The Support Automation Show: Episode 27

In this episode of The Support Automation Show, a podcast by Capacity, Justin Schmidt is joined by Dan Steinman, Chief Evangelist at Gainsight. They discuss the difference between support and customer success and how businesses should apply automation to both.

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Justin Schmidt: Welcome to The Support Automation Show, a podcast by Capacity. Join us for conversations with leaders in customer or employee support, who are using technology to answer questions, automate processes, and build innovative solutions to any business challenge. I’m your host, Justin Schmidt.

Hey, it’s Justin. Before we begin into this episode, I want to apologize for the audio on my end during the interview. I forgot to record a separate audio track for myself, so we’re probably going to end up using the Zoom audio. Dan still sounds great. The conversation is amazing. You would think after 40 years of writing the word “Schmidt” every time I wrote my name, I’d know how to dot an I and cross the T, but I forgot to get my audio set up. In any event, I hope you enjoy this episode. It’s a good one. Good morning, Dan Steinman. Welcome to The Support Automation Show.

Dan Steinman: Justin, it’s great to be with you. Glad to be part of this. Thanks for asking me to join.

Justin: Absolutely. Where does this podcast find you?

Dan: I am in Saratoga, California, which is the southern end of Silicon Valley, south end of the San Francisco Bay Area.

Justin: I spent two years in San Francisco myself. Absolutely love it there. How about to get started, give a little bit of your background, your journey to Chief Evangelist at Gainsight? I know you’re involved in some other things, but maybe give the audience just a little bit of your story.

Dan: Sure, but I won’t tell the whole thing because it’s been a long one, and it’ll take the whole time. I’ll skip over most of it. I gravitated, in the early part of my career, towards interacting directly with customers. That was a sweet spot for me. I did a whole bunch of roles that have, today, become known as customer success. I had a whole bunch of titles like account manager, customer relations, customer advocacy, and all sorts of other things that were dancing around that same idea of taking care of customers. In the early 2000s, it became customer success because once Marc Benioff decides that’s the name of something, then that becomes the permanent name of something.

I started doing same roles, but they were now called customer success, including VP of Customer Success at Marketo, and then I left Marketo shortly before their IPO to join this little company called Gainsight. It was actually called JBara Software back then became Gainsight because I thought that was the next big thing because it was tooling for customer success, meaning, how do we develop a platform that helps us take better care of our customers?

I joined as Chief Customer Officer, then I became Chief Evangelist when I stepped out of that role, then I went to Europe, ran our European operation for four years. I had the GM title and then I came back a couple years ago and went back to the Chief Evangelist title, which just means anytime there’s a group of more than two people who want to talk about customer success, I’m happy to join into that conversation or even one-on-one like I’m doing with you right now. That’s basically, at Gainsight, what the Chief Evangelist role means.

Justin: I love it. We’re very familiar with Gainsight here in St. Louis, Missouri. That’s one of our claims to tech success. Here on The Support Automation Show, the first question I ask everybody after we get past our introductions and welcome is the following; when you hear the words “support automation”, what does that mean to you?

Dan: The first thing that comes to my mind, because I have managed support teams as Chief Customer Officer, at Gainsight, support was one of the things under me, it says to me, “How do we automate the functions of the customer support organization, the CSRs, or whatever we might call them?” That usually involves starting with something like Zendesk or Service Cloud, or maybe something smaller, Freshdesk, or something like that. How do you turn what is oftentimes, early in a company or early in an organization, an ad hoc, reactive role into something that’s much more process-oriented, rules-based and scalable?

When you say automation, to me, that’s saying, “We’re doing something that makes it scalable.” That’s what I think about when you say “support automation.”

Justin: It’s interesting you think about scale because scale it’s the thing that basically every function in a business is chasing after. I have yet to talk to a business leader, an entrepreneur, an operator that doesn’t want to deal with scale problems. In customer-facing roles, whether it’s frontline support, or you’ve got customer success account management-type functions layered on top of that, as the amount of business increases, obviously, the support and success functions increase with that.

There’s a particular opportunity for technology to come in and provide either relief or extra bandwidth or provide additional value to these particular functions because, as you well know, the customer relationship can be a deep and complicated one. One of the things that I’m really interested in talking with you about especially considering you’ve seen the lifecycle and the value chain of Chief Customer Officer oversees success, support, and I’m sure several other things. Where support and success blend together, where they’re separate, how do you look at that from an organizational design standpoint?

