Wesley Craft

Cross-functional operations and technology executive with 20+ years of experience leading organizational transformation, operational scaling, workflow modernization, digital platform evolution, and cross-functional execution initiatives within technology-driven businesses. Experienced aligning strategy, people, processes, and systems to improve operational effectiveness, execution visibility, organizational scalability, and long-term business resilience. Recognized for bridging executive leadership, technical teams, creative organizations, operational stakeholders, and business functions to drive modernization initiatives, reduce organizational friction, and build scalable operational frameworks.

Combines deep technical fluency with systems-oriented operational leadership, AI-enabled workflow modernization, and practical execution across fast-moving, resource-constrained environments.

Chief Technology Officer at Inside Lacrosse Holdings, Inc. (2010-01 – Present)

Serve as senior operational and technology leader for a national sports media organization spanning publishing, advertising, events, digital products, data operations, and e-commerce initiatives.

• Partner directly with executive leadership on strategic planning, operational modernization, workflow optimization, infrastructure evolution, and organizational scaling initiatives.
• Lead cross-functional coordination across technical, editorial, creative, finance, operations, advertising, and vendor teams to improve execution alignment and organizational effectiveness.
• Established scalable operational workflows, deployment standards, accountability structures, and modernization initiatives supporting long-term platform reliability and organizational execution.
• Guide organizational modernization efforts involving AI-assisted workflows, process optimization, communication systems, prototyping, development acceleration, and operational coordination.
• Architected and oversee cloud infrastructure operations, deployment systems, operational security, identity management, VPN access, DNS systems, endpoint management, and business continuity environments.
• Manage operational ecosystems including contractor/vendor coordination, budgeting visibility, resource planning, and operational continuity initiatives.
• Coordinate payment operations and reporting workflows supporting more than 700 contractors and vendors annually.
• Implemented workflow visibility and project coordination initiatives using Jira and collaborative operational systems.
• Mentor technical and non-technical staff while helping improve organizational maturity, operational discipline, and cross-functional collaboration.
• Oversaw multiple major digital platform modernization initiatives, including long-term evolution of scalable publishing and data delivery systems.

Director of New Media / Technical Director at Capital-Gazette Communications (2000-01 – 2010-12)

Led organizational transformation and digital modernization initiatives across a regional publishing organization supporting more than 60 newspaper properties during a period of major industry disruption and digital transition.

• Directed a cross-functional operational division responsible for development, editorial, advertising support, video production, and online product operations.
• Managed divisional operational planning, staffing, budgeting, vendor coordination, and P&L responsibilities.
• Successfully integrated previously siloed digital and traditional publishing teams through collaborative execution strategies and shared operational workflows.
• Rebuilt and modernized multiple large-scale publishing platforms while maintaining operational continuity and improving long-term scalability.
• Developed new digital product initiatives supporting audience growth, advertising expansion, and operational efficiency.
• Helped drive organizational change management efforts by building collaborative relationships between resistant operational groups during the industry's digital transformation.
• Oversaw operational coordination across editorial, advertising, technical, and production teams to improve execution consistency and organizational alignment.

Programmer Analyst at L3 Communications Titan Group (2005-01 – 2006-12)

Developed workflow applications and operational support systems for National Institute for Literacy initiatives.

• Collaborated with operational stakeholders to improve reporting visibility and application usability.

Bachelor of Science in IT Management – Western Governors University

Associate of Science in Computer Science – Anne Arundel Community College