How to get Customer Success and Sales on the same page, without stepping on toes - Glide Consulting
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How to get Customer Success and Sales on the same page, without stepping on toes

Have you ever had a customer who just wasn’t a good fit? Whether you sell monthly subscriptions to a marketing automation app, or complicated annual contracts for an enterprise compliance and risk management solution, supporting these customers can quickly become a nightmare.

Whether their use-cases aren’t a good fit for your product, or they’re just plain incompetent in the relevant skill-set, these customers steal resources you could be using to help other accounts grow.

A lot of CS teams just deal with it, but fighting to retain problematic customers isn’t a long-term solution.

If Sales and Customer Success aren’t on the same page, problematic customers will bury you.

For most of the past two years, I was Director of CS at a startup that grew from about 60 customers to over 2000 in 18 months.

A significant amount of customers who signed up during that time were beginners, and didn’t fully understand the scope of the problems they were solving for. Sometimes they churned days after signing up; other times they struggled with the account for months before cancelling.

Beginner customers overload support, have the highest user-churn of any cohort by a significant margin, and account for 80%+ of the firefighting most CS teams do every week. If you sell to small businesses, you know exactly what I’m talking about.

As stressful as dealing with beginner customers can be, nothing compares to the feeling of getting an urgent email from a mega-account asking for a refund and cancellation. These “rage quit” scenarios usually happened for one of two reasons:

  1. the customer bought in thinking our tool lacked the problems their current solution had, and felt upset when our tool just introduced different problems
  2. the customer bought in thinking they were getting functionality we didn’t actually have

If you’ve had friction with customers for either of those two reasons, some critical marketing and Sales processes failed. In growth-driven companies (like startups), the Sales mentality can sometimes be reduced to “bring them in now, we’ll figure out how to deal with them later”.

That might be a great way for Sales to make their top-line growth numbers, but the Customer Success team usually gets stuck with the “we’ll figure out how to deal with them later” part. This is an incredibly expensive way to do business, and puts Sales and Customer Success at odds. Even worse, the customer gets caught in the middle.

This crazy time led me to the following Customer Success maxim:

Just because somebody has budget for your product doesn’t mean they’d be a good customer.” Click to share this quote on LinkedIn

Unfortunately, very few VPs of Sales or growth-focused CEOs will take that maxim too seriously. However, elite CS leaders don’t just take it seriously, they know how to influence others in their organization to take action on it.

What if you could get Customer Success and Sales on the same page this quarter, without stepping on toes?

The friction between CS and Sales boils down to a failure of communication processes. In a lot of companies, there’s an unclear (or non-existent) communication process in place between Sales and Customer Success. This results in ad-hoc decision making, unclear expectations, and a lack of accountability.

If that sounds about right to you, then it’s time to do something about it. All you have to do is put on your Strategy hat.

Step 1: Define the symptoms.

Most of the CS teams I’ve worked with had some variation of the following symptoms:

  1. “Several of our big customers are pretty unhappy and probably won’t renew.”
  2. “Churn is creeping up in a couple of our cohorts.”
  3. “The time it takes us to resolve issues is getting out of control.”
  4. “My team is working a ton of hours, but our efficiency is dropping every week.”

Step 2: Define the problems beneath the symptoms.

The first premise we have to agree upon here is that the symptom is not the same thing as the problem, even though the symptom feels quite urgent and real.

We can uncover the problem beneath the symptom by adding the word “because” to the end of the symptom – like this:

  1. “Several of our big customers are pretty unhappy and probably won’t renew¬†because Sales promised them functionality that our product just doesn’t have.”
  2. “Churn is creeping up in a couple of our cohorts because they lack competence in the skill-set necessary to generate value from our product.”
  3. “The time it takes us to resolve issues is getting out of control because we have to spend a ton of time sorting out the bad deals Sales keeps pushing down the pipeline.”
  4. “My team is working a ton of hours, but our efficiency is dropping every week¬†because we’re starting to get burned out from all the firefighting.”

Step 3: Dig into the data.

Now that we have the problems written down, let’s compile the data we used to come to the conclusion that the problem exists in the first place. We’ll continue with the examples from steps 1 & 2.

