Dave Derington, Head of Customer Education at Outreach, On Training High-Performing Sales Teams

      In this episode, we’re joined by Dave Derington, Outreach’s Head of Education. At Outreach, Dave helps guide customers on their journey. Dave has led a multi-disciplined career with roles in laboratory science, game development, higher education, and SaaS – all of which he combines to drive product adoption and customer education for Outreach.

      Show Notes

      How to Make Customers More Successful

      “Here's an exercise I used to do in consulting: Sit down with a whiteboard, and have your team think about what it is that a customer really needs to be successful.” (6:35)

      “There are a lot of tools, but the biggest, most powerful one is to actually simply sit down and figure out what you want a customer to be able to do and how to get joy in that; how to get them through those steps.” (8:39)

      What Makes Selling to Sales Different

      “I'm a very data-driven person: I like to demonstrate a hypothesis, and then find either supporting or negative countering arguments to that case, so we can move on. And the hypothesis I set forth, based off of conversations we had at Outreach is [that] sales is a little different.” (10:14)

      “What I'm finding is salespeople are properly motivated, they want to use your product... But you only have so much time from them. They are busy, they're trying to sell, and every minute away from their desk is time away from having another opportunity closed. So, for us, time is immensely important.” (13:03)

      Measuring Success in Customer Education

      “How you typically measure success of a customer education program is time to first value... if they're appropriately consuming my content, I'll see that time to first value to be a lower number.” (15:05)

      “Learning a new product, it's kind of like a map, right? It's kind of like a GPS. So we're programming the GPS for a customer to know how to proceed in their journey. They may want to go fast, or they may want to go slow...there might be things that you want to figure out for the cities to go visit on the map. But our job in education is to help you chart your own journey to success.” (17:59)

      “The biggest thing that's important to anybody that's going to use a product successfully is to think about what [customers] want to achieve.” (25:12)

      How COVID has Transformed Sales

      “Normally I'm gonna come to you, we're gonna have a meeting. Let's have dinner, you know, let's talk, let's do that personal thing. Guess what? COVID came. That's all gone. Now, we're trying to figure out how to navigate in the space where all the rules have changed. Now we only have online [...] So the biggest trend that we see is predominantly around sales organizations who now are needing to be scrappy.” (19:37)

      “That's the biggest trend: How can I do more with less? How can I be more efficient?” (20:20)

      “There's a way you can change your selling motion to be in this cloud-based COVID reality, but it's gonna take some work.” (27:27)

      Full Transcript

      Michael Pollack 00:01

      Hello, everyone, and welcome to selling in the cloud, a podcast about the business of cloud sales and marketing brought to you by Intricately, THE authoritative source of digital product, adoption usage, and spend data for sales and marketing teams. I'm Michael Pollack here with Sarah E. Brown. And we are your co-hosts.

      Sarah E. Brown 0:39

      Michael, great to be with you here on the show today,

      Michael Pollack 0:41

      Sarah, it's great to be here with you.

      Sarah E. Brown 0:43

      This week, we're talking to Dave Derington, the Head of Customer Education at Outreach. Excited to chat with him about how cloud sales and marketing leaders are using outreach to be successful. Shall we dive in?

      Michael Pollack 0:56

      Let's do it. Dave, welcome to the show.

      Dave Derington 0:58

      Hello, thanks for having me on. It's great to talk with you.

      Sarah E. Brown 1:01

      Tell us a bit about your background and give us a brief history of how you got to be where you are today as Outreach's Head of Customer Education.

      Dave Derington 1:08

      All right, so now you've got it. We're in for a long journey. I'll try to make it short. You know, I'm really thankful to have had the opportunity to join Outreach and a lot of the kinds of jobs that you have in your career are these, – gosh, how is it put – happy little accidents, happy little mistakes, you know, you'd go one place and you lean another place, and then bam, you end up at a pretty awesome, amazing work environment. That's what Outreach is.

