AI-Driven Digital Customer Success in App Form
The Digital Customer Success Podcast
Hosted By Alex Turkovic

With Guest Dickey Singh, CEO at
Reproduced here with permission

Watch on YouTube

Listen to the podcast on Apple Podcasts or Spotify

51 minutes.

Listen on Apple Podcasts
Listen on Spotify


(upbeat music)

...Talk about numbers, talk about things that matter to him.

Every user at the same account should get a separate subject, separate body, separate email, separate actions.

Because at the end of the day, you're trying to communicate as a digital CSM to them, not as customer marketing.

We want to send emails and texts like how a human would write, "Hey, I'm concerned about this. Your number dropped by XYZ. Do you wanna talk to me about this?"

Put that as part of the subject.


And once again, welcome to the Digital Customer Success Podcast with me, Alex Cherkovich.

So glad you could join us here today and every week as I seek out and interview leaders and practitioners who are innovating and building great scaled CS programs.

My goal is to share what I've learned and to bring you along with me for the ride so that you get the insights that you need to build and evolve your own digital CS program.

If you'd like more info, wanna get in touch or sign up for the latest updates, go to

For now, let's get started.

Hello and welcome back to the Digital Customer Success Podcast.

It's so great to have you back for episode 40.

I can't believe I'm saying that, but it has been 40 episodes since I first said hello to you.

And today I'm bringing you an off-cycle extra episode for the week with none other than Dickey Singh of

You will likely have heard of Dickey before because he's very active in CS circles and is CEO of, which is such a cool platform because it is one of a few emerging AI-based and AI-driven CS platforms out there.

And it's essentially digital customer success in app form.

So we have a lot of great conversation about digital CS, but also personalized motions and the future of AI, current state of AI, such really great and timely information in this episode that I just couldn't wait to share with you.

So please enjoy this conversation with Dickey Singh of 


Just aged myself. (laughs) - Same here, man.


Yeah, I remember very distinctly sending my first email.

I was, I don't know, I guess I must've been in high school maybe or something. (laughs) And I remember sending it and calling my friend that I'd emailed and say, "Hey, did you get it?"


(laughs) - Nothing has changed.

Now you would text him, "Hey, did you get my email?”


'Cause you sure as shit ain't reading it. (laughs) - That's funny. - Well, Dickey, hey, I really appreciate you coming on the show.

It's a pleasure to have you.

I know we had to reschedule a couple of times on my end, I think once on your end. - Yeah. - But we made it happen and I'm really excited because not only are you doing awesome things for the CS community, but you have just a crazy background as well.

And I wanna dig into that a little bit, but welcome to the show. 


Thank you so much, Alex.


Yeah, for sure.

So speaking of background, I do wanna kind of maybe rewind the clock a little bit.

You spent some time at MIT.

From the looks of it, you did some cool stuff at MIT. 


Yeah, I did an AI course over there before all this new stuff that came out and learned a lot, right?

I mean, we wanted to use AI everywhere.

So, yeah.

I'll tell you more about it.

Like, right now we are using AI as an assistant, right?

So then we're talking about using AI as a peer.

Then we're talking about like using AI as a manager that manages me.

And then there were even like things like distributed organizations, right?

Like the AI would run the organization and it'll just give you tasks.

And there's like distributed organizations and all.

So we were very futuristic and we thought like, you know, this is 30 years in the making.

Then OpenAI came out and everything, like in six months, seven months, right?

So things have changed. 


- Yeah, crazy.


And you know, everybody kind of thinks that the OpenAI thing was like, it's like the first thing that is AI, but it's, I mean, there's a long history there that has led up to this event in history, right? 


Absolutely. (laughing) We were using OpenAI obviously before it became popular and other, we used like four or five different services models.

And we ended up like training OpenAI with a whole bunch of stuff, right?

Like we said, like, you know, our CSMs don't know how to write SQL.

Why can't they just describe it in natural language?

And it will, hey, it'll connect with GainSight, it'll connect with Salesforce, it'll connect with Snowflake and write a query across platforms.

And the CSM just has to look at the results of the digital CSM in our case.

Has to just look at the results.

If it looks fine, click a button and it'll be used to gather data, right?

So we ended up doing that.

We had to train it quite a bit, but now it's available to everyone because, you know, I guess we didn't have business accounts at that time, right?

So, you know, early on.

So whatever you train, it's available to everyone. (laughs) 


Yeah, exactly, exactly.

Well, so tell me a little bit about your, I guess, what led you up to, I mean, today, you're, you know, very well known in CS circles because of CastApp that, you know, you're founder of, been about like four, but you have this crazy rich history of engineering and product leadership across all kinds of segments, right?

