Customer Success trends and predictions: An interview with Dickey Singh

In this article, Annette Franz reviews some Customer Success trends and predictions posed by Deloitte and asks CEO, Dickey Singh, to weigh in with his thoughts on what he’s seeing relative to each trend or prediction.


The role of your Customer Success team is to ensure that customers receive the value they expect — and achieve their desired outcomes — as a result of using your products. More specifically, in Wayne McCulloch’s book, The Seven Pillars of Customer Success, he notes that Customer Success has five main responsibilities:

  1. Eliminate churn through value attainment
  2. Drive increased contract value through value expansion
  3. Improve the customer experience
  4. Gain customer acquisition through building advocacy
  5. Proactively lead the customer to success

So, as we think about how to ensure those responsibilities lead to desired outcomes for both customers and the business, let’s take a look at some of the trends and predictions that Deloitte posed for the profession. While they published them at some point in 2021, they offered that, “Over the next 12–24 months, the adoption of a Customer Success-led approach is poised to transform how enterprise-scale companies deliver long-term customer value.” I think we’re still in that 24-month window, so let’s see how we’re doing today compared to what they proposed.

1. Dynamic and Adaptable Customer Success

Right now, Customer Success teams are mainly brought into customer relationships after the sale/purchase is completed. Not ideal, as those handoffs and introductions are often clunky, and sometimes they just don’t happen. If they do happen, there may be multiple individuals from different teams involved in the transition meeting, creating much confusion for the customer. I’ve seen this happen. The next thing customers do is ask, “Who do I reach out to if I have a question?”

Here’s the prediction from Deloitte.

“We predict that in the coming year, the role of Customer Success will grow to become truly dynamic, with the ability for Customer Success resources to flex into multiple domains of customer experience as needed, regardless of whether the customer is in the early stages of the sales cycle or years into using the product.

This dynamic relationship will require a more flexible staffing model that includes a group of Customer Success overlay resources who are not dedicated to assigned accounts, but instead are available to be targeted where there is the greatest customer need at any given time.

The dynamic model allows Customer Success to become adaptable in scaling to serve more customers, and it also creates an opportunity for these overlay resources to become highly skilled specialists in responding at high-impact moments across the customer journey, such as onboarding, renewal, or incident resolution.”

Dickey, where do you think Customer Success teams stand with regards to this today? Are they truly dynamic, as Deloitte posits?

First, several companies have already embraced a pool-and-pod model, where skilled Customer Success specialists step in as needed. Second, Customer Success teams are already involved earlier in the sales process.

The pool-and-pod Customer Success Model, now mainly based on skills versus availability, helps the service provider bring in the right Customer Success Manager (CSM) to the right task. This model is the norm now and a natural progression for service providers looking to provide better and scaled service to their customers.

We also see post-sales customer-facing teams, including Customer Success, getting involved in the sales process earlier – when the customer is still a prospect – across the board. Prospects are far more likely to become customers if they see committed and engaged Customer Success teams eager to solve customer problems.

In sales-led go-to-market motions, instead of the handover being a flip of a switch it becomes more of a collaborative effort between sales and the Customer Success department. Customer Success involvement gradually increases as customers progress through the sales process, and more specialized CSMs become involved.

In product-led go-to-market motions, applying Customer Success principles to free/freemium users helps convert them into paying users.

Of course, Customer Success leaders who do not use productivity or automation tools may find it much harder to get CSMs involved early on. Automation techniques can help scale Customer Success to prospects and customers in both sales- and product-led motions.

2. Customer Success as a Packaged Product

When you think about productizing your service offerings, Customer Success doesn’t necessarily fall into that thought process. I’m not sure that I can think of Customer Success as a packaged product. Sure, there might be specific consultative offerings that you might have or undertake that would be outside of the standard Customer Success responsibilities (see the start of the article!), but do these offerings fall onto Customer Success Managers?

Deloitte notes that they’ve seen some of these offering set up within companies, including: “setting up product management capabilities with Customer Success teams; building multiple offerings tailored for specific customer segments; and packaging multiple components of Customer Success, professional services, support, and learning together will become more widespread.”

To do this, Deloitte predicts…

“… that companies will need to build structured engagement mechanisms across the multiple teams involved and establish strong feedback loops. We also see companies continue to invest in the capability to deliver Customer Success motions digitally inside the product. Additionally, the integration of Customer Success into a packaged product has also enabled Customer Success teams to scale with cost-efficiency and increase the ability of companies to drive business outcomes for a broader set of customers.”

Dickey, how important is productization critical to scaling Customer Success?

