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From Academy to Community: Exploring the Evolution of Customer Education

with Dave Derington, Dir. of Customer Education at ServiceRocket

The key to customer success is customer education. And the way digital solutions and tech are blending with one another is creating an exciting convergence of possibilities for the space.

“It's another font and resource for success. And I think that's the first driver. Don't think about the money. Think about the success thereafter, the engagement that can help drive that success,” says Dave Derington, Director of Customer Education at ServiceRocket and Co-Host of CELab Podcast.

Dave Derington Guest

In our latest Practitioner episode of LEARN, Dave chats with Ted about how category convergence could work in the customer education space. Along the way, he and Ted also talk about the potential for AI to disrupt processes and how professionals and leaders can push the industry forward through communities.

In this episode, you'll:

  • Understand how different categories could blend together in customer education
  • Harness the power of AI and automation to make customer education tasks much easier
  • Find like-minded peers in customer education is crucial for your growth, as well as the growth of the industry

Don't get left behind. Hear how the customer education space is evolving. Listen on your favorite podcast app.


04:07] What’s next for the academy market

[08:29] Understanding communities in B2B

[11:05] Ranking B2B community outcomes

[15:04] Predicting the future of convergence

[22:37] LEARN Rapid-fire round


Dave: Community I really strongly feel as a part of our educational enablement stack. what is the community and in service to B2B? what is a community in the first place, If I go back in time, I was there back in the day when a community was a BBS was AOL and then you have these forums and platforms and you have all these things what a community is for B2B.

Is a place where we encourage not just our customers, but our partners, our team members, and everybody to have a home base

Ted: Hi, I'm Ted Blosser, CEO and co-founder of WorkRamp, where we're redefining the corporate learning space with the world's first all-in-one learning cloud for employee and customer learning. Welcome to the Learn Podcast, where we learn from the biggest leaders in SaaS and hear what makes them successful.

Hope you enjoy the show.

Hey, what's up, everybody. Welcome back to the LEARN podcast. We have a special guest today. Dave Derington, Director of Customer Education at ServiceRocket. Dave, welcome.

Dave: Hey, how you doing, Ted? Thanks for having me on.

Ted: I was joking in our pre-interview here. The tables have turned, Dave. You invited me to your podcast CELab, which we could promote here as well. And now I get to interview you, which should be really fun.

Dave: It's going to be great. I'm really looking forward to this when we talk together; magic happens. So let's, rock and roll.

Ted: Alright, let the audience know a little bit about you. Let's do an elevator pitch on you, what you're doing right now, and then we'll jump into the core topics today.

Dave: Yeah, cool. I will start from my day job. I work at ServiceRocket. Like I said, Director of Customer Education. What does that mean? I come to ServiceRocket after being a customer and, I've been at outreach. I've done all these programs and now what I've been doing is working.

To help people like your audience to strategize, to plan, to articulate, a roadmap for their educational program, doing it with the principles that we believe in that have come out of programs like C lab, the six principles, like the manifesto that we have, and it's working. It's great.

We do advanced partner training I've learned a lot of new things in this opportunity. There's a lot of stuff going on out in the market right now. This is a great time for customer ed I think we're ripe for good things. So this is where I'm at.

I'm passionate about helping people. To do the kind of work we do.

Ted: Well, we were joking offline that I truly think you're probably one of the leading thought experts. In customer education, almost an entire world. Your podcast is a huge


Is it the number one ranking podcast in the category of customer education?

Is there anything that even competes?

Dave: No, we're doing pretty good. The podcast is actually just right about that five-year mark. We're in our fifth season. And it's taken on a life and an existence of its own in a place of the community. So I will be honest there are not a lot of voices in customer education.

And we're one of them. I'm actually doing a lot more work, and elevating the mission of what customer education is, because I believe it's a core of customer success. It affects enablement, we're partners. We're up there, but there aren't many competitors in the market.

Ted: Well, thanks for leading the charge regardless. And that's why I think it's gonna be so fun today to actually spend time with you to get your perspectives. On the market overall, the main topic I want to talk about today is the concept of convergence what I'm personally seeing on the market is the convergence of multiple different, categories that typically used to be standalone.

Think about the academy, think about the community, think about the knowledge base, think about Digital adoption platforms. And they're all converging right now. So I want to have that as a main theme for our discussion today. But the first place I'll start is on academies themselves, because I think that was really where you grew up.