And I'm curious to get your take on kind of what led you down this path.

What was the evolution to get you into, you know, serving the CS community with software? 


Yeah, so my background mostly been like, you know, like an SVP product or a CTO with six or seven venture-backed companies in Silicon Valley.

As I said, like I've been here since '95 and before that I was in Virginia.

And naively I had no idea about customer success before I started Cast.App.

And I think that helped in a way as well, but there are like two stats that I read that kind of were in the back of my mind, right?

75% of the revenue of most companies comes from existing customers.

And there are like eight to 10X more tools for pre-sales.

So it's like, you know, the exact opposite, right?

73% in Salesforce, 75% in UiPath.

Like you look at Slack 75%. Look at any company, look at PLG companies or SLG companies, it's the same thing, right?

So, but the number of tools you sell to pre-sales or to salespeople is like 10X more.

So I always wanted to like understand it more.

So, you know, what I did is like, I bought every book on CS and on Post Sales, like, you know, read them cover to cover, made yellow marks all throughout.

And I tend to like read the books again and again, like, you know, because sometimes I'm like, oh, I missed this or something.

No, that's absolutely wrong.

That doesn't work.

That's like, he's just, the author is just selling the company or just selling his services, right?

So that's not.

So I always kind of thought that way.

But then something interesting happened.

I was just having lunch with my, one of my ex-CEOs at CustomerSat, where we kind of mostly served customers like Apple, Yahoo, Salesforce, BEA, WebLogic, AMD, and those kinds of companies.

And he mentioned something, about Mary Alexander.

And I said, oh, she was a board member.

So he said, yes.

So I said, I want to meet her.

And I had lunch with her.

And then she told me she formulated, or she pioneered, or coined is the right word, customer success in 1990 for Vantive CRM.

And, you know, and I read all the blog posts from everyone, like, oh, Salesforce, this is, I didn't believe her to be honest, right?

Then she followed up and connected me to another person.

And he was her indirect report, like maybe two, three levels down or something.

And he shared with me his customer success manager business card.


He showed it to me, like it was like, you know, in a bad shape, yellow and all that stuff.

Then I said, okay, she's telling the truth.

So basically, so I got together with like a few executives and I did, what did I do?

We did an interview with her and we kind of actually posted on our website,, you have to find it.

It's pretty interesting is, even in her mind, it was a way to add revenue, not just service the customer.

And it's like full circle after so many years, now it's going back to talking about revenue.

Even if you're not selling or upselling, you're influencing the sale, right?

So that thing was pretty, to be honest, yeah, that's how I got to know CS from her original experience.

I always thought it's about like doing better for the customers and doing better for the teams, right?


Yeah, yeah, that's a cool genesis.

I like that, where literally you started with the genesis of CS.

I think a lot of people, you know, work backwards into that, but yeah, that's really cool.

Well, you know, so fast forward to today,, pretty well known.

The reason why I'm crazy excited to speak with you is because essentially what you're doing is digital customer success in app form, which is very just like meta and cool.

But like, and so this is a question that I ask all of my guests, right?

Which is this notion of what is digital customer success?

Because it varies from absolutely everybody I talk to. 


Yeah, that's an interesting question.

I think it's, whatever the company is selling is digital CS in my mind, right?

Like that's how most people think of it.

But I mean, it could be webinar software, it could be like community software, even email marketing, you know?

So I guess everyone's jumping into the bandwagon, but seriously, I think to me, digital CS is, using technology to help customers and even the customer success team members to grow and preserve their revenue—but, here’s the kicker—with a magnitude higher speed, accuracy, reliability, consistency, and scalability.

And by magnitude higher, I mean like 10X, 20X higher.

And that's what advanced automation and AI really get you, is like, you know, our customers have like, I'll share with you later, I guess, like 30X ROI on some of the products.

I mean, we take the credit, but at the end of the day is like combining automation and AI and making sure that your AI does not hallucinate.

We spent a lot of time doing that, but we'll talk about that as well. 




I personally see digital CS as three things.

One is the very simple one to many, even like a blog post or infographic, or even a webinar or a webcast that you do, you do it once you share it with multiple people.

This podcast is two people talking and sharing it with multiple people.

And the second is what I kind of started calling many to many, like early on.

And there are just two things in there.

One of them is multiple people helping multiple people, like communities.

And the second thing that's becoming really popular these days is customer and customer success manager collaborative wikis.

In other words, they would write some posts, the customer would comment on it, the other CSM would comment on it and end up becoming like a collaborative article.

So that is many to many.

