are you playing the wrong game?

Customer success leaders are an empathetic bunch. We tend to prioritize the customer over just about everything else. But as an executive, you have a dual mandate.

On one hand, you must prepare the customer for success.

On the other, you have a fiduciary responsibility to increase enterprise value.

As my friend Daphne Lopes says, “There is no customer success if the company is bankrupt.”

Most professional stress stems from a single disconnect: when your strategy doesn't align with the game the owners are playing. The specific game is dictated by your majority shareholders. Whether they are individuals, VCs, or institutions, they have specific desired outcomes. If you try to run a "white-glove, high-cost" playbook in a company built for "low-touch efficiency," you will fail. Not because you're bad at CS, but because you're playing the wrong game.

Before you take a job (or build your next strategy), you need to know which of these five games you're in:

1. The Bootstrapped Founder Game

• The Goal: Sustainability, autonomy, and cash flow.

• The Reality: Budgets are tight. Growth expectations are moderate but profitable.

• Your Play: You need to be scrappy. Every decision must support long-term cash flow. You won't have endless resources, but you’ll likely have the autonomy to make customer-focused decisions that drive long-term loyalty.

2. The Venture Capital Game

• The Goal: "Go big or go home." Aggressive scaling for a 10x-30x return.

• The Reality: Speed is everything. Cash burn is expected, but growth must be exponential.

• Your Play: Expect immense pressure to hit short-term expansion targets. You are running wind sprints, not a marathon. Job security hinges on meeting aggressive growth metrics, not just keeping customers happy.

3. The Private Equity Game

• The Goal: Maximize value for an exit in a 3-5 year window.

• The Reality: It’s about EBITDA. Operational efficiency and profitability rule the day.

• Your Play: You may need to lead cost-cutting efforts while maintaining retention. This is often about standardization and automation. If you're trying to hire expensive CSMs here, you're fighting gravity.

4. The “Strategic” Ownership Game

• The Goal: Support the "mothership." (When you've been acquired).

• The Reality: You play by the parent company's rules. Decisions take longer.

• Your Play: Success is about being accretive to the parent company's cash flows. Your autonomy will be limited, and your ability to navigate "red tape" and align with broader corporate systems becomes a core skill.

5. The Publicly Traded Game

• The Goal: The quarterly treadmill. Steady, predictable growth.

• The Reality: The markets hate negative surprises. Scrutiny is intense.

• Your Play: Compliance and predictability are paramount. You need to hit the number exactly. The upside is often stability and liquidity; the downside is the relentless pressure of the 90-day cycle.

When your skills and strategy align with the desires of your owners, you can do your best work. When they don't, you are constantly swimming upstream.

Before you finalize your strategy for the coming year, ask yourself:

Do you know exactly what game you’re playing?

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