About Me
Monica Gillespey
Founder & Strategic Transition Architect
Monica Gillespey is a seasoned People and Organizational Strategy executive with more than 25 years of experience helping companies navigate growth, change, and transformation with clarity and purpose.
Throughout her career, Monica has partnered with executive Teams, Founders, Private Equity Sponsors, and Senior Leaders to align People, structure, culture, and execution around what matters most. Her experience spans high-growth environments, private equity-backed companies, healthcare technology, mergers and acquisitions, organizational integration, executive leadership alignment, compensation strategy, performance frameworks, and employee experience through both US and global based settings.
Why Monica Gillespey?
Executive People leadership, integration judgment, and practical support built for PE backed growth.
People side expertise
M&A, integration, organization design, compensation, HR readiness, and Leadership alignment.
Built from operator experience
Not theory heavy. The work is practical, clear, and designed for Leaders who need to execute.
PE relevant judgement
Focused on risk, speed, scalability, decision clarity, and value creation.
20+
Integrations. Not theory heavy. The work is practical, clear, and designed for Leaders who need to execute.
25+
Years in HR operating lens and executive presence.
Relevant Experience
Supported integration across organizations ranging from about 50 Team Members to several thousand, including both US based and Global environments.
People side expertise
More than 25 years in HR and People leadership across healthcare technology and other growth-oriented businesses.
Deep operating experience
Led due diligence, post close integration planning, organization design, compensation strategy, and executive support through complex change.
M&A leadership
Experience supporting founder led, high growth, and private equity backed companies through transition, growth, and operating pressure.
Scale across stages
Core Expertise
People due diligence
Leadership alignment and operating cadence
Compensation and People infrastructure
Integration strategy and readiness
Organization design and accountability
Executive coaching and trusted partnership
Change management