The third is what we are doing, which is, which is going back to the roots of customer success, which is one-on-one personalized digital experiences for customers, but one-on-one.

In other words, if I'm talking to a C-level executive, my tone changes, my conversation changes.

When I'm talking to a CFO, I'm a little bit more professional.

I'm talking about ROI.

When I'm talking to a CCO, I'm talking about like ROV or things like that.

But when I'm talking to a user, I'm talking about, hey, learn this, do this, watch this video. And surfacing and making summaries of those blog posts and showing it to them, that's what we do.

And then also when you talk to a power user, like don't teach them how to click the mouse or anything.

Say, hey, you have too many users in your SMB segment.

You should sub-segment them.

And don't believe in a single segmentation model.

Have several segmentation models.

It's okay, can handle it.

So those are the kind of things that we talk about. 


Yeah, I love that.

And it is really kind of one of those kind of golden opportunities in digital is to get to the point of sophistication where you can be persona-specific.

And that's hard.

It's hard to get to.

You know, you gotta know who your users are and you gotta have some data to support that and all that.

But once you do it, it's so powerful. 


Yeah, I think persona is the most important thing you can talk about when you're talking to people.

But one advice that I figured out is don't go by titles.

And the reason I say that is an SVP at Salesforce may not have that much authority, but like a head of customer success at a very small company would have a lot of authority.

So it's a different thing.

Don't go by titles, go by responsibilities, go by roles.

Go by user profiles, right?

Like go by interests.

And then we use all that data to like figure out behavior.

Like, you know, we have so much AI built in even to our player kind of thing.

So if we notice that someone always skips over support slides or something, we move that away that they can click on and access it, for example. 


Yeah, so, you know, making it intelligent and really specific to that person, that's super important.

You know, in a previous episode, I had a really great conversation with Dan Ennis.

I don't know if you're familiar with him, but, you know, he's been doing some pretty amazing work around data analysis of specific personas where he's essentially building a data profile of what an admin might be versus what an end user might be versus what an exec might be or whatever.

And then applies that across, you know, the user segments to where he doesn't necessarily need to like ask them or know for sure what they are, but based on, you know, their usage and their behaviors and things like that can get a pretty good sense for, you know, what the persona is.

And I love that level of sophistication.

It sounds like y'all are cracking that very similar thing. 


Yeah, yeah, absolutely.

And the only thing I would add, don't go by titles, go by responsibilities.

Like a CEO of a startup would do support and customer success and bring good rights for the team. 


From mopping the floors to signing the checks. 


Yes, there you go. 


Probably at the same time too.

So I wanna get a little bit deeper into Cast because, you know, I don't like to kind of, I hate having founders on and then basically tell them what their app does.

I'd much rather hear it from the founders themselves and kind of, you know, and let you kind of, you know, speak about not only the genesis of it, but at its core, what are you solving for? 


Yeah, what we are kind of solving is, we only see little like two major problems for every B2B company.

It's a huge thing.

They're like—before I say that, there are three types of companies.

Companies that are very simple products.

They don't need CSMs.

They'll never need CSMs.

It's a very simple idea.

They will just build it into the product.

And these are like young PLG companies.

And then there is the whole mass of B2B companies and SaaS companies, which kind of rely on CSMs and account managers and subject matter experts to provide, you know, adoption and usage and, you know, sales and upsells to customers.

So that's what we kind of focused on.

And the last category is companies that take like nine months to deploy and they have an army of professional services, technical services, and all those kinds of things.

And so, so we are kind of focused on the middle, which is luckily 95% of that 5 million B2B customers.

They're 5 million B2B companies.

So, so we're trying to help over there.

And there are two things we realized 

The CSMs and account managers, each have too many accounts.

On the other hand, not every account has a CSM.

So we are just trying to solve those two problems.

And the way we did it is we think it's very unique, but you know, everyone has his own opinion.

So in the traditional way of doing customer success, you put a customer success manager in between the customer and the playbooks and the data, and you need a CSP tool, you need CRM tools, you know, support tools.

So what we did is, what if we could elevate that CSM to a more of a consulting role, and maybe so he or she can focus on relationships with customers and new challenges, and in his place, bring in a digital customer success manager, or an AI driven digital customer success manager in our case, who executes playbooks, digitizes playbooks, executes playbooks, and communicates with the customer in the manner that is approved by salespeople or the VP of sales is approved by the CCO, and uses like automated benchmarking to upsell and cross sell and uses like things like, hey, customers your size, use these four features, you're only using three.

Do you wanna talk to your CSM Scott Adams to see if they wanna, you know, learn more about this, or same thing for sales, right?