      Dave Derington 1:30

      I like to say that I'm kind of a mutt when it comes to career aspirations, things I've done in my history... I started off as a chemist, I was a scientist, worked in the pharmaceutical laboratory for many years. And, you know, I've always been a lover of computer technology and software. So I found myself pretty quickly gravitating out of that, and ended up working to implement. I don't know if either of you have seen laboratory information management systems, I call them LIMS, kind of like "LMS," but you put an "I" in there.

      Dave Derington 2:01

      I started working with, implementing that kind of technology and other kind of laboratory software where we didn't have training, we were getting an environment where people were like, "Okay, what does the software do? I'm not going to use it, I hate this, I don't want to change." And I cut my teeth on software training. When someone said, "Hey, Dave, can you help me look like I have an aptitude for this? Can you help us get adoption in the laboratory?" And when I say laboratory, I don't mean just a small group, I mean hundreds of people in the facility that we are at.

      Dave Derington 2:34

      So that's where I got really excited about this confluence of software and technology, and how do we help people do their job better? So since that time, I've done all kinds of things. I've had my own company, I used to run large-scale video game tournaments for companies like EA and Nvidia. I taught at a university as an adjunct professor for many years. And I taught everything from event management to my bread and butter was game design, video game design, and did a lot of things in between.

      Dave Derington 3:02

      So I had started working at a software company called Tripos back in the day in the early 2000s. And we built molecular modeling software, which is like CAD for chemists, it's really cool.

      Dave Derington 3:12

      Where this all clicked though, I had spent several years as a Fortune 100 consultant traveling all over the place, and got an opportunity to join a company called Gainsight. And Gainsight, you know, kind of like everything we're seeing today was coming out of the woodworks, a really exciting place to be, new technologies.

      Dave Derington 3:30

      And this is what got me into this field: I was interviewing for a job as a project manager. And in the middle of the interview, my future manager said, you know what, we're stopping this interview, and I panicked for a moment. And she said, we're gonna interview you for something else right now.

      Dave Derington 3:47

      And I got hired on as the basically a manager of the education program there. I was at Gainsight for three years. And then I went over to another company, it was smaller called Azuqua, and Azuqua got acquired by Okta, and now I'm here. So, that's my journey – long-winded but it's really interesting to find how your career goes.

      Michael Pollack 4:07

      I love that background. And I think, you know, a lot of what you do has relevance for what we do in that, you know, Intricately is focused on digital product usage. And so our customers are using our data to try and find their best prospects.

      Michael Pollack 4:21

      But it's interesting, our data, our product, fundamentally is helping sellers and marketers take advantage of some information.

      Michael Pollack 4:28

      And so one of the challenges we have is teaching people to use a new tool – which is an incredibly hard problem, because software, oftentimes, particularly enterprise software, isn't always innately obvious.

      Michael Pollack 4:42

      So I'd love for you to share kind of maybe with our audience, how you approach that challenge. I'm very familiar with Gainsight. We're an Outreach – a very happy Outreach customer, but I'm curious to hear from you about what your toolbox is to help people learn to do something that maybe they haven't done before. How do you teach somebody to use a tool for the first time with software when it's maybe not quite as obvious as a hammer and a nail?

      Dave Derington 5:06

      That's a really great question, Mike. It's, it's hard. And I like to preface this. So I'm a co-host of a podcast called the Customer Education Laboratory, or CELab, for short. And I work with Adam Avramescu, so he's Head of Customer Education at Slack. So together, we've been thinking about this problem a lot: How do you get people to understand a complex piece of software?

      Dave Derington 5:30

      If we put our product manager hat on, and our developer hat on, we like to think our product is super easy. So, Mike, how often is that actually the case in experiences that you've you've seen, right? Not that easy. It's because we have this fluid model of software.

      Dave Derington 5:48

      So I think the big differentiation and something I also like to talk about going in and talking about what customer education is, is it's new, and it's not new – it's a field that's emerging. It's kind of like we're customer success was several years ago.

      Dave Derington 6:00

      There's this pressing palpable need for people like me, like Adam, like a number other people I can, you know, build a shard, I would, I would say, you know, Sarah, you know, build really well, that these are the people that were looking at software and saying, "Hey, I have an idea of how I can help educate you."

