How to Build a Sales Org That Doesn’t Break at $100M

Published 4 days ago • 2 min read

September 13, 2025 | Read online

How to Build a Sales Org That Doesn’t Break at $100M

by Kevin 'KD' Dorsey

There’s a brutal stat floating around tech: The average VP of Sales tenure is <18 months.

Not because they aren’t talented. Not because they don’t work hard.

It’s because they’re leading by results.
And here’s the truth: you can’t change results.

Revenue is already in the past. Pipeline is already in the past.
By the time you’re talking about them in the boardroom... it’s too late.

So what separates the execs who build $100M+ orgs from the ones who get cycled out?

They stop obsessing over outcomes and start mastering inputs.

Math Is Your Friend

Too many leaders set quotas on “gut feel” or board pressure. That’s vaporware leadership.

Here’s the reality:

If your ACV is $25K, a rep needs 4 deals to hit $100K.
With a 20% close rate, that’s 20 qualified opps.
Which means you’d better have 100 opps in pipeline to make the math work.

If you can’t map the path to quota in under 60 seconds, your team is set up to miss.
And when they miss, attrition and board pressure spike.

Stop arguing about headcount. Start with pipeline capacity.

Diagnosis Before Prescription

Bad sales leaders look at low revenue and say: “Close more deals.”
World-class leaders ask: “Why is close rate low?”

Every metric has a behavior, process, or skill behind it.

Low opp creation? → Prospecting time blocked?
Deals stuck in evaluation? → Is discovery surface-level?
High slip rate? → Follow-up discipline missing?

Without diagnosis, your “coaching” is just noise.

Think like a doctor:

Symptom: Revenue is down.
Diagnosis: Close rate at 17% vs. 30% benchmark.
Prescription: Fix follow-up cadence, coach DM alignment.

Don’t just measure. Diagnose, prescribe, and track the cure.

Responsibility > Accountability

Execs love to talk about “holding reps accountable.”

But accountability is just the tax you pay when reps don’t take responsibility.

In elite orgs, reps own their metrics. They run their own calculators. They walk into one-on-ones with answers, not excuses.

Your job as CRO isn’t to babysit. It’s to create the system where responsibility is the default.

Micro-awareness (spot trends).
Micro-prescription (fix inputs).
Macro-results (board confidence).

That’s how you scale without burning yourself - or your managers - out.

How to Apply This Week

Audit your quotas. Can every rep mathematically hit it with inputs in their control? If not, fix it.
Run a diagnosis session. Pick one underperforming metric and trace it to the real cause.
Flip accountability. In your next one-on-one, have the rep bring their own metric diagnosis and action plan.