When you use competitive benchmarking, so that kind of comes for free with our product.

So what we are solving, just two simple use cases, a digital business review with a purpose, you know, what good is a digital business review when you cannot upsell, cross sell, or recommend products, right?

So, and then advanced onboarding, which includes like pre-boarding prospects, onboarding accounts, onboarding users, onboarding different personas differently, re-onboarding a previously bundled product, when a new hire happens at your customer, onboarding the users again when the account has already been onboarded.

So the more complex the onboarding, that's where we kind of come in.

So two simple use cases like a digital business reviews could that grow and preserve your revenue, and accelerating value realization through pre-boarding, onboarding, re-boarding, and even off-boarding, although we don't have a single customer that's using our off-boarding part.

So. (laughs) 


I love that so much because it speaks to what, you know, digital CS has kind of evolved to over time.

Whereas, you know, and regular listeners will have heard me talk about this before, but like, you know, a few years ago, the notion of digital CS is, okay, we need, you know, this thing, and of customers.

And that's definitely evolved into what it is today, which is to say, okay, yeah, we're doing a lot of customer facing things, but a big part of it is automating things so that your CSMs can be more strategic, provide more value, and less time doing like the mundane things, sending the same emails, like doing those kinds of things.

And I love that you're fitting right into that level of kind of sophistication and automation to where it is removing the burden so that your CS, I hate saying can do more with less, but can be more valuable with less, I suppose. 


Yeah. (laughs) Yeah, people have started hating that term, right?

Doing more with less, but you know, I guess efficiency is like built in, right?

So yeah, absolutely. 





And you may have heard of that term, like, you know, death by campaigns, right?

What that really means is like, you have to write your own campaigns, and the campaigns that the customer marketing team wrote versus the campaigns that the CSM is putting together or versus the campaigns that the marketing department, they don't talk to each other.

Even your four campaigns don't talk to each other.

Now, the biggest problem with such environments is like if the campaigns don't talk to each other, you're sending too many emails, too many things.

And if you upsell or cross sell in an email, you're gonna be banned as a spammer, right? 




Because, you know, and then you get like, start getting really poor results.

So the trick over there is to not upsell and cross sell in an email, but like take them into an environment, whether which is in-app or out-of-app, via email or text.

So the executive does not have to ever log in? 

If the executive has to remember how to log in, you're not gonna be able to reach a CFO or a chief administrative officer.

I'm trying to say it's like non-line of business executives who are very influential, whether to keep their product or not keep your product.

If they don't know about ROI or ROV, they're not gonna continue that.

So that's the underlying thing.

Like, you know, instead of asking everyone to come into your product, just so that you can claim like higher monthly active users or daily active users, what if you could take the product to where the user is?

If they send an email or text, reach them over there.

If they log in like power users and users, show them in-app kind of thing.


Yeah, it's interesting too, that executive persona, nine times out of 10, they're not gonna be in the app at all.


Like they're not your users, they're not your intended kind of audience for regular users.

So why expect them to log into the app just to kind of see how things are going.

And one thing you hit on that I think is something that is very often overlooked is text messaging and SMS.

I don't think a lot of people are doing that because I think there's an automatic assumption that it's kind of creepy or it's invasive or whatnot.

My argument has always been that if someone wants to be communicated via text or if somebody wants to be communicated via email or whatever it is, or Slack message, like we should give our customers that option so that if they wanna be communicated with text, they can be, but I think that's for a lot of people. 


Yeah, you're absolutely right.


So it's one distinction that we like to make is like, let's say you use HubSpot or so for email marketing.

You don't have a relationship with the people that you're sending your mails to.

When you are talking to a customer, you have a relationship with the people.

They're like kind of opted-in in your terms and conditions that you can communicate with them.

So use transactional emails and that's what we do.

And honest to God, we get like minimum of 2.1X to 4X the industry average when we send out conversations.

Like, we can HP, they use CSP platforms, but send emails to us, Pure Storage, Aruba, same thing.

So the interesting thing is in the presentations or digital hubs that we generate and send, we ask them, would you like to opt in for getting text?

So you have to do an opt-in.

So what we notice is like C-level execs prefer text, whereas operators and everything prefer email and users and power users prefer to just log in into the product or so. 


It's like a no brainer, but there's a huge aversion to that.

I don't really get that, but I think it's extremely powerful because your executive, they've got their phone like all the time, right?

What do you recommend when folks are setting up the system and doing those kinds of things?

Do you make recommendations on what they should send via SMS versus email? 


Yeah, you let your end customers choose SMS, but you reach out to executives over email, but give them an option to switch to SMS.

