Our Leadership

TIM SHOOP

CEO

As Digital Boardwalk’s CEO, Tim oversees all activities of the business as well as co-chairs our business development efforts. Tim’s innate passion for entrepreneurship, marketing, and partnership development helps drive Digital Boardwalk’s strategic growth and development.

With decades of professional experience building successful businesses, and a commitment to entrepreneurial mentorship through community involvement and team empowerment, Tim helps solidify Digital Boardwalk’s culture of hard work, dedication, and devotion to the ultimate customer experience.

BRIAN WILKEY

COO

As Digital Boardwalk’s COO, Brian oversees all operating activities of the business as well as chairs our business development efforts. Brian’s deep-rooted passion for continuous change and progress helps drive Digital Boardwalk forward as an innovative industry leader.

With over a decade of professional experience in information technology and business process development, Brian brings an unyielding pursuit of high-quality, efficient, and innovative technologies and processes to create a customer experience like no other.

KATHLEEN SHOOP

CRO

As Digital Boardwalk’s CRO, Kathleen oversees all new and existing customer relationship development activities as well as directs our innovative channel partner program. Kathleen’s passion for building meaningful relationships helps her lead our team of vCIOs, account managers, and channel partners.

With decades of experience in human resources and customer service, Kathleen reintroduces a human element into an otherwise technology-driven industry, helping Digital Boardwalk deliver a unique and refreshing customer experience.

JAMES TODD

CTO

As Digital Boardwalk’s CTO, James helps our customers navigate the ever-changing technology landscape by architecting solutions that simplify and accelerate their path to success. James’s passion for cybersecurity and privacy also helps guide our customers towards resilient technology environments that adhere to some of the strictest compliance requirements in the industry.

With over a decade of professional experience in the information technology industry, and a persistent commitment towards continuous learning, James brings a fresh perspective to customers looking to anticipate future challenges and stay ahead of their competitors.

Jimmy Guest

Vice President, Information Systems Management

As Digital Boardwalk’s Vice President of Information Systems Management, Jimmy oversees our Implementation, Help Desk, and Cybersecurity & Compliance teams. Although these teams are functionally separated, Jimmy’s leadership brings all the staff together as a single unit pursuing a common goal for the good of our customers.

With decades of professional experience in the information technology industry, Jimmy brings an unmatched level of wisdom and expertise to the team. Along with his relentless work ethic and commitment to customer satisfaction, Jimmy helps drive the evolution of Digital Boardwalk in its endless pursuit of being a true industry leader.

COLBY SULLIVAN

Senior Implementation Engineer

As Digital Boardwalk’s Senior Implementation Engineer, Colby is the technical lead for complex customer projects involving major infrastructure changes, cloud migrations, and more. Colby’s deep passion for technology helps him quickly adapt to changing technologies and mentor the rest of our implementation engineers.

With decades of professional experience in the information technology industry, as well as a lengthy tenure with Digital Boardwalk, Colby brings a great deal of wisdom and expertise to the team and helps them deliver some of the best technical support in the industry.

Tim Edge

Training Coordinator

As Digital Boardwalk’s Training Coordinator, Tim drives our culture of lifelong learning, continuous growth, and knowledge sharing. Tim also leads our customer training efforts, ensuring businesses get the very most out of the technology solutions we implement.

With over a decade of professional experience in the information technology industry, as well as a lengthy tenure with Digital Boardwalk, Tim brings a great deal of wisdom and expertise to the team and helps them deliver some of the best technical support in the industry.

Matt Foust

Implementation Engineer

Prior to joining Digital Boardwalk, I Worked as an IT Analyst for a heavy equipment dealer, providing software, hardware support, systems access, and software licensing for over 500 employees and corporate staff.

Hali Cherry

Customer Engagement Specialist

As Digital Boardwalk’s Senior Technical Advisor, Tim assists our Information Systems Management team with technical escalation support, training, and customer service. Tim’s deep passion for technology helps him connect with Digital Boardwalk’s engineers as a mentor and invaluable support system.

With over a decade of professional experience in the information technology industry, as well as a lengthy tenure with Digital Boardwalk, Colby brings a great deal of wisdom and expertise to the team and helps them deliver some of the best technical support in the industry.

Michael Riggleman

Technical Account Manager

As Digital Boardwalk’s Senior Technical Advisor, Tim assists our Information Systems Management team with technical escalation support, training, and customer service. Tim’s deep passion for technology helps him connect with Digital Boardwalk’s engineers as a mentor and invaluable support system.

With over a decade of professional experience in the information technology industry, as well as a lengthy tenure with Digital Boardwalk, Colby brings a great deal of wisdom and expertise to the team and helps them deliver some of the best technical support in the industry.

Ryan Oleszkiewicz

Project Manager

As Digital Boardwalk’s Senior Technical Advisor, Tim assists our Information Systems Management team with technical escalation support, training, and customer service. Tim’s deep passion for technology helps him connect with Digital Boardwalk’s engineers as a mentor and invaluable support system.

With over a decade of professional experience in the information technology industry, as well as a lengthy tenure with Digital Boardwalk, Colby brings a great deal of wisdom and expertise to the team and helps them deliver some of the best technical support in the industry.