You built an awesome academy, for example, Outreach. That's when we first met, but tell us about the academy market. How do you think the academy? Market is going to evolve. I'm assuming you'll probably say something around convergence, but tell us more in a vacuum, the academy market, and then we'll move on to a few of the other categories and then maybe tie them all back together here.

Dave: First off, I'm going to go back and channel the discussion that we had, a year or so ago where this came up. This was emerging we're at a concrescence.

I'm thinking about right now, I wish I could get my Crossing the Chasm book out. Because one of the things I'd like to frame up and propose to our audience is we think of education like it's this linear thing,

It's like, oh, I just build some stuff and I get out there, and I train my team, and I help them grow and they're going to help other customers grow. It's not like that. The felt experience, Ted. You know this because you're like me.

We're working in these startups, working these ecosystems and you as a leader see it even more So where we're at with that in context of an academy, An Academy is like your second step in an educational enablement program.

And I think we can speak to that whole market. Where are we at? When you get to the point, Ted, and you want to do an Academy, you've realized I got enough people that I can make some content. I can organize that content. I have WorkRamp, I have the tools, the stack that allows me to build out a self-service approach.

And that's important. Think of it like a Jeopardy board. I'm going to take admin for 200 Alex, you pull the card off, and then we go down that path and we have the questions and we learn. So I have might have one path, another path, another path.

So you can put a matrix up it's kind of linear, in the modern era, the workflow and the persona. Of whomever is using our product. I think it's a baseline. It is where you start and it's where you grow and it will always be part of your ecosystem because it characterizes and tells the story of how I put all these ideas together to use the product or to work as a team.

Ted: That's a great start. When you think of it as a baseline, the WorkRamps of the world, the thought industries of the world. When you just think about the academy itself I'll take a technology bent to this.

It seems like we all have the baseline. We all have courses that are available within whatever hierarchy, a folder structure on a landing page there. Do you see that evolving into something even greater over the next couple of years? For example, Extreme degrees of personalization. what do you think's next?

And again, this is just the Academy's lens from a technology standpoint, beyond the baseline?

Dave: It's going to be about this concrescence, we keep seeing these things happen, like, chat GPT appears, it just lands in my door, like a cat that, came in from the wild, these emergent technologies are so helpful. The big new thing is how we are grappling with it. Artificial intelligence and machine learning. What I mean by that, it's not necessarily chat GPT, but that's a good place to start. It's these scaling resources, these things that help you and me, maybe you started writing out something that you're going to share with your customers about your new value prop for work ramp over the next year.

If you're like me, Ted, sometimes my thoughts are disorganized. I'll throw everything down on paper, and I have a couple of resources, and I go, okay, ChatGPT helped me. And then we pull a few things for you and get you started. Like what was a four-hour job for me as a marketing person, a leader, an education person now truncates into something that's more linear.

I think you want, I know I want this assist. I want to be able to build and automate content. I will talk about one platform that I think is really cool, which is video. Where we can create and construct videos on the fly with audio, with translation. And if you want me to really hardcore nerd out, those things could be hooked into your continuous delivery or continuous integration platforms like Jenkins or whatever, whereas like I automatically strangle these things up. So product changes that hits a threshold of, I've got to maintain all this content and all this stuff in my academy.

What if those things were just automatically updating and there's no human involved or there's a human involved. Who is now a subject matter expert that can make sure to refine. they're not necessarily an education person. We've taken all that best practice mindshare and pooled it into templates and things that work and things that drive success.

Now I'm thinking like Gainsight, I'm thinking like Outreach, I'm thinking like all this automation I can talk about a lot of stuff, but I think that's the core of it.

Ted: You're spot on. I think about where the innovation is going to happen. You've talked about this before, where, customer education doesn't always get the investment it should and we need to figure out how to scale our efforts content might be. One of the highest leverage points, maybe I was thinking about it wrong.

And I thought your answer is going to be something more on the front end. What was the customer experience? And maybe that has a little bit of innovation. But you're saying is on the backend. And how do I scale long-term?

Let's shift gears. So I think an area that has a lot of momentum right now, which is communities. You've had guests on to talk about communities. I wouldn't say it was in your immediate sweet spot.

I could be wrong when you start seed lab, but it's starting to get there. Give us your thought on B2B communities, how you feel like It's evolving right now, what they should be. Give us your rundown there. And then we'll talk about the conversions between academies and communities.

