Our Mission
Windward solves Service-Centric IT challenges throughout our clients’ organizations by
providing the best minds and proven solutions. We believe in an engaged workforce to build a stronger company by operating with integrity, honesty, transparency and teamwork.  We are accountable for our actions and are empowered to be innovative.  We are committed ​to
excellence and to continually deliver ​solutions that result in high value for our clients.
Our History
The term ‘Windward’ refers to the nautical requirement to always be aware of the direction and strength of the wind, especially when racing or maneuvering a sailing ship. During the days of classic naval warfare, the windward vessel was always more maneuverable, thus, entering the battle from the windward direction gained an important tactical advantage over the opposing warship. Windward provides our clients with the ‘windward’ advantage by using IT as a strategic and tactical advantage in the marketplace.
Since our inception, Windward has supported over 500 clients around the globe with more than 2000 projects. With initial roots in the Communications Service Provider sector, Windward has diversified to provide solutions to commercial sectors such as Financial Services and other large enterprises.
In 2001, Windward was selected by a member of the intelligence community to bring commercial best practices to the Federal Government. Since then Windward has grown a significant presence within the Federal Government and continues to provide innovative solutions to the Department of Defense, Intelligence Community, and other civilian agencies.
Meet Our Leadership Team
Sean McDermott
President and CEO
Founder of Windward Consulting Group. In addition to Windward, Sean was the Founder and CEO of RealOps, Inc., the pioneer in enterprise management Run Book Automation solutions which was acquired by BMC. Before starting Windward, Sean held senior positions with Predictive Systems and Booz Allen Hamilton.
Mafa Amr
General Manager

    ​​​   Mafa is responsible for revenue generation and sales opportunities, as well as overall P&L for all business units. Prior to rejoining Windward, Mafa held a Management position at Nexius Solutions, Booz Allen Hamilton and Predictive Systems and previously spent a decade with Windward where he led the Commercial Sales Team.
Pete Tony
Pete is responsible for maximizing the return on financial assets by establishing financial controls, policies, procedures, and reporting systems. In addition, Pete monitors and confirms financial condition through both internal and external audits and achieves budget objectives by scheduling expenditures, analyzing variances, and initiating corrective actions. Prior to moving to the role as controller, Pete spend 15 years as the general accounting supervisor at Windward.
      Charles Semones
Managing Director
Fortune 500
Charles is responsible for managing all staff and resources within the Enterprise Services vertical, as well as program and project delivery, and business development.  Prior to joining Windward, Charles spent 26 years at Xerox, responsible for the development of network and monitoring technologies and product development.
Chris Demory
Managing Director
Government Solutions
​Chris is responsible for all revenue generation, sales opportunities and project delivery for Windward’s Government Solutions business unit.  Prior to joining Windward, Chris held leadership positions for systems integration and software companies such as TechTrend, IBM, Software AG, and Accenture.  Chris brings 20+ years’ experience in the areas of distributed computing, cloud infrastructure, and business process solutions.
Bob Henderson
Managing Director
Communication Service Providers
Bob has overall P&L responsibility for the Service Provider business unit. Prior to joining Windward, Bob operated a successful consultancy at ProcessNow delivering IT services to large service providers such as AT&T and Cox Enterprises. Bob brings over 20 years of experience in IT Infrastructure Management, Service Deployment and Service Desk Optimization for the Telecommunications Industry.
David Ragsdale
Consulting Director
Fortune 500
David is responsible for managing project delivery and leading business development efforts for his financial and insurance clients in the Enterprise Services vertical, as well as managing staff and resources in the Enterprise Services business unit. Prior to joining Windward, David spent 10 years at Freddie Mac working a majority of those years in the operations management and service management areas.
Daniel DeSandre
Consulting Director
​Fortune 500
Daniel is responsible for managing day to day targeted client projects, increasing revenue and growing the business. Prior to joining Windward, Daniel has been in the ITSM realm for over 18 years has experience in areas of Project Management, ITIL training, education and process design. Implementing large projects and designed processes for public and private corporations to improve their overall quality, efficiency and effectiveness of service.
Aaron Allgeyer
Consulting Director
Government Solutions
Aaron is responsible for business development, capture, sales, partnerships and customer engagements for our Federal practice. Prior to joining Windward, Aaron was a USAF Officer for 20+ years specializing in Intelligence, Cyber, and IT. He is ITIL v3 certified and holds Master’s Degrees in Management and Strategic Intelligence.  Aaron has advised our most senior government and military leaders in the U.S. and Allied nations.
Bill Anderson
Consulting Director
Communication Service Providers

Bill is responsible for business development and services delivery for Windward’s Communications Service Provider business unit. Prior to joining Windward, Bill spent 13 years leading business development, service delivery, and partner alliance teams focused on IT consulting and professional services.
Chris Sobray
Director of Recruiting
Chris is responsible for all talent acquisition and resource management. Prior to joining Windward, Chris held senior positions at various commercial and government companies where he has overseen and led successful recruiting departments.  Chris brings over 17 years of experience and expertise in IT recruiting.
Michelle Reilly
​Director of Strategic Partnerships

Michelle is responsible for strategic partnerships for all business units. She actively manages partnerships with a focus on revenue growth and success for both companies involved. Prior to joining Windward, Michelle held multiple executive positions with global corporations that spanned several industries including technology, communications and legal.  Michelle’s area of expertise is in business development, marketing and branding.
Michele Darwin
Director of Corporate Social Responsibility
​Michele is responsible for Windward’s overall CSR strategy to identify, ideate and execute philanthropic, charitable and cause-related initiatives including the Windward Foundation. She maintains all donor and partner relations, fundraising and communications for the Windward Foundation and organizes the District Music Benefit, the foundation’s annual fundraiser. Previously, Michele spend 7 years leading marketing efforts for Windward Consulting Group.