      Dave Derington 6:17

      It's a combination of a lot of things. So what's in my toolkit is course an LMS, learning management system. But beyond that, it's super awesome people, subject matter experts throughout the company, they may be in Product, they may be in Marketing, they may be in professional services – who know the platform.

      Dave Derington 6:35

      And my approach has always been, let's build a foundation. Let's understand that... here's an exercise I used to do in consulting, which really transfer as well to our market, sit down with a whiteboard, and have your team think about what it is that a customer really needs to know, to be successful. Right?

      Dave Derington 6:56

      I think I could tell you a story about how learning a piece of software can really help you and help you even you know, not just in your normal state, but emotionally to deal with the kind of work that you do.

      Dave Derington 7:09

      So here's an example, I was working at a company where we had one sales development rep, one SDR. And that person was sitting there all the time trying to figure out how to build their own strategy, they didn't have a lot of help, they didn't have a lot of support, didn't have any software, right?

      Dave Derington 7:22

      And eventually, this person was so frustrated, he left the company. Not very long afterwards, we had another individual who who joined the company. And he said, I found this thing called Outreach. And he wanted to show particularly me because he wanted to train me who was a trainer, and educator, and why this made a difference in his job.

      Dave Derington 7:41

      And he went through and he gave me a demo and a pitch and a spiel. And this was such a meta experience, because what you're looking for in software education, and customer education is that somebody can grok what you put together, they get the high-level picture. And he says to me, you know, Dave, my biggest problem is I don't know what my book of businesses and who my best prospects are. And with Outreach, I figured all that out, it helps me prioritize, and sort that and helps me figure out who the people are in the moment, that would be the best person I can talk to.

      Dave Derington 8:10

      And I have all the information in my fingertips like you're talking about, Mike, and that changed everything.

      Dave Derington 8:17

      And really, it's a matter of a combination of some video, some audio, short, you know, job aids and things like that. And we constellate an approach, where we have an on-demand presence and virtual instructor led or live training, we have all the things to receive that customers questions.

      Dave Derington 8:33

      It's not support, right? Because support shouldn't be treated as education or training, it's not documentation.

      Dave Derington 8:39

      So if that answers your question there, Mike, it's that there's a lot of tools, but a lot of the biggest, most powerful one is to actually simply sit down and figure out what you want a customer to be able to do and how to get joy in that how to get them through those steps. And that's almost entertainment, an entertainment value, too. You can't have boring, stale content to do that.

      Dave Derington 9:00

      The last note, I'd say is that when you're in a company like us Intricately you're, you're new, you're emerging, you're growing, how are you building your training program? Are you going to hire somebody and do long drawn-out development content? Are you going to do a quick and dirty and get it out there? Because, you know, the customers just needs the content? They don't care that looks perfect.

      Michael Pollack 9:20

      You can't see me but I was nodding my head, the vast majority of what you were saying and I think you raise a couple of interesting points.

      Michael Pollack 9:26

      Number one, when you're teaching software to somebody, you need to make the process obviously somewhat interactive, and that person has to be participatory in it. But you know, I'm curious to dive into a really specific point here.

      Michael Pollack 9:40

      We similar, to you, work very closely with Sales and Marketing. Marketing is predominantly our customer that tends to be our economic buyer is, but we also build tools that individual salespeople use similar to Outreach. So many of our customers are also our Outreach customers.

      Michael Pollack 9:57

      In your experience, you know, when you talk to training scientists teaching scientists how to use LIMS software tools, or some of these programs versus teaching salespeople, do you find a big difference between teaching one type of human versus a different type?

      Michael Pollack 10:14

      And by type, I just mean by role and do you find that, hey, salespeople are way better at learning X than Y, I'm curious. Have you had to tune your approach? As you deal with one constituency versus the other? How do you tackle that? How do you think about that?