Dave: I really strongly feel as a part of our educational enablement stack. I'm going to shift the language a little bit more and talk about how we incorporate these technologies and thought process. It doesn't mean that we don't have an expert of community, But this stuff isn't particularly hard. What is the community and in service to B2B? What is a community in the first place, If I go back in time, I was there back in the day when a community was a BBS was AOL and then you have these forums and platforms, and you have all these things what a community is for B2B.

Is a place where we encourage not just our customers, but our partners, our team members, and everybody to have a home base just like I go to Facebook or something where I have a community of people that I care about and I interact with, or I just want to fight with Communities as a service of B2B is a little bit harder, you go to whatever platform you like, and there's people there, and there's content there, and there's stuff that's happening.

If I go back and I think about Gainsight, it was kind of a nascent, state of communities for B2B. And we had built a platform and then it was like, Where is everybody?

We had to build that as a part of our platforms, a part of our customer success program fill it with content, And then it started really serving us as a way where people were promoting ideas and natural things were happening.

And it works. But I want everybody to think seriously about it. That it's not a panacea. You can't just throw a community out there. You have to have an executive sponsor and you need to start integrating that into other of your stack.

Ted: Let me ask you this, what do you think the top outcome should be from your community? So for example, you will have the influence of the world who have their flavor. That's a little more on the referral-driven side. Let's call it top of funnel.

Let's go generate money from your communities. Then you have the discourses, which is a little bit more forum-like application. That's all about product support, making a better product user. If you had to kind of stack rank your personal opinion, cause you're going to come at it with a lens of customer education, where would you stack rank in the B2B world, the outcomes you should try to drive from your community?

One is engagement.

Dave: What does that mean? You can measure it in terms of engagement metric. How many I may use?

What monthly active users, daily active users? That means something for success. So I want to, speak in the language that we need to be thinking about. And, I know some of the customer success thought leaders out there will say, we're all driving to outcomes.

Those outcomes are typically, you and I get a new product. And. Well, we've got to do something tomorrow with it, and we got to get in able to do that where community comes into that is it's transcendent. It's a little more meta, and it's a little more evolving. The outcome that I want to see, one, is that everyone in your business space, your customers, your partners, are able to ask questions broadly. The whole market and not just a support agent, they have other things to do they're focused on break, fix any problems and real issues.

You get on, and you go, Oh, Dave, that's easy. Let me show you. And you screenshot something guess what? That gets pinned. Then that gets liked 10, 100, 1,000 times. And then we convert to a blog and then we do an education and enablement material for it for different teams.

It's another font and resource for success. And I think that's the first driver. Don't think about the money. Think about the success thereafter, that engagement that can help drive that success. And then, we want a lead generation to solve the problem.

That's generating more revenue over time because we have longer lifetime value of our customer. You know, I was a scientist and I think about calculus. I think about all the area under the curve and all the little things we do. This is one of those playbooks where we can actually see the effects and the outcomes of helping

Ted: Everyone I want to take a second to talk a little bit more about WorkRamp right now. You are listening to Dave Darrington, who's talking about the convergence of technologies in the customer education category. If you're looking for the ultimate platform to converge all of your learning needs, look no further to WorkRamp.

WorkRamp is what we call the all-in-one learning cloud where you can converge your employee, your sales enablement, and customer education efforts. All on one unified platform. If you want to learn more, visit us at work ramp. com. Now back to the show.

Dave: Drive value to the community members, answer their questions. let's make them product experts. Let's make them highly engaged. That's number one. Once you do that. You can drive, top-line goals.

This is them retaining, this is them referring, this is them doing case studies for us.

But first and foremost, just make them as successful as possible on the product and engaging on that.

Ted: That's great. Stackering. Cause I do have that debate. It's like, if you ask a marketing leader or a sales leader, they'd be like, where are my referrals from the community?

That's their number one thing. but I love the customer success lens to this first, which will then breed.

Dave: I'm going to parent this again. I did a talk at Gainsites Pulse this year. What was important is that we're thinking in the lens of B2B businesses and successful outcomes.

Customer education, in my thinking, is the core of customer success. It's all the things we do and we never talk about, but we're trying to now package all of this stuff up. So that these are legitimate plays that go into your playbook. And this is customer success.

Ted: Love that. Let's, combine these two topics. Now I'll talk about a few trends that we're seeing in the market. So I want to get your opinions on these. actually listened to your podcast, with, Adam from Docebo, really good, episode, loved his vision. I think you knew him even previously and he was talking about the convergence of communities.

