The iPayment Executive Leadership Team

OB Rawls, IV

Chief Executive Officer and President

Joining iPayment in April 2016, Rawls is a proven sales leader and manager with a record of significant achievement in the payments, banking and technology sectors. Prior to joining iPayment, Rawls served as the Senior Vice President and General Manager, Partner Solutions, First Data Corporation. His vast career also includes executive leadership roles with Hypercom, Caredata, Unified Merchant Services and Bank of America. Mr. Rawls earned a Masters of Business Administration from Queens University of Charlotte and a Bachelor of Science in Social Work from East Carolina University.

Robert Purcell
Chief Financial Officer

Mr. Purcell joined iPayment in October, 2012. He has held numerous executive leadership positions throughout his career, most recently with Intuit Inc., where he served as Vice President Finance, Intuit Financial Services. Purcell also served as Executive Director, Finance-Global Operations at Amgen, Inc. and was Audit Senior, Business Assurance and Advisory Services at Deloitte & Touche. He holds a Master’s in Business Administration from the University of Southern California and a Bachelor’s of Science in Business Administration from California State University, Northridge. He is also a licensed CPA.

David Cronin
Executive Vice President & Chief Human Resources Officer

Dave joined iPayment in September, 2011 and brings a wealth of experience across multiple industries building and leading best-practice HR organizations. In his five years with iPayment, Dave has been instrumental in transforming the culture and talent level of the organization. Through his leadership, mentoring and coaching we have a management and employee team fully capable of meeting the many exciting challenges facing iPayment. Prior to joining iPayment, Dave held several senior level positions within the healthcare industry where he transformed traditional HR functions into best-practice business advisor models. Dave holds an M.S. in Leadership from Northeastern University in Boston, MA and a B.S. in Engineering from the United States Military Academy at West Point, NY. Dave is an Adjunct Faculty member in the MBA program at Cal Lutheran University.

Phil Ragona

Phil Ragona
Executive Vice President & General Counsel

Philip Ragona has a highly-distinguished legal career spanning over 20 years. Prior to re-joining the iPayment team in early 2017 as General Counsel, Ragona served as Executive Vice President and General Counsel for Lighting Science Group, a global leader in next-generation LED lighting solutions.

Ragona’s career began in private practice, where he worked for over 10 years, serving as an Associate with both Paul, Hastings, Janofsky and Walker LLP and Cahill Gordon & Reindel LLP. In 2002, he made the move to corporate, joining Atrium Corporation as Senior Vice President and General Counsel, a role he held for more than nine years, then joining iPayment for just over three years, serving as Senior Vice President and General Counsel. Ragona earned his JD from Columbia University School of Law. He also holds a BA in Political Science from University of California, Los Angeles and he is a member of the New York State Bar Association and the Dallas Bar Association.

Mark D'Ambrosio
Senior Vice President, Direct Sales

Mark D’Ambrosio started in the payment processing industry in 2004. As Director of Sales for Flagship Merchant Services, Mark was instrumental in building one of the top inside sales organizations in the industry. Most responsible for managing and motivating the sales team on a daily basis, he assisted with training and developed the internal analytics for employee performance. In his current role, Mark now works closely to integrate digital, referral and strategic partners into the direct brands of iPayment. Mark received his Bachelor of Arts from Colby College.

Guy DiMaggio
Senior Vice President and Head of Operations

Having joined iPayment in January, 2013, Guy has overall responsibility for Operations and Customer Service. A senior executive with in-depth knowledge in building/leading world class operating environments, Guy combines extensive operational expertise with deep business development and client relationship skills. Prior to joining iPayment, Guy held numerous executive leadership positions within the Financial Services/Payments industry (e-commerce, merchant acquiring, credit/debit/prepaid cards, money transfer). He was the Senior Vice President of Integration & Indirect Business Channel for Vantiv and preceding experience as the Vice President of Operations for Europe, Middle East, Africa, Asia, & Pacific at Western Union. Guy has led organizations both domestically and internationally in key areas such as operations, customer care, sales support, technology, integration, and business development. Guy earned his Masters of Business Administration degree from the University of Denver, Daniels College of Business and his Bachelor of Arts degree in Communications from Shippensburg University.

Christa Shook
Senior Vice President, Partner Support

Christa has been with iPayment since its inception and after achieving success in each position she has held, now leads the organization in the area of full service ISO integration and Relationship Management. She leads and manages the sales support function and provides critical input in the areas of strategic planning, problem solving, training and residual profitability analysis. Christa works closely with IT to build custom programming, custom reporting and any other tools that help our company focus on sales. She provides high-level consulting and support for all of iPayment’s ISO and Agent offices.

Marcus Smith
Senior Vice President, Risk Management

Marcus has been with iPayment since its inception and has aided in the growth and evolution of the organization. As SVP of Risk Management, Marcus plays an integral role in the company’s success and manages one of the best performing merchant portfolios in the industry. Mr. Smith has also served iPayment as SVP of Merchant Operations and contributed to the development of the company’s infrastructure, policies and procedures. Marcus was introduced to merchant bankcard in 1997 when hired by Electronic Card Systems to manage the company’s High Risk merchant portfolio. He quickly rose to the rank of Director and eventually headed the company’s Operations and Risk Management divisions. Prior to merchant bankcard, Marcus held positions at GE Capital Corporation / Residential Communications where he participated in a joint venture established to provide telecommunication services to corporate clients. Marcus received his Bachelor of Science in Business Administration: Finance, from the California State University at Dominguez Hills.

Jennifer Terrill

Chief Information Officer and Senior Vice President, Information Technology

Jennifer joined iPayment in late 2014 and is responsible for leading the organization’s Information Technology software development, technology services and security strategies. Prior to joining iPayment, Jennifer served in Information Technology and Security executive roles for True Religion Apparel, Digital Insight, and FiServ. Throughout her 25-year career, she has successfully lead enterprise application, infrastructure, project management, security, and software development teams. In 2013, the Los Angeles Business Journal named Ms. Terrill as the Enterprise CIO of the Year. In addition to her professional duties, Ms. Terrill has served on technology leadership boards and committees, including the NRF CIO Advisory council. She received her Bachelor of Science degree in Computer Science from Cal Polytechnic University, Pomona, and earned a Certified Information Systems Security Professional (CISSP) credential in 2011.