The Many Faces of "The Plan"
How smart operators tailor targets to fit the game they’re playing
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Let’s get one thing straight: there’s no such thing as the plan.
There’s the plan you show your reps.
The one you take to the board.
The one you lock in with your lenders.
The one you parade in front of VCs.
And the one you hand over during diligence when it's time to sell the company.
Each one is tailored for a different stakeholder—because each one serves a different agenda.
If you're an operator in a growth-stage or PE-backed company, understanding these tradeoffs isn’t just helpful. It’s survival. Give the wrong plan to the wrong person and you’ve zapped away enterprise value, which is in many ways a game of managing expectations.
1. The Street Quota Plan
Purpose: Motivate the team and de-risk reality
Audience: Sales Reps
Tone: Aggressive
Offset: +10% from board if you are of scale (+$200M in revenue), up to +30% if you are subscale and growing rapidly
This is the sum total of quota capacity assigned to reps in the field. But it’s also a hedge.
In the words of a CFO I texted this morning:
“Any aggressive plan is typically pointed to our internal teams.”
This isn’t “mean” or “nefarious”. It’s an exercise in de-risking the company.
You're uplifting the plan to account for:
Big deals slipping a quarter
Reps quitting (leaving quota gaps)
New reps ramping (and not yet productive)
Macro risk (budget freezes, buying hesitations)
The goal? Protect the company from execution volatility. It's not a forecast—it’s a coverage map.
2. The Board Plan
Purpose: Set bonus targets and show credible governance
Audience: Board of Directors
Tone: Conservative, but achievable
Offset: 0%. This is the baseline for everything else
This is the official operating plan. It's tied to exec bonuses and serves as the benchmark for performance reviews.
Miss this plan, and your personal wallet feels it. Trust erodes amongst the C-Suite. And forecast credibility tanks with the board.
So you build in a margin of safety—while still showing ambition.
3. The Lender Plan
Purpose: Stay within covenants
Audience: Venture Debt Providers / Banks
Tone: Ultra-conservative, MUST HIT
Offset: -5% to -10% from board, depending on how well you know your company’s seasonality
Lenders don’t care about upside. They care about downside protection. You hand them a plan you can hit—even in a downturn. Even with your eyes closed.
Why so sandbagged?
Because if you breach covenants, they can call the note or ratchet up terms. Suddenly you have a problem much more existential than not getting bonuses.
As Catherine Jhung, Managing Director at Hercules Capital said on Run the Numbers:
“You might even go more conservative with a lender plan than the board plan—because they can enforce covenants.”
This is the “no surprises” plan. Lenders HATE surprises.
4. The Fundraise Plan
Purpose:
InflateEncourage healthy valuationAudience: PE / VC investors
Tone: Aspirational
Offset: Probably the same as the “quota on the street” plan. Raising on a number “as if everyone hit 100% of quota”
This one lives in the pitch deck. CAC magically goes down. Margins expand. Revenue hockey-sticks into the stratosphere. By year 5, everyone is at $100M, right?
This isn’t about conservatism. It’s about selling the dream—backed by a narrative and selective metrics.
Investors know it’s aggressive. You know it’s aggressive. But everyone plays the game.
“This is 20% higher because I know you are going to discount me 20%.” - any good CEO / CFO
5. The M&A / Diligence Plan
Purpose: Avoid price erosion during exit
Audience: Potential Buyers
Tone: Realistic, defensible, slightly conservative
Offset: -3% to -5% from board, depending on how well you know your company’s seasonality
Here’s the rub: if you hand a buyer a plan during diligence and then miss those numbers mid-process, expect a re-trade on price.
This version must hold up under the weight of reality, in the moment:
Is retention real?
Are your GTM assumptions replicable?
Can this scale without heroics?
WILL YOU HIT THE PLAN?
You want to show upside—but only if you can walk the talk during diligence.
The numbers may be similar. The variables they are built on is the safe. Yet, the intent behind them is not.
Sophisticated operators tailor the message, not the mission. The truth? Every plan is a tool. Use it wisely.
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If you want to get smarter on how venture debt works, check out this podcast I did with Catherine Jhung, Managing Director at Hercules Capital.
The venture debt landscape has changed dramatically over the past few years, and execs can’t afford to be left behind. Catherine Jhung, Senior Managing Director at Hercules Capital and a seasoned expert in venture lending, joined me to explore the landscape of venture debt in 2025.
The delicate balance between rate and flexibility
A surprisingly overlooked use case for venture debt
When not to raise debt
How to determine the right amount for your capital stack
What really separates banks from private debt funds
And the complex dance between VCs and debt providers.
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