And, customer, education academies. Cause they just bought pure board Then you have Nick Metta, your former boss over at Gainsight who literally just last week, bought North pass who were very familiar with as well too. So you see this convergence and we've also been watching it as well.

Now let's talk about that convergence. What's your opinion on the convergence? Where you think it should go. Love to just ask you that open-ended question and we can navigate from there.

Dave: The day of that announcement, it was weird. I got all of these pings on my phone, and it woke me up. is there an emergency? Is something happening? But everyone's like, Dave, Did you see this? I'm like, no. What? And that day was very interesting. And the rest of the day we just went to Lowcon, which is a conference for customer education enablement, this whole thing. And everybody there was talking about this and like, what does this mean? I had about kind of an analyst who's been working in this market for 10 years and trying to help the market.

I think this is the shot across the bow for the industry. you've got Nick Mehta standing up and saying, look, this concept of customer education is a tool. It's a framework. I want to actually, incorporate customer enablement or user enablement or partner enablement. I don't like to differentiate these things because, my friend Sam Anthony Murray said this, knowledge governance, curation of. All the materials that go into supporting a customer at a scale. You talk about Nick and Gainside and North Pass, and the language that's emergent from this is this concept of scaled digital success, scaled customer success, digital customer success, digital customer education.

They're all evocative of one thing, which is, in this context, a trend of a push or a drive to allow people in their own place at their own time, whenever, wherever and whatever language, whoever they are to get the help they need to get a successful outcome. And my feeling about that is education in its role.

We could call that enablement. We could call that engagement. A lot of times what a CSM does is help teach. They don't think about it. We all teach So going back, reframe this acquisition happened. On one hand, I'm a little scared, and everybody should be.

All of us are going to benefit by cooperation, We have our own tracks and our own goals and stuff, but we have to do a little give and work with each other, but we all slot into the space, the ecosystem differently, we can constellate a series of best practices and thinking off of a framework that embeds into our overall gain site stack platform of technologies.

We mentioned community. Inside it is a part of that package, right? You've got gains IPX, what's happening in the platform. And how do I capture that? And what can I do with that? So all of that, I like to call telemetry, what did you do to it? Oh, you click the button and then you didn't do anything after you click the button.

And what does that mean? I see this as building out the framework with a platform. And LMS is a database. That's almost pejorative. at the core of everything that's behind WorkRamp, It's People and what they did and how they did it and what they got and constructed in a learning program. So I think what this does to us is it helps contextualize how the effect of education impacts successful outcomes over an entire market in an on-demand or self-service play. I have to emphasize this too.

At Outreach, when I built my program and this was on the Skilljar platform, we had a small team working. On the scale place, But we had a massive team working on training live. What I saw, though, and this was fascinating is this push away from the live, away from one to many.

It's still there. And the system can allow us to pay for people to pay for that and get that ROI and get that one-on-one intention. But the bulk of those people are maybe inattentive, busy, don't have time, got the kids at time, and they're going to come back and say, Can I have the recording? go to the academy, go to the platform, go to the integration, build this whole on demand platform that is there.

It's that dashboard, that portal that is there for you any time of day. that's the excitement that I have as an analyst strategist it's here and important. Now what?

Ted: So have you formed an opinion? I don't know if people are coming to you, but when you think about, and the core technology pillars right now, academies, community platforms, knowledge bases. Do you feel like those. Are going to converge and do you recommend that, buyers or your brethren that you work with start thinking about that convergence and factor that into their, decisions?

Dave: Yeah, I like to think about. All of this stuff as A stack, what's a stack, my educational stack is that thing that when I walk into a job or a role, I go, okay, what is my community?

Do we have an LMS? We have three. Why? And which one works? how do we measure what a customer is doing? Where is my CRM? What's our data lake or data warehouse where we can bring this together?

What tools can I use myself? I want to work with a BI person to get all these sources put together in one place let's just put in context of Nick Meta at Gainsight. And this is something we did together when I was working there.

Thanks to Nick and an amazing team of people were able to put together my LMS data in and merge that with the CMS data. And I merged that with the product data. We had dashboards that he, Nick, could go to the board meeting with real-time accurate and showed usage and BS of the education program.

All this stuff. Why I say this is that our stack allows us to interconnect all of this information. That's, happening in a digital world. Now we've got these data sources, we are pushing them, compressing them,

And building a constellation of interpreted data that tells us what a customer is actually able to do, where they're stuck, and the gravitas of that is I can make a trigger or some kind of a call to action or some automated response.

