Digital-Led Customer Success
Use High-Touch Strategies to Inform Your Digitally-Led Model

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A conversation with Dickey Singh
by Chris Hicken, CEO and cofounder 'nuffsaid

According to Dickey Singh (CEO & Cofounder of, most Digital CS approaches including low- and tech-touch models today aren’t effective.

Customers in this segment are usually overwhelmed with automated emails, pdfs of reports, and dashboards - instead of being sent meaningful, tailored content at the right time.

Dickey came on the Nuffsaid podcast this week to share how Customer Success teams can take a working high-touch model to inform their digitally-led CS practices. That's why this week he shares how Customer Success teams can take a working high-touch model to inform their digitally-led CS practices.

Listen to the podcast on Apple Podcasts or Spotify

Approximately 16 minutes.

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AI-generated and edited for clarity.

Chris Hicken (CEO and co-founder' nuffsaid):
Hey, this is Chris, co-founder of 'nuffsaid, and on today's show, we talked to Dickey, the CEO of about why most low-touch models aren't effective.

And here's what we learned.
1. You just can't create great low-touch experiences by automating content.
2. It's best to start by taking the most effective high-touch programs, and then figuring out how to automate them.
3. It's important to empower low-touch CSMs with both productivity and automation tools.
4. Upsells and cross-sells should still continue to be a big focus, even in the low-touch model.

So that's the TLDR. Let's jump in.

Dickey Singh (CEO and co-founder
Hi everyone. My name is Dickey Singh, and I'm the co-founder and CEO of, a company laser-focused on scaling Customer Success, Renewals, and Revenue Expansion.

I am delighted to be here with you, right after Thanksgiving!

Awesome Dickey. It's great to have you joining us today. And you know, the low-touch Customer Success program is interesting. It's very [effective]. Lots of companies are focused, right now, on doing more scaling in their customer success, but in your view, low-touch Customer Success Programs are broken today.

So what's your philosophy behind how to effectively scale Customer Success?

It's a very interesting question. And I get that a lot.

Let's take a look back at Customer Success.

Why did Customer Success become important? One reason is that it is easier to retain and upsell to existing customers than acquire new ones. The cost of acquiring customers is 6.4 times the cost of retaining and upselling to existing customers. This metric comes from Bain.

Of course, the product should work, and the customers need to find continuous value from our products to keep renewing and buying more features, products, and services.

But there is a fundamental shift happening!

First, Profitwell did some interesting analysis. The cost of acquiring new customers has increased 60% in the last five years, while the willingness to pay for features has dropped by 30%.

Second, because of the increased competition — and easier to onboard, use, and adopt products — the time, money, effort, and emotional cost associated with switching from one product to another continues to fall.

Third, most SaaS businesses targeted an ARPA of hundreds of thousands of dollars. With PLG and self-service products, that's changing to serving more accounts at the ARPA of tens of thousands of dollars, or as Chris Janz from Point Nine Capital would put it a shift from elephant-hunting to deer-hunting.

Now with lower switching costs, rising acquisition costs, lower ARPA, coupled with lower willingness to pay means as your CAC goes up, your profitability goes down. Therefore, you need to serve more accounts to sustain as a SaaS business.

To me, that means that we have to provide a magnitude higher value and ROI (Return on Investment) to our customers.

That also means that we have to scale customer success and revenue expansion.

In the last decade, we scaled reactive customer service.
In this decade, we have to scale proactive Customer Success and Revenue Expansion.

So I think lots of companies have realized that they need to introduce more of a scaled approach, meaning automation self-service. So what's what is broken about today's implementations of that model.

If you look at today's models of tech-touch, what are they really doing? They are sending automated emails and automated PDFs of reports. And when was the last time you opened an email or looked through a PDF and understood everything that the vendor was telling you? It's very hard. And that's why people rely on presentations being made to them and going deeper understanding what it is.

We tend to overwhelm our customers with 20 recommendations every day. You get a new, do this, do this, do that. At the end of the day, the customers turn off the emails that you're sending them because you're not sending meaningful content. You're just overwhelming them with content — the same thing with dashboards.

We overwhelmed our customers with dashboards. Now we are overwhelming them with emails and reports.

Yeah, that sounds very true, if I think about programs that I've seen other people implement.

