Guest: Dickey Singh – Scaling Customer Success with Automation

Guest: Dickey Singh - Scaling Customer Success with Automation
The Jasons Take on... Logo
The Jasons Take On...
Guest: Dickey Singh - Scaling Customer Success with Automation

Episode Description

Join us with guest Dickey Singh, CEO & Co-Founder of,a company focused on scaling customer success and post-sales.

Today we are talking with Dickey to learn how to scale Customer Success with Automation. We will explore new and emerging areas of automation, such as using advanced technology to offer on-demand, personalized automated business reviews. We discuss other opportunities, challenges, and implications for using automation tools to scale your CS reach and impact.

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Meet Our Guest

Dickey Singh

Dickey Singh

CEO & Co-Founder,

Dickey Singh is the CEO and co-founder of, a company focused on scaling customer success and post-sales.

Cast drives success, health, adoption, retention, and impactful outcomes for your customers and expansion revenue for you.

Previously, Dickey was the founder and CEO of two companies, and earlier, he was SVP of product, CTO, or operator creating customer-facing products at several venture-backed companies serving Apple, Google, Salesforce, SAP, and other customers. He has ten patents and lives in the SF Bay area with his wife, twins, and an English Lab Elektra.

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[00:00:00] Jason Whitehead: Hi everyone. And thank you so much for joining us today. I’m Jason Whitehead. One of your co-hosts of the Jason’s take on podcasts over here in sunny, Washington, DC. And I am joined by my co-host Jason Noble, the UK say hello, Jason.

[00:00:11] Jason Noble: Hello? I’m one of the other or the other co-host so really excited to be here for this podcast, talking about a really exciting topic, but I’ll let Jason introduce this and our guests.

[00:00:21] Jason Whitehead: Awesome. Thank you. And today we are excited to be joined by our guests Dickey Singh, who is the CEO and co-founder of, a really exciting company with a really neat tool to help customer success, move forward with automation and scale and do some great things. And we’re going to talk about scaling CS with automation and looking at everything from what are some automation tools and how do they help you to even some exciting things they’re doing with on-demand business reviews and other ways to continuously add back.

To the full automation engine. So really excited. I’ve had a chance to catch up with decay a couple of times now and love what he’s doing this organization. So I guess before we jump in Dickie, why don’t you go ahead and introduce yourself and tell us a little bit about your background, your company, and then what.

[00:01:03] Dickey Singh: Awesome. Thank you, Jason and everyone else over here. Yeah, I’m digging saying, as you mentioned, and I’m the co-founder and CEO of gas startup, and GastroDigest is laser-focused on scaling customer success, renewals, expansion, advocacy, and everything that goes with customer success, but using automation.

So we have an automation tool and happy to talk more. That’s great. Thank

[00:01:30] Jason Whitehead: you. To kick us off here, we often hear people talk about scaling with automation or at least historically in the CS space. I think a lot of the go-to assumption has been that it’s going to be low touch, digital touch, a lot of automated emails or in-app engagement, like surveys or videos or links to help that.

Yeah, or those kinds of things, but it sounds like we’re moving beyond that now. And in your website, talked about automate personalize and humanize every user experience and interaction throughout the user journey. And I thought that was really an interesting take because in my mind, that’s very different than just sending off some automated emails and moving things quicker.

Can you tell me a little bit about what you mean by this and what does it look like? And how’s this different from what we typically talk about CS and what is the new version of sales

[00:02:12] Dickey Singh: automation? Yeah, actually great question and diving right in. That’s amazing. If you think about it how often have you opened an email that was sent to.

Or how often have you opened like a PDF or a report that was emailed to you? And I’m talking about like in a traditionally known one too many, right? Yes, we do open emails, but our vendors are like, we tend to overwhelm our customers with so many emails and so much information and we want to try to cover every point.

Like I want to give you 20 recommendations. I missed one or so. But the problem with that is, is the same problem we had with dashboards. Why don’t executives was their dashboards because we give them eight tabs. We are showing. Pretty graphics per tab. And we tend to overwhelm our dashboard users.

And then we tend to overwhelm our users with like email. So how we think of it is instead of overwhelming our account or sending the same thing to everyone at the account, why can’t we personalize this for each user and account? The reason I say that is the needs and the. Oh the outcomes that a CEO or a C-level person desires versus a V level person or an operator, or an individual contributor desires are like totally different, right?

