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Dataprise Leadership

Meet the team of leaders that are dedicated to being the strategic IT partner and employer of choice

Our People Make the Difference

Leadership is vital for both building the strength and power of the organization and in helping to manage relationships and resources. Our leaders have led Dataprise to continuous growth since the start of the company in 1995 and they continuously embody our corporate culture and company values.


One of many ways that we aim to keep providing customers with the best possible service is our continued investment in the education and growth of our people. We only hire the most highly-skilled professionals, and continually train and keep them updated in the latest technologies so we can help you win and grow your business.


Explore the leaders of Dataprise below to discover just how the people of Dataprise truly make the difference.

Leadership Team

William Flannery serves as the Chief Executive Officer (CEO) of Dataprise, where he plays a pivotal role in shaping the company's strategic direction and overseeing its operations. In this capacity, he is responsible for charting Dataprise's course towards continued growth and success in the dynamic IT services industry. William's leadership encompasses strategic planning, operational excellence, and fostering a culture of innovation to ensure Dataprise remains at the forefront of delivering top-tier IT solutions to clients. His role involves driving corporate initiatives, cultivating client relationships, developing associates' careers, and navigating the evolving landscape of technology services with a keen focus on operational excellence and client satisfaction.

With a distinguished professional background, William brings a wealth of experience to his role as CEO. Prior to assuming this leadership position, he held various executive roles, including Chief Operating Officer, General Manager, and Executive Vice President of Global Operations at Ensono, where he demonstrated an exceptional ability to improve Client satisfaction, drive growth, streamline operations, and lead diverse global teams. William has a track record of transforming organizations, expanding market presence, and delivering results in fast-paced, complex environments. His extensive leadership experience equips him with the skills and insights needed to guide Dataprise to new heights.

William's academic journey includes an MBA in Information Technology/Management Systems from Fordham University and a BS in Civil/Structural Engineering from Lehigh University. Beyond his professional endeavors, William is dedicated to mentoring high-potential leaders and actively engages in community involvement, further emphasizing his commitment to personal and professional growth.

William Flannery

Chief Executive Officer and Board Member

John A. Raos is the President for Dataprise overseeing our business operations and premier services including Cyber Security, Network Operations, Global Service Desks, Professional Services and Field Engineering.

Mr. Raos has over 25 years of experience in mid-market service delivery management for multiple MSPs and VARs. For the last decade Mr. Raos’ focus has been on integrating AI and Automation tools to enrich Infrastructure support programs with the goal of improving the customer experience.

In 1994 John worked as an Advanced Systems Manager for Dataflex Corporation where he served as a principal advisor to their Healthcare and Pharmaceutical customers with respect to the continuous improvement of service quality and process efficiency. In 1996, he joined CompuCom Systems, one of the nation’s largest IT services providers, as a Professional Services Manager eventually becoming a Regional Director. After helping the business grow tenfold during his tenure, John co-founded Innovative Technology Solutions, LLC in 1999 (Acquired by ATS) and became the company’s Chief Information Officer and Vice President of Professional Services, initially building the technical solutions team, implementation methodology, operations, and internal information systems teams for the company. In 2018 he became the Vice President of Operations for the IT Services division of Advanced Technology Services where he was responsible for driving innovation and increasing operational efficiencies.

John Raos


Clinton Weaver is Dataprise’s CFO and responsible for the company’s financial oversight. Previously, Clinton was VP Finance & Accounting at security company Ntirety, where he rebuilt finance and accounting functions, implemented new systems, and completed several large and small acquisitions and mergers. Prior to Ntirety, Clinton served as Controller at Civtas Learning, a pre-revenue SaaS startup, where he authored their accounting policies, presented financials, led tax prep and budget creation.

Clinton holds a bachelor’s degree from Indiana University and MBA from Indiana Wesleyan University.

Clinton Weaver

Chief Financial Officer

As Chief Marketing Officer, Mary Beth Hamilton leads with a customer-focused and insights-driven approach to branding, communications, demand generation, customer engagement and partner marketing. Mary Beth is a passionate leader with 20 years of experience that spans marketing and communications at industry-leading organizations.

Prior to Dataprise, she was Vice-President of Marketing at global IT provider Eze Castle Integration where she was instrumental in building the brand, marketing strategy and demand generation engine that powered the company’s growth. Previously she managed public relations programs for leading technology companies including HP and BMC Software.

Mary Beth holds a bachelor’s degree from Loyola University New Orleans and an MBA from Boston College.