  1. Compile the emails you’ve exchanged with the customers who were promised one thing but got another. Pull out their exact verbiage, and put them into a Google Doc. Use comments to explain what your team had to spend time on in order to salvage these accounts.
  2. Dig into the unit-economics of the problematic cohorts. Figure out how much these customers cost to acquire and support, then compare that number against the revenue you expect to generate from them over their lifetime. You might actually be losing money hand over fist on these high-churn, low-value customers.
  3. Compile response time/time-to-resolution metrics and plot them on a graph to see how they’ve changed over time. Figure out the exact dates you worked on salvaging bad deals, then plot them on the graph. Bad deals may drastically affect your team’s productivity, and this is an extremely compelling way to show this.
  4. This one’s especially important for Directors of CS, because it requires you to have rapport with your team, strong leadership skills, and tact. Interview your CSMs, and actually listen to them. Use their words as leverage to construct arguments for why these problems exist. Your CSMs are incredibly observant. Use their observations to your advantage.

Step 4: Specify your conclusions.

Now that you have the data to back you up, this step can be as easy as writing down a list of if/then statements. Again, based on the hypothetical examples above:

  1. If my team has to deal with another customer this quarter who feels like they got duped, we might lose one of our CSMs because of the stress. That will cost us $70k and a lot of credibility.
  2. If our highest-churn, lowest value customers cost us $50 to acquire and $150 to onboard, but their LTV is only $170, then we’re losing an average of $30 per account, plus 40 man-hours a week in opportunity cost.
  3. If Sales pushes a bad deal through, then it reduces my team’s productivity by 30%, and bumps our response and resolution times above 700 minutes for up to a week, which is 600% above baseline.
  4. If bad deals come through, my implementation CSM has to split time between implementation and support, which drags out implementations by up to 25%. 2 of the 4 new customers this week are already in red status as a result.

Are you starting to see how powerful this process can be?

Step 5: Propose some executable solutions.

It’s one thing to be able to point out problems, it’s another thing to have the expertise to propose reasonable solutions. Here’s what some solutions could look like to the problems I outlined above:

  1. Let’s get Director of CS, Product, VP Sales, and Marketing Director in the same room for 25 minutes this week to review the latest bad deals, assess where the sales process failed, and get on the same page about the feature set and product roadmap.
  2. Let’s invest in an automated, video onboarding series to help our lower-tier customers get their first use-case implemented faster. Here’s a script outline based on the most common use case. I think this could reduce support overhead for this customer tier by 30% or more.
  3. See #1
  4. See #1

See what we just did there? We used an objective process of assessment to define a couple of really painful problems more clearly, then succinctly proposed the first step on the path towards solving them. Now the only thing left to do is communicate our findings to the right people.

Step 6: Communicate with confidence.

If you rigorously follow steps 1-5 in this process, you’ll be able to use the information you gathered to disarm even the most hard-headed managers and sales executives. By putting all the work in up front, you’ve shown everybody involved that you’re committed to the process of communication. The more objectively you present your findings, the more respect, trust, and loyal cooperation you’ll earn from your peers and managers.

If you’re a CSM, present this information to a Director you have good rapport with. A good Director will know exactly how to escalate your findings. If you’re a Director or a VP, flex your leadership muscle and go to the decision makers who rely on your judgement and expertise to keep the machine running. When you walk into that conversation, try to remember: this is not a personal issue, this is a process issue. The point isn’t to throw anybody under the bus, or display how smart and strategic you are; it’s to use your natural strengths to make the lives of your teammates and customers better.

This level of communication isn’t easy, but it’s one of the most important things you can do for your career this quarter. It’s also a huge step towards aligning the interests of Sales and Customer Success at your company, which would have a massively positive impact on the health of the entire business.


When people give me pushback on this model, it sounds something like this:

“Hey DanG, this sounds pretty awesome, but who the hell has the free time to spend digging through emails and making pie charts? I barely have enough time for lunch.”

Here’s my answer:

Unless a customer dies, goes out of business, or finds a way cheaper/better product, they churn because your business processes consistently failed to deliver the value they were expecting.

Therefore, if you’re aware of a business process that fails to deliver the value your customer is paying for, it’s your fiduciary and ethical duty as a Customer Success professional to assess the failure, communicate your findings, and assist in the resolution.

If you work in CS, a significant part of your job requires you to make time for this.

Further reading…

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