OSG Executive and Leadership Team

June, 2026

Leadership Overview

OSG has 7 executives leading key functions including strategy, marketing, technology, human resources, legal, operations, and revenue.

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

  • President & 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
  • Dean Cherry - President & Chief Executive Officer

    Dean Cherry, the President & Chief Executive Officer at OSG, directs the overarching corporate strategy and operational execution. Cherry guides the company's vision, ensuring alignment with market demands for customer engagement and payment solutions. This leadership role involves optimizing the delivery of electronic billing, invoicing, and statement services, alongside document printing and marketing solutions. Cherry's strategic direction drives innovation in how OSG interacts with its client base, fostering growth and enhancing service offerings. The President & Chief Executive Officer ensures robust financial performance and sustainable expansion across all business units. By focusing on client success and operational excellence, Dean Cherry solidifies OSG's position as a leader in the industry.
    Dean Cherry

    Gabriel Tilley - President

    Gabriel Tilley, the President at OSG, drives strategic growth and operational oversight across key business segments. Tilley focuses on expanding OSG's market presence and enhancing its suite of customer engagement and payment solutions. This involves leading initiatives in electronic billing, invoicing, statements, and document printing services. The President collaborates with other executive leaders to align departmental goals with the company's overall mission. Tilley's leadership ensures that OSG remains at the forefront of innovation within its industry. By fostering strong client partnerships and exploring new market opportunities, Gabriel Tilley contributes significantly to the company's sustained success and revenue generation. Tilley champions business development.

    Sarah Guckes - Chief Marketing Officer

    Sarah Guckes, the Chief Marketing Officer at OSG, architects and executes comprehensive marketing strategies. Guckes drives brand visibility and market penetration for OSG's suite of customer engagement and payment solutions. This involves developing targeted campaigns for electronic billing, invoicing, statements, and document printing services. The Chief Marketing Officer analyzes market trends to identify new opportunities and refine existing service offerings. Guckes oversees all aspects of marketing communications, digital presence, and lead generation initiatives. By fostering strong client relationships and communicating the value proposition of OSG's solutions, Sarah Guckes significantly contributes to revenue growth and market leadership. Guckes ensures marketing efforts directly support the company's strategic objectives.

    Joel Weinfield - Chief Information Officer

    Joel Weinfield, the Chief Information Officer at OSG, oversees the company's technology infrastructure and digital transformation initiatives. Weinfield directs the development and implementation of secure, scalable IT systems supporting OSG's customer engagement and payment solutions. This includes managing the technology behind electronic billing, invoicing, statements, and document printing. The Chief Information Officer ensures data integrity and cybersecurity across all platforms, safeguarding sensitive client information. Weinfield drives innovation in technology adoption, enhancing operational efficiency and service delivery. By aligning IT strategy with business objectives, Joel Weinfield enables OSG to leverage technology for competitive advantage and superior client experiences. Weinfield's leadership ensures technological robustness.

    Kathryn Marocchi - Chief Human Resources Officer

    Kathryn Marocchi, the Chief Human Resources Officer at OSG, leads all human capital management strategies and initiatives. Marocchi cultivates a high-performance culture that supports OSG's mission in customer engagement and payment solutions. This involves talent acquisition, employee development, and fostering an inclusive work environment. The Chief Human Resources Officer ensures compliance with labor laws and develops competitive compensation and benefits programs. Marocchi drives organizational effectiveness by aligning HR policies with business goals, supporting the delivery of electronic billing, invoicing, and document printing services. By focusing on employee well-being and professional growth, Kathryn Marocchi strengthens the workforce, enabling OSG to achieve its strategic objectives and maintain operational excellence. Marocchi champions employee engagement.
    Kathryn Marocchi
    Ronald Lambert, the Chief Legal Officer at OSG, provides expert legal counsel and oversees all legal affairs for the organization. Lambert ensures OSG operates in full compliance with all applicable laws and regulations governing customer engagement and payment solutions. This includes managing contracts, intellectual property, and corporate governance related to electronic billing, invoicing, and document printing services. The Chief Legal Officer mitigates legal risks and advises leadership on strategic decisions impacting the company. Lambert's role is critical in protecting OSG's assets and reputation. By providing sound legal guidance, Ronald Lambert supports the company's growth and operational integrity, ensuring all business activities adhere to the highest ethical and legal standards. Lambert safeguards corporate interests.

    Michael Barenklau - Chief Operations Officer

    Michael Barenklau, the Chief Operations Officer at OSG, directs the company's operational functions to ensure efficient and effective service delivery. Barenklau optimizes processes for OSG's customer engagement and payment solutions, including electronic billing, invoicing, statements, and document printing. This involves overseeing production, logistics, and service delivery teams to meet client demands. The Chief Operations Officer drives continuous improvement initiatives, enhancing operational scalability and cost-efficiency. Barenklau ensures seamless integration of technology and workflows to support business objectives. By focusing on operational excellence, Michael Barenklau plays a vital role in maintaining OSG's reputation for reliability and quality in the market. Barenklau manages day-to-day operations.
    Michael Barenklau

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    Frequently Asked Questions Regarding OSG Top Executives and Leadership Team

    Who leads OSG?
    OSG is led by Dean Cherry (President & 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 (President & Chief Executive Officer), Gabriel Tilley (President), Sarah Guckes (Chief Marketing Officer) and other senior executives.
    How many executives does OSG have?
    OSG has 7 executives leading key business areas.
    What roles are included in OSG’s leadership team?
    The leadership team of OSG includes roles such as President & Chief Executive Officer, President, Chief Marketing Officer, Chief Information Officer, Chief Human Resources Officer.