So how do you take a working effective high-touch model and then apply some of the same fundamentals to a low touch model that creates a good experience for customers?

This is a great question. And I might add, it's not that straightforward and easy.

But the ROI is amazing! So in other words, even if you start with just a couple of use cases and implement them, you get a rewarding ROI.

If you step back and look, our customers have several interactions with our business. So all customer interactions have to be positive, whether you're talking to a salesperson, the CSM, support person, or have office hours with an exec. Or even digitally on the website or in your product.

Now, CSMs can maintain these intimate relationships with customers when you have named CSMs and a small portfolio of customers. The problem is you cannot replicate white-glove experiences in environments when you have several customers — from thousands to millions — especially when you don't have that many CSMs for all those accounts.

So automating even the top positive interactions or what the industry calls Moments of Truth or emotional experiences can be very financially rewarding.

For one instance, if you have playbooks that work for one-onone named accounts, consider digitizing the top few — these could be automated.

You could send a notification directly to the customer. You could send a notification directly to the CSM.
You could send an explanation. Ask the customer to fill some forms. So anyway that you can think of, but taking the top few playbooks that really work, you can scale them.

I must add not every interaction can be or should be automated. With several workflow-based automation tools — and I'm thinking of Braze and Autopilot that work very well for prospect marketing — you can take several complex multi-step interactions resulting from a playbook trigger and then automate them. So it's the same kind of philosophy, but what works for prospect marketing may not work for customer marketing.

Also, when you start, you don't have to boil the ocean.

A lot of people think let's automate everything. You don't have to do that. You can start by automating maybe just the QBR, or, what we call that the Digital Business Review or one playbook for a specific segment. And then, you can iteratively digitize additional playbooks or additional segments. But it's always good to start small, understand how your market responds, and then take it further. And very soon, you can kind of end up with your own sophisticated automated engine that works for your business and your users, freeing up CSMs to be strategic advisors — what they signed up for!

The concept of automating a playbook that comes from a high-touch model, I think, will be very attractive to both high-touch and low-touch segments.

Can you give an example of a playbook that you've seen automated in the high touch that's worked actually across both segments?

Yes. I'll give you an example — and also give you a problem associated with it.

When Customer Health drops a number, or you see it spike, we usually create automation going out to the CSM. And then the CSM goes in and looks in to the data and sees, oh, this was a false positive. But if you want to digitize that, one difference would be — yes, digitize based on Customer Health — but look at the metrics that made up that Customer Health. In other words, you have, leading indicators and lagging indicators — look at both — use a weightage or so, but it doesn't have to use the same thing that you use to calculate the CH (Customer Health) but look at various components to trigger.

For example, if the Customer Health score drops, two metrics may be canceling out each other. So you may never see that metric. But if you look at the metrics that make up the customer health, it's very easy to automate that particular part because you know exactly what to send to the customer or what to send to the CSM, depending on the use case.

Nice. And you've talked about, you know, when you're thinking about tooling for the low-touch model, you've talked about productivity versus automation tools, and you speak about them differently.

And I think a lot of people might think of them as the same thing. So what's the difference in your, in your mind?

I'm going to give you an example, but very broadly, before we go in, Slack may be an excellent productivity tool. In contrast, Braze or Autopilot may be perfect automation tools. Yes. Both are needed, but in the spirit of Thanksgiving, I'll give you an example.

So there's a group of us, five families, who feed the homeless at Glide Memorial Church in San Francisco every year. And there is a lot of food prep, cooking, hauling the food to San Francisco, serving, and cleaning. So every year, 20 chefs spend a lot of hours making flatbread. That kind of looks like tortillas, right? They may have the best knives, or the best utensils, to make them productive. But you think about it flatbread isn't even the essential part of the entire meal. I'm thinking about the meats, the vegetables, and the desserts.
So what we did is one of the years we invested in a tortilla-making machine. So instead of 20 folks making those flatbeds, one person could use this product to create flatbeds for almost everyone. And the remaining 19 chefs could focus on improving the quality of the vegetables, the meats, the desserts. And we added more items to the menu. And we got so many thank yous and blessings from the people.

So without productivity and automation tools, our CSMs are just flipping flatbreads.