Dan: It’s such a great question, Justin, because there’s an evolutionary answer to this. Early on, when we started doing customer success, one of the most important things that we did, and I had to do this at Marketo, was differentiate it from support because human beings do this thing whenever they hear something new, they try to pattern-match it with something that either sounds like it or sounds like it might be like it. When you say “customer success,” 15 years ago, people were like, “Oh, that must be a rebranding of customer support, or it’s a level to customer support, or it’s something like customer support.”

In fact, I did presentations that were all about how customer success is not customer support. In fact, in so many ways, it’s the complete opposite. One is totally reactive. The other one is intended to be totally proactive. One is a cost center. The other is a revenue-generating organization, and so on like that. That was early on. We had to draw really clear lines so people didn’t get confused.

Now, what’s happened over time is that people have figured out and understand now what customer success is, that it’s different than customer support, both are necessary. Especially as a CCO, when I was doing that role, I had good clear lines between onboarding, customer success, customer support, and professional services in training and development. Those are the organizations that were under me, even renewals at some point.

When you’re in a bigger role like that, you have multiple organizations. Your mind has to change about how you think about those orgs because now, there’s some value in differentiating those works, but there’s way more value in looking at all of those people as a pool of resources. My job is to deliver the highest value possible to my customers. When you put that hat on, you’re like, “The organizations don’t matter at all.”

A simple example, more often than not, a customer support person on average is paid less than a customer success person. Something we define as customer success, and you could be really rigid about that, might be better off done by a customer support person because they’re more equipped to do it, they’re less expensive, they have the bandwidth to do it, and it enhances their job because it becomes something that’s proactive. For a lot of support people, one of the things they’re looking for often is, “How can I be less reactive and more proactive?”

You have to start getting those lines to be a little bit fuzzy, or early on, we had to have those really clear lines so people weren’t confused about whose job was what, but then over time, I think making those lines fuzzier can actually add value because now you’re just saying, “Who’s the best equipped to deliver this value to the customer?” It doesn’t matter what organization you sit in.

Justin: I loved your bit there about proactive versus reactive and how over time, that wasn’t necessarily a bifurcation between customer success and customer support. The ability to be reactive and proactive, and having the organizational and operational excellence to be able to be adequately both of those is definitely something where I think technology, and especially recently, AI in those areas becomes really apparent.

One of the things that I was thinking about this morning actually is, when it comes to automation in the customer lifecycle, there’s automation, and, let’s just say automation AI and just bundle that together for a second, that is seen versus felt. When I go onto a website and I engage a chatbot to get a question answered, that is automation that I see. It’s usually branded as some sort of bot and I know what I’m talking to bot before I’m handed off to a human.

Then there’s the automation that I feel, which may be because the vendor is using– they’ve got all their customer data and all my signals of product usage and adoption and whatever, feeding into a CDP, predicting when I may run into troubles, and my CSM reaches out to me to help me understand whatever it is, in the platform, I’m not using, feeling that maybe more than directly seeing it.

When you look at the adoption of technology inside of organizations, do you think the better place to start is with maybe some of the more reactive stuff, with maybe some of the more proactive stuff? Or does it not matter so much as which end of that spectrum you go after, but rather, that you identify the places where you can drive the most value and start there? I’m just curious when you look at bringing technology into a customer organization, where to start. That’s a very long-winded way of asking a simple question, but it’s an interesting topic.

Dan: It’s actually not a simple question. Philosophically, when you’re building a post-sales business, I don’t like that term “post-sales”, but everyone understands what it means, you have to know that both of those things are necessary, reactive and proactive. That means a lot of people are going to have to do both of those things because it’s easy to say customer support is a reactive organization, which is how it was born and it’s still probably largely true, or the primary differentiator of customer support is that their on-call. A customer has a problem they could call them.

The best support teams do a lot of proactive stuff as well, and the best customer success teams have to do some reactive stuff as well. As much as we’d love to have everything be proactive, it never works that way. I think you have to start with the premise that you’re going to have to do both reactive and proactive. I wouldn’t say one is more valuable than the other.

