Driving strategic transformation and exits
STRATEGIC BUSINESS & TECHNOLOGY CONSULTING
Board Advisory | CEO Leadership | Business Restructuring | Software Architecture | Strategic Exits
"Transforming visionary ideas into market-leading enterprises through strategic execution and technological innovation."
"Generative AI and autonomous agents are driving the next wave of enterprise productivity, unlocking new value through scalable, intelligent systems."
— Gilmore & Company
About Gilmore & Company
Gilmore & Company is a premier strategic advisory and investment firm led by Craig Gilmore, focused on high-impact business transformation, capital structuring, and AI-driven digital innovation for forward-thinking organizations.
With over 25 years of executive leadership experience, Craig specializes in building, scaling, and positioning companies for high-value exits, while creating systems that drive measurable performance improvement and ROI. Our consulting approach combines deep business acumen with technical expertise to deliver transformative results.
Current projects span AI-driven platforms, scaled analytical systems, enterprise software architecture, and strategic integrations in weather intelligence and social infrastructure. We work with boards, CEOs, and executive teams to navigate complex business challenges and capitalize on emerging opportunities.
CEO Advisory Services
Strategic Leadership Consulting
Our CEO advisory services provide executives with strategic guidance, operational insights, and leadership development to navigate complex business challenges and drive sustainable growth.
- Executive decision-making frameworks and strategic planning
- Leadership team development and organizational alignment
- Crisis management and turnaround strategies
- Succession planning and leadership transitions
- Performance optimization and accountability systems
CEO Performance Acceleration
We help CEOs maximize their effectiveness through personalized coaching, strategic frameworks, and proven methodologies that enhance decision-making and leadership impact.
With experience leading multiple companies through successful exits and transformations, we provide practical, results-oriented guidance that addresses the unique challenges facing today's executives.
Our approach integrates business strategy, technological innovation, and leadership development to create sustainable competitive advantages.
Board Advisory & Governance
Strategic Board Consulting
We provide comprehensive advisory services to corporate boards, helping directors navigate complex governance challenges, strategic decisions, and organizational oversight responsibilities.
- Board effectiveness and governance structure optimization
- Strategic planning and oversight frameworks
- CEO performance evaluation and succession planning
- Risk management and compliance strategies
- Technology governance and digital transformation oversight
Board-Management Alignment
We facilitate productive relationships between boards and management teams, ensuring strategic alignment, clear communication, and effective decision-making processes.
Our board advisory services draw on decades of experience working with public and private company boards across various industries, providing practical guidance that enhances governance effectiveness and strategic impact.
We help boards navigate complex challenges including digital transformation, market disruption, and organizational restructuring with confidence and clarity.
Core Expertise
CEO & Board Leadership
Strategic vision, operational execution, and market-driven leadership for high-growth organizations and corporate boards.
AI & Digital Innovation
AI systems, software architecture, and automation strategies that scale operations and increase efficiency across enterprise environments.
Business Transformation
Comprehensive restructuring, go-to-market strategy, growth acceleration, and strategic repositioning for sustainable competitive advantage.
Strategic Exits & M&A
Structuring and preparing companies for acquisition by strategic buyers with optimal valuation and favorable terms.
Capital Strategy
Capital raising, investor alignment, and fund management to support scalable growth and strategic initiatives.
Software Architecture
Building scalable software frameworks and integrated platforms for enterprise growth, operational efficiency, and technological innovation.
Business Restructuring
Comprehensive Restructuring Solutions
We provide end-to-end business restructuring services that optimize operations, improve financial performance, and position organizations for sustainable growth.
- Operational efficiency and process optimization
- Financial restructuring and cost management
- Organizational redesign and talent alignment
- Technology infrastructure modernization
- Strategic repositioning and market focus
Transformation Management
Our restructuring approach combines strategic vision with practical execution, ensuring that transformation initiatives deliver measurable results and sustainable improvements.
We've successfully led multiple organizations through complex restructuring processes, creating more efficient operations, stronger financial positions, and enhanced competitive capabilities.
Our methodology integrates people, processes, and technology to create holistic solutions that address the root causes of performance challenges.
Software & Technology Consulting
Enterprise Software Architecture
We design and implement scalable, resilient software architectures that support business growth, operational efficiency, and technological innovation.
- Cloud infrastructure and platform design
- Microservices and API architecture
- Data architecture and analytics systems
- AI and machine learning implementation
- Legacy system modernization
Technology Strategy & Implementation
We help organizations align technology investments with business objectives, ensuring that software and systems deliver measurable value and competitive advantage.
Our software consulting services combine technical expertise with business acumen, bridging the gap between technology capabilities and strategic requirements.
We've successfully designed and implemented enterprise software solutions across various industries, creating scalable platforms that support business growth and innovation.
Current Ventures & Projects
AI & Automation Platforms
Building scalable AI-driven infrastructure for business intelligence, process automation, and operational efficiency across enterprise environments.
Weather Intelligence
Developing a platform delivering AI-enhanced extreme weather and ecological impact analytics at scale for government and enterprise clients.
Analytical Systems at Scale
Building integrated data pipelines and reporting engines to support large-scale modeling and analysis for strategic decision-making.
Social Platform Development
Creating digital ecosystems for niche engagement and monetization with advanced user experience design.
Successes & Impact
Strategic Acquisitions
Led multiple successful exits, including EXTEN Technologies and VetDepot, delivering exceptional returns to stakeholders.
AI & Software Innovation
Deployed AI solutions that increased operational efficiency by 35% and reduced costs by 28% for enterprise clients.
Capital Management
Managed a $500M acquisition fund for a NYSE-listed corporation, identifying and executing strategic investments.
Strategic Partnerships
Closed major strategic deals with IBM, Intel, Broadcom, and Costco, creating sustainable value and market expansion.