Strategy · Operations · Consumer Experience
Most organizations have the vision. Fewer have the strategy, the infrastructure, and the consumer experience to back it up — consistently, at scale, where your audience feels everything and your investors track every result. That's not a gap. That's an opportunity — and it's where I start.
225+ Events Produced & Counting
What We Do
Three engagement models built around one belief — that strategy without execution is just a plan, and execution without emotion is just logistics.
Engagement 01
A structured diagnostic of your strategy, operations, and consumer experience. You'll walk away with a clear picture of where the gaps are, where the opportunities live, and exactly what to do next.
$8,000 – $12,000 · 2–3 weeks
Engagement 02
Embedded strategic and operational leadership without the full-time cost. I function as your COO — shaping strategy, owning execution, and keeping the consumer experience at the center of every decision.
$15,000 – $20,000/mo · 3-month minimum
Engagement 03
Deep, sustained transformation for organizations in transition. I bring strategic clarity, operational rebuild, and consumer experience redesign — together, in sequence, at the pace your organization can hold.
$22,000 – $35,000/mo · Custom scope
Not Ready For A Full Engagement?
Strategy Session
A focused 90-minute working session on the operational or strategic challenge that's keeping you up at night. Walk away with clarity and a concrete next step.
About
VP-level experience. Founder-level drive.
I'm Kaitlyn Greenleaf — founder of The Inflection Advisory Group and a strategic operations leader with 15+ years of VP-level experience in sports, live events, and consumer experience.
My work sits at the intersection of strategy, operations, and consumer experience — and that intersection is exactly where I thrive. Strategy sets the direction. Operations makes it executable. Consumer experience makes it worth remembering. These aren't three separate disciplines to me — they're one integrated approach, and the magic happens when all three are working together. When all three click, organizations don't just perform — they endure.
Most recently, I led a $90M+ business unit at USA TODAY Network Ventures — 270 staff, 225+ annual events, and an 82% YoY EBITDA improvement. Before that, I scaled an endurance division from $21M to $36M, integrated six acquisitions, and navigated a full virtual event pivot during COVID.
I don't advise from a distance. When I take on an engagement I'm inside your organization — in the meetings, in the numbers, in the decisions. I learn how your team operates, where the friction lives, and what your consumers actually experience versus what you think they experience. Then I build the strategy and the systems to close that distance. This isn't a transaction. It's a commitment.
"Strategy sets the direction. Operations makes it real. Consumer experience makes it matter."
Open To
Get In Touch
Whether you're looking for a fractional COO, exploring a full-time hire, or just want to understand what embedded operational leadership looks like in practice — I'd love to hear from you.
Kaitlyn Greenleaf
kgreenleaf@theinflectionag.com