About Us
Our Leadership
Dean Cherry
President & Chief Executive Officer (CEO)
Dean Cherry was appointed President & CEO of OSG in January 2023, bringing more than 35 years of executive leadership experience in the print and mail industry. Renowned for driving growth, profitability, and operational excellence, Dean has consistently enhanced customer satisfaction while building high-performing, employee-focused cultures.
Throughout his career, Dean has demonstrated a strong customer-first mindset and a deep understanding of market dynamics. His strategic acumen has enabled him to scale businesses across the print, manufacturing, and B2B services sectors successfully. Prior to joining OSG, he served as CEO and President at several industry-leading organizations, including RR Donnelley, Cenveo, World Color, and Pharmaceutic Litho & Label Co.
Dean has also played an active role in corporate governance, contributing to strategic decision-making as a member of various corporate boards. He joined OSG’s Board of Directors in September 2022, reinforcing his commitment to the company’s long-term vision and growth.
He holds a Bachelor of Science in Finance and an MBA from Murray State University. Dean’s proven track record in operational and financial leadership, combined with his passion for delivering customer value, continues to guide OSG’s innovation and strategic expansion.
Bob Nelson
Chief Revenue Officer (CRO)
Bob Nelson was appointed Chief Revenue Officer (CRO) in February 2023, bringing more than 25 years of leadership experience and deep expertise in driving revenue growth across sales, product, and client-facing teams. His career spans both U.S. and European markets, with a focus on print and digital solutions.
Throughout his career, Bob has held senior leadership roles at R.R. Donnelley, Moore, and Moore Wallace, where he built a strong track record of increasing revenue, enhancing profitability, and driving EBITDA growth. His strategic leadership has consistently accelerated business performance and fostered strong client relationships.
Most recently, Bob served as a key leader at IonQ, a quantum computing start-up, where he led the sales organization and formalized the company’s strategic business development plans for its hardware, software platforms, and services.
Bob holds a Bachelor of Science in Business Administration and Management from the University of Southern California. His proven ability to scale organizations, optimize revenue, and enhance client engagement continues to support OSG’s strategic growth and market expansion.
Mike Barenklau
Chief Operating Officer (COO)
Mike Barenklau was appointed Chief Operating Officer (COO) in February 2023, bringing extensive operational leadership experience in print and digital communications. Known for driving efficiency, enhancing customer satisfaction, and implementing innovative technologies, Mike has consistently delivered exceptional results across large-scale operations.
Prior to joining OSG, Mike served as Senior Vice President of Operations at R.R. Donnelley, where he oversaw seven operational facilities generating $400 million in annual revenue. In this role, he successfully increased productivity, streamlined costs, improved customer quality and loyalty, and leveraged advanced technologies to deliver superior service and outcomes for clients.
Earlier in his career, Mike held senior operational leadership positions at Moore Wallace and Brown Printing Co., where he managed multiple print facilities across the U.S. and Canada, further strengthening his expertise in large-scale manufacturing and operations management.
Mike holds a Bachelor of Science in Electrical Engineering from South Dakota State University. His operational excellence, strategic vision, and commitment to delivering client value continue to play a pivotal role in OSG’s ongoing growth and innovation.
Brett Shroll
Chief Financial Officer (CFO)
Brett Shroll was appointed Chief Financial Officer (CFO) in August 2022, bringing more than 25 years of global executive leadership experience across Finance, Accounting, Operations, and Business Development. Brett’s strategic financial acumen and operational expertise span multiple industries, including Consumer Packaged Goods, Manufacturing, Building Automation, E-commerce, and Financial Services.
Throughout his career, Brett has held key leadership roles at prominent organizations, including Spectrum Brands, Johnson Controls/Adiant, Miller Brewing Company, VF Corporation, Fanatics, and, most recently, Zenith American Solutions. His extensive experience includes driving global business development, evaluating and integrating acquisitions, streamlining operations, and building high-performing Finance and Accounting teams that support long-term growth and profitability.
Brett holds a Bachelor of Business Administration (BBA) in Finance and an MBA from the University of Wisconsin-Whitewater. His forward-thinking leadership and deep financial expertise continue to strengthen OSG’s financial strategy, operational efficiency, and growth trajectory.
Gautam Anne
Chief Information Officer (CIO)
Gautam Anne has over 25 years of experience leading global technology strategy and digital transformation across Healthcare, Financial Services, Manufacturing, and High-Tech industries. As Chief Information Officer (CIO) at OSG, he is responsible for application and product development, infrastructure, cybersecurity, compliance, cloud operations, and client delivery. Gautam is passionate about building agile, accountable, and innovation-driven teams that drive operational excellence and deliver measurable business outcomes.
Gautam has successfully led multi-million-dollar initiatives, modernized enterprise systems, and scaled secure, cloud-first platforms. He brings a collaborative leadership style that fosters cross-functional alignment, enhances service delivery, and improves both top- and bottom-line results.
Prior joining OSG, Gautam held senior leadership roles at Pitney Bowes, Oracle, Quadient, Endava (Cigna, Express Scripts, Zelis Payments) and Prudential Financial, where he led complex technology initiatives that supported innovation and growth.
Gautam holds a Bachelor of Science in Electrical Engineering from the University of Madras and a Master of Science in Computer Science from the University of Bridgeport.