If I had to pick I would say early on, you have to build a support team because there’s got to be a place that makes the customer feel comfortable, that they can call and get somebody to respond to them. You probably don’t want that to be the customer success person who, in the long run, you want them to be proactive. You don’t want to get them in the habit of answering customer calls like, “I can’t log in,” or, “I think I’ve got a bug,” or whatever.

I think, build the customer support, organization, or whatever you want to call it because maybe it’s only one person doing multiple jobs, but think about that first and what that requires, and then once you have that established, then introduce customer success so that when a customer does have something that should be funneled through the support organization, if they come to the CSM, CSM can say, “Let me open a support ticket for you because this is really a support issue and our support person will call you back on this or respond via email.”

Now you’re starting to guide the customer through their journey and how to best interact with you as a company, which is a really important thing. I always say, if you as a company don’t own the customer journey, the customer will create their own journey, which results in one of two things, either chaos or silence. Neither of those is good.

You have to build a journey and then you have to manage your customer through that journey. Part of that is describing that journey to the customer, “Here’s when you call support. Here’s what’s going to happen. Here’s what a P1 is, versus a P2, versus a P3. Here’s how the customer success is going to operate. Here’s the data we’re going to watch. Here’s when we’re going to call you when you haven’t logged in two weeks, or when you open 12 support tickets on the same day. We’re going to get proactive and try to help you figure out how to get more value or to use our product better.”

Mentally when you think about both of those things, as if I was building an organization from scratch, I think I’d start with support and then tag success onto that once I’ve got established that there’s a support organization to do some of the reactive, repetitive kinds of things that customers are going to need.

Justin: That’s a really interesting point you made about the journey where if you don’t lay that out, they’re going to make their own, and then you’re not going to have insight into it, which is silence or you’re going to feel the fallout of it, which is the chaos. It reminds me of one of the big trends in marketing that I think about a lot and that is, this concept of the dark funnel, where you’ve got people interacting with your brand, having discussions about your product, doing all these stuff, outside of the locus of control that you have with your messaging and marketing, and whatever it is.

This has led to the advent of community marketing, every SaaS company has a podcast, and a lot of Slack groups and LinkedIn groups and all that other stuff. This is something that always interests me when you think of customer success at scale, and that is, how much engagement with the customer needs to happen within the channels and QBRs and within the MO, that an organization wants? Maybe what are a couple of ways you could design that customer success manager relationship to ensure you keep most of that conversation in the places you can manage?

Dan: Yes, a good question. It comes back to creating and then managing the journey with the customer because, at a simple level, there’s two aspects to the customer journey, when you think about customer success. One is, there’s a set of what I call date-driven events.

You could put it on a calendar, “This is a high-touch customer. We’re going to meet with him every week. Every month, we’re going to review our metrics. We’re going to do quarterly business reviews. We’re going to do an on-site visit once a year. There’s going to be three executive outreaches during the year.” There’s a set of things you’re going to map out and say to the customer, “Here’s what you could expect from us.” That’s the date-driven stuff.

The second thing is data-driven interactions and that is, “Here’s the data that we’re going to watch and when these triggers go off, we’re going to call you. You haven’t logged in two weeks. It’s renewal time, you’re not using the new feature that we shipped six weeks ago in our release. You’ve never touched the reporting and analytics part of our product,” whatever those things are. It’s all about managing customer health. The simple locus of this whole thing is, there is a health score for every customer. The only question is, do know what it is? If you do know what it is, then you’re managing that.

The analogy is customer health score is to the post-sales team what pipeline is to the pre-sales team. Pipeline is the leading indicator of the result we’re looking for, which is sales. Customer health score is the leading indicator of the result we want from a customer, which is renewal and up-sell. You have to start this process by understanding the journey and mapping out the journey for the customer. Once you do that, then you can start to automate that journey.

By the way, the journey is going to be different for different segments of your customer base for one simple reason, because you can’t afford to treat all your customers the same. A customer paying me $1 million a day could get a very different level of touch from me than a customer who’s paying me $6 a year.

Justin: Literal white-glove support. Yes.

Dan: Literally everything is high-touch, and then at the low end, which is a much more challenging thing, how can I manage a set of a very large set of customers without ever talking to them? I always joke with people like, the high-touch customer success manager and the digital customer success manager have the same title, but if you put them in a room together, they have nothing in common. One guy talks to all five of his customers every single day. The other guy has 3,000 customers and never talks to any of them because the minute he picks up the phone, he breaks the model as digital and scalable, not high-touch.