      Dave Derington 10:29

      That's interesting. Yeah, there's always a difference. I'll share a strategy that I've used, that sometimes gets a little pushback. But, Mike, I'm a very data-driven kind of person, I like to demonstrate a hypothesis, and then find either supporting or, you know, negative countering arguments to that case, so we can move on.

      Dave Derington 10:50

      And the hypothesis I set forth, based off of conversations we had at Outreach is sales is a little different.

      Dave Derington 10:57

      I'll answer your question about scientists, you would think scientists are often some of the most the sharpest, you know, knife in the drawer, and super, super talented. And it's not always often the case, scientists may conceptually know a lot of stuff, they struggle with software as much as anybody else.

      Dave Derington 11:13

      I think the cohort of people that I would say are easier to train are often people that are developers, and they often don't need our training, they want to look at raw documentation.

      Dave Derington 11:23

      So the last cohort I work with was last two cohorts, three cohorts. Let's let's put it this way, I'll tell you some differentiation points between all the kinds of people that we've been working with.

      Dave Derington 11:32

      Gainsight: Customer success managers, they're very much their salespeople, they're post-sales salespeople, right? They're there to get you excited to get you to adopt to help you out to be your spirit guide, you know, be your Sherpa. They're there to coach you along the way so that you love that product. and you can grow with that product, ideally, expanding seats. But they're a little bit different than a salesperson. I'll get to that in a second.

      Dave Derington 11:55

      The next cohort I worked with was more kind of business development people. So Mike, I'm sure you have people on your team that you've worked with that use an integration platform like it could be as simplistic as something like Zapier, or If This Than That, you're doing a couple different things and doesn't take a lot of chutzspah to do that.

      Dave Derington 12:16

      But on the high end, if you are working to integrate, okay, somebody logs into your product, and you want to know if they've looked at training, and you could build a use case around that through tooling. And those kind of people that are the developers have this savvy mind, and they can grasp on to these technical concepts pretty quick. So looking for a doc, not necessarily training.

      Dave Derington 12:37

      Sales is a little bit different. And my hypothesis going in was that I think they're going to be a lot more hands-on and interactive, then I'd say that after a year and a half here at Outreach, I can definitely tell you that. We have worked hard to develop a lot of on-demand content. But, you will see a lot of people really love that live interactive content, they want to have somebody there to discuss with or ask questions or challenge.

      Dave Derington 13:03

      What I'm finding is a lot of sales people that are properly motivated, they want to use your product, right. But you only have so much time from them, they are busy they're trying to sell and every minute away from their desk is time away from having another opportunity closed. So for us time is immensely important.

      Dave Derington 13:22

      And we've restructured a lot of our training courses, both bespoke custom training. And we've dropped down the amount of time that we've had in these sessions, so people don't get bored. And we've extended to have multiple sessions instead of one. So you have time to go and try things.

      Dave Derington 13:36

      So for example, what we do to really help the customer that's trying to learn the software, like the sales development rep, or BDR, or account exec, etc., is we do in our live sessions. Okay, I'm going to turn the table, Sarah, you're going to be driving right now you're going to show me how this works. Mike. Okay, you're next, what do you think? You know, you answer a question. So we have this interactive spirit. And it really helps retention because you have your peers there, you want to be paying attention. That helps a lot.

      Dave Derington 14:03

      And then we've used the on-demand content, because people often go through that live training, and go, gosh, I miss something, and they'll go back look at it, or they don't have time. So we've developed a scaffold, with a lot of different kinds of training to help the customer in their moment of need, rather than sitting through a training session two months before you ever use a product. You know?

      Michael Pollack 14:24

      I have one more question on this thread. And then I'm sure Sarah has a whole bunch of questions, and we may switch topics here, but in your role, when you think about it, is your mandate to operate like a dean or more of like a facilitator or this is a you know... it's like, effectively, you're trying to operate a university, of sorts in which you have survey courses, you have interactive courses, and you have a number of different things.

      Michael Pollack 14:47

      But at the end of the day, the goal is to graduate, conceptually, the largest number of constituents through the program, curious how you think about it, and then internally, how are you measured on that? For our audience I think that's a that's an interesting way to understand: How does your success get measured here?

