August 9, 2025 | Read online
How to Lead a $100M+ Sales Team Without Burning Out
by Kevin 'KD' Dorsey
A VP of Sales I worked with recently was crushing it… or so it seemed.
Top-line revenue was growing, the board was happy, and reps were “busy.”
But when we looked under the hood, things were shaky: quotas set without math, close rates falling, and managers chasing results instead of fixing the causes. Pipeline was drying up. The same reps who looked like rockstars one quarter were struggling the next.
The truth? He wasn’t leading a sales org. He was babysitting a chaos machine.
We fixed it in 90 days - without doubling headcount or grinding people into dust.
Here’s how.
Big Idea #1: You Can’t Change Results, You Can Only Change What Causes Them
Most leaders spend 90% of their energy talking about results: “We need more revenue,” “We’re missing quota,” “Pipeline is down.”
That’s too late. Results are lagging indicators. By the time you see them, the work that created them is already done.
The BIPSY mindset flips the script:
- Behavior → Individual → Process → Skill → You (leadership)
- Find the result behind the result — keep asking “What’s behind that?” until you hit the controllable driver.
Example:
Revenue down → Close rate low → Weak discovery → Poor 2nd-layer questions.
When you fix the controllable input, you fix the output.
Big Idea #2: Quotas Without Math = Fantasy Football
A lot of quotas are based on “we need X% growth” rather than “what’s mathematically possible.”
From your metrics toolkit:
- Start with Pipeline Over Everything — how much pipeline is needed to hit your annual revenue goal?
- Stress-test quotas by deal size, close rate, and opportunity volume.
If ACV is $10K and close rate is 20%, hitting a $200K quota means 100 opps per rep per quarter. Do you have that pipeline?
If you can’t find a math-based path to quota, you don’t have a quota - you have a wish list.
SPOTLIGHT: HighLevel
Every rep and company needs a “pillar piece”. One signature asset.
Something you can become known for.
An asset that punches above its weight in value. That you just give away.
That pillar piece → becomes 20+ pipeline machines.
I have quite a few now. I leverage them all the time in outbound to just provide so much value.
I just dropped a new playbook to show you how to do the same for yourself.
It will help get you started. How to structure it. How to write it. How to splinter it.
It comes with a ready-to-go template so you can start building it in HighLevel.
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Big Idea #3: Build a Culture of Responsibility, Not Just Accountability
Accountability is reactive - you chase people when they miss.
Responsibility is proactive - they chase themselves because they own the number.
How to shift:
- Make the rep the primary owner of metrics, issue diagnosis, and action plans.
- When prescribing actions, include the how (calendar blocks, lead sources, call prep) - not just the “do more.”
- Get peer-to-peer accountability in play. The strongest orgs I’ve seen? Reps call each other out when someone isn’t living the team’s standards.
How to Apply This Week
- Pick one result to improve: then dig 3–4 layers deep to find the real cause.
- Audit quotas with math: ACV, close rate, opp volume, capacity. If the path doesn’t exist, rebuild it.
- Run an issue diagnosis workshop: give managers a checklist so they stop treating symptoms and start fixing causes.
- Shift ownership: have reps self-report metrics in 1:1s, and review actions, not just outcomes.
Sales leadership isn’t about pulling harder on the rope — it’s about pulling the right rope at the right time.
Do the math. Diagnose the cause. Build the culture.
The results will take care of themselves.
KD
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