From the outside looking in, Customer Success can feel like a risk mitigation, damage control guessing game.

In fact, Customer Success as a discipline has grown, evolved and come into its own as businesses – particularly SaaS businesses – are embracing the value of net recurring revenue and the huge upside of maintaining and growing existing customer accounts.

Differentiated SaaS businesses are embracing the education, engagement and experience of their customers.

You need only look at a leader in the space, HubSpot, and their emphasis on customer learning through academy or their huge investment in community. In fact, I started my career in SaaS with HubSpot and consider my onboarding experience with the company and early time there as a “SaaS University” for me and many others that started and grew there over the years.

Tools like ChurnZero or Gainsight are set up to give Customer Success teams more insight into their customer’s usage, health and activity so they can better serve and support them.

And more and more marketing teams are investing in supporting customer success relationships with customer lifecycle, growth marketing and customer marketing roles.

But the way we measure the success of, well, Customer Success can feel like it’s stuck back in its rudimentary days. Particularly when it comes to the final indicator: a customer’s renewal.

Which is what we ultimately want as a business, right? A customer to be getting enough value that they renew and grow?

But can we, as Success leaders, confidently say our teams know who is going to renew because they’re getting value? Or do we know who isn’t likely to churn? The aforementioned tools might give us an indication based on product usage – but that’s never the whole picture.

You have to ask.

Customer Success plays don’t match the outcomes we want

When we spend time in a fixed mindset – mitigate and limit risk exposure, decrease bad interactions, do damage control – the plays we run don’t match our ultimate outcome: Customer. Success.

So, before we start asking customers point-blank “do you plan to renew next year?” (which can be a scary question, I get it), we need to adjust our methods so that we earn enough trust to be allowed to ask that question.

When we think about a customer’s success in terms of what their stated goals are, our:

  • Onboarding and kickoff calls become stronger and more tailored to customer outcomes
  • Ability to interpret questions, hesitations and “fire drills” from customers is more informed
  • Insight into who in a customer’s organization is important to engage is sharper

All of these insights, the art and science of Customer Success, are important because they center what the customer is trying to accomplish in doing business with you.

Using qualitative and quantitative leading indicators

The list of metrics you can and should measure for visibility into the health of your book are long. For example, we tend to look at:

  • Product usage (by frequency, # of users, and depth)
  • Behavior changes by main points of contact
  • Actual changes in your main points of contact title, scope or even position in the company
  • Satisfaction scores and self-reported happiness indices
  • Past renewal or account activity
  • Firmographic and industry-specific data for that customer’s particular use case
  • Intent signals like competitive tool usage

But all of these metrics are predictive of a future action, and aren’t complete unless your customer success team is:

  1. Charting activity plans based on customer’s stated goals
  2. Proactively and properly setting expectations and, consistently verifying whether expectations are being met
  3. Adapting their success plan based on a customer’s business need changes
  4. Planning for turnover or disruptions in a customer’s business by multi-threading and expanding the pool of contacts getting value

When you combine both the predictive data and the customer-led insights, you’ll have a better sense for what customers can’t live without your product and which ones feel there’s still area to improve.

So, we’ve proactively managed expectations, implementation and the day to day usage for a customer.

We’re feeling great about the relationship.

And we’ve got a hunch – a strong one, in fact – that they’ll renew next year. They may even buy more.

But we don’t ask. We’re hesitant to even broach the topic (and don’t get me started on customers that don’t seem satisfied, engaged or like they’re getting value. We’re definitely not asking them…)

Why we don’t ask for renewals earlier

Part of our hesitation to find out “bad news” comes back to human psychology. Whether we’re naturally optimistic or pessimistic, a future definite that we can’t do much about can be hard to stomach. Our natural inclination, and our fear of rejection, is the voice inside our head that says if we know earlier, it’ll extend out the “pain” that we’ll feel, from the time we find out that a customer won’t renew to the time that they actually cancel or stop using our services.