But then the campaign should also change.

As I was mentioning earlier, right?

Like you don't have to create multiple cameras because we have a generative platform.

So not only the presentations are generated, the digital hubs are generated, but even the campaigns are generated, right?

So if I take one 30 second departure, why is that helpful?

Because if somebody has already done steps eight and 12, the campaign won't get stuck.

It will overlook that, tell them to do steps one to seven, and then as of two, step nine, and then move on, right?

Because it's a generative platform.

Since it is generative, don't write like really long emails, put like really short emails, give them a single call to action button, right?

Or if you have several call to actions, they should point to the same result, which is like watch the presentation or view your digital hub or so.

And then if you're sending it by text, should be like one or two lines, right?

We have come up, like we call it like anti-patterns of email so everyone puts the name of the customer on the top in the subject and that does this.

No, talk about numbers, talk about like, you know, things that matter to him.

Every user at the same account should get a separate subject, separate body, separate email.

Because at the end of the day, you're trying to communicate as a digital CSM to them, not as a customer marketing.

We support customer marketing also in our product, but we wanna send emails like how a human would write, "Hey, I'm concerned about this.

"Your number dropped by XYZ.

"Do you wanna talk to me about this?"

Put that as part of the subject, right?

So, and again, you can do that with generative platforms.

It's very hard to set it up when you're kind of creating campaigns separately, right? 


Yeah, yeah, exactly, exactly.

Are there some like particular like success stories or really cool like use cases that you've come across and customers that are using it particularly well? 


Yeah, absolutely.

There are quite a few.

There's a paper on our website about Pure Storage.

This is the first division that signed up.

They are making over $400,000 a quarter and they're attributing it to digital CSMs. 




And another division of them, Pure Excellence, they do 6-sigma training for customers.

They save over 150 hours per account by switching from a self-service LMS to cast personalized learning.

Now, the difference in LMS is like, you know, yeah, you have a 30 minute video or you watch that, we can generate like a four minute conversation, five minute conversation, that goes over and teaches you the five Whys of Six Sigma, but also teaches you how to use fish boning and all those kinds of things in case you have forgotten.


Because the prerequisite is you need to know fish boning before you do this, right?

So the presentation video that goes out is custom created for Alex.


Because we know that Alex has taken these four courses.

He got three A's and one D.

So we'll talk more about the thing that he got a D on. 


Yeah, right.


So it's like personalized because we know this, we know, and it's much shorter, right?

Like what is four or five minutes?

And there's an option to look into that.

So those are some of the…


Yeah, that's a cool combination of kind of the concept of micro learning and AI generated kind of content curation is essentially what it is, yeah. 


Yet another example, this customer RouteThis, and I tell this to all my customers because they've given me permission to share some of their analytics.

They get like 4X the other people as far as like success metrics are concerned.

And they have a very simple philosophy, “less is more."

They don't wanna tell more things to a customer.

They show like two or three slides, but they let them ask questions.

They let them, so I don't know whether you're aware or not that our product, it trains on every tech stack and your products automatically.

So what that really means is like, when you are giving a presentation, you usually show seven to 10 slides, but on your eighth slide, the CCO has 20 questions, right?

So what normally people do in a QBR or something, they create like a 50 page deck and have a big appendix and all that stuff, right?

But that's not the right thing.

Just keep it very small, but when the people ask questions, answer their questions live using an AI agent, right?

So that's what we do.

It's quite interesting.

It was very well received by HP, Pure Storage, Aruba, Vcom, RouteThis.

And yeah, I mean, HP shared something that engaged customers by 90% more often and spend 60% more per transaction.

So, I mean, yeah, they have been using digital and our product for a long time.

They were one of our design customers and yet another customer, which I should be able to mention early next month, they showed us that a CSM can handle 2.17X, the number of accounts across segments.

And I have to read this, while improving the CSM NPS by 16% and improving the onboarding CES by 21%.

So at the same time, right?

So basically what I'm saying is the CSM can handle 2.17X, the number of accounts across segments and the CSM's NPS improved by 16% and the onboarding exports CES, customer effort score improved by 21%. 

To me, what this boils down to is finding those key moments and just really digging in on those and being like hyper-focused on the outcome and the metric behind the outcome.

Because again, to the earlier SMS example, right?

If you can text your executive and say, "Hey, your team is doing this well, your team isn't doing this well, this is your ROI, et cetera, et cetera."

In like one or two lines.

I mean, how impactful is that versus the 20 page deck that we talked about that has the huge advantage in it? 


Yeah, and that's the difference.

Why just inform the user, right?

Tell them what to do.