The individual contributor may be focused on, Hey, how did my email campaign go? The operator may be focused on how is this business doing versus this business doing? And the C-level guy is usually focused on the. Or, all those kinds of things like, am I getting the ROI? And once you, we all know, once you solve that ROI, problem renewals become a no brainer.

[00:03:48] Jason Whitehead: Yeah, th that’s interesting too, because you’re talking about the different user roles and levels where I think a lot of times when I hear people talk about automation they talk about low touch and high touch and medium touch.

Oh, ready. You’re looking at this, I think in a different way.

[00:04:00] Jason Noble: Yeah. I think the really exciting thing is it does apply. We’ve saying at the beginning, we want to carry the preamble. It applies to any type of customer, and this can add value to any customer. I think automating and adding this intelligent automation to the right parts of the customer journey is critical and it applies to every single.

And I think one of the key things I’d be interested in getting your thoughts on Dickies. I know you guys offer some services where you automate business reviews or on demand business reviews. How do you go about doing that? Cause that is something that a lot of companies spend a lot of time and effort preparing them to, to your point that sometimes they’re not read the information is not looked at, but how do you go about automating that and putting that information?

[00:04:41] Dickey Singh: Yeah. Another great question, right? QPRs and EBRs are, the TBRS for the stakeholders and EBRs for the bosses of the stakeholders. That’s how I think of them. If you think, there are two or three problems with those right. One there we hear from our customers, they are infrequent.

Yeah. Because are quarterly or yearly. And then we stayed there too long, 45 minutes to 60 minutes. And then we have a date. Which says that the C-level people stop showing up for QBR after the first two, the V level structuring. And after the first four, and then you are, again, talking to the champion who helped you create that QBR in the first place earlier in the day.

So what we are thinking is we started calling it a traditional business review, which is two to four minutes. Just it’s to the point, it’s the right message to the right person at the right time of where the user is in the journey. Not notice. I did not say customer is in the journey.

User is in the journey. The reason I’m saying that explicitly is because when a new hire comes in, they need to be like drained. They need to go through the adoption. They need to go through the same retention cycles. So these digital business reviews are automatically generated from data.

We go depending on how mature the organization is like larger organizations that have a data warehouse. We get the data directly from our data warehouse, or anyone can get the data from the warehouse, or if they don’t have a date of arrows, you can go get it from a customer success platform, the CRM platform, your Zendesk, or whatever ticket management system and your advocacy platforms.

You get the data. Put it together as a digital business review, but it doesn’t stop there. Digital business review is interactive. In other words, when you show some information to a user and we show it as a recommendation instead of thinking of like an absurd or across a, or anything similar.

When they take an action after you show them something, it gets recorded directly in the same system of record, where we got it from. For example, if they are interested in learning more about an recommendation that you made, oh, you should look at these features, they click on it, it gets recorded into your CRM, said this person has addressed it in this feature.

So it becomes like a more end to end system versus just a QBR that you do. Once a quarter or EBR once a year, something like

[00:06:58] Jason Whitehead: that sounds fascinating to me, it seems a couple things come to mind with that. One is that it’s that concept of microlearning. And just in time, here you are a small enough chunk that trying to get a C-level executive to a 30 minute meeting or an hour long meeting on a regular basis is a challenge, but give them some, Hey, can you spend.

Four minutes between meetings, just to prep for your next one about this would be huge. A lot of the work consulting work that I do and have done over the years has been working on with buyers of software. And, half of my business is customer success. Half is hands on with the buyers of software to help them drive adoption internally.

And one of the things that we routinely have to do is help the executives figure out how they’re going to monitor and then drive effective usage of a platform within their own organization and cascade that down. And many times they’re like, all right, I can put it on the agenda for my meeting. And I have a weekly meeting with my team, but I need to know.

Before that what I should be asking them where I need to get, go, and I could see arming them with this kind of information, three minutes before my meeting, I can come in and see what I need to see and have a more effective meeting with my team to cascade from my organization. I could see where that’d be a huge thing a, in a very dramatic change from what I think most CS teams are doing today.

So it’s,

[00:08:04] Dickey Singh: it’s exciting. And I’m nodding my head over here because product adoption is not about adopting for the users of the system is also for the people who are paying for that system, the economic buyers of the executives. And all right. So once you get them aligned about the usefulness of the product, they will make sure that the.

The individual contributors or ever have time to adopt the product. So it still comes up.

[00:08:28] Jason Whitehead: Yeah. And when I keep finding is the, if you can give the executives clearer evidence and clear actions that they can take to make sure they’re solving their underlying business problem, that’s what’s really going again.

