Strategy. It's the buzzword that never goes out of style. Board decks overflow with it. Executive off-sites revolve around it. Annual plans can't exist without it.
But for all our talk about strategy, how much of what we call "strategy" fits the definition?
According to Jason Cohen, founder of WP Engine, "Strategy is: How we will win."
Simple enough, right? Yet most so-called strategies are vague, wishful thinking exercises, written once and never seen again. They're full of aspirational statements like "be customer-centric" or "lead with innovation" that everyone can agree with — and that's precisely the problem.
Let's explore what strategy is, especially when it comes to your customers, and why the difference matters...
Listen, we’ve been there. Meeting with your biggest customer and have no idea how they’ve been doing… we built a ChatGPT prompt to help you do just that.
We are developing an AI Prompt library with various day-to-day prompts that customer success leaders can utilize. Email jeff@chiefcustomerofficer.io if you have any ideas.
A proper strategy requires actual decisions — choices with real consequences, especially for your customers.
Consider these common "strategic" statements:
Sound familiar? The problem isn't that these are bad ideas. The problem is they're not decisions at all. No company would proudly claim the opposite.
A real customer strategy makes clear, specific choices with tradeoffs that other successful companies might reject:
These statements tell you something about how the company plans to win. They involve real choices and acceptable consequences.
When developing a strategic approach to your customers, you need three critical elements:
Which customers will you prioritize, and which will you consciously deprioritize?
This isn't about excluding people from buying your product. It's about being clear on who you're optimizing for, which customer segments receive your best resources, and which "good customers" you're willing to disappoint when priorities conflict.
The 98/2 principle applies here: 98% of companies talk about customer segmentation but don't make the hard decisions required, and only 2% follow through with differential treatment.
What problem do you solve better than anyone else for those target customers?
This isn’t about the positioning and marketing spin. It’s product differentiation. As Seth Godin says, “Making something remarkable is making something worth remarking about.”
The key word is "better." Not different, not unique, but better in ways that matter to your chosen customers. This requires brutal honesty about your actual capabilities versus your customers' alternatives.
As we covered in Cost to Retain, retention costs skyrocket when your value proposition doesn't align with customers' real-life experience with your product.
How will you deliver value to customers in a way that creates sustainable advantages over alternatives?
This is about designing a customer engagement model that becomes more powerful over time, not less. It's creating a system where your advantages compound with scale while competitors face diminishing returns.
The best customer strategies include what Jason Cohen calls "asymmetry," where your upside vastly exceeds your downside, so even partial execution success generates positive outcomes.
For example, a community-led approach where each additional customer improves the experience for everyone or a data advantage where each customer interaction trains your system to deliver better outcomes.
This is why Covering Your Bases matters so much. Your strategy must leverage your best strengths across industry, product, engagement management, and commercial expertise.
Most executives can articulate what their company does and explain how they do it. However, few can clearly state how they'll win with customers in a way that accepts real tradeoffs.
So the question is simple: Can you articulate, in one or two sentences, how your company will win with customers in a way that makes hard choices explicit?
If not, you might have a plan, a roadmap, or a vision — but you don't have a strategy.
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We’re grateful you choose to read each week.
When you’re ready for more, there are a couple ways we can help:
» Cover Your SaaS is a financial literacy course for go-to-market leaders. Grab your copy here.
» Promote your product and services to over 4,000+ senior SaaS Sales, Marketing, and Customer Success pros by sponsoring our twice-weekly newsletter and podcast.