It’s really important to understand that yes, you’ve mapped out a customer journey, but that journey is really a cost model that says, “We can afford to be high-touch with this customer, but this customer, we have to have this very low-touch or purely digital touch a model.”

Justin: This is one of my favorite corners of the customer organization with regards to the business writ large conversation because we’ve gone through this conversation in capacity too, and this is why you have to– I like making my little continuums here, and I’m going to pick two very successful businesses, one of them, maybe more so than the other but still, you have ServiceNow on one end and you have Countly on the other.

The average ServiceNow contract is almost mathematically infinitely higher than the average Countly deal and the customer organizations in those companies are built entirely differently because of that.

To your point about you don’t want to have your support and success cost outweigh the revenue that an incremental new user brings on, there’s product discussions that have to happen, there’s go-to-market, do you need to raise your prices? Do you need whatever it is? My feeling is, this is one of those questions that startups deal with quite often in the lead-up to product-market fit, and the– I like the phrase that NASA uses of max q, when you reach the escape velocity, or whatever, of product-market fit and getting into ServiceNow, and you’ve got it all figured out, it’s just a matter of scale.

My question to you, and I know you advise a lot of startups, how do you approach that conversation with the founders and with the operators in those businesses on trying to strike that balance between where you need to solve some of this in product, where you need to solve some of this with people in the success and support roles, and then where you just need to look at the revenue model to right-size all this stuff?

Dan: It’s such an important conversation, Justin. I’m glad you brought it up. I have a mantra that I’ve preached to thousands of CSMs, and it goes like this, it’s really simple, product is your number one priority. Now, you’re a CSM, I know what you do all day, every day, and almost none of it has to do with thinking like a product manager. The point I’m trying to make is, this is a reality. The only scalable thing in your business is your product, period. It is the only scalable thing in your business.

Second point, the companies that own their markets have the best product, period. You could own a market for a little while with a great sales and marketing team, but in the long run, the only way to own the market is to have the best product. Therefore, as a CSM who sits at the most important intersection in your company, which is the intersection of your product and your customer, if you, every week, are not helping us make our product better, then you are not doing your job.

The only negative thing that’s ever come out of the world of customer success is that it has removed product managers from customer interactions because early in the days of SaaS, there were no customer success teams, but every company was doing customer success because you still had to get renewals. How was it being done? It was being done in a mad scramble of executive involvement, and consulting, professional services people getting involved, and support people trying to do success, but mostly, it was product managers having to bail out customers who were struggling to use the product. They had a ton of interaction with customers.

When I joined Marketo, there was no customer success team, I built the first team. The product managers were on six calls a day with customers trying to make sure that they were doing customer success. We built a customer success team over time, built that expertise. One of the things that happened was Product Manager started spending way less time on the phone with customers. Therefore, this idea of figuring out product-market fit and what the market needs, et cetera, became a little bit more in a vacuum, a little bit more theoretical.

Customer success people have to figure out how to transfer the knowledge of what’s happening with their customers in the product to the product team so that the most important thing in your company can actually get better, and that is your product.

This is really important. I always draw this picture of the golden triangle for success in a SaaS world, and the golden triangle is customer success, product, and sales. Those three pieces of the business have to collaborate in a really high level. They also have to butt heads all the time. They cannot agree on everything or they’re not doing their job because, as the VP of Customer Success, if I’m not in the product guy’s office all the time putting pressure on him to improve performance and to refine this part of the product so that my customers actually get value and renew their contracts, I’m not doing my job.

At the same time, if the VP sales isn’t in the Product guy’s office saying, “Hey, our competitors have these three features, we don’t have those,” you better build them or we’re all going to starve to death. Both people need to be putting pressure on product and then customer success and sales need to be putting pressure on each other in the exact same way. I need sales to do their job better, set expectations better, transfer knowledge better, stop showing a demo that isn’t how the product works.

You have to set us up for success, and

then sales has every right to say to me, “I’m going to sell customers that aren’t perfectly in our sweet spot. I need you to make them successful so that we can make our numbers.” That’s a legitimate request. We need this healthy tension between these key organizations, otherwise, we don’t grease the wheels of the company that drives us forward in a successful way.

