About Sadie Shepard

Advisor. Operator. Speaker. Human first, always.

Hi, I'm Sadie.

I'm not here to fork over an AI-generated template.

I’m here to help you see what’s really going on, and do something about it.

  • Most people execute strategy. I question whether it’s the right strategy.
  • Most analyze symptoms. I diagnose root causes.
  • Most give general guidance. I bring a hands-dirty lens from high performance operating & leading implementation.

My role is helping you pause & think critically—
so you can see clearly, ask the right questions, and create the outcomes you're actually after.

My Lens

My work starts with clarity, and it ends with sustainable momentum.

In partnering together, we:

  • See what’s broken. Question the systems, spot the gaps between theory and reality, and start addressing what's quietly dragging things down.
  • Fix what matters. Focus on leverage points that create real traction—whether that's strategy, operations, or leadership habits that actually stick.
  • Build what lasts. Create structure and aligned capacity so you're not solving the same problems six months from now.
My Experience

Strategic Operator, Practical Leader

I'm strategic enough to architect the plan & operational enough to implement it.

I use ongoing discovery to zoom out and look at the why before the how. I’ve worked across 30+ companies at nearly every stage—from failed unicorns to sustainable, quietly scaling businesses—and within roles that span the full customer lifecycle, operations, leadership, and everything in between.

 

Whether I was the solo salesperson launching a global brand in a reluctant local market or presenting an integration strategy to executive VC-backed teams, I’ve protected revenue, growth, and customers from the inside.

 

I’ve also rebuilt customer success programs post-acquisition. I’ve architected GTM strategies, compensation models, and internal ops for multi-brand rollups. I’ve trained teams, restructured functions, and helped high-growth companies build trust where it was broken.

 

I’ve worked behind the scenes to clarify focus and make vision executable—whether a leader is navigating M&A, scaling sustainably, or reevaluating strategy entirely.

I understand how growth-stage businesses actually operate, not just how they look on a slide deck or in an Excel spreadsheet.

A woman with straight blonde hair and a white button-up shirt smiles at the camera, standing outside near a brick wall.

What I bring to the table, every time

I spot what's hiding in plain sight: the patterns and pressure points everyone else walks past.

Then I help you turn that mess into something that actually creates traction—not theory.

 

And because I've been inside so many different functions and business models, I can see around corners.

I catch problems before they become expensive headaches and design solutions that grow with you.

I started this practice to bring the lens I wish more leaders had: strategic, operational, & grounded in real-world context.

My Jerk-free Policy

I'm not for everyone, and that's intentional.

I work with smart people where respect is reciprocal. I work best with:

  • Business leaders at an impasse: they need someone to move them forward, even if they can’t name exactly what’s hindering them [yet]
  • Visionaries, execs, & founders who've thrown specialized consultants at the "obvious" problems or hired mindset coaches only to miss out on meaningful progress
  • Ops leads & team builders who want to contribute meaningfully, but are caught up in BS performance systems & mindless tactics inside fractured orgs
My Promise

Having me in your corner guarantees a few things.

I meet you where you are, not where some methodology says you should be. I weave in my own challenges and wins because real transformation requires real honesty.

I'm pragmatic without being fussy about how something gets done. We get to the heart of it, make it workable, and keep momentum without performative productivity.


 

If you're building something meaningful & ready to move forward with what's next, let's talk.