Mary Beth Hamilton

Chief Marketing Officer

Christian Fulmino joined Dataprise in 2022 as a Senior Vice President and Head of Corporate Development and M&A. He is responsible for driving inorganic growth by identifying and acquiring the best companies in our space. Additionally, Mr. Fulmino works closely with the rest of the executive committee on strategy and growth initiatives.

Mr. Fulmino has over 20 years of experience in buyside M&A. Christian has extensive experience leading complex acquisitions in both publicly traded and private equity owned businesses with a track record of successfully identifying potential and viable business acquisitions that support the growth strategy of the organization.

Christian has a bachelor’s degree in Finance from Rider University and an MBA from Cornell University.

Christian Fulmino

Senior Vice President, Corporate Development 

As Senior Vice President of Sales & Business Development, Keith Moses leads Dataprise's Sales organization with a customer-centric focus and consultative approach using analytics and tools to drive hypergrowth and promote our core values.

Keith Moses brings 14+ years of successful sales leadership experience to Dataprise. Prior to joining Dataprise, Keith served 6 years as one of the Enterprise Sales Leaders at Comcast Business where his focus was leading a hyperscale mid-market and Enterprise team driving revenue for Ethernet, Managed Services, Professional Services, Voice, and other complex solutions. He was a President club winner and prior to that led other hyper-performing teams at Clearwire, AT&T, Verizon and T-Mobile. Keith has an integral strategic focus on helping to curate a winning culture, recruiting, and DE&I.

He attended Pennsylvania College of Technology studying Business Management where he met his wife and they have a son and daughter that keep them very busy.

Keith Moses

Senior Vice President, Business Development and Sales

As Dataprise’s Senior Vice President of Human Resources, Amanda Gill leads the company’s human resource and talent acquisition and retention strategies, ensuring they are closely aligned with overall business objectives while fostering a best-in-class associate experience.

 A passionate leader with 25+ years’ of human resources experience, Amanda has an extensive background in HR operations, retention planning, M&A integration, and talent acquisition, with recent roles serving as the Head of Talent Acquisition for North America and Latin America at Nokia and Vice President of Talent Acquisition for Oracle. Her skillsets and responsibilities extended beyond recruitment to include strategic collaboration, stakeholder management, and shaping initiatives in compensation, benefits, retention, DEI, and L&D.

Amanda holds a Bachelor’s degree in Psychology from Florida Atlantic University and has completed Accelerate Executive Insight (AEI) programs through University of Michigan and IESE.

Amanda Gill

Senior Vice President, Human Resources

Our Team
Finance team
Sales team
HR team
Senior Leadership
Board of Directors
Al Castrillon
Vice President, National Accounts

As the Vice President of National Accounts at Dataprise, Al Castrillon, leads the customer facing technology consulting services for Dataprise which includes the execution of server, network, VoIP, Security and cloud projects as well other professional services.

Prior to joining Dataprise he was the Director of Pro Services for Innovative Technology Solutions and was responsible for high-touch projects for critical clients in the Northeast region. He has led several technology groups for Dow Jones and Hearst Magazines. Alfredo also served in the United States Army as a commissioned officer in the Military Police Corps after he graduated from Hofstra University with a BBA. He also holds an MBA from Hofstra University.

Alfredo is married and has two boys ages 14 and 16 respectively. He and his family reside in Long Island, New York.

Chaz Chalkley
Vice President, Channel and Strategic Partnerships

As Dataprise's Vice President, Channel & Strategic Partnerships, Chaz Chalkley leverages his 20+ years of technical consulting and customer service expertise to ensure Dataprise’s strategic partnerships receive the engagement necessary to help empower sales teams and grow revenue share across their customer base. He's focused on building strong relationships with Dataprise partners, clients, discovering new opportunities, and delivering IT guidance on Dataprise’s broad suite of managed and professional services.

Chaz has been instrumental in the overall growth of Dataprise through his work in operations, service delivery, and account management. Before joining Dataprise in 2005, Chaz managed operations for a small IT consulting company specializing in carrier and managed services. He holds numerous technical and executive management certifications, as well as a bachelor's degree in Integrated Science and Technology from James Madison University.

Jon Coughlon
Vice President, Global Service Desk

Jon leads a passionate team of individuals who focus on delivering best-in-class IT support to  Dataprise's global client base. 

Andrea Chaidez
VP Mobility Services

As the VP of Mobility Services at Wireless Watchdogs, a Dataprise company, I have more than five years of experience in delivering exceptional mobility solutions and fostering an inclusive and diverse culture. I oversee the strategic direction, execution, and growth of our mobility services, serving clients across various sectors and regions. I also lead the service delivery and help desk operations, ensuring quality, efficiency, and customer satisfaction.