It says, Nick, you're my customer. You and your entire team have not been using WorkRamp like you did. Total usage is down rather than me have being a CSM Finding that out three months later at renewal, that's already in my playbook. I'm an enablement coordinator and I'm seeing my team internally not engaging with my material and they're, using it down and I still am using a gain site,

I can build triggers internally for that to go to my internal team, to my managers and staff. And now I'm not fighting L&D-type stuff. It's all integrated. So I'm pausing intentionally. Think about that stew like a, pinball machine and I'm upside down. I'm stringing it all together. And you have this experience of, you're an exec and you're walking out of a meeting and you've got your admin there who knows all of your stack, and they can pull up, Gainsight and look at the dashboard.

Yeah, that's a problem. Hey, can you write me a report on this? And we've got all the data there. It's all together in one place.

That's convergence.

I want to go a little bit further and say, there's another end of this. That's the worry end, I like to position myself, like you said, as a thought leader, but it's more than that.

I'm a practitioner. I still edit my own stuff and make my own content, As a hobby and I keep motivated. If you're a thought leader, let's keep, busy. But what I see is this next layer of integration; why couldn't you swap out the learning platform with another learning or connect to it via an API framework or a connector?

But the things we could do behind the scenes now are, I'm going to join my enablement data into the Gainsight stack. And, here's the API here's the connector. Boom. Here, just turn it on. It goes in, it sees your schema. Your database, it pulls the right things in. Now it can look at.

My partners are enabled like this. My customers are doing this in this LMS that's over here. The swap and plug-and-play modularity of an integrated tech stack around education and enablement learning is. Perhaps to me, the Holy Grail.

Ted: That was a great monologue, Dave. I think we have this really nice theme from the top of our conversation around, the academy market going and a lot of that's on the content creation side and hopefully AI can help out there.

But you pulled this all back together really well where this convergence. Is not just happening because of better content creation or better academies, but it's really the unified data set that a business now has visibility to that could take action on. It could be on your gain sides of the world, a catalyst of the world's sales force of the world.

But if you have that, unified data set, that's really what you're gunning for. So, Dave, I know we're running up on time here. I love to move over to learn rapid-fire round to close this out.

This is a section where we just ask a few questions, one to two-line answers from each. Especially from someone like yourself, what is one podcast, book, or blog that is top of mind for you right now?

Dave: I keep watching or listening to Greeking Out, which is a Nat Geo podcast about Greek and Roman mythology, and, more because my kids listen to it. Best darn podcast I've listened to. I've learned so many things from it. It's just fun.

Ted: Probably beefing up your vocabulary. I think I've learned four new words in our short

30 minutes together. All right. Next one. If you could learn from one person alive or dead, who would it be?

Dave: Ryan Reynolds. Because I really love how he's taken that humor and business strategic thinking. And I want to see us do that for education, like on TikTok and YouTube, these micro things,

I want to learn how he's doing this and what he's thinking about in the back end. What a business strategist and a great actor.

Ted: This is Deadpool, Deadpool Ryan Reynolds. That's a great answer. I don't think we've heard that one. And maybe he does listen to this podcast.

We'll see. All right. Last one. one tip you would give to all the other customer education professionals out there.

Dave: That is to find the others. Ask for help. Connect with your peers. You really should be finding resources, or if you are so motivated, share your opinion, share your ideas, get out there and share what you've learned. One thing I've learned, Ted, over the past few years, in particular, one of my friends, Brian Childs, who runs Learning Outcomes, said to me, Dave,

There are so many people that know customer education enablement out there. They know way more than any of us. And I believe that. And I know it experiences I've had this weekend, like low-con learning outcomes. This is a conference C lab is focused on sharing that knowledge.

I'm inviting people to come on that show, have the knowledge, right? Doing things like this. So get out there, find the others, get connected. You won't feel alone. You'll feel supported. And you'll feel like this all is starting to make sense.

Ted: Dave, thanks so much for jumping on love talking through the various topics here, especially on this concept of, convergence in general, but appreciate you taking the time. We'll have to catch up soon. And thanks for being a guest on today.

Dave: Anytime Ted, you're one of my favorite people to rap with about technology and learning and enablement. So keep doing this. It is wonderful to see. And I got your back.

Ted: Thanks for listening to the Learn Podcast. If you're a fan of the podcast, do us two favors. One is to subscribe to it so you can get the latest updates of our most recent episodes.

And two, write a short review of the podcast. This helps us get discovered in the broader podcast community. Thanks again.