They don’t care about adopting your product for the sake of it. They care about it for a venue to solve a business

[00:08:42] Jason Noble: need that they have. I think that’s something that’s often overlooked. You make a good point there document it. Isn’t just about. User adoption. It’s about adoption of what we’re trying to deliver adopting.

How are we going to help them address their outcomes or get to their outcomes? And there’s too much focus quite often on just the user analytics, how are people using this? What does that mean? And I throw organizations that I’m a customer of, and they’ll just send me usage information and it doesn’t tell me anything.

I want to know, how is this helping me get the value and I’m expecting for me,

[00:09:13] Dickey Singh: Exactly. And the other beauty of this, which I forgot to mention this it’s asynchronous, right? So you don’t have to all come together and resume or a meeting or inverse to do this. You can send this and someone who wakes up at five for an exec, they can watch it at 5:00 AM.

Somebody can like, watch it at like midnight or whatever the scenario maybe. Yeah. That’s huge.

[00:09:33] Jason Whitehead: I’m wondering as you help organizations automate their CS platform or program, I should say. The go-to instinct has typically been, oh, that’s a low touch or a digital touch approach. And is that, how does automation, especially some of the things that you guys have worked on or seen over the years fit with meme and high touch customers as well too.

And do you have people typically come to you and say, I just want to automate my low touch. They don’t realize they can do it for medium and high touch, or how does this typically work?

[00:09:58] Dickey Singh: Most organizations. So when we talk to customers, the first thing we try to figure out is like how they’re segmenting their user base or customer base.

And and depending on like how they’re like segmenting it we answer the questions differently if they’re using like a traditional approach, which is ARR or potential err, based then they would have. A lot of some accounts in the top, which are paying them a lot. And there they have like CSMs named CSMs or so.

So if you take and then that could be anywhere from companies like pipe drive and Google and notion that’s as small as a two to 400. And whereas, if you look at some other companies, they have 60% of the customers are in the top tier and it depends on what ARPA or what annual revenue you’re getting per account.

So the smaller the are the bigger, the low touch, medium touch and no. Sure. So we tend, we always start with let us help you with anything. That’s not named accounts, which is usually low touch, medium touch, and no touch because that’s so easy for us to show immediate value for the no touch and the low touch Lot of customers we ask so what are you doing for the, so note notice a lot of times they say nothing and let’s say the cost of doing nothing versus doing something what’s the difference.

And they immediately understand what the advantage, and then it’s easier for us to sign them on with at the end, There are several customers who segment very differently and I’m going to plagiarize some of the stuff that Wynn McCulloch has put in his book, which is you put like wages and you put not other factors, just like how you calculate like customer health, you calculate there may be a big customer like Coca-Cola or so they may have.

So many employees that they don’t need that much customer success going on, but there may be a very small customer that may need it depending on how you segment it. We can tell them like where you should start, but everyone kind of starts with a digital business review of some sorts, which is interactive and moves on to a full automation engine because they learn more.

And when they move on to a full automation engine, a lot of times they involve the top tier What they say to the top tier is different to what they say to the other tiers. We were talking about a low MIDI. No, And who the message goes to could also be different and that I’m going to make it clear.

So we send typically you should send the conversations to your customers where they are like, for example a user who logs into the product, show it or. Whereas an economic buyer or an executive who will never log in into a potential product, right? Stop talk to them over text, talk to them over email or slack or wherever they are.

What, but having said that you can also send these notifications or whatever to the city. And that works great for the high-touch deer. You send us so that he or she has stopping points immediately and they can conveyed into to their customers using their own PowerPoint or using their own ways of communicating as an email, or how would they do,

[00:12:58] Jason Noble: What are some of the other, the on demand business reviews that the kind of automation that is a huge value add, I like the idea of digital businesses.

But what else can people do organizations do around automation that can really help scale customer success, both in terms of kind of the reach of your customer success teams, but also the impact. And I think the reach is always a challenge, as businesses grow from one to two to three to 20, 30, 40 customers that their revenues go up, their ARR goes up.

Is it all about adding more CSMs or is there a way that we can use automation to scale more efficiently, still drive value for customers?

[00:13:34] Dickey Singh: Yeah yeah it’s not about always adding more CSMs because it does not make financial sense. At CSM, especially for the segments, we’re not paying a customer back much.