Dara Eisner
Senior Corporate Counsel

Dara Eisner began the in-house legal department when she joined Dataprise in 2014 as Corporate Counsel. She oversees all aspects of Dataprise’s legal affairs while working collaboratively with Dataprise Leadership and across all departments. In her role as Director of Legal Services, she manages all Dataprise’s legal functions including compliance, contracts, legal drafting, risk management, complex transactions, employment law, as well as managing outside counsel.

With her law firm experience and prior work in litigation and employment law, Dara brings practical legal guidance to the team. She holds a Bachelor of Science from Vanderbilt University, and a Juris Doctor from the Columbus School of Law.

Colin Hastings
Vice President, Internal Operations

Colin Hastings’ career began with 20 years’ service in the Royal Air Force as Fast Jet aircrew, operating the Tornado GR1, a multirole combat aircraft. He departed the RAF in 2000 as a Squadron Leader after a final tour as Program Director of Electronic Warfare on the Headquarters staff at Strike Command. Colin then joined the telecommunications industry as a Project Manager. During that 17-year career in the complex business of telecommunications, in Europe and North America, he developed into an accomplished executive with vast international experience and deep technical expertise. His skills are numerous with expertise in change management, customer operations, service delivery, team development and program management.

As Vice President of Internal Operations, Colin is responsible for the delivery of an outstanding and consistent level of service to our customers through continuous improvement, customer advocacy and employee engagement.

Colin holds a Master of Business Administration degree from Open University in the United Kingdom, a large distance-learning and research university, and one of only three United Kingdom higher education institutions to gain full accreditation in the US. He earned his Bachelor’s Degree with Honors in Electrical and Electronic Engineering from the University of Edinburgh, UK. He was awarded Membership in The Institution of Engineering and Technology (MEIT), a highly selective and prestigious multidisciplinary engineering institution.

Mike Wendt
Vice President, Professional Services

Mike Wendt joined the Dataprise family in 2011 as a Technical Services Manager. He currently serves as the Vide President of Professional Services where he oversees a talented team of IT strategy consultants, project managers, and subject matter experts in a variety of technical areas. Professional Services helps Dataprise and our customers win with IT by understanding and mapping business drivers, managing change, and overcoming complex technical challenges.

Mr. Wendt holds a B.A. from Martin Luther College and an M.S. in Management of Information Technology from the University of Virginia. The focus of his studies at U.Va. was delivering business value through IT. This continues to be a focus for him at Dataprise. Mr. Wendt has over 15 years of experience in IT operations and management.

Tim Krueger
General Manager: Mountain Region

Tim founded and led PEI for 35 years as President and CEO before joining Dataprise in November 2023.  He's been a serial entrepreneur his whole life with a number of businesses in real estate, property management, capital financing, and cattle.  His hobbies include hunting, fishing, competitive trap shooting, hockey, ranching, and fast cars.  Tim is the proud father of three grown sons and their wonderful wives. 

Jason Silva
General Manager of Central US

Jason Silva joined Dataprise in 2023 with the acquisition of RevelSec, where he served as CEO.

Now serving as General Manager of the Central US business for Dataprise, Jason leads the region

to deliver value and best-in-class services to clients while working closely with the executive team

on strategy and growth initiatives.

With over 20 years of experience in the solution provider and managed services industry, Jason has served

in an entrepreneurial capacity since 2011 where he successfully founded and led the RevelSec business.

Jason holds a bachelor's degree in Finance from the University of Houston Bauer College of Business.

Dan Dickenson
Field Vice President & General Manager, West

Dan, the CEO and founder of Reboot Networks, a services-based Information Technology firm established in 1997, is now focusing on fostering comprehensive excellence at all levels and in all aspects of company operations. Reboot Networks has recently merged with Dataprise, expanding its reach and services.

Industry Presenter and Technical Enthusiast

Dan has been a regular presenter at major industry conferences on KPI reporting and cloud services business models in IT Service Providers. Although his role today is primarily team, peer, and customer-facing, Dan still relishes the technical aspects of IT, including the design of cloud-first architectures for small and medium businesses, data reporting and dashboarding, and R&D related to this constantly evolving business.

Personal Interests

When not engaged in technical pursuits, Dan enjoys outdoor activities with his family or indulges in high-speed adventures on asphalt, snow, or water.

Nima Khamooshi
Vice President, Cybersecurity

As the Vice President of Cybersecurity at Dataprise, Nima Khamooshi leads Dataprise’s security operations, spearheads security product development and innovations, and delivers advanced security advisory services and consulting to clients.