In other words, "Hey, great job on this.

Your team is doing really good.

This is the next thing that you should focus on.

Really bad job on this, you should consider going to this training."

So the purpose is not like informing, the purpose is like an action that was generated on the fly.

We take credit, but it's the AI doing it, right?

So on the fly, telling them what to do.

So never show them negatives, always use the negative to tell them what to do.

And nine out of 10 times, you are right, right?

But there may be times you're not right, but still you gave a suggestion and you can always say, "I don't have a suggestion.

Do you want to set up like 30 minutes with a CSM?"

Right, we do that all the, you know, we do that, as I was saying earlier, right?

AI tends to hallucinate.

So what we do is like we figure it out with every answer.

We ask for how confident are you?

If the confidence level is less than 0.36, we say, "We think this is the answer, but we are not sure."

But if it is less than 0.26 or something, we say, "We don't know the answer, but here is the Calendly for a CSM."

Like when we introduced like these, being able to connect CSMs and people basically, "Yeah, so I can put this in my database and everyone can connect to Calendly, so it's not no big deal."

But this is the reason why we did that is 'cause the AI tends to hallucinate and then we can bring in the CSM as needed. 


As the human backup, yeah.

Do you feel like your newness to customer success and you coming at this from an outside of CS perspective has served you well in this?

'Cause I mean, that's my impression because you have this other view and you're not bogged down by the, by the like, I guess, traditional sentiment of what a QBR is or whatever.

Do you feel like that served you well in this whole thing? 


I hope so, I believe so, I hope so.

But you know, see whatever happened in customer service, like 15 years ago is happening in customer success now.

So in customers, you cannot ask for help without having, when you start typing a question, it starts giving you suggestions, right?

You go anywhere.

But the problem is they're going against a static document.


In other words, they're going through your help documents and or your whatever, like, you know, university documents or whatever.

We call it

So they're going through that.

So what we are doing different from over there is we are reading account information and helping the information, but that's an aside.

But that's the point that I'm making is like whatever happened in customer service will happen in customer success, which is like more automation and more AI agents answering your question and bringing in an expert, which is like the person who did the customer service agent later on.


So for that to happen, what happened in that industry is they started paying more to customer service agents, right?

The humans.

I call them coffee-driven CSMs and AI-driven CSMs.


So that makes it easier for me to explain. 


I love it.



The same thing is going to happen.

Like the AI-driven CSM is going to request the coffee-driven CSM to like come in and help him or, right?

So I'll see, we'll see a lot more of that. 



If you haven't trademarked that already, I would do that immediately. 

(both laughing) 


I should. 


Well, I mean, speaking of seeing more of that, I think, you know, arguably AI has been around for a while, but we're now getting into a level of usability of Gen AI that is obviously unprecedented.

And a lot of people are coming to terms with that, some better than others.

But what is, in your opinion, what is, what are the next few years look like in terms of the adoption of this technology?

And I guess specifically to CS, like where do you see all this going? 


So, I mean, we have been noticing this since early October [2023] already, right?

Adopting AI. Even like we're signing up a customer, just sent up a document early morning, and he said, "We'll sign as soon as I pick up the kids.” So even security companies are adopting AI.

You know, obviously they ask us tough questions.

And then I have a demo where I put his name and I say, "Who is such and such?"


The CCO's name.

And in the past, we have tried to answer that.

No, we cannot answer that because this person is talking to me.

So it says like, "I don't know, do you want to connect with our CSM to answer?"

So that gives a good way to tell them that people are getting comfortable with this AI thing.

At the end of the day, I don't think, so there are still few people who are resisting, right?

Like say, "Hey, human touch," and all those kinds of things.

But I feel it can do more service to you and make your job as a CSM or as a CS leader a lot easier.

And you can look at like minimum 12X to 40X ROI with the products that you use, instead of using a system of record tool that put data in it and you run reports, and then you create campaigns and reach out to people and say, "Nobody's clicking on my campaigns."

You know, things like that.

So things that can learn can really help you take it to the next level.

And if I may, a lot has changed.

When I was at the MIT AI thing, we were focused on supervised learning and unsupervised learning.

We even have unsupervised learning in our player because it learns if you always skip over support and it will move it to the side, right?

But then again, semi-supervised learning was a big thing at that time.

Like we were like, "Oh, we're waiting for it to like show up."

And then we were talking about like one-shot learning or few-shot learning, which is like, just give it a few samples and it learns.

And that's what OpenAI was like just a year and a half ago when we were like training them how to generate SQL from commands or we were telling it how to have a combination, generate code from liquid, which we do that today also.