And that’s why you see executive sponsored on the top. And then you see like high-touch, which is number two. And these two have like CSMs assigned. And if you are a company like Palentier or a big company, a $22.5 million contract with the NSA. You can assign, sorry about that. But you can assign six CSMs to the same account.

You know what I’m saying? Whereas if the customer is like paying you tens of thousands of dollars or so it may not make sense to assign a CSM and they can use automation over there. But when the automation is too dumb to solve a problem, bring honesty. Or bring on a specialist or in the capacity of an advisor, right?

That’s what the CSMs are headed to. Instead of doing all the grunt work, they are becoming advisors. So you can do that. Did I even answer your question?

[00:14:34] Jason Noble: You did. And I loved the way he finished. Cause Jason is something that we’ve spoken about before. The idea of it’s not a customer success manager, it’s almost a business value concept.

And you can then get into the whole debate about whether I, as a customer would pay for a customer successful. If you’re driving more value for me getting that value. Yes, I would pay and it becomes miss, like our last podcast. It becomes a real professional service that there’s a lot more volume with it.

So you absolutely answered it. And I love the way you finished that.

[00:15:04] Jason Whitehead: Yeah. So Dick, as I’m listening to you, I’m also

[00:15:06] Dickey Singh: just thinking about how would you

[00:15:09] Jason Whitehead: position like the Texas CS automations and. Digital business reviews and the other things that you’re talking about and that you guys focus on versus some of the things more like the traditional CS automation platforms, you have the gang sites and the, this and that other world.

When should a company start with this type of automation that you’re talking about, is this something, Hey, you’re an early stage startup, we’ve got a little bit of funding. This will help you scale without adding more headcount, more CSMs, or is this more of a situation? You need to have your program established.

You need to have things pretty much solidified what you want to do, and then you’re ready to scale it and automate it more now that you know what you’re doing and how you’re going to do it.

[00:15:43] Dickey Singh: There’s no good answer for this, but I can divide it into segments, right? If you are a product leader, The company you are already thinking from day one, how you’re going to automate this.

Why? Because you’re going to have like hundreds of thousands of customers to millions of customers. So you have to start thinking of scale, but whereas if you are like sales lead, and then you have higher ARPA, then you were, you’re thinking about okay, having CSM. Early on for the larger accounts, but as you grow downmarket into SMB or other, you have to think about like automation, but for for the first one we have customers like who.

20 customers, 25 customers. And they’re thinking they’re talking to us for the second one. We recommend like anywhere between two 50 or higher customers, or so to think about, start thinking about automation. And again, as I was saying there’s it’s a mindset kind of thing, right?

If, once you have enough CSMs, then any problem that’s shown to you, you will try to solve with the same hammer, like address it. Whereas if you have like a productivity tool or an automation tool, then you tend to solve those problems with the tools that you have. So that’s why PLG companies think of it like very early and other companies, like when they get into a, when they get into like smaller accounts, they start bringing on.


[00:17:07] Jason Noble: yeah. W we’re seeing kind of automation, AI popping up in a lot of different business areas, and there’s a huge amount of investment going into it. A lot of new ideas and visions that are coming from it, but there’s absolutely been a nice trending customer success customer experience, and really helping customers.

I think self-serve, I never liked the idea of self-serve just as a concept, I think but there’s a better way of doing it. And I think AI is helping us. But there’s lots of other business areas as well that really adding value back for CS, or you a, you guys looking at other areas of the business as well, and be really interesting.

Your thoughts on what other business areas might have impact over the next couple of years. So let me,

[00:17:47] Dickey Singh: let me. Sorry. Yeah. So AI in my mind is our toggle to whatever view, whatever anyone does. I don’t think we should. At this age, 20, almost 20, 22, we should talk about whether somebody wrote the program or somebody took some training data and looked at the outputs and like use that to like train clean the train they’re using.

Or so I think we use in our product, we use a combination of AI and manually coded stuff. So that’s how everyone is doing it these days. But so let’s take the ad take like customer health calculation. You can do it. Like rules-based why, how we can take the leading indicators.

The lagging indicators apply some wastage and add them up and you can have a composite score Salesforce users, 128 variables and, wages, which they keep tuning every now and then there are other

[00:18:41] Jason Noble: companies isn’t it.

[00:18:44] Dickey Singh: That’s why they haven’t been able to productize it. If you think about it, right?

They keep tuning it and they’re using data scientists and all those kind of things. And there are other companies who say Hey, if a company uses feature a feature C and feature E. They’re adopted, there’s no way they’re going to leave. So they use that kind of preference.