To return the favor, that was a very long-winded answer to what probably wasn’t that long-winded of a question.

Justin: No, that was great stuff. It’s interesting hearing you. As you were going through that, I was thinking in my head of a conversation I had with our VP of Customer Success and a conversation I had with our VP of Product. It was interesting because hearing the two of them go back and forth with different issues, but I think it could have been over the same issue if the words are slightly different. That is, there is this journey that a business is on to the pot of gold at the end of the rainbow, the exit or the IPO, whatever that is.

There’s this zigzag push and pull where sometimes it’s the customers pushing you in a certain direction, sometimes it’s the market pulling you in another, and it’s just this ping pong until you get there. There is a very concerted effort here at Capacity to try to make sure that we are being customer-led in the advancement of the product. We’ve added features because people have asked for it and then simple end.

Overall, I think it’s a good piece of information for any budding leader customer success, even customer support leader listening to this, that product is you need to get into their ear. To your point with the golden triangle, I love that phrase of sales, product, and customer success working together and providing that healthy tension.

One thing I wanted to ask you, just looking at your career and all the different things you’ve done, and it’s everything from what you did at Marketo, just even before that when you were working at some of these other places in customer roles, with all the advisory you’ve seen, with Gainsight’s growth that you were there, over that journey, when you think of what has changed, and what has stayed the same, what’s maybe something that, looking back on after 20 years of doing this work, you’re surprised it’s still the same? Maybe what’s something that changed that you’re surprised it did?

Dan: I want to say the thing that stayed the same is actually not a surprise because when you boil business down to its simplest form– I was having this conversation yesterday with a CEO that I’m advising as we get a brand new company off the ground. He talked about so many different things, “How do we market this? How do we sell it? How do we price it? Should we have these features?” et cetera. At the end of the day, there’s a really simple equation, I learned it at my very first startup.

One of the engineers asked our CEO this question when we had about 12 people in the company. He said, “What’s our exit strategy? Are we trying to do an IPO? Do you think we’re going to get acquired?” It’s way too early to even think about that, but the CEO had this perfect answer. He said, “Here’s what I think we’re going to do, we’re going to build a really great product that customers are willing to pay real money for, and then we’re going to make sure they get value out of it. If we do those three things, I’m pretty sure everything else will take care of itself. That will be a really good exit if you can continue to do those things.”

That’s the one thing that hasn’t changed. If you bring business back to its core, are you building a really good product, the product that actually works, delivers real value to the customer that you can charge a fair market price for? If you do those three things, all sorts of great things are going to happen. That’s the thing that stayed the same. I think sometimes it’s really helpful in all the complexity of our daily lives, running companies, building products, whatever, just bring it back to those core things.

What’s changed, I guess it’s a pretty obvious answer. To me, the rapid evolvement of technology is probably the primary thing that’s changed. Scalability is more achievable, more quickly than it’s ever been before because that’s what automation is, that’s what technology does. It says, “We can do more with the same number of people or we can do it better.”

At some point, I always ask VPs of Customer Success this, I said, “What’s your customer-to-customer success manager ratio?” “Oh, on average, we have 15 customers per CSM.” I’m like, “Do you think that number is going to go up or down next year?” Guess what? It’s going up every single year. It’s not going from 15 to 12, it’s going from 15 to 20. How do you do that? You ask your people to work harder, and then the next year, you ask your people to work 90 hours a week. No, that’s not the answer.

The answer is, is there a part of it that we can automate? That has become so much better and easier in our technology world today, the advent of SaaS has changed the world in some ways. One of the primary ways is, you can now buy departmental solutions. 20 years ago, there was no such thing as a departmental solution because it all had to be hosted on sites, so you had to buy Oracle or SAP or Microsoft or whatever. Today, you buy Marketo, you buy Zendesk, you buy Salesforce, you buy Gainsight, you buy Countly, you buy Box, and you Workthere or whatever. It’s like you can truly buy these departmental solutions.

You can scale your part of the business potentially really quickly, and you can add automation to it in a way that isn’t disruptive to the whole business that you still have to worry about security and all sorts of IT things, but it is much easier to buy and implement software for your department. Scalability is more readily at our fingertips than it ever has been before. Scalability was always there, you have to do it. It’s just much easier to do it now. I think you can do it much faster.