We were doing that.

But now you don't even have to train.

As part of the prompt, you can give an example.

Here are a couple of examples.

It just needs two or three examples.

Yeah, we wanna take credit because we trained it, but at the end of the day, everyone can use those kinds of things, right?

Few-shot learning.

So I think that's where the world is headed.

And this whole OpenAI, Sam Altman fiasco, whether it was because of AGI or whatever the real reason is, hopefully we'll find out when he writes his book. 


But 'cause you know it's coming, yeah. (both laughing) 


But yeah, I mean, again, Wall Street is saying one thing, the Silicon Valley is saying another thing, but at the end of the day, more AI is coming, more useful AI.

And I'm not talking about what MIT should teach us, like using AI as an assistant and eventually a peer and eventually your manager and eventually it runs the corporation and just gives you tasks or distributed code.

We are far from that, but at the end of the day, any tool that's available, I mean, look at the thing.

No one's hiring a chief of staff because this OpenAI, this tool is your chief of staff. 


Yeah, yeah, yeah, absolutely.

So I think back to kind of Google and early kind of search engines and back in the day, I mean, we were dating ourselves earlier, right?

Given our early influences of the internet or whatever, but back in the early days, you kind of had to know how to search for something like on Google to get accurate results.

Whereas today, Google's pretty smart.

It knows kind of what you meant to say or what you meant to search for.

And it has contextual history and all that kind of fun stuff.

And I feel like I is still kind of in this place where you kind of have to know how to prompt.

And I kind of feel like I need to educate my on, prompt engineering a little bit, but I don't know that that's always gonna be the case, right?

Because at some point


You're right.

Prompt engineering is gonna go away. 


And so, yeah.

So, I mean, is that really a thing?

I mean, you see all the posts about like, top prompts for CS professionals and all this kind of stuff.

Like, is that gonna be a thing in 10 years or five years?


No, not really.

I think that'll go away.

What they're doing is like reusing the same, how to write an email, they're putting that inside the code.

How to create the initial workflow, like diagram, they're putting, everyone's putting in there, but those are like barely scratching the surface, right?

So, yeah.

I mean, like, why can't you create the prompt right when, like in our case, like we have like a narration was generated and then we can click on a button and say, make it humorous for peers, but keep it professional for the CFO, right?

So, we do it with just by one button, but we have made the prompt behind the scenes to do all those kinds of things, right?

So, yeah, I think prompt whole thing is gonna go away.

It's gonna become more of a, hey, ask the user.

But along with that, we have to be very careful because if you put the prompt in front of the end user, they can ask anything.

It can ask you to expose, hey, what is the underlying platform?

What security systems are using?

What you can even ask, like, what was the question that one of my engineers asked?

Like, hey, what security patches have not been applied and how can I use them to infiltrate?

He's asked something like this and he was shocked that he got a really good answer, right?

So, we were shocked, right?

Like he did it in a short meeting.

Like we went for like lunch and all this stuff.

He just put it up his laptop and did that.

So, we have to be very careful around that.

And that's why the security companies, they come to us, they ask first question, do you have SOC 2?

Yes, we have SOC 2 and SOC 3.

Okay, then this, I wanna have a conversation. (indistinct) (laughing) 


Yeah, it's very interesting.

And you hear about like AI being now used in a collegiate setting, you having to like cite your prompts and how you got there and those kinds of things.

It's very interesting to me because I think there are all kinds of implications from a plagiarism perspective and whatnot.

So, it'll be interesting to see where that goes. 


Yeah, but don't get me wrong.

There are already prompts available that will say, you can prompt and say, only give me answers that you can cite and then it'll put the citation also.

So, it's easy to do that.

I mean, don't try to solve an AI problem outside the realm of AI.

Just ask the same thing, like how we do here, how confident are you with your answer?

And if the answer is between 0.22 and whatever, 0.36, then we say somewhat confident. 


I think that's very important for people to hear because I think there's a, I've talked to a lot of people who just have a general distrust for it. 


Because it's this little black box, you don't know behind it.

And so, what I know is to figure out what's behind it is important. 


Yeah, so there are three types of people.

Like, the one in the middle could be the open-minded people.

They're looking for answers, so ignore them.

And the one is like, who's a skeptic.

So, when a skeptic writes a word, he's looking for that answer that is wrong so he can advertise that.

Whereas the other end, like people like me, they only look at the positives and they like advertise that.

But the right person is like, who has an open mind and say, knows the limitations of AI, but still is willing to give it a try to use it to her advantage.

So, that's the key thing. 


Yeah, I love this. 


Because both extremes are bad.