      Dave Derington 15:05

      Oh, wow. Okay. So I think there's two things to unpack there. Right? So the latter one, I think, is relatively easy. Let me answer that first. And we'll go back, how you typically measure success of a customer education program is, we want to look at key metrics. And here's the metric I like to use time to first value, right?

      Dave Derington 15:25

      First value can be measured as, alright, a customer went and they did something meaningful for the first time on their own. Now that might be in the context of Outreach, I went in, I loaded in if I don't have them, already automatically loaded all my prospects for the week. And I've organized them and I've sorted them, so that I could see who are the top candidates that I have the best information of, have the most interest in our product, and I think I can have a reasonably good opportunity to sell, right?

      Dave Derington 15:55

      So I could look at the product telemetry, the product adoption data and say, okay, a customer that has had a decent attach rate to my training material. If they're appropriately consuming my content, I'll see that time to first value to be a lower number, meaning time to first value is in days or months, right, in contrast, with someone who hasn't taken any training at all.

      Dave Derington 16:18

      At Gainsight, I saw a pretty phenomenal, I think, off the top of my head, it was, you know, double digits of a difference between those individuals. So imagine you have an account, you onboard them, you didn't give them any training, or you onboard and gave training to an admin and not the end users, somehow people slipped through it.

      Dave Derington 16:34

      It's the fact of being aware of things and having several touch points. That's what builds the adoption and even more, so it's about, well, I know I'm getting measured on how many customers are actually using the product is our adoption going up?

      Dave Derington 16:48

      How many people if I had complete some of the training, but that's a lesser metric for me, because I care more that you saw the training, and you know where that training is, right? And you've done at least the first couple things. Because that tells me, okay, well, I've set up, I've configured, I know what to do next. And then I like to make sure that it's less about completion, it's less about, did I get everybody through everything, I want to know that it's there just in time. So that when a customer does have a problem, they know where to go.

      Dave Derington 17:19

      And you should be able to see that as you know, I'm getting some adoption, but I'm not getting a lot of support tickets. I'm not calling my CSM a lot. So things like that. So Mike, I forget the first part of the question. I'm sorry, I was focused on the second part.

      Michael Pollack 17:30

      The first part of the question was just in your role, do you think about yourself like you're the dean of this program? To some extent, are you the facilitator? Are you a professor? Are you all the above? How do you generally introduce yourself?

      Dave Derington 17:44

      For me, you know, because I'm a leader now, and I have a group of trainers and a group of instructional designers, I'm more of a facilitator. I could call myself the dean – I kind of like that.

      Dave Derington 17:57

      It's yours, run with it!

      Dave Derington 17:59

      I tend to not worry about myself so much in my position, I'm more of us facilitator, I want to make sure that actually, let's put it a different context, Mike, I'm the map maker. Education is to learning a new product; it's kind of like a map, right? It's kind of like a GPS.

      So we're programming the GPS for a customer to know how to proceed in their journey. They may want to go fast, or they may want to go slow. Contrast, things like documentation or just simple webinars might be destinations, there might be things that you want to figure out their cities to go visit on the map. But our job in education is to help you chart your own journey to success.

      Sarah E. Brown 18:38

      Dave, as a leading provider in the space, I know Outreach has a lot of data and insights into what the trends are within this market. And I'm curious without naming names or giving specifics, can you talk about some of the overall trends within the industry? Sales and marketing leaders who are adopting Outreach? How their teams are adopting? The software trends in terms of data that you see that maybe other sellers and marketers could benefit from knowing?

      Dave Derington 19:02

      Yeah, first off, let me answer this by saying we are very security-minded. So we have a really great team, we have to be protective of content. So I'm not going to give you any names. Of course, like you just said, but I can't give you we're not here to like watch what everybody's doing. But we do know in aggregate, what direction we're going.