And then there are yet a third category of companies who say, okay if you look at all this variables and and these and these guys kept on renewing what was common between them. So use that data, like train their models and come up with. And there’s a fourth category, which I won’t go into. It’s like self supervised learning and all where you easiest way to explain that is cat’s eyes will always be above the nose, right?

So you don’t have to train a system. It can just train itself. It can get the signals. If I’m going too deep into it, I stopped me. But. Yeah. So you can claim that the system can train itself. Which is and I’ve written a paper about that in MIT. So that’s why I’m referring it but that’s the future, right?

Just looking at the data and like self supervising and like creating those things. I think that’s where we are going to head to not only for customer health, but also for like segmentation or other things that we do for every customer facing product, not just instance.

[00:20:00] Jason Whitehead: Yeah. It sounds like there’s a lot of exciting things that are happening and will continue to happen, where do you see automation having the biggest impact next two to five years? And where should companies start? Where should you know, we’re thinking about it. We’ve got a certain amount of CS expertise that we’re getting ready to scale. Where do we go for it?

[00:20:14] Dickey Singh: Yeah, so I think again, if you’re a PLG led and if you have like low ARPA-E customers, you need to start thinking very early on.

But if you have customers who are providing you a lot of toddlers and everything start with CSMs, and when you go into a smaller accounts, you can think about automation at full scale, but also remember. Both of you mentioned earlier automation lag or ritual that is not just for the low touch or the note touch it’s form the entire customer base.

How you surface it could be different. You surface it directly to the. To the customers, or you surface it to the CSM or you automated and like the customer takes care of it. A CSM is notified. So there are so many ways of surfacing insights and bringing it to the customers, bringing recommendations to the customers.

[00:21:03] Jason Whitehead: Right? Absolutely.

[00:21:05] Jason Noble: I think what we always like to do, like a huge, thank you for this. This is I’m, I, for one, I’m going to have a look in more detail at kind of what you guys do. The app itself. I think there’s a massive value to organizations. I know. And this has been a great conversation. What we always like to do with our guests at the end is give them what we call a bowl challenge question.

So really this is a non rehearsed. We want to give you a question. We’d love your feedback on this and the kind of question we want to give you. What are the bold actions that customer success or business leaders should take today to quickly use automation to scale their reach and impact within customer success?

So what are really those top few key actions that they can do?

[00:21:45] Dickey Singh: I think they should understand the difference between a productivity tools and automation tools. And that the reason I say that is productivity tools will bring you like like a percentage improvement, right? Like you said, Certain productivity tools, you get a 10%, 20% improvement.

But if you look at companies like braise and autopilot, which is for like prospect marketing, not for customer marketing. But but if you look at them, you get like a return of 10 X, two 40. We had to stand next to 40 X compared to 15%, 20%. So considered the tools that you want to use and have, and don’t be afraid to try newer ways of communicating with customers and we, and then also don’t overwhelm your customers with data, actually send them less information, but more meaningful information.

And by that, I mean is if you’re already sending an email to them, Why can’t you just attach a digital business review at the end of it, right? Or things like that, versus as like creating a new email for every interaction that you have with the customer or sending them a text or sending them anything that you want to do or showing for example, all our digital access platforms adoption platforms, rather, you can show all the digital business review directly in the product as a button or embedded within the websites, all those things.

[00:23:08] Jason Whitehead: Wow. I think that’s great. And I love, taking some chances and try new ways to engage with customers. So you’re going to find some things that really work better than you thought they would. And you’ll learn a few things that probably didn’t work as well as you’d hoped. And the only way to do it is to take the bold action.

So I think that’s great. Dickie, thank you so much for being here and being with us before we go, we want to. It did give a shameless plug for your company, your product, your tool. I can tell everyone out there too. I saw a great demo of it and was blown away by what you guys are doing.

And you immediately see where this can be extremely valuable to a lot of folks, but we’d love for you to add your own shameless

[00:23:39] Dickey Singh: plug. Yeah, actually just, was it. And or connect with me on LinkedIn I’m Dickey Singh. And then you can sign up for a demo or you can sign up for a forever free version of that you can use for your customers. is the website to go and.

[00:24:00] Jason Noble: I think that’s the best plug ever sign up for free forever version. Absolutely love it. As Jason said, look around, this has been really cool, really exciting conversation. I really look forward to it to see what you guys do in the future. Thank

[00:24:13] Dickey Singh: you, Jesse. Nice to be here with you.

Thank you, sir.


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