 Nima has over twenty years of leadership experience in cybersecurity and most recently was Global Information Security Practice Leader at Lumen Technologies. Previously, he also held leadership roles at Booz Allen Hamilton, The College Board, and Conference of State Bank Supervisors.


Khamooshi holds a Master of Science in Cybersecurity from the University of Maryland University College and a Bachelor of Science in Business Administration, Information Systems, from the University of Arkansas. He is a Certified Information Systems Security Professional (CISSP) and holds several prestigious certifications in the field of information technology and security. 

Board of Directors

Blake Apel joined Dataprise’s Board of Directors in December 2019. As a Partner at Trinity Hunt, Mr. Apel serves on the firm’s Investment Committee and leads investment evaluation activities in the IT Services industry. Mr. Apel also sits on the Board of Directors of Improving, which provides outsourced custom software development services to Fortune 500 and mid-market clients across the US and Canada. Blake currently sits on the Board of three additional Trinity Hunt portfolio companies.

Mr. Apel began his career at Trinity Hunt in 2007. His responsibilities include deal sourcing, deal execution, and portfolio company growth initiatives. Before joining the firm, Blake worked in management consulting at Bain & Company where he focused on corporate strategy, operations, and other value-creation projects. Mr. Apel has investment experience in the IT services, legal services, and healthcare industries, among others.

Mr. Apel graduated magna cum laude from Vanderbilt University with a BA in Economics, and received his MBA from the University of Chicago Booth School of Business, where he was awarded the Elfman-Wareham Private Equity Fellowship.

Blake Apel

Chairman of the Board

David Eisner founded Dataprise in 1995 and led its growth from tiny technology start-up through becoming a recognized leader in providing managed IT services to small and medium-size businesses nationwide.

In 2019, Mr. Eisner led Dataprise through a successful transaction with Trinity Hunt Partners. In 2020, after twenty-five years of leadership, Mr. Eisner transitioned to the company’s Board of Directors where he remains a strategic advisor focused on growth related initiatives.

Mr. Eisner is a past recipient of the Ernst & Young Entrepreneur of the Year Award® and the Tech Council of Maryland’s Executive of the Year award. Mr. Eisner has also been named to the MSPmentor’s 250 Top People in Managed Services. In 2015, Mr. Eisner wrote Build Your Business Not Your IT Department: A Guide to Selecting the Right Technology Partner, a guidebook for small to medium-sized business on how to select the right IT partner. The book is available at In 2018, Mr. Eisner was honored with the inaugural MSP 501 Lifetime Achievement Award from Channel Futures.

Mr. Eisner holds both a bachelor's and master's degree in computer science from the University of Maryland and The Johns Hopkins University, respectively. He is an alumnus of the Entrepreneurs' Organization and a member emeritus of the Board of Visitors for the College of Computer, Mathematical, and Natural Sciences at the University of Maryland.

David Eisner

Founder and Board Member

John Martin joined Dataprise’s Board of Directors in January 2022. As a Vice President, Mr. Martin is responsible for supporting deal sourcing and execution as well as portfolio company growth initiatives. He joined Trinity Hunt in 2018 after working for Piper Jaffray & Co. in the Diversified Industrials & Services Group, where he focused on mergers and acquisitions across a variety of sectors including business services, transportation and logistics, specialty manufacturing, and building products.

John is actively involved in the portfolio management of Dataprise, Aperture, Improving, IMS ExpertServices, Juris Medicus, Lone Star Fasteners, MainStreet, Miller Environmental, Unity MSK and Exclusive Concepts. He received his B.S. in Accounting and Business Administration cum laude from Washington and Lee University.

John Martin

Board Member

Chip Register joined the Dataprise Board of Directors in 2023. Chip is the CEO of Argano, a next-generation business and technology services provider that builds the Digital Foundations™ that make businesses run better. He is responsible for providing end-to-end digital solutions to help clients transform business operations and optimize their competitive position.

Previously, Chip served on the Executive Board of Publicis Groupe, one of the three largest media and communications holding companies in the world, and Co-CEO of Publicis Sapient, its digital transformation division. He joined Publicis Groupe when it acquired Sapient Corporation in 2015. At Sapient, he was CEO of Sapient Consulting, one of its two operating divisions focused on industry-led consulting and IT services.

In 2010, he was named one of the Top 25 Consultants in the World by Consulting Magazine.

Chip also serves on several Boards of Directors and Advisory Boards for companies innovating enterprise and consumer technologies and services.

Chip Register

Board Member