Like me, like everything positive about AI is also bad.

And the other person who's like, hey, no human touch, no nothing, AI is gonna take over our lives, that's also bad. 


Right, yeah, yeah, yeah, balance.

It's all about balance. 


I could have just said that instead of giving a long story. 


No, it's perfect, yeah.

It's fascinating.

I think I could talk about this stuff all day.

But the unfortunate thing about the fact that it is eight till the hour is that we are running out of time and that sucks.

But I do have a couple of just kind of round out questions for you.

The first one is what are you paying attention to, listening to that informs kind of who you are?

It could be business, could be non-business.


I'll be honest, I think I'm spending a lot of time on TikTok these days.

And somehow it had figured out that I read a lot about entrepreneurship and I kind of look at like AI hallucination problems and AI.

So those three things it talks a lot about.

And it also talks to me about boots and sunglasses because it knows that I collect sunglasses and it knows that I collect shoes. Or boots and all this stuff.

So between these five topics I use like TikTok.

But then when I go for walks, I'm usually have an airpod and I'm listening to books.

I tend to listen to the books that I've read before because I'm trying to look for more things that I missed or I've started to disagree with a lot of stuff that I re-listen to now.

I guess as I'm evolving as my concept, so I kind of figured out like, okay, they're just saying the norm, right?

They're just, like for example, their product is for CSMs.

So there is no way they are interested in having a low ratio or a high ratio of account to CSM, because they're charged by the CSM.

So that's why they're gonna say this.

So I've become skeptical.

So instead of just learning from that, I'm saying, why are they doing that?

So I've started to think like that, which I think people should listen or read books that they have read before again, after like a three or six month period.


Yeah, I think that's really helped the fact that you're reading it and then listening to it, because I feel like, I mean, I know our brain very differently, whether it's auditory input or visual input, right?

You're absolutely right.

You're probably picking up on stuff just because of that very thing. 


Yeah, and what you were describing is, and this is one of the research that we did when we started CAST.APP

So University of Washington, some biomedicine doctor, he said like, if you just use one modal, which is like reading a blog post or listening to a podcast, you retain 10% of the information.

If you add one more, like visuals as well as reading, it goes to 65%.

And I have the research too, I've actually paid for it.

But if you add a third one, it goes to 73%.

You add a fourth one, 73.5%.

So it doesn't matter.

But minimum two, or three, that is the reason our avatars have lip movement when they talk.





So you're listening to something, you are watching and you see the lip movement and all.

This came directly from the professor.

But I'll be very transparent, like 50% of our customers turn the avatar off and 50% like wanna label it, name it.  Hi, I'm Amy or Hi, I'm Mark, depending on the gender.

So they do all sorts of things.

But you're absolutely right.


No, it's great.


I'll look up the research.

Actually, it might be linked on our website also at the bottom, but I'll look it up and see. 


Well, I mean, you know, even in editing this, you know, these podcast episodes, you know, I do edit the video and the audio at the end.

I notice that when I'm looking at it and I've even had this feedback when people are listening on YouTube versus just on their podcast app, they pick up different things.

Because obviously so much of our communication as humans is visual. - 



So yeah, you know, I have CarPlay and recently the podcast app in CarPlay enabled the 1.5X, 1.75X, speed.

Like, so what I noticed, like if I listen on 1.75X speed, I'm driving much faster.

So I had to like go back to 1.25 or 1.5 because, you know, I'm into sports cars a little bit, but I tend to drive a lot faster when I'm listening to something really fast.

So it's like, that was the reason why it switched back to 1.5 or, you know, versus like 2X. 


That's really funny.

Apple's probably gonna have to update their terms and conditions for that. (both laughing) 


Just for me, just because of this guy I tend to drive faster when I'm listening to faster podcasts. 

Exactly, exactly.

Well, look, I've enjoyed this conversation tremendously.

I'm sure people can find you on LinkedIn.

Are there other resources or places people can


Yeah, yeah,, D-I-C-K-E-Y.

And the best way to reach me is like my email.

So D-I-C-K-E-Y

I think those are the two best ways to reach me. 



Well, again, I appreciate it.

Thanks for the time.

It's been a pleasure.

Thank you for joining me for this episode of the Digital Customer Success Podcast.

If you like what we're doing, consider leaving us a review on your podcast platform of choice.

It really helps us to grow and to provide value to a broader audience.

You can view the Digital Customer Success definition word map and get more details about the show at

My name is Alex Terkovich.

Thanks again for joining and we'll see you next time. (upbeat music)

Want a 1:1 demo?

Book a Demo

Try for free...

Try for Free

Signup for updates: