadership Overview

Square has 5 executives leading key functions including operations, organizational strategy, marketing, revenue management, and financial services.

Focused on empowering merchants through accessible payment technology, Square delivers robust point-of-sale systems that simplify commerce for businesses across global markets.

Leadership Roles at Square

  • Chief Operating Officer - Reith Kabois
  • Chief Operating Officer, Square Financial Services - Samantha Ku
  • Chief of Staff - Sarah Schramm
  • Chief Marketing Officer - Lindsey Irvine
  • Chief Revenue Officer & Manager - Shweta Chiplunkar
  • Reith Kabois - Chief Operating Officer

    Reith Kabois, the Chief Operating Officer at Square, directs all internal business processes and infrastructure scaling. Overseeing the daily execution of payment product delivery, the Chief Operating Officer ensures seamless integration between hardware and software systems. This leadership role involves optimizing supply chain logistics to support rapid merchant adoption across North American markets. By streamlining operational workflows, Reith Kabois directly impacts the efficiency of the entire organization. The Chief Operating Officer maintains rigorous standards for service reliability, ensuring that every point-of-sale system functions at peak performance. Through constant monitoring of operational metrics, the Chief Operating Officer identifies bottlenecks and implements scalable solutions. Kabois drives the internal culture of excellence, fostering cross-departmental collaboration to meet aggressive growth targets. Ultimately, the Chief Operating Officer secures the operational foundation necessary for sustained market expansion and long-term stability within the competitive financial technology landscape.

    Samantha Ku - Chief Operating Officer, Square Financial Services

    Samantha Ku, the Chief Operating Officer, Square Financial Services at Square, directs the operational framework for banking and lending products. Overseeing the integration of financial services into the existing payment ecosystem, the Chief Operating Officer, Square Financial Services ensures compliance and operational excellence. This leadership role involves managing the risk assessment protocols and the delivery of capital solutions to merchants. By optimizing the lending process, Samantha Ku directly impacts the financial accessibility for small business owners. The Chief Operating Officer, Square Financial Services collaborates with regulatory bodies and internal teams to maintain high standards of service and security. Ku monitors the performance of financial products, ensuring that the offerings meet the specific needs of the merchant base. Through strategic oversight of financial operations, the Chief Operating Officer, Square Financial Services drives the expansion of the company into broader banking services, solidifying the position of the firm as a comprehensive financial partner.

    Sarah Schramm - Chief of Staff

    Sarah Schramm, the Chief of Staff at Square, manages executive communications and strategic alignment across all internal departments. Overseeing the prioritization of corporate initiatives, the Chief of Staff ensures that leadership objectives remain synchronized with the broader mission of simplifying commerce. This leadership role involves facilitating high-level decision-making processes and managing the flow of information to the executive team. By coordinating complex projects, Sarah Schramm directly impacts the speed and accuracy of organizational responses to market shifts. The Chief of Staff acts as a primary liaison between the C-suite and various business units, ensuring consistent messaging and goal attainment. Schramm monitors the progress of key performance indicators, providing actionable insights that guide resource allocation. Through meticulous planning and oversight, the Chief of Staff maintains organizational focus, enabling the company to navigate the complexities of the global payment industry with agility and precision.

    Lindsey Irvine - Chief Marketing Officer

    Lindsey Irvine, the Chief Marketing Officer at Square, architects the global brand strategy and customer acquisition programs. Overseeing the development of marketing campaigns, the Chief Marketing Officer ensures that the value proposition of payment products reaches diverse merchant segments. This leadership role involves analyzing market trends to refine messaging and enhance brand visibility across international territories. By leveraging data-driven insights, Lindsey Irvine directly impacts the growth of the user base and strengthens market positioning. The Chief Marketing Officer collaborates with product teams to align promotional efforts with new feature releases, ensuring a cohesive customer experience. Irvine manages the creative direction of the brand, maintaining a consistent identity that resonates with small and medium-sized businesses. Through strategic partnerships and targeted advertising, the Chief Marketing Officer expands the reach of the company, driving sustained demand for point-of-sale solutions in an increasingly digital economy.

    Shweta Chiplunkar - Chief Revenue Officer & Manager

    Shweta Chiplunkar, the Chief Revenue Officer & Manager at Square, directs all sales strategies and revenue generation activities. Overseeing the expansion of the merchant portfolio, the Chief Revenue Officer & Manager ensures that sales teams meet aggressive targets for payment product adoption. This leadership role involves managing regional sales operations and optimizing the conversion funnel to maximize profitability. By implementing innovative pricing models, Shweta Chiplunkar directly impacts the financial health of the organization. The Chief Revenue Officer & Manager coordinates with product development to ensure that sales offerings remain competitive within the evolving fintech landscape. Chiplunkar monitors revenue streams across diverse markets, identifying opportunities for cross-selling and upselling to existing customers. Through rigorous performance management and strategic planning, the Chief Revenue Officer & Manager secures the financial trajectory of the company, ensuring that revenue growth remains consistent with the long-term vision of empowering merchants everywhere.

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    Frequently Asked Questions Regarding Square Top Executives and Leadership Team

    Who leads Square?
    Square is led by Reith Kabois (Chief Operating Officer), along with executives such as Samantha Ku (Chief Operating Officer, Square Financial Services) and Sarah Schramm (Chief of Staff).
    Who is part of Square’s executive team?
    The executive team of Square includes leaders such as Reith Kabois (Chief Operating Officer), Samantha Ku (Chief Operating Officer, Square Financial Services), Sarah Schramm (Chief of Staff) and other senior executives.
    How many executives does Square have?
    Square has 5 executives leading key business areas.
    What roles are included in Square’s leadership team?
    The leadership team of Square includes roles such as Chief Operating Officer, Chief Operating Officer, Square Financial Services, Chief of Staff, Chief Marketing Officer, Chief Revenue Officer & Manager.