About Sadie Shepard

Hi, I'm Sadie.

I walk into high-functioning messes and figure out what’s actually in need of repair.

Over the last decade, I’ve led sales, customer success, and ops through unicorn chaos, mergers, and scaling pains — spotting what others miss and fixing it before it costs revenue, trust, or talent.

Buzzwords and Band-Aids are not my remedy of choice. I bring clarity, strategy, and a no-BS approach that turns complexity into traction.

When Things Stop Making Sense

I’m the leader people call when things stop making sense.

Not because I have all the answers, but because I’ve sat in several seats where systems, customers, and growth collide — and I know what breaks when they don’t align.

My Path Here

I started in enterprise systems and security marketing, then moved into account management and expansion sales. At WeWork, I launched a new market while learning how quickly growth stalls when systems and metrics are misaligned.

From there, I worked across sales, customer success, and operations — from early roles inside a Kansas City unicorn, to managing $60M ARR during a 7-company merger at Pathlock, to rebuilding CS programs across seven acquired brands.

Eventually, I went out on my own after realizing the same patterns kept repeating: leaders knew things were breaking, but not what to fix first.

What That's Looked Like in Practice

Across 30+ companies — from failed unicorns to quietly scaling firms — I’ve helped leaders fix the problems that quietly drain revenue, trust, and energy:

  • Stabilized retention across 7 acquired brands by rebuilding customer success post-acquisition

  • Uncovered $3.2M in missed upsell opportunities and protected millions more from leaking

  • Aligned GTM, comp models, and ops frameworks to support high-growth rollups

  • Rebuilt trust and priorities inside fractured orgs so teams could execute instead of stall

At every stage, my role has been the same: find what’s actually broken, and help people fix it without losing their minds or their margins.

Signals I listen For

Problems don't announce themselves neatly.

They usually sound like:

  • “Growth is outpacing our systems and teams are flying blind.”

  • “Everything’s breaking and we don’t know what to fix first.”

  • “We’ve tried the fixes, but nothing sticks.”

  • “We’re successful, but everything feels chaotic behind the scenes.”

My edge is translating those signals into the real issues underneath — and solving them before they spiral.

Call me when...

  • Growth is outpacing your systems

  • A merger or rollup just made everything messy

  • Revenue is leaking or upsells are getting missed

  • Exec meetings keep circling the same problems

  • You’re debating an expensive hire but not sure it’s the answer

If you're building something meaningful and need a co-pilot to advise or execute, let's talk.