Meet Kirsten Osolind
Kirsten Osolind, MBA
CEO / Architect / Co-Founder
Practice Specialties: Business Transformation Metrics • Change Management • Data-Driven Transformation Narratives • Agentic AI • Retail, Healthcare, CPG Strategy
Kirsten Osolind is a business transformation leader who accelerates ROI and value realization with advanced data analytics, AI-driven metrics, execution governance, and orchestrated Agentic AI. 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™.
She has led enterprise-wide transformation initiatives for global leaders including 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 co-founded, advised, and successfully exited AstroPrint — the universal 3D printing OS SaaS startup (a 500 Startups Batch 11 portfolio company). She’s advised numerous startup incubators and high growth startups.
Who Calls Kirsten and When
- Fortune 500 executives under pressure to transform business transformation investments into ROI and operational clarity
- Private equity firm leaders facing portfolio company underperformance or chaos post-close or integration
- Mid-market companies ($500M–$1B) wrestling with strategy to execution drift, team and tech misalignment, or delivery failure
Unblock Your Stalled Execution
- Execution Readiness Audit: get a quick diagnostic revealing where people, process, tech, and priorities have fallen out of sync—with a clear, actionable roadmap in 10 days
- 90-Day Business Transformation Sprint: gain traction, alignment, and results in 90 days. Fix what’s broken and install the systems and tools you need to move faster and smarter
- Fractional Business Execution Architect: An embedded execution partner driving results without overhead. Improve transformation, change management, AI readiness, or tech ROI recovery
Results You Can Expect
Relentlessly focused on results, Kirsten has:
- Led $100M+ P&Ls and enterprise-wide business 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
Education & Credentials
- MBA – Duke University, Fuqua School of Business
- BA, Organizational Behavior – Michigan State University
- Certified/Trained: Agile, PROSCI, Lean, PMP, Design Thinking
Osolind’s insights have been featured in WSJ, Fortune, Bloomberg/BusinessWeek, Ad Age, INC., Silicon Valley Business Journal, Motley Fool, San Diego Business Journal, Crain’s Chicago Business, Chicago Tribune, and leading academic journals.
Endorsements
- “Kirsten has a terrific gift of picking up on important ideas and putting them together into practical frameworks to help managers make sense of the problems they face and how to address them.”
— Former CMO of Strategy& and Editor, Harvard Business Review
- “Kirsten’s unique ability to distill complex challenges, analyze data with precision, and foster innovative thinking enables her to craft actionable strategies and implement them seamlessly.”
— Former President, Frost & Sullivan
- “Kirsten is a consummate leader who gains results by producing at an incredible level as a role model and then empowers others to catch up.”
— President, Diversity in Boardrooms
“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.”
If you’re ready to stop drifting and start executing, let’s build the system that powers your future.