Meet Kirsten Osolind
Kirsten Osolind, MBA
CHIEF STRATEGY OFFICER / ARCHITECT / CO-FOUNDER
Practice Specialties: Retail Execution • Healthcare CX • Business Transformation Metrics • Change Management • Tactical Execution Playbooks • Data-Driven Transformation Narratives • Agentic AI
Kirsten Osolind is a business transformation leader relentlessly focused on turning strategy into measurable, execution-first outcomes through AI-driven metrics and Agentic AI models. She is the architect of RE:INVENTION’s proprietary Science of Change® Ethos and the AI-Driven Infinite Knowledge OS (IKOS®), Business Transformation Metrics Model®, 13-Step Agentic AI Process™, and Singularity Tools™.
As Chief Strategy Officer and lead Architect, Osolind partners with Fortune 100s, private equity firms, and high-growth ventures to close execution gaps, forecast outcomes using real-time and historical data, and deliver prescriptive actions that transform stalled investments into ROI.
She has led enterprise-wide transformation initiatives for Microsoft, Vanguard, Genworth, Builders Insurance, and Magna International. Previously, she held senior roles inside Whole Foods Market, WebMD, General Mills, and Coca-Cola, where she owned $100M+ P&Ls and delivered business transformation with speed and precision. She also co-founded, advised, and successfully exited AstroPrint — the universal 3D printing OS SaaS startup backed by 500 Startups.
Notable Achievements:
- Led $100M+ P&Ls and enterprise-wide transformations
- Engineered a 150% efficiency gain during a Fortune 100 cloud migration
- Doubled enterprise resilience during two Fortune 100 mergers
- Increased project success rates by 122% for a global grocery chain
- Slashed operational costs by 140% for a 30-location restaurant group
- Boosted division profitability 1550% for a Fortune 50 food & beverage company
Osolind’s insights have been featured in WSJ, Fortune, Bloomberg/BusinessWeek, Ad Age, INC., Chicago Tribune, and leading academic journals.
Education & Credentials
- MBA – Duke University, Fuqua School of Business
- BA, Organizational Behavior – Michigan State University
- Certified/Trained: Agile, PROSCI, Lean, PMP, Design Thinking
Advice from Osolind:
“Companies — and human beings — are instinctively good at generating ideas. Their greatest weakness? Execution. Implementation is hard — and the pressure to execute flawlessly is unprecedented.”