Justin: The department-in-a-box nature of SaaS is an instrument. It’s funny you say that because actually, the last person I interviewed for this show was a gentleman by the name of Lee Cockerell who– talk about a career. He ran operations at Disney World for 40 years, and it is interesting talking to him, where we’re having this discussion and he just kept going back. He said the same that you did, that the fundamental laws of business haven’t really changed. You’re providing value to a customer, you need to make that experience the best thing as possible.

Hearing you talk, just made me think like, if ServiceNow was around in 1890, Rockefeller would have probably invested in it for standard oil, but the fundamental of what they were doing is still the same, is managing expectations and delivering value.

This has been a fantastic conversation, by the way, Dan. I can talk to you all day, but I need to land a plane. When we think about going into the future, what excites you the most about where support automation and just automation in the customer world, in general, is going?

Dan: I think we’re in the middle of one of the more dramatic shifts, at least in the technology world, that’s ever happened. If I paint the history, we’d go back 20 years. We lived in a transactional world. I sell you Oracle, you write me a check for $3 million, I put all that money in the bank. No one ever logs in to Oracle for two and a half years because that’s how long it takes to implement it. I have your $3 million in my bank account. You are working for me the whole three years. That’s the exaggeration, but that’s the old transactional world.

Then we moved into SaaS, where suddenly, we don’t collect all the money upfront. We collect a small chunk of it and we have to earn the rest of it. Now, in theory, lifetime value for a SaaS customer can definitely be higher than it was in the old transitional world, but you don’t get it upfront, you have to earn it over time. Now, to a certain degree, we’re moving out of the subscription model into what I call the consumption model, which is a model where we don’t collect money upfront. In fact, we don’t collect a subscription, we collect money only when you use our product.

The simple way to think about this would be, let’s take cloud storage as an example. Let’s say I’m Box, and I sell you Box today, and your subscription is $2,000 a month to use my software or not use it. There’s tremendous value if you use it. Here’s the new future for Box, potentially. You don’t pay me any money on a subscription basis, you pay me a penny every time you download a file, another penny every time you upload a file, and another penny every time you share a file.

Now, here’s what’s happened in this transition over 25 or so years. We’ve gone from a world where all revenue is completely driven by sales. You could argue that the only thing that mattered for Oracle back in those days was sales and marketing, and that’s the way they acted. Everything else was an afterthought because to make next quarter’s number had nothing to do with renewal or up-sale or any of that, it had to do with, “Can I sell 25 new customers my three-million-dollar software?” It was all sales-driven. Everything else was literally the tail of the dog, and sales was the dog.

Fast-forward to that consumption model, we don’t collect any money upfront. You ask yourself the question in that model, “What is sales?” There is no financial transaction that happens. There’s still a sales motion to find customers who are willing to try our product. Think about how much easier that is when you say, “You don’t owe me any money unless you think this has value and you start using it.” Now who’s the dog, and who’s the tail?

The dog now, are the people responsible for helping the customer use that product and consume more of it every single day. This is a shift unlike anything I’ve ever seen in my career, where we went from sales being the kingpin, and I’m not picking on sales, because it’s still so incredibly valuable, but they ran everything, and the only way to become a CEO was to be the VP of sales prior to that, to a world where it’s hard to even define what sales is in a world where the consumption of the product is what drives all of the revenue.

I look forward to that because I think it’s such a shift in the way companies have to think about their business. It’s the way things ought to be. Subscription is closer to the way ought to be, which is, you shouldn’t have to pay me any money unless I’m delivering value to you. In a consumption world, that’s even more true than it is in a subscription world. When you decide that the product is not working for you, you don’t have to say, “I’m not going to renew my contract,” you just say, “I’m done,” stop using the product, and the money stops going to the vendor. You install a competitive product and you start using that one.

What it does is it keeps centralizing our focus on customers, and delivering customer value. In that old-school world, we just didn’t have to worry that much about whether customers were really getting that daily value. We wanted them to, but our business model wasn’t dependent on it. Our business model was dependent only on, “Could we sell more customers?” Today, if we move into that consumption model, our business model is fully dependent on customers seeing enough value to use our product more today than they did yesterday.

