About Sadie Shepard

Hi, I'm Sadie.

I’m a steady, strategic operator who walks into complex, high-functioning chaos and quickly figures out what’s going on beneath the surface.

For the last decade, I’ve sat inside the parts of the business most leaders don’t have the time — or the visibility — to untangle: GTM, customer operations, revenue systems, post-merger integration, and cross-functional decision flow.

I’m the person companies bring in when the symptoms are loud but the cause or solution is unclear; when momentum has stalled under the weight of competing priorities.

My edge?
I can hear what people are saying, map what the business is actually doing, and translate the gap into a plan everyone can execute.

I’m not precious about where problems “belong.”

Whether it’s sales hygiene, CS fire drills, forecasting logic, CRM definitions, onboarding debt, team structure, pricing confusion, or handoff misalignment — none of it is isolated.

Every decision lives inside a larger system, and that system tells the truth.  My job is to surface that truth without drama, blame, or ego.

I’ve worked across scale: bootstrapped teams trying to stabilize early traction, post-Series A orgs outgrowing their tooling and processes, and mid-market leaders facing margin strain, misaligned accountability, or the operational drag that happens after acquisitions or aggressive hiring cycles.

I’ve built and rebuilt customer success engines, untangled seven-system mergers, architected revenue workflows, designed forecasting and reporting, and repaired cross-functional trust after a breakdown.

Through all of it, my approach is consistent:
〰 Translate complexity into clarity.
〰 Make the real problem impossible to ignore.
〰 Design the systems and decisions that keep teams aligned.
〰  Build structures that protect margin, momentum, and talent.

I work best with leaders who value clarity over theatrics, and who care about the long-term health of their business as much as the next quarter’s targets.

If you want someone to sugarcoat, over-polish, or bypass the hard conversations, I’m not your person. If you want someone who will tell you the truth, maintain your trust, and move your business forward without burning people out, I usually am.

Leaders hire me because I’m the safest set of hands they can bring into a messy, high-stakes environment.

I'm someone who can diagnose flawlessly, make order out of noise, and get the business back to running the way it should.

If that’s what you need, you’re in the right place.

Thanks for being here.
— Sadie

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