Sarah Guckes
Chief Marketing Officer (CMO)
Gary Gregg
Chief Product Officer (CPO)
Gary Gregg brings over 26 years of experience in the Customer Communications Management (CCM) industry, where he has established himself as a visionary leader and a driving force in the transformation of customer experience. As the Chief Product Officer at OSG, Gary has played a key role in evolving the company into a leader in Customer Experience Management (CXM), blending innovative print and digital strategies to create solutions that elevate customer engagement and streamline communication processes.
With a passion for pushing the boundaries of innovation, Gary is dedicated to driving product strategy and ensuring that OSG consistently delivers cutting-edge solutions to meet the evolving needs of its clients. His deep understanding of the intersection between print and digital technologies enables him to deliver holistic solutions that foster deeper connections between businesses and their customers.
Gary holds a BA in Business Administration from the University of California, Santa Cruz. His leadership in driving OSG’s product innovation positions the company for continued market success, delivering solutions that not only address today’s customer needs but also anticipate tomorrow’s challenges
Ron Lambert
Chief Legal Officer
Ron Lambert joined OSG as Chief Legal Officer in January 2023, bringing more than 25 years of legal and business experience in high-growth technology and SaaS organizations. Known for his expertise in navigating complex legal, regulatory, and corporate matters, Ron provides strategic legal guidance to support OSG’s continued growth, innovation, and operational success.
Before joining OSG, Ron served as Senior Vice President and Deputy General Counsel at CSG Systems International, a NASDAQ-listed global provider of revenue management, digital optimization, payments, and customer engagement SaaS solutions. In this role, he advised on a wide range of global legal matters, including corporate governance, compliance, mergers and acquisitions, and strategic transactions.
Earlier in his career, Ron held General Counsel roles at several high-growth technology companies and a private equity firm focused on fintech and sports-related businesses. He also practiced law at Mayer Brown, a leading global law firm, where he specialized in global technology transactions, corporate law, and mergers and acquisitions.
Ron earned his Juris Doctor (JD) from DePaul University in Chicago. His extensive legal acumen, business insight, and commitment to driving value make him a key contributor to OSG’s leadership team.
Kathryn Marocchi
Chief Human Resources Officer
Kathryn Marocchi is a seasoned Chief Human Resources Officer (CHRO) with over 20 years of experience in human resources leadership. As the CHRO at OSG, she plays a central role in shaping and nurturing a people-centered culture that aligns with the company’s vision and strategic goals. Kathryn is deeply committed to supporting OSG’s employees, recognizing them as the organization’s most valuable asset, and driving initiatives that foster growth, engagement, and overall organizational success.
With a strong focus on employee relations, Kathryn is skilled in managing the full spectrum of HR functions, including talent acquisition, employee development, performance management, organizational design, and change management. She excels at creating an environment that not only attracts top talent but also promotes an inclusive, dynamic workplace where employees can thrive, innovate, and reach their full potential.
Kathryn holds an MBA from Eastern Illinois University. Known for her strategic thinking and collaborative leadership, she focuses on building high-performance teams and cultivating a positive organizational culture. Her efforts play a key role in driving OSG’s continued success, both in terms of employee satisfaction and overall business performance.
Matthew Oakes
President, Real Estate Services Group
Matthew was appointed President of Real Estate Services in April of 2023 after 6 years with OSG. In this role, he leads all aspects of the Real Estate Services division, including sales, customer service, partner relationships and revenue growth, with a focus on driving innovation and delivering superior client experiences.
Matthew’s executive leadership experience includes previously held positions as Chairman of the Board, CEO & President for both private and public software and eCommerce companies including Paybox Corp, Direct Insite Corp, Direct Media Networks, Mall Net Media Corp., and Westinghouse. His diverse background spans corporate strategy, operations, legal, and financial management, positioning him to drive growth and operational excellence in his current role.
Matthew holds a B.S. Degree in Business Finance and Management from Cornell University, and Juris Doctor of Law from Nova Southeastern University.
Matthew is a veteran having served in the United States Marine Corps for six years attaining the rank of Sergeant. He was deployed with the 3rd Marine Division serving multiple tours overseas as a Scout Sniper, and at Parris Island, SC as a Drill Instructor with the 1st Recruit Training Battalion.
Daniel Durie
Chief Technology Officer (CTO)
Daniel Durie is the Chief Technology Officer (CTO) at OSG, having been promoted to the role in 2024 after joining the company in 2021. With over 15 years of experience in technology leadership, Daniel brings extensive expertise in driving innovation, leading high-performing teams, and implementing cutting-edge technology solutions. In his role as CTO, he is responsible for shaping OSG’s technology strategy, focusing on building scalable, secure, and efficient platforms that enhance the customer experience and support business growth.
Daniel is passionate about leveraging emerging technologies to solve complex problems, improve operational efficiency, and deliver impactful solutions. He leads OSG’s technology vision and roadmap, overseeing the development of new products and services that address both current and future client needs. His approach emphasizes collaboration, agility, and forward-thinking, ensuring OSG stays ahead of technological advancements in the industry.
Before his promotion to CTO, Daniel held senior technology roles at leading companies in the financial services and SaaS industries, where he played a key role in driving digital transformation and implementing solutions that supported business growth.
Daniel holds a Masters of Science degree in Computer Science from the University of Alabama, Birmingham. Daniel’s vision and innovation are key to furthering the future of technology at OSG, enabling the company to better meet the needs of its clients both today and in the future.