Justin: It puts an extra bit of shine on the product side of the golden triangle too, because, in a consumption usage-based model, to your point, if people aren’t using it, you’re not going to drive incremental value. Product and customer need to really get themselves aligned there.

Dan: To double down on that point, just really quickly, if you go back to that transactional world, I keep saying Oracle, I’m not picking on them, because-

Justin: Shout out to Larry Ellison.

Dan: -we’d all love to be as successful as Oracle, think about that model where all revenue is driven by my ability to sell new customers. Ask yourself this question, “What’s more important to my success as a company? The demo of my product, or the way the product actually works?” The answer is the demo was literally more important than the way the product actually worked.

Today, it’s the opposite. If you demo it, and that’s not the way the product works, you’re setting your customer success team up for failure because the customer sees that immediately and says, “Hey, this isn’t what I got in the demo. Why was that?” That’s why I say one of the things that’s incumbent on sales in that golden triangle is set expectations properly with customers by showing them the product as it actually works, and not exaggerating what it can do, or what it might be able to do three months from now.

Justin: Love it. Dan, this has been an incredible conversation. I’m going to close with a quick-fire round. I’ve got two questions for you. The first one is, what is the book that you most often recommend to people who are going down the same career path you have?

Dan: You set me up for an ego-driven response. That’s the book I wrote, which is the seminal original Customer Success book. I didn’t write it myself. Nick, my CEO, and another guy named Lincoln Murphy are the co-authors. It is a really high-level picture of, we call it customer success, but it’s really philosophically customer success. It’s not how to do day-to-day customer success, it’s written for CEOs of every company in the world, how to think about the new world, where customers matter way more than they did previously.

That’s the book I recommend because I think that’s where the world is moving to, where the customer really is becoming our central focus from a product to sales and, I suppose, sales standpoint.

Justin: Love it. The final question for you, you’ve led very large teams, you’ve advised a bunch of founders and CEOs on leadership and growing companies. Part of that is managing time and managing your productivity. When you think of all the different productivity tips or hacks if you want to use that word or just tools that you’ve gathered over the years, what’s one that you would recommend everybody adopt in their practice?

Dan: I’m old school, so I don’t adopt a lot of personal productivity tools. I just never got into that mentality. When you ask the question, I’m harkening back to the really simple two-by-two thing that we used to talk about all the time where the upper right quadrant is urgent and important.

Justin: Eisenhower matrix. Yes.

Dan: The lower right quadrant is urgent, but not important, et cetera, with the four pieces of it. Am I spending enough time every day on the things that are in that upper right quadrant? Because in our worlds, it’s so easy to spend all of our time on urgent things, many of which are not all that important. I go back to a simple drawing of a two-by-two thing instead of some fancy productivity tool.

Justin: The Eisenhower matrix, as it’s also known as, is incredibly powerful. Funny enough, I’ve got a notion notebook set up to manage all my tasks, and it puts things in [unintelligible 00:41:26] for me, so I’ve [crosstalk]

Dan: That’s the key thing, to look at your calendar and say, “Just a week of 30 hours of meetings and 50 hours of time spent, am I spending at least 30 of those on things that are both important and urgent?” I don’t know what the right number is, but some high numbers like that.

Justin: Absolutely. Steinman, thank you so much for coming on The Support Automation Show. If people want to know more about you and Gainsight, where can they go to find that information?

Dan: Yes, gainsight.com, of course, if you want to know about Gainsight, and find me on LinkedIn, happy to connect with anybody listening. I’m way more open than you might think to having one-on-one conversations, especially if they’re about leadership, startups, founder mentality, or customer success. Those are my things, and I love talking about them. All you’ll owe me is a cup of coffee at Starbucks someday when we could get together.

Justin: Dan, next time I’m in the Bay Area, I’ll look you up, and I’ll get you that cup of coffee.

Dan: I’ll take you up on that. Sounds great. This was really fun, Justin. Thanks for inviting me.

Justin: Thank you for coming, really appreciate it, and have a wonderful afternoon.

Dan: Yes, thank you. My pleasure.Justin: The Support Automation Show is brought to you by Capacity. Visit capacity.com to find everything you need for automating support and business processes in one powerful platform. You can find the show by searching for “support automation” in your favorite podcast app. Please subscribe so you don’t miss any future episodes. On behalf of the team here at Capacity, thanks for listening.

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