The game you’re playing

We had an influx of new members this week. If you’re one of them, welcome. This is a weekly newsletter where we explore relevant insights for SaaS chief customer officers and those who aspire to the role.

We’re just a couple weeks away from unveiling a new name and website. Keep an eye out for that.

For now, I want to talk with you about the games we choose to play in our careers. And how those choices dictate our professional success and job satisfaction.

Let’s go…

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Customer success people are an empathetic bunch. As such, they tend to prioritize the customer over just about everything else in a business. At first glance, most of us would consider this a good thing.

But customer executives have a dual mandate. On one hand, it’s your job to prepare the customer for success. To anticipate their needs and provide the resources and structure to move them toward a better future.

On the other, you are an employee, and perhaps an equity shareholder, of a company to which you have a fiduciary responsibility to increase enterprise value over time. After all, “There is no customer success if the company is bankrupt,” says my friend Daphne Lopes.

And she’s right. Your job is to help strike the appropriate balance between the needs of customers and the needs of the business.

In the early stages of your career, finding a great boss is crucial for professional growth. Even in a struggling company, a talented leader can make a positive impact on your mindset, judgment, and professional habits. Their guidance is invaluable for early success.

But, as you climb the leadership ladder, the companies you choose to work for will define the ceiling of your professional success and personal financial achievements. And perhaps the most crucial aspect of those companies to understand is who owns them.

Like it or not, the business strategy of most companies is dictated by its majority shareholders (for whom executive managers work), and their desired outcomes. Whether the owners are individuals or institutions, they are playing a specific game that you need to be aware of. A game you become a participant in when you join the company.

Are the owners in for the “long haul” based on the CEO’s compelling vision of the future like early Amazon.com investors were? Or are they short-term stewards who plan to exit their position in the business as soon as pre-defined investment return hurdles are reached?

You might have ambitious goals to provide top-notch, high-touch service to customers and create a phenomenal culture for your employees. But the company’s balance sheet, financial performance, and exit timeframe could limit the range of possible product, process, and people investments you can make in these areas.

I’m convinced that most of the professional stress in our lives stems from the disconnect between our perception of reality and the actual truth. Long ago, a mentor taught me this simple formula for customer satisfaction:

When it comes to your satisfaction, as an employee, the following corollary formula holds true:

When your expectations, interests, talents, skills, and experience align with the will and desires of your employer’s owners, you will be able to do your best work as a leader.

So, when you take a new job or when your company goes through an ownership change, you need to be clear on the game you’re playing. Here are some of the common games you might encounter as a SaaS executive:

The Bootstrapped Founder Game

Steady, measured, profitable growth. In founder-owned companies, the horizon is long, and the focus is on sustainability. There’s a moderate growth expectation, but the founders prioritize cash flow and autonomy. They want to stay in control.

As a CCO, you’ll need to be scrappy. Every decision must support long-term sustainability. You won’t have endless budgets, but you’ll likely have the freedom to make customer-focused decisions that drive lasting results.

The Venture Capital Game

Go big or go home. VC-backed companies are all about fast growth and a high return. The goal is often to scale aggressively and achieve a 10x-30x (or higher) return on investment. In this environment, speed is key. You’re running wind sprints, not a marathon.

As a CCO, expect pressure to hit short-term metrics and expand the customer base rapidly. It’s exciting, but also risky. Job security may hinge on meeting aggressive targets. Cash burn rate will be a major concern, and each quarter will bring new challenges in terms of growth, scale, and efficiency.

The Private Equity Game

Short-term growth and efficiency. Private equity (PE) firms aim to maximize value in a 3-7 year window. They’ll expect a solid return, typically 2x-5x. PE-owned companies focus heavily on operational efficiency and profitability.

As a CCO, you may need to lead efforts in cost-cutting or operational efficiency while still driving customer retention and expansion. You should be ready for frequent changes, as PE firms often sell the company when they’ve maximized its value. Job stability can vary, and your leadership role may shift depending on their strategy.

The “Strategic” Ownership Game

Beholden to the mothership. When a larger company acquires your company, you’ll need to play by their rules (they may be playing any of these games!). The time horizon is typically longer-term, but depends on the parent company’s overall strategy. The goal here it to be accretive to cash flows and profitability of the business.

You might benefit from increased resources, but your autonomy could be limited and there will almost certainly be some “red tape” to deal with.

Decisions might take longer, and you’ll often need to align with the parent company’s broader goals and systems. As a CCO, balancing the needs of your teams and customers with the priorities of the larger organization will be key.

The Publicly Traded Game

The quarterly treadmill. If you’re at a publicly traded company, the game is all about quarterly results. There’s less freedom to make long-term plays because shareholders demand steady, incremental growth. Oh, and no surprise bad news. The public markets hate negative surprises. Public companies face intense scrutiny from both institutional and retail investors.

As a CCO, you’ll need to focus on compliance and meeting short-term performance metrics while still driving customer satisfaction. The upside? Public companies often offer more stability—but with high accountability. (Oh, and probably stock grants that are worth real money).

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Each ownership type has its own objectives, risks, and rewards for you as an executive. Before accepting a CCO role, make sure you know the game you’re signing up to play. Understand the expectations, time horizons, and return rate expectations of your owners because they will shape the company’s strategy.

When you know the game, you can lead with purpose and win for your company, your employees, your customers, and for yourself.

Do you know what game you’re playing?

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