And although this has some clear drawbacks – it’s hard to know a decision about continuing purchase of services before it’s made, you can’t clear up any confusion about product capability before it’s too far gone and you can’t adjust your approach and time spent on the relationship unless you know where they stand – so many of us default to a wait and see approach.

We should stop doing that.

We should ask.


  • Because it establishes a level of trust and credibility with your customers. When it comes to communication, clarity is kindness. And when you speak openly and clearly to your customers – including asking them what they expect your relationship to look like in 3, 6 or 9 months – it builds credibility and allows them to reciprocate the clarity and directness.
  • Customer experience is a differentiator. In tech, features and solutions are becoming more interchangeable, the landscape is becoming more crowded and switching costs are at an all time low. 
  • You’d be surprised at the answer. More often than not, that customer you’re sure is going to cancel is on the fence. Especially if they are the primary user, the champion of the purchase or have expressed dissatisfaction in the past. They want the tool/solution that they paid for and had intentions of using to work. Help them help you.

How to ask for a renewal

Expectation setting is the name of the game in Customer Success, and I’m certainly not suggesting we ask customers if they are planning to renew on every single call.

But, we can prepare our customers to have renewal conversations from the very first call. 

Connecting success to customer outcomes is the first step, and it also opens the door for you to understand if there are any other factors that might affect a future renewal – things like changes in leadership, changes in budgets or budget owners, etc.

Have you ever been on the other end of a “Discovery Call” that felt like an interrogation? Chances are, some of our customers feel that way, too. But if we take the steps to tell them why we are asking certain questions, then we set an expectation that this is not an interrogation, rather, a set of questions aimed to help you help them, better. 

Make the most of milestones. When we have our kickoff calls and we align on what success means for the customer, we focus on their outcomes. But those outcomes are also what will drive greater usage and future renewal. And it’s okay to tell customers that. 

That opens the door for your teams to ask questions like, “if your renewal was tomorrow, how likely would you be to move forward?” earlier in the relationship, instead of actually asking that question when it’s too late. If a customer completes onboarding, hits a 3 or 6 month anniversary or agrees to a quarterly business review … don’t miss the opportunity to ask them if they plan to continue using your services. 

Check in on progress to goals. No, I don’t mean you should be “checking in” with your customers. But you should be checking in on the goals you set together throughout your entire relationship. If you’ve done the hard work to align your Success motions to what the customer is trying to accomplish, celebrate when they’ve achieved a goal. And use it as an opportunity to set new ones. And also plant the seed for future renewal or growth.

Proactively address account challenges, business challenges. Ahead of a downturn, or coming off the heels of a tough customer service or product experience, it can be tempting to put your head down and even let a customer cool off. But it’s really one of the best opportunities we have to temperature gauge a renewal, because a customer whose been through that tough experience is probably going to be feeling strongly about whether or not they want to move forward with your team when it comes down to it. Find out which way they are leaning in that moment, and give yourself time to plan.

Understand your value, especially as it relates to how customers view you compared to alternatives. Feature to feature switching costs may be at an all time low, which is why implementation, customer experience and interactions with your company are more important than ever to create a “moat” and differentiate doing business with you from all of the other options in the market.

But leaving it at “we provide a delightful customer experience” sells your customers short. Consider all of their alternatives, even if they want to stay with you.

  • How might a competitor provide the specific value they need at a lower cost?
  • How might other options provide a better solution, in your customer’s eyes, as they grow or change their use case for why they purchased your product in the first place?
  • How do you show up compared to your competitors in the minds of your customers? And how can you ensure that you’re approaching it from a value-add perspective, and not disparage the alternatives?

Customer Success professionals don’t need to feel uncertain about the state of their book or not know whether they’re going to reach quota for the month or quarter. In fact, those that wait and see are often left the most disappointed.

Make a list and start asking your customers for renewals. Today. 


Sales Assembly can help your business scale better, faster, and smarter. Contact us today to find out how we can help your SaaS business grow quicker and more profitably.