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

Results-Second Leadership

“Safety third”. Sorry, what?!

Mike Rowe, from Dirty Jobs, popularized the Safety Third concept. Eye-catching, right? Who will argue safety is anything but first? 

In a conversation with a mentor, I was challenged to consider ways to be a better (people) leader. I wanted to improve:

  1. Giving people autonomy and holding those accountable
  2. Being more human and more charismatic

In talking through these concepts he, again, challenged my thinking on what this would look like. To think of specific and practical outcomes, yet bigger. Eventually, we settled on these two goals of what I want to become:

  1. People-first leader
  2. Results-second leader

I purposefully wrote “Results-second” this way because I knew it would both agitate me (in a good way) and be awkward to say anything other than “results are our number one goal”. After all, a company has to be (or plan to become) profitable. A company much continue to exist. A company must drive results. Without that, it will fail and then fail all employees, vendors, and customers. Massive ripple effects. We see that, especially in recessions

Culturally, we have values statements such as “people are our biggest asset”, “our people matter the most”, and “our employees are always top of mind for us.” But are those statements true? How do our actions line up with our words? For some leaders and companies, yes, they are true. For many other companies, however….it’s a mixed bag.

Many say and act on “people are our biggest asset” because they recognize they can’t get results without happy employees. However, that is seeing people as the input to achieve the output (results). Effectively, we must do certain things to ensure efficiency with our biggest asset for maximum output. That mindset is thinking about “them” as property, plant, and equipment, not as human beings. We even use the analogy of people as “assets” — taking care of cars through regular maintenance such as oil changes, or caring for factories by keeping them clean and replacing machinery to avoid stoppages. Again, this mindset of “people are our biggest asset” while intended as a good thing, has negative repercussions. People have become replaceable cogs. Do we see people as souls, or as one-time-use disposable items?

Related but distinct, we decouple making money from being compassionate, generous humans. Our business culture seems to live under a dichotomy of “we need to make money” and then “I will become a philanthropist” to change the world for the better (this is similar to the mindset “I’m going to work ruthlessly hard now so I can have an amazing retirement” which is also damaging). Instead, we ought to lead integrated lives where we make money (perhaps being okay with less) and live our philanthropism daily. In the office. At the work site. In our commute. At the DMV.

I don’t have all the answers. Being a people-first leader is putting people first and results second. That is fine in great times but will be very tense in hard times. It will also be awkward in seriously stressful seasons such as when we are behind on a deadline and you are tempted to throw everything at it and begin barking orders at a faster and more sharp pace. That’ll help in the short term. Bryan Loritts, a pastor, has said “Anxiety is a fuel that helps drive further, but it is a dirty fuel. It will pollute your life and be bad for you long term.”

To be honest, I don’t know how I would react in these cases and I don’t pretend to have the answers. But I do know this is the road that must be pursued. If I truly believe humanity matters, there aren’t other options: there is no Plan B. We ought to care about our neighbors — even in a remote environment where your coworker lives on the other side of the planet — and put their interests ahead of results. Even ourselves. It’s not about “we need to care or pretend to care so we get the maximum out of people” but “we must care about people because that is a high and honorable good” because people are created beings. Virtues can be stated in good times. Virtues are tested and proven in difficult, trying times. Let’s continue to think and dialogue on what being a People-first, Results-second leader looks and acts like.

Mike Rowe’s point is that we truly do not believe in “Safety First” because we’d never take any risks; we take calculated risks for the intended outcome. Imagine if we always shied away from any risks because of safety. Would we ever fly on an airplane or send a shuttle to space? Now, imagine if we truly put people first and results second. What could this world become?

Fire Yourself — a multi-year process of self-renewal

Self-reflection is a difficult skill. If you’re struggling with an honest reflection of your (work) life, start here: fire yourself. Seriously, act as if you just fired yourself from your role. Now what do you do?

In 2016 I listened to a podcast episode titled Fire Yourself. It changed my perspective. The key difference was I could stop clinging onto projects, dreams, goals, or past accomplishments and open my mind to new ways of viewing the world. Effectively, a restart.

You will ask yourself many of the same questions you would have asked but from a very different vantage point.

Think about it this way: pretend you fired yourself. It’s done. It’s over. Now, that job role is open and the new you applies to be re-hired into the role of your old self. What would you do? You cannot coast along on your past accomplishments — those were performed by someone else (the old you). How would you pitch yourself for the role?

In going through this process this year, I made a number of changes to my 2023 strategy. Truth be told, this process took me over a month to build my pitch and strategy to be re-hired. Here are a few 2023 strategic changes:

  1. Rethink a team’s alignment to our revenue growth. It may be commonsensical that teams should generally grow bigger with a company’s revenue growth, but the old me was so stuck in a mindset that it took “fresh eyes” to see not just that this should happen, but how the ratios and metrics should be constructed. I wish I saw this six months sooner.
  2. Be okay with letting go of initiatives with your name on it. There were two initiatives I oversaw and if someone had asked me three months ago, “we’re moving/changing XYZ” I would have had a very hard time with that. With detaching myself emotionally, I am now open to that happening and why (epilogue: no structural changes will happen, but it opened my eyes to several really great opportunities for my team to take on more autonomy, make better and faster decisions, and a better vision setting approach). What can you let free? How will it make you a better leader?
  3. Provide feedback to leadership. Remember when you wrote a performance review and suddenly you had clarity on the performance? That’s analogous to what happened here. By firing myself and re-entering that role, I saw how certain leaders could improve: whether they’ve been more reactive, they need to be more collaborative and less combative, they need to slow down and listen more, or they need to ask different, better questions. We’re often too afraid to give feedback to others — I’m speaking of those who “rank” higher than you — but it’s so valuable to you and especially them. 
  4. Show appreciation to my team. 2022 was a year of “hair on fire” at many times and I allowed myself to be pulled into the fray. I lost perspective. Truthfully, I work with a terrific team of people who are kind, caring, brilliant, hard working, creative, and collaborative. They need to hear that I care and that their work matters and is highly esteemed. They need to hear how amazing they are and to know I think highly of them!
  5. Quitting projects. There were several projects that I doggedly pursued. I should have listened to the team and agreed to pause or eliminate them months ago. Instead, I wasted much mental energy and the team’s time on trying to make it work. Know when to be stubborn, and when to let go.
  6. Work life considerations. We’ve praised “work life balance” for years as a utopia. Sometimes it truly is a balance, and sometimes trying to maintain balance leads to imbalance. I must return to taking needed holidays and vacations (even staycations), and return to doable hours. Bonus: holding yourself accountable to a set amount of hours greatly improves your own view of your worth, and forces you to focus on the critical few because “I now don’t have enough time for those things that don’t matter”.

Those are my learnings. Fire yourself. Learn from it. What are your takeaways? What would will you do differently upon being re-hired?

Focus and Meeting Time

I don’t recall being a person who “hates meetings”. In fact, early on in my career I sometimes leaned toward joining meetings because I was in the camp who believed that’s where the “important stuff happened.” Now that my calendar is full of meetings and, within the Covid-era, we have even more meetings, I’m actively focused on eliminating, shortening, and deferring meetings. It’s not that meetings are bad — they are very good and effective! — it is too much of one thing can the exact reason we have meetings: to drive results.

Meetings are to align, discuss, and jointly work through problems. That’s the beauty of diversity: hearing different voices. 

We also need uninterrupted hours of focus time to reflect, contemplate, think through, develop proposals and plans, and execute much of that work agreed-upon during said meetings. A balance is required; that balance is different for every person, role, and company (that makes setting any sort of “standard” as nigh impossible).

A couple years ago, my company embarked on Focus Fridays where we elected to not have meetings on Fridays. They serve as days to get work done, catch up, review projects, plan, etc. Over time, they’ve mostly remained as no-meeting-Fridays, with some exceptions. 

However, I don’t know that it reduced the number of meetings as much as crammed them into Mondays-Thursdays, thereby exasperating an existing problem: enough hours spent in meetings, preparing for meetings, or following-up from meetings so as to mitigate thoughtful and proactive thinking. Put differently, we need to meet, and, after re-evaluating the purpose of our roles, determine if we ought to be leading meetings 6-7+ hours a day (perhaps a VP or executive?), or if our role is more like a Manager or Director where we need to execute on the VPs plan and carefully think through the strategy pieces. Then again, the executive needs focus time, too.

I’ve seen people come away from Focus Fridays feeling refreshed and rejuvenated! However, by reallocating the meetings to Mondays-Thursdays, people are pretty wiped out by Friday and it becomes a recovery day. Maybe a catch-up on work day, if lucky. Rarely a “let’s think about the future” day. Then the weekend hits, then Monday and the cycle begins again. 

This is not about whining or some sort of Millennial (or Gen Z, perhaps?) diatribe on how the world owes employees something; it is about creating an effective and healthy work environment to promote high productivity, employee retention, and stellar company results (whether building products, selling products, etc.). Those meetings are costly.

Let’s try a different analogy. Let’s say we go to a full week in-person training seminar or conference where our schedules are jam-packed, content-rich, and from sun-up to sun-down. Two weeks later, how much of that content do you remember? Did it change your processes and approach the way the speakers and workshop leaders intended? Did it make you a better person? Did your company train you so now you know how to use the software, or what to do in a given situation? My guess is, in short, “no”.

That leads me to accepting that “maybe a Focus Friday or No-Meeting Friday isn’t the answer” — or, at least, isn’t the complete one. Is there a better way?

But first, a disclaimer. There’s no perfect solution; we live in an imperfect, imperiled depraved world. Perfection will not be found here.

A coworker and kind friend blocks off afternoons for at least two hours per day. I’ve appreciated watching him develop a more healthy day where he incorporates time to reflect, think about problems, reach out to stakeholders, and do all the other things that we normally do by “multi-tasking” during meetings when we’re neither paying attention to the speaker in the meeting, nor fully to the person we’re Slacking or emailing. Not only have I been watching, but I’m taking notes, too, friend.

I can do a few days of 6-8 hours of meetings a day, but I can’t last forever — I’m no robot. Now, having begun incorporating 2-3 hour blocks of time per day in the mornings or afternoons has changed my attitude, made me more excited about the future at my company, and has begun a healing process from freneticism — constantly running to and fro without the time to slow down and reflect. It’s also helped put into context any new meeting so I can better challenge it: “is this required? Do we need to do this now? Would this be urgent three weeks from now, or is it a flash in the pan? Can you prepare a proposal first, and then we meet to discuss the well-researched proposal?”

Be encouraged to start small. Perhaps even take a Saturday or Sunday morning or evening to reflect on your week. 

  1. Where do you get energy? 
  2. Do you find yourself making intelligent and wise decisions, or are you reacting? 
  3. Are you less capable in afternoon meetings and either struggle to make great decisions or be the captivating leader you aspire to be? 

From there, make changes in your calendar. Perhaps you can’t start the following week, so start three weeks out when your calendar is a bit freer (or could be six weeks out). From there, set boundaries and hold others accountable: “I appreciate you want to meet soon, but to give this project the appropriate focus and energy, I need time to prepare for it. Let’s meet _______ date instead of this week.” That’s taking the hard path. As Henry Townsend says, “Boundaries are what you create an allow.” Be sure to know what you allow for.

PROVE Value to Your Customers

Visibility into customer accounts always seemed to the “holy grail” of Customer Success. While a fully-fledged Customer Health Score can require years of work and refinement, here are some ways to get started and finding value in 1-2 months (or less!).

My company recently completed the first version of our Account Health Scoring methodology (more here). The exercise helped frame each metric as directly linked to the customer’s value.

Disclaimer: As of the writing of this blog post, I am employed by GitLab. The views expressed are my own. I will be highlighting pages that are publicly available.

The acronym, PROVE, serves to remind us internally that the point of the Health Score is not for our own internal desires and goals, but to ensure that the way we analyze customers is to PROVE value to them and us. PROVE stands for:

  • P: Product
  • R: Risk
  • O: Outcomes of the customer
  • V: Voice of the customer
  • E: Engagement with the customer

With this, as we build each component we ask ourselves, “but does this PROVE value for the customer?” The acronym is more than a handy mnemonic — it serves the greater story of ensuring we always think about the customer, the most important part!


You can find more context on the handbook page, yet the reason is when companies create a Health Score, it’s often conflated as they are trying to solve several questions. Here are just a few:

  1. What is the likelihood of my customer churning? (predictive analytics)
  2. What does their adoption journey look like? (product adoption)
  3. Have they adopted all of the product? (product adoption)
  4. Is my customer achieving their desired outcomes? (outcome)
  5. Is this an early warning indicator? (predictive analytics)
  6. Are they a promoter of our product? (predictive analytics)

Different stakeholders expect to solve different — and often competing — questions. It is necessary for your team to be crystal clear on what you’re solving. And then revisit that likely every couple of weeks as alternative definitions will sneak up in a variety of ways.

In our case, we opted for understanding customer adoption. We revisited PROVE and chose adoption as that will best benefit the customer. That may change over time, though, it is what we’ve agreed on, have commitment for, and our health measures are in sync with that approach; this isn’t a Swiss Army knife Health Score. We’re not solving everything.

Health Score Components

What should a Health Score include? What measures should we include in the calculation and why?

The components should necessarily derive from the purpose: the purpose defines the direction we take and needs to be thoroughly debated. Since customer adoption is the purpose, that defines and shapes the components. Specifically, we want to know if the customer is achieving their primary goals with GitLab. This goes beyond the product. We want to know if they’re achieving their intended use cases with the product, but we also need to heavily weigh their outcomes and sentiment. For instance,

  • Product: Are customers using the product as they intended from their purchase reasons? Are they finding intended value?
  • Outcomes: Is our customer achieving the results they set out for? This is generally more easily solved at the high-touch segment, but can be operationalized for the Digital customer segment
  • Sentiment: Is our customer responding to surveys and providing helpful feedback? How’s their experience with Support, with their CSM, with our content (LMS, knowledge base, video trainings, etc.)?
    • Note: we called this “Voice of the Customer”

These aren’t the only way to go, but these are three great starting points for a company to begin or expand their work into Customer Health. We’ll expand on these below.