      Dave Derington 19:19

      One of the things that I've really seen – and let's talk COVID –  this is a really powerful and impactful time for us. And it's been very useful for the software market. It's useful because it's actually showing us that some of the things we had been doing, like let's talk about an account, except, hey, I'm going to try to sell you, Mike, Sarah, on new product.

      Dave Derington 19:37

      What am I going to do? Normally I'm gonna come to you, we're gonna have a meeting. Let's have dinner, you know, let's talk, let's do that personal thing. Guess what? COVID came. That's all gone. Right?

      Dave Derington 19:48

      Now, we're trying to figure out how to navigate in the space where all the rules have changed. Now we only have online.

      Dave Derington 19:56

      So the biggest trend that we see is predominantly around sales organizations who now are need to be scrappy, maybe they've lost all of their SDRs. And the AEs are now what we call full stack. Right? meaning they're not only in charge of closing deals, but now they're actually in charge of prospecting too. Or, it could be the opposite. Right? You could have an SDR team that is focusing now on everything.

      Dave Derington 20:20

      That's the biggest trend is, how can I do more with less? How can I be more efficient? So we're seeing that uptick in people turning to products like ours, particularly in the high end? Right? Enterprise businesses are saying, we need tooling. And this is good for you, right? For Intricately. We need to link to help us learn as much as we possibly can about a customer. And it's not just about their businesses and what they're doing. It's about where they need to go. Right? How do we make them more efficient?

      Dave Derington 20:51

      And one thing that I think is relevant here, you know, if I were to say, training does have an impact on our customers, and we're right in the middle of it, some of the reports that I've been reading lately show that even a 25% increase in customer acquisition when you have training, right, and that sales channel, a lot of prospects say to me, training is important.

      So more people are looking at that we're looking at training as being a part of the aspect more people are asking about like, well, how do I get better, because obviously, you don't have a lot of time, and you're spending a lot of money on a product. But that's the biggest thing. We're using digital systems like ours, sales, engagement platforms, a lot more, because we have to do more with less.

      Sarah E. Brown 21:32

      So are you seeing that people are creating, let's say, more sequences and Outreach that are targeted for account based sales and marketing programs? Can you talk a little bit about how you also train people to think about doing account based sales and marketing, certainly using your platform, but also as a best practice in the industry?

      Dave Derington 21:48

      Yeah, I think it's, I have to pull up actual specifics on like the number of sequences. But that's not always the indicator of a company that's being successful in their sales enablement, or sales engagement practices.

      Dave Derington 21:59

      There's a lot of best practices that we use when we're talking with sales leaders, and how to coach them through the change management of learning this application. In particular, when you talk about practices here, I think that's hitting it on the head, what do you use the product, or like any of ours, there are reasons for why you'd want to use that, right. And we really want to help you understand how to use it most effectively.

      Dave Derington 22:24

      So we're not necessarily going to say we see an increase in the number of sequences, a sequence in the context of Outreach is kind of like a conveyor belt of all these different interventions and activities that you can do. So it's not necessarily making more sequence That's better. But what we do to help our customers understand the value of Outreach, his pitch more on like, how to optimize that sequence, right? You may need fewer sequences,

      Dave Derington 22:49

      Because one of the big objections that we have when people come to learn our product is, "Hey, I'm a really great salesperson. And I crushed my quota every month, every week, and I'm doing great. Why do I need your product? You tell me." Well, it's not necessarily just for that superstar person. But that superstar person's included, because hey, what happens if your strategy next month doesn't work anymore?

      Dave Derington 23:14

      You know, like, in our case, with COVID, strategists, we had part of COVID working great, and then all of a sudden, guess what, now it's a whole different reality. So the best practices in there are things like understanding A/B tests for, let's say, have an email that's going to be sent as a part of a sequence and, or an assembly line.

      So you might send a couple automatic emails. And the third thing might be a phone call. And the fourth thing might be a LinkedIn, though, so you have all these different verbs or a text message.

      Dave Derington 23:39

      One thing that we have that's super cool is that you can do an A/B test on a sequence or an email, an email might have a different subject line, and then you can start testing these things. So the best practice is really use the data that you have in front of you to introspect, how your selling motion is functioning.

