What is Strategy? Examples In Customer Success

I was introduced to the book Good Strategy, Bad Strategy through Dave Kellogg in his book review. Before this, “strategy” was a term once used to sound smart, to appear capable, and to act confidently. I believe it still is. So when I came across the book, I devoured it and re-read sections (unusual for me). 

Below is what I’ve shared with my team. Before we get there, keep in mind the presupposition that strategy is a response to known events. A strategy’s first section is called “The Diagnosis”. In the same way a doctor examines a patient, they’re diagnosing the patient’s current situation to understand and establish a baseline. However, just like a doctor prescribes a change, a strategy can and must be forward-thinking to identify trends, market movements, and other economic situations to drive forward.

With that, let’s jump in.


This document is intended to assist in defining many of the core requirements to develop a holistic strategy. This will help lay out the framework, assist in outlining the core topics, determine requirements, and establish what alignment needs to take place.


The Strategy DRI will be owned by the lead, with the support of the director as GitLab operates under the premise of a Manager of One.


What is Strategy?

Strategy can be broken down into three areas:

  1. Diagnosis (of the problem, situation, or opportunity)
  2. Beliefs (key assumptions about the situation to connect the diagnosis and guiding policy — note, Dave Kellogg added this section and after using it, I 100% agree)
  3. A guiding policy (for dealing with the problem)
  4. A set of coherent actions (designed to carry the guiding policy)

Strategy is knowing what you’re pursuing so you know when and to whom to say “no”. 

Strategy is the outlined goals. Tactics are the steps to execute the strategy. An analogy could be an OKR: you have the objective (goal) and key results (tactics). However, to develop a strategy, you must first know the Mission.

Example Strategy

Let’s make up an SMB churn and contraction issue as an example:


  1. Product experience: we cannot throw bodies at problems in SMB; limitations in the product will increase churn
  2. Retention goals: in SMB, we are unclear whether our North Star is dollar retention, logo retention, contraction, or something else
  3. Brand and packaging: because of a poor signup experience, customers are less likely to renew


  1. We must maintain a greater than XX% Net Retention and YY% Gross Retention to stay on track
  2. SMB is critical to our long-term success since these accounts today will be Enterprise tomorrow
  3. Succeeding in SMB is voluminous, necessitating automation, rich analytics, and a significant decrease in manual intervention

Guiding Policy

  1. Prioritize vs. boil the ocean: be selective with our time and resources; prioritize and execute
  2. Scientific method: Hypothesis-> Analysis —> insights (confirm or deny the Q) —> proposed actions
  3. Forecasting drives awareness: to improve gross and net retention, identify why customers have already left, and forecast what will likely happen to take preventative actions for future quarter risks

A Set of Coherent Actions

  1. Establish a North Star; know our target and pursue it
  2. Define the top five reasons customers churn and align the organization to solve that
  3. Create a feedback loop of insights that lead to action
  4. Narrow forecast range to within +/- x%

That’s the example: take what you already know, know your key assumptions, develop your policy to guide you, and create actions to accomplish, fix, or avoid.

Where Should It Live?

The best place is generally whatever the most accessible medium as you want to share the high-level goals across many teams and divisions (such as slides or a document). Slides also rely on a combination of text, images, and video, making it easy for the audience to digest.

What Are the Best Practices?

Creating a strategy is neither easy nor quick. It is something formulated over weeks and months and is continually refined. It is evergreen. Several recommendations:

  1. Realize these are big challenges! It’s not simple.
  2. Go offsite. Minimally quarterly but best monthly to take 2-5 hours in a day and de-couple from your computer and have a notebook or something that will relieve you of distractions (Slack, email, etc.). Take this time to do a retrospective on how it has been, what’s currently working/not working, and where you’d like to go. Then update your strategy.
  3. Ask for feedback as it is collaborative, but you are the DRI. Your internal customers don’t dictate your strategy. You do. 
  4. Draft and take a break. After a few days, come back and ruthlessly evaluate it. Make it a shining example through eliminating non-essentials, jargon, and even great, detailed content. It should be easily understood by executives.

Creating Your Strategy


First, before sitting down to write out your strategy, first understand the mission and vision of your company, division, and team. To develop a strategy within Customer Success Operations, here’s the recommended flow:

  1. GitLab
    1. Mission
    2. Strategy
  2. Customer Success
    1. Vision
    2. Strategy (internal only)
  3. CS Operations
    1. Strategy (internal only)

With this, ask yourself these questions:

  1. What are the top-level objectives that my department best aligns with GitLab, Customer Success, and CS Operations?
  2. What does success look like?
  3. If my department could only do 1, 2, or 3 things in the next 12 months, what would they be? 18 months? 
  4. How does GitLab and Customer Success measure itself (KPIs, for example)? How can I measure my department for clarity for CS, Sales, Company Leaders, and others to understand?
  5. What are the 20 things I must say no to, so I can give an exuberant YES to one, two, or three must-haves?

Develop Strategy

Now that research is complete, create a slide deck or document from the GitLab template or use the CS Operations deck as a template to clearly and succinctly address the following questions:

  1. What purpose does [x] department/team/initiative serve?
  2. What are your high-level plans?
  3. Why does it matter to me? Why does it matter to others?
  4. How will you know if it is successful?
  5. What is the roadmap to get there?
  6. How will you communicate this to others, now and ongoing?
  7. What do you need and what are your risks?

To address those questions, you can follow this format (improv is encouraged):

  1. Mission statement
  2. Executive summary (like a book intro)
    1. Extremely high level with 1, 2, or 3 easy-to-read takeaways in under 10 seconds
  3. KPIs and Success Criteria
  4. Optional: team(s) we support
  5. Optional: WIIFM if the strategy isn’t absolutely clear to someone off the street
  6. Strategy deep dive/areas of focus
    1. This is where the deck will get into some of the details — again, high level
  7. Timeline or Roadmap
  8. Asks
  9. Risks, Concerns, Blockers
  10. Appendix (if there are additional non-essential slides)


  1. Demystifying Strategy – HBR
  2. GitLab Strategy
  3. Strategy Means Saying “No”
  4. Strategy vs. Tactics: Why the Difference Matters
  5. Book Review of Good Strategy, Bad Strategy by Richard Rumelt
  6. Book: Good Strategy, Bad Strategy

Published by Jeff Beaumont

I love helping companies scale and grow their organizations to delight customers and employees, enabling healthy teams, fast growth, and fewer headaches. Scaling quickly is wrought with potholes and plot twists. When you’re running a company, losing customers, and employees are on their way out, and don’t have your systems running smoothly, then you’ll be at your wits' end. I've been there and hate it.

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