Let’s unpack Customer Success. We may think of it as three vital elements.

  1. Growing the usage, adoption, retention, and renewals of products and features customers are already paying for;
  2. Driving direct and indirect revenue expansion in the form of upsells, cross-sells, and add-ons for products customers could benefit from and should pay for; and
  3. Driving overall satisfaction and advocacy to promote referrals.

You achieve the above by ensuring customers get value from the product, have the best experience at every step of their journey for every interaction, and are continuously reminded of the value and ROI they are getting from products or services they pay for.

We already have several Digital Adoption Platforms that have productized adoption for users, delivering adoption digitally inside the product. Digital Adoption Platforms target active users of a system but cannot reach the economic buyers or executives who do not necessarily log in directly to products. Executives, decision-makers, and even users prefer information presented to them., for instance, is an automation platform that generates personalized presentations from data and shares and explains customer insights to every persona, from users to executives, to engage and influence them. It ties customer insights to actionable recommendations and practical advice.

Another point is that, more often than not, we work in silos. Product, Customer Success, Customer Marketing, Customer Service, Account Management, and Implementation teams all communicate with customers during the customer lifecycle. Account Management teams get activated three months before a renewal. With all these various touches, a unified way to communicate with customers becomes essential.

3. Partner-Driven Customer Outcomes

For B2B companies who deal with consumers via/through partners or resellers, their focus has traditionally been on the relationship with the partner, often with very little visibility into the end-customer experience. This is definitely changing, and we’re seeing a new trend in the marketplace: the shift from B2B to B2B2C. This shift is ultra-critical, for a variety of reasons.

You can have all the partners you want. You can satisfy their needs all you want. But if the product you manufacture doesn’t add value, doesn’t sell, or isn’t something the end customer actually cares about, both you and your partners are going to go out of business.

With regards to partners, Deloitte predicts:

“… as partners increasingly take ownership of the outcomes that customers want to realize, they will require greater access to customer data to deliver those outcomes and grow customer lifetime value. We see partner-led Customer Success as a significant area of opportunity that can allow companies to tap into the power of their ecosystems to drive retention and growth while creating additional monetization opportunities for their partners. This will become a material revenue source for both companies (through greater expansion opportunities) and their partners as they become more involved in the sales cycle.”

I believe there’s a balance there between partner-led Customer Success and the need for brands to have access to that customer data and customer understanding, as well, to ensure that they develop products that actually deliver value for customers.

Dickey, what are your thoughts on this one?

The more people you have between you and your end customer, the harder it becomes to make them successful. However, partner-led Customer Success may become a feasible option as you scale. With access to data and the right tools, partner-led Customer Success can be successful. A  company doing this well that comes to mind: MarketSource. They partner with organizations and take over critical parts of Customer Success.

4. Collaborative Approach to Value Realization

A couple months ago, hosted a webinar titled, “Modern Customer Segmentation and Future of Customer Health” with Wayne McCulloch (CCO, WalkMe), Jeff Heckler (Director of CS, MarketSource), Dickey Singh (CEO,, and me. We talked about different ways to segment customers as well as important metrics when it comes to Customer Success, including customer health (CH) scores and what’s needed to calculate those scores.

Deloitte noted that they see “increasing maturity is adopting a unified customer health score across all product categories to enable a holistic approach to customer engagement. We are seeing a continued focus on identifying the right set of metrics to drive the customer health score and articulate value realization, specifically business value realization. However, identifying the right metrics, which are unique for every company, currently presents the most substantial challenge for companies.

They also see customers “playing a larger role in informing their own health score. Customers can exercise this influence through joint development of success plans, informing its key milestones and identifying business value metrics in a collaborative manner with their CS teams. Further, the digital maturity in Customer Success operations will allow customers to have access to an on-demand dashboard that will give them visibility into their success plans and account health at any given time, thereby driving greater engagement and collaboration.”

Metrics are always a hot topic, and Customer Success metrics are no exception. In the webinar, we talked in detail about customer health scores, including addressing:

  • What is broken in today’s health scores and what should companies focus on in the future?
  • Does customer health always = retention?
  • Do good health scores mean they’ll stay, and vice versa?
  • Why isn’t there a fixed formula for CH that everyone can use?
  • what should it include? CSM sentiment, Product Usage, Financial health, Relationship health, Service health.
  • How is CH calculated?
  • Salesforce’s 128 variables seems overwhelming. Why did it work for Salesforce, and does everyone need that many variables in a CH score?
  • CH can be simple too — usage and adoption of core features

If you haven’t listened yet, it’s definitely time well spent!

Dickey, any additional thoughts on this topic?