      Dave Derington 23:59

      If I do this, if I do A, which is I said, you know, open this message now versus B, which is some other statement. I can't make it up. Why? But it's the little things like that the attentiveness.

      Dave Derington 24:13

      In science, you change a limited number of variables as you're trying to understand a space, right? So this is kind of a scientific approach to that. And that's the kind of best practices that we want to implore people to use. It's, let's get above our day to day or individual heroics. Let's start thinking about where am I going? I want to see us close 10 more deals a week or a month. I want us to see we have 100 more calls per rep.

      It's those kinds of things which we're trying to get to because the way we're teaching the product is helping to elicit that or facilitate that fewer sequences or fewer people making sequences, fewer people making a lot of the copy, so a seller can focus on selling and not all the copying. things around.

      Sarah E. Brown 25:01

      What are some of the specific tangible things you've seen people use Outreach to actually do recently, particularly since COVID? Maybe that's different than how they were doing it before?

      Dave Derington 25:12

      I don't interact directly with the customer use cases, I'd have to pull up a couple of case studies. But, you know, just speaking generally, it's really the customers that sit down and focus first, a lot more of their time, on understanding what their outcomes need to be. Right?

      I think the biggest thing that, and this is not directly answering your question, I think the biggest thing that's really important to anybody that's going to use a product successfully, is to think about what they want to achieve.

      Dave Derington 25:43

      So I wish I had the slide in front of you have a really great slide that shows you kind of a funnel of when you're going to use Outreach, and I talked about this a little bit before, there's certain metrics that are table stakes, you know, number of calls, the interest in a in a buyer, you know, that's done by like semantic understanding of the text, natural language, query type stuff, you know, all that kind of stuff is like, if I want to double this or triple that, that's the kind of thing that's important. And customers do all kinds of different things. And a lot of the plays, there may be in your sequence itself.

      Dave Derington 26:16

      Because how you interact with your customer base may be very different, how you need to check on those for sure. So let's flag those to come back to.

      Actually, there was one customer – and I'll extract this a little bit more so I don't name names...

      Dave Derington 26:30

      There's a customer that has a very traditional kind of a selling background, one that is really in person, very high touch, meaning you go to a store, and you have an experience. And this is actually a really good use case, in this case, this customer was going to go out of business, complete completely, there's no way that you can take a storefront type company, and literally pivot overnight to start selling in the cloud.

      Dave Derington 26:58

      That's what we're talking about here. This is a really good case to understand. Because what they did is they sat back and inspected their reality. The reality is, look, I'm not going to get the people in the stores, they're scared to come in. How do we fix this. And what they did is they used Outreach to implement a process, you know, sequence based process that they can engage these people that were normally you know, in person customers, and completely saved that kind of a business. So that's, that's a good case that I remember,

      Dave Derington 27:27

      There's a way you can change your selling motion to be in this cloud-based COVID reality, but it's gonna take some work.

      Dave Derington 27:35

      And those customers that we've seen that done it most successfully have done the hard work of figuring that out. And they've got all the tools with our platform and other platforms like us to do that.

      Michael Pollack 27:45

      You made a comment earlier about, you know, reticence of certain sellers to use a tool like Outreach, and I hear that and I just scratched my head. I mean, prior to us being an Outreach customer, we used a product that was similar, but I'd say slightly inferior.

      Michael Pollack 28:00

      And the idea again, the same kind of thing, email augmentation. I'm a CEO, and I love Outreach because it lets me manage my inbox more efficiently or really manage my outbox, I guess more effectively, is the way to think about it. So I'm just like flabbergasted that any seller, whether you sell in person, or you sell over the phone, or you sell over email, why wouldn't you want a better way to manage that? And for what most people is the cesspool that is their inbox and or outbox?

      Michael Pollack 28:29

      So I'm surprised that Outreach has to even articulate to people hey, here's how this could help you. Like I desperately would take anything that would help me manage my inbox and outbox better. So, I find that to be crazy, but I want to lead to a specific question with that, which is, if that's the case, and maybe that's kind of the universe that's out there.

