Driving strategic transformation and exits
Operating Leadership for Value Creation, Scale, and Complex Situations
Executive transitions · Turnarounds · Board-directed execution · Capital and transaction support
Hands-on operating leadership during leadership transitions, control events, and periods of elevated execution risk. Engagements focus on stabilizing operations, establishing operating cadence, aligning resources to priorities, and driving disciplined value creation.
About Gilmore & Company
Gilmore & Co. provides hands-on operating and execution leadership to boards, investors, and management teams during leadership transitions, control events, and execution-risk periods. Engagements focus on stabilizing performance, resetting operating priorities, and driving durable outcomes.
The firm brings experience across transformational CEO roles, board-directed operating mandates, and investor-led situations, including turnarounds, strategic repositioning, and completed exits.
Work spans software, tech-enabled services, and asset-intensive businesses. Operating approaches are designed to translate across industries, emphasizing governance, capital discipline, operating cadence, and accountability, with technology applied where it materially improves execution.
CEO Advisory Services
Embedded Operating Strategy
Execution-focused operating leadership for CEOs and investors during transition and scale inflection points. 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
Leadership of pivotal transitions where execution, structure, and accountability must be reset quickly. 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 integrated execution that addresses the root causes of performance challenges.