Driving strategic transformation and exits
Strategic Growth & Execution for Founders, Boards &
PE-Backed Companies
CEO Leadership · Business & Revenue Transformation · Capital Strategy · Scalable Tech Execution
"We turn high-potential companies into scalable, investable platforms — with operational clarity, repeatable execution, and AI-integrated systems that work."
"We help founders and investors turn promising businesses into scalable, high-margin platforms — with clear priorities, repeatable execution, and systems that support growth."
— Gilmore & Company
About Gilmore & Company
Gilmore & Co. is a hands-on operating and strategic advisory firm led by Craig Gilmore. We help founders, boards, and private equity-backed companies scale intelligently — with systems-level execution, modern capital strategy, and AI-enhanced business architecture.
With over 25 years of experience as an operator and CEO, Craig has built and exited multiple companies, led turnaround and growth initiatives, and guided leadership through transition, funding, and platform-building milestones.
Current work spans consumer, tech-enabled services, software platforms, and data-driven infrastructure. We specialize in fixing underleveraged execution, repositioning businesses for scale, and structuring growth that attracts capital or strategic interest.
CEO Advisory Services
Embedded Operating Strategy
We provide execution-focused leadership support to CEOs and investors. Our work spans restructuring teams, unlocking growth levers, and aligning operations with realistic funding and exit paths.
- Market-driven operating priorities
- Team reset & accountability systems
- Interim leadership or go-to-market buildout
- Organizational clarity & structure
- Capital-aligned growth strategy
Strategic Transitions & Turnarounds
We lead companies through pivotal transitions — from stagnation to scale, from chaos to execution. Whether advising boards, stepping in alongside founders, or supporting PE-backed transformations, our goal is practical progress, not presentations.
Board & Investor Alignment
Strategic Board Consulting
We help boards and lead investors align around commercial clarity, operational planning, and critical control transitions. Focused support for situations that require decisive action and forward momentum.
- 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-Focused Execution Support
We support boards through CEO transitions, strategic pivots, and underperforming management situations. Our focus is execution: helping directors reset priorities, manage risk, and drive value through aligned, accountable operating plans.
Core Expertise
Growth & Operating Strategy
Structured priorities, scalable execution systems, and high-leverage operational design.
Go-To-Market & Sales Systems
Build or reboot customer acquisition, channel models, pricing, and delivery platforms.
Capital Strategy & Structuring
Equity story, unit economics, and execution plans aligned with investor goals.
Turnaround & Transition Leadership
Interim support or direct execution for stalled or underperforming teams.
AI-Enabled Business Architecture
Applied AI, automation, and software workflows to drive margin, speed, and value.
Exit & Strategic Value Planning
Positioning for acquisition or recap through investor-grade operational readiness.
Execution
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.