OSG Executive and Leadership Team

May, 2026

Leadership Overview

OSG has 8 executives leading key functions including strategy, marketing, technology, human resources, legal, operations, product development, and overall company direction.

Driven by innovation, OSG provides comprehensive customer engagement and payment solutions, shaping market dynamics through advanced document management and communication strategies.

Leadership Roles at OSG

  • Chief Executive Officer - Dean Cherry
  • President - Gabriel Tilley
  • Chief Marketing Officer - Sarah Guckes
  • Chief Information Officer - Joel Weinfield
  • Chief Human Resources Officer - Kathryn Marocchi
  • Chief Legal Officer - Ronald Lambert
  • Chief Operations Officer - Michael Barenklau
  • Chief Product Officer & Chief People Officer - Gary Gregg
  • Dean Cherry - Chief Executive Officer

    Dean Cherry, the Chief Executive Officer at OSG, directs the company's overarching strategy and operational framework. Cherry guides the integration of OSG's diverse service offerings, including electronic billing, invoicing, statements, document printing, and marketing solutions, ensuring cohesive delivery to clients. This leadership role involves setting the strategic vision for market expansion and technological advancement within the customer engagement and payment solutions sector. By fostering cross-departmental collaboration, Dean Cherry ensures that all business units align with the company's core mission of enhancing client communication and payment processes. The Chief Executive Officer's focus remains on driving sustainable growth and maintaining OSG's competitive edge in a rapidly evolving industry landscape.
    Dean Cherry

    Gabriel Tilley - President

    Gabriel Tilley, the President at OSG, holds a pivotal leadership position overseeing key strategic initiatives and operational segments. Tilley drives the execution of OSG's comprehensive customer engagement and payment solutions, including electronic billing, invoicing, statements, and document printing services. This executive focuses on enhancing market penetration and client satisfaction through effective management of core business functions. By fostering strong relationships with stakeholders and leading cross-functional teams, Gabriel Tilley ensures alignment with the company's growth objectives. The President's role involves significant oversight of operational performance and strategic planning, contributing directly to OSG's sustained success and market influence.

    Sarah Guckes - Chief Marketing Officer

    Sarah Guckes, the Chief Marketing Officer at OSG, architects the company's brand positioning and market outreach strategies. Guckes oversees the development and execution of campaigns that highlight OSG's capabilities in electronic billing, invoicing, statements, document printing, and marketing solutions. This executive drives initiatives to enhance customer acquisition and retention by communicating the value proposition of OSG's integrated engagement platforms. By analyzing market trends and customer needs, Sarah Guckes ensures marketing efforts directly support business objectives and revenue growth. The Chief Marketing Officer's responsibilities include managing digital presence, content strategy, and public relations to solidify OSG's market leadership.

    Joel Weinfield - Chief Information Officer

    Joel Weinfield, the Chief Information Officer at OSG, directs the company's technology infrastructure and digital transformation initiatives. Weinfield oversees the development and maintenance of secure, scalable IT systems that support OSG's comprehensive suite of customer engagement and payment solutions, including electronic billing, invoicing, and document printing. This role is critical in ensuring the reliability and efficiency of all technological operations, safeguarding sensitive client data. By evaluating emerging technologies, Joel Weinfield drives innovation to enhance service delivery and operational effectiveness. The Chief Information Officer's strategic focus includes optimizing data management, cybersecurity protocols, and the integration of new platforms to support OSG's evolving business needs.

    Kathryn Marocchi - Chief Human Resources Officer

    Kathryn Marocchi, the Chief Human Resources Officer at OSG, leads the strategic development and implementation of human capital management initiatives. Marocchi oversees all aspects of workforce planning, talent acquisition, employee relations, and organizational development to support OSG's mission in customer engagement and payment solutions. This executive focuses on cultivating a high-performance culture that aligns with the company's values and business objectives, ensuring the attraction and retention of top talent. By designing comprehensive HR programs, Kathryn Marocchi enhances employee engagement, professional growth, and overall organizational effectiveness. The Chief Human Resources Officer's purview includes compensation, benefits, and compliance, ensuring a robust and supportive work environment.
    Kathryn Marocchi
    Ronald Lambert, the Chief Legal Officer at OSG, provides strategic legal counsel and oversees all legal affairs for the organization. Lambert manages corporate governance, regulatory compliance, and risk mitigation across OSG's operations, which encompass electronic billing, invoicing, document printing, and marketing solutions. This critical role ensures that all business activities adhere to applicable laws and industry standards, protecting the company's interests. By advising on contractual agreements and intellectual property matters, Ronald Lambert supports business development and operational integrity. The Chief Legal Officer's responsibilities include managing litigation, advising the executive team on legal implications of business decisions, and maintaining strong relationships with external counsel.

    Michael Barenklau - Chief Operations Officer

    Michael Barenklau, the Chief Operations Officer at OSG, directs the company's operational efficiency and service delivery across all functional areas. Barenklau oversees the execution of OSG's customer engagement and payment solutions, including electronic billing, invoicing, statements, and document printing, ensuring seamless client experiences. This executive focuses on optimizing workflows, enhancing productivity, and implementing best practices to maintain high standards of service quality and operational excellence. By managing resource allocation and process improvements, Michael Barenklau drives cost-effectiveness and scalability. The Chief Operations Officer's strategic imperative involves ensuring the reliable and timely delivery of all services, directly impacting client satisfaction and operational profitability.
    Michael Barenklau

    Gary Gregg - Chief Product Officer & Chief People Officer

    Gary Gregg, the Chief Product Officer & Chief People Officer at OSG, spearheads the strategic direction of product development and human capital management. Gregg guides the innovation pipeline for OSG's customer engagement and payment solutions, ensuring products meet evolving market demands for electronic billing, invoicing, and document printing. Concurrently, this executive shapes the company's people strategy, focusing on talent development, organizational culture, and employee engagement to foster a high-performing workforce. By aligning product roadmaps with workforce capabilities, Gary Gregg ensures OSG remains at the forefront of technological advancement and operational excellence. The dual role emphasizes a holistic approach to business success, integrating product innovation with robust human resource management.

    Explore Leadership Teams in Business Services

    Frequently Asked Questions Regarding OSG Top Executives and Leadership Team

    Who leads OSG?
    OSG is led by Dean Cherry (Chief Executive Officer), along with executives such as Gabriel Tilley (President) and Sarah Guckes (Chief Marketing Officer).
    Who is part of OSG’s executive team?
    The executive team of OSG includes leaders such as Dean Cherry (Chief Executive Officer), Gabriel Tilley (President), Sarah Guckes (Chief Marketing Officer) and other senior executives.
    How many executives does OSG have?
    OSG has 8 executives leading key business areas.
    What roles are included in OSG’s leadership team?
    The leadership team of OSG includes roles such as Chief Executive Officer, President, Chief Marketing Officer, Chief Information Officer, Chief Human Resources Officer.