That was a notable webcast, and one of the most listened to on our website. Thank you for hosting it, Annette.

I now think there are various ways to measure and determine customer health for different customer segments that incorporate a customer’s maturity. In addition, it’s perfectly acceptable to update, improve, or completely replace how you calculate CH over time as your business and customer needs change.

Again, CH is a metric to report on, similar to NRR, but you need to pay close attention to the metrics that make up your CH score in order to make substantial improvements.

5. Digital-Led Customer Success is an automation platform that uses a bot to help scale growth and revenue from existing customers. The bot surfaces, shares, and explains customer insights for each persona and ties them to actionable recommendations and practical advice at scale.

The automation-first just-in-time approach helps businesses scale across all customer segments and personas – not just the lower-paying accounts or active product users. They can reach, engage, and influence every persona – from executives to product users – without hiring additional Customer Success Managers, account managers, and customer marketers. And they can scale experiences across customer maturity and user journeys – from pre-boarding to retention to renewals and expansion – without setting up rigid drip campaigns.

So we love that Deloitte’s fifth trend/prediction revolves around digital-led Customer Success across all account types, i.e., high touch, low touch, and self-serve, and notes that this is the wave of the future. The future is here today!

Specifically, Deloitte predicts:

“… that automation of workflows and customer touchpoints is a key enabler to drive scale in Customer Success coverage. Even in high-touch models, we expect Customer Success teams to leverage digital tools to drive personalized communications and more frequent touchpoints, point customers to the appropriate content, and leverage conferencing tools to bring the appropriate subject-matter advisers at the right time. Interactive dashboards will enable CSMs to share customers’ success plans and health scores in real time with them. For low-touch motions, a menu of resources, made available online and complemented by automated communications triggered by specific events, will allow companies to take Customer Success practices deep into small and midmarket layers.”

Dickey, I know you love this particular trend/prediction. Anything you want to add to Deloitte’s explanation of this one?

We have been saying this for two years now. And it seems like they wrote this with in mind! Ha ha.

Here is the thing. When you hire many CSMs, every problem looks like one that can be solved by adding more CSMs. That is not a wise decision, regardless of the current economy.

Consider these three scenarios:

  1. When you have a few customers with sizeable annual revenue per account (ARPA) values, you can have several CSMs reach out to customers. High-touch Customer Success works because you make hundreds of thousands of dollars annually from your customers.
  2. However, if you have many customers, or the ARPA is roughly in the $70K-100K range, productivity tools may help your CSMs; for instance, these tools can create presentations for CSMs to present to customers.
  3. Finally, when you have several customers or a lower ARPA, automation tools that automate the generation of presentations and explain customer insights, tying them to appropriate and personalized recommendations and advice, make way more sense, mainly because they provide a magnitude higher ROI.

What’s interesting to note is that automation and digital personalized Customer Success are not just for tech-touch customers. We don’t have a single customer account that does not enable Digital Customer Success and Automation across all of their segments within a couple of months of becoming a customer. A little more than half start with the lower customer tiers, but then the CCO and VP of Customer Success get involved, and we end up enabling across all segments.

No doubt, if something works well, you want to enable it for all your customers.  


Thanks, Dickey. I couldn’t agree more!

Customer Success is a critical role and responsibility within the organization. Its prominence has evolved and grown, especially over the last couple of years. The work that Customer Success Managers do is rooted deeply in a customer-centric culture because that’s “how we do things around here.” First and foremost, that is critical to success – for employees, customers, and the business. A customer-centric organization is one that puts the customer at the heart of all it does, always acting and responding with the customer’s best interests in mind. Let’s first and foremost focus on designing and delivering a customer experience that solves customer problems and delivers value for them. That in and of itself is a great first step in helping CSMs not only do their jobs with greater impact but also help every constituent achieve desired outcomes.

The biggest barrier to customer success is CEOs not making it an important part of the culture. ~ Nick Mehta
Annette Franz

Annette Franz is an advisor at, founder and CEO of CX Journey, and an internationally recognized customer experience thought leader, coach, speaker, and author. She recently published her first book, Customer Understanding: Three Ways to Put the “Customer” in Customer Experience (and at the Heart of Your Business); it’s available on Amazon in both paperback and Kindle formats.

In 2022, she published her second book, Built to Win: Designing a Customer-Centric Culture That Drives Value for Your Business (Advantage|ForbesBooks), which is also available on Amazon.

She is one of the Top 3 Customer Experience (CX) influencers, one of the Top 100 Strategists in Customer Success, and one of the 100 B2B Thought Leaders and Influencers. This article originally appeared on