Yes, But How Do I Deploy Something Now?

For the PROVE methodology, here are several tips for which ones to prioritize. But first, let’s address some presuppositions of the PROVE methodology:

PROVEDescriptionPriorityPrioritization Assumptions
ProductBy far one of the toughest setups of the PROVE acronym. This should include:
1. License Activation
2. User Engagement
3. Use Case Adoption (are they using the product in key, specific ways?)
4Product Analytics (telemetry) come from integrations (your own product, or another system) which requires time and resources. Also, the metrics need to be assessed for predictability. Note: this is likely the toughest to measure given it typically requires integrating telemetry data to make calculations. While the first of the PROVE acronym, consider this a long-term solution
RiskIs there risk in the account, relationship, or opportunity that causes concern for your company?1Relatively speaking, this is easy to deploy. Measured by hand, which requires a CSM, Sales Rep, or another person. Great for high/medium touch but not for low/tech touch
OutcomesIs the customer truly achieving their desired outcomes through your company? This means they purchased your software and were able to perform their actions in a shorter time period, they saved money, their team became more efficient (cost savings), they became more effective (better campaign targeting, analytics, etc.), or some other bottom-line financial outcome. This is measurable, noticeable, and traced to the financial statements.5This is tough as measuring the outcomes (not activities) often requires either a well-trained CSM team to spot value outcome achievement and/or highly focused product analytics. Can include survey data measuring, “Are you achieving _____ objective with the product?”
Voice of the CustomerSurveying customers is an effective way to keep a pule on onboarding, renewals, expansions, customer lifecycle, and more. For instance, use it in conjunction with Tech Touch campaigns (“is the content helpful?”), assess the value of your company (NPS), and the customer’s interactions with your personnel (Support, CSMs, Sales, etc.).3Can be deployed relatively quickly with NPS, CSAT, CES, and other feedback methods
EngagementThis is one of the first measures to deploy (after Risk) as it is relatively quick with High/Medium touch customers. The math is fairly straightforward as you are looking for what a typical cadence should be with your customers. If your CSMs/Sales teams aren’t engaging with your High/Medium touch customers frequently enough, that can be a warning signal. Note: as a v2, you can have different calculations for High vs. Medium touch where you expect a more frequent engagement with High touch. Again, a v2.2High touch: requires measuring if the customer is engaged with their CSM or other company contacts
Low/Tech touch: necessitates tracking webinars, open/click rates, product analytics, or other resources (note: Engagement could be excluded for Tech Touch as there is no human-to-human interaction)


There are several areas where we in Customer Success Operations are liable to become stuck. It is tempting to, boil the ocean (attempt to solve everything), become paralyzed by analysis, or focus on less meaningful initiatives. Let’s break each of those down.

Boil the Ocean
It’s really easy to believe we can build it all. Except…there’s a lot of thinking, algebra to solve for, research to do, studies to evaluate, and change management to see through. The best approach is to ensure you have someone who has done this (or similar), you’ve hired professional services, or you have a really good assessment of what it’ll take to build. And time.

Paralyzed by analysis
This is the most common. There is always the possibility of making a better decision with more and better information. GitLab helps us address this by following the Make Two-Way Door Decisions popularized by Jeff Bezos and Make a Proposal. Especially the “Make a Proposal” sub-value where our team is clear the decision is a proposal, but it gives something for others to work with, debate, refine, or refute; it’s a lot simpler than calling several brainstorm sessions — not to mention makes immediate progress. Most of all, it unblocks work and progresses us forward.

Setting The Correct Focus
Do we put our time to what we know, or don’t know? To what is easy, or has a high reward potential? Do we focus on product analytics, support analytics, or something else? Do we say yes to all? Or which segment do we start with? All?

Sadly, this is where the response is “it depends”. Customer segmentation, B2B or B2C, high/low/tech touch, and other factors play into account. For us, we started on our Enterprise segment given the revenue attribution and then have been working downstream. That allowed us the luxury of our CSMs getting used to Gainsight with setting the health for their accounts (CSM Sentiment).


In summary, your health score should help your customers better themselves — to grow, go faster, be more consistent, predictable, and scalable. It should factor in what’s important to them and if it happens to align to renewal goals, then great, but it should not be conflated with a churn score. What if your doctor only considered procedures and prescriptions based on whether they could retain you?

What to do now? Start with one step. Build your vision, but take one step at a time. Keep your vision before you (print and stick it on your wall!) and give yourself grace when it’s not built in a day. You’re building something great, sustainable, and vital for your customers — make it great and do it with joy.