Productivity tools save hours for CSMs, helping them do more with less. And you typically measure ROI as a percentage for productivity tools, but everything adds up right for using over an Excel spreadsheet may give you a 20% boost in productivity. And we talk about like 20% increase and productivity, which may mean like the CSM can support 20% more accounts.

But if you look at automation tools, obviously, they go beyond saving hours. You are helping every segment with renewals, expansions, recommendations, and a lot more.

These automation tools do require an investment in learning how to use the tool to maximize the gain. But you get a magnitude higher ROI. 10x to 40x increase in ROI is possible with automation tools like Braze and autopilot. That's for prospect marketing, but those are real numbers.

Again automation, however, is not for everyone. If you're making 20 flatbreads only, or you're just serving 20 accounts, automation may be overkill. And if you're just storing the data in Excel spreadsheets, maybe it is way too early for you to look at automation tools,

This might be related, or it might not. But, I'm curious what you're thinking is, how do upsells and cross-sells work in a low-touch model?

It is a very controversial topic when you say, "who should own the upsells and cross-sells"? We agree that renewals and add-ons usually belong to CSMs, but should upsells and cross-sells be with CSMs, or should they go into sales?

I've seen all extremes, and it usually depends on whether the company has a strong CRO or a strong CCO, and how's the relationship between the CRO and the CCO. And it also depends on how big are the upsells and cross-sells are. Cross-sells could be a totally different product and an upsell could be small or really big.

I've concluded that I'm comfortable with the "It depends" answer. It's not a cop-out because I've seen so many customers have different opinions at the end of the day.

It does not matter who swipes the credit card because the customer account is one.

So the last thing I would want is an account manager coming out of hibernation right before a renewal update, or CS teams become activated just a few months before.

So I think Wayne McCullogh his book, Seven Pillars of Customer Success, introduces these terms called up-telling and cross-telling, which is (by the way, I highly recommend that book) essentially, even though CSMs are not making the sale, they're influencing that sale. They're telling people what to get.
And so how do you — your question was — how do you scale that?

So the way you scale those up-tells and cross tells is by making relevant recommendations and making those recommendations, not to the entire account, but to the person who has the renewal authority, to the person who has the upsell and cross-sell authority. And it's just getting a little bit of data about your user. You can, instead of giving 20 recommendations to an account, you can provide two or three recommendations, a different one to the C-level guy, a different one to the VP operator, and different one to that individual contributor who's working on that email campaign. So all three of them feel that they got two or three recommendations that are very useful to them instead of people rolling their eyes on 17 out of 20 recommendations.

So look at this podcast; we are talking about scaling CS and post-sales. Several of your listeners may have questions and feedback, and they may want to connect directly with us. Similarly, we can scale post-sales by making inbound easier. We can show highly relevant and personalized calls to action or "Personalized Recommendations" to the right user at the right time in their journey of using our products.

The right time to ask for an upsell or renewal may be right after a positive Moment of Truth. Note again, Moments of Truth, according to Wayne, are emotional experiences or interactions we have had with our customers. The right call to action, coupled with a positive Moment of Truth, and personalized for the right user is what I am calling "Personalized Moments of Action."

So Personalized Moments of Action, are well thought through data-driven recommendations, driven by usage, personas, journeys, stage needs, segment and cohort, user-level desired outcomes shared when the user is engaged and has had a positive Moment of Truth.

Awesome. And Dickey, obviously you've spent a lot of time thinking about high-touch versus low-touch and how to make low-touch, a more effective overall program automation productivity.
So for people who are listening in, I assume that helps automate or helps companies roll out low-touch models in an effective way. So for people that are interested in learning more about your company, where should they go after listening to this podcast?

Yeah, you can reach me at Dickey Singh on LinkedIn. And so what does is, we automate several interactions that you have with your customers in the low- and the no-touch models. And we do that by using the concept of virtual CSMs, which are very similar to human CSMs but are focused on accounts where you do not have human CSMs.

Amazing. Well, thank you for joining us today for sharing your thinking about low touch. As many of us are planning and thinking about our low-touch models in 2022. So, I really appreciate you joining us and sharing your knowledge and wisdom with us today, and helping us level up.

Thank you so much, Chris, for having me — this was a wonderful conversation!

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