      Michael Pollack 28:49

      What's something you often spend a lot of time teaching people? Who are salespeople always say that you wish they knew? Right? What are some of the things that you find yourself educating outbound sellers that Outreach or sales leaders there that you think they should know? Or they seemingly don't? It isn't as obvious to them as it is to you?

      Dave Derington 29:09

      That's a really good question, Mike. I think I've peripherally answered this in some of my comments before where I think one of the biggest things that we want everybody to have cognizance about going into using like a sales engagement platform is this change management process?

      It's kind of meta, Mike, it's kind of about like, how do I really think about do I want to be a really great seller going to go beyond? In thinking about like the outcomes again, I keep coming back to outcomes. We want to think about what you want to do.

      So if I was an SDR, and I was by myself, and I maybe had just a manager and they didn't have a tool like Outreach, what am I trying to do? I'm just trying to close meetings. I might have a simple metric like that.

      But with Outreach, now I'm able to see I can compare on my team. How am I standing up against you know And Jim and john and Joan, in my team, how am I doing better or worse? Why, you know, what are the things we're doing? So things I want to share with our audience here is that being aware of the bigger picture is what's going to help you sell better, right?

      Maybe you might have some ups and downs. But generally, when you start getting a standardized methodology, a practice that you've implemented, that takes into consideration your unique character, too, right? We're not saying that you can't have fun and joy and show your persona. We're trying to build structure. So I want people to understand that.

      Yeah, it's a little bit painful, at first, to use a system that you haven't used before, because you've been using what Mike? What did you use before you had Outreach? And before you had any technology, to work and manage your your book of business and talk to your prospects? You're asking me before I even had CRM before I had spreadsheets? Yeah. What was the start when you were the first time you went to sell? What tools are you using to understand and connect with your prospects?

      Michael Pollack 31:04

      Well, I'd say I was limited by probably an underpowered brain. So I had to work through that. I think that was limited asset number one, but I think it was a notebook and pen and paper, and then trying to kind of keep track of mentally where things were, in all these various transactions, right?

      Because each transaction is a series of steps. So sequences and Outreach is a logical way to think about it that's in relation to just email conversations. But in each of these sequences, I try and keep track, where was I? And then what's the next step? And then trying to keep all these things going concurrently is I'd say how I probably characterize that,

      Dave Derington 31:42

      Yeah, and I think that really blends well into what we're trying to say here, the things that I'm going to try to express my team is going to try to expense for us and get people to understand is, number one, you need to understand who your prospects are, and understand your own ability to to address those prospects. So one of the biggest challenges for some people as they come into us Outreach is, you might load 1000 prospects in at once and start working them through a sequence, guess what happens? I can't keep up between phone calls and emails and customization, you'll lose your mind.

      Dave Derington 32:16

      So you have to kind of figure out what is your cadence. And you can do that by tuning it. Maybe I'll load 50 people, maybe alone 100 a week, and I work those prospects, right. So it's part of knowing your own limits, and having a software like Outreach and other platforms, it helps you to throttle head so that you don't burn out.

      Dave Derington 32:35

      Because I see this a lot, you know, str has worked really hard. And they're going to do a lot to close a deal. But having a systemic approach, where you have your notes, you have a chronicle of all the emails that have happened in the platform, not your inbox, right? You have all these things that help you out.

      Dave Derington 32:52

      Other things, you know, there's a tool we use called templates and snippets. And I'm sure you've used them before, if you're a power user of about reaching us Outreach, a couple different ways.

      One, you could use your inbox, that's the standard convention, because you're living in your inbox, and there's an add-on, and you plug in and you have all this additional information. The thing I love the most is the ability to schedule meetings really quickly, right?

      Michael Pollack

      I'm an Outreach power user. That is my most used feature ever. And I just want to sidebar here for a second for our audience, which I imagine we have lots of Outreach users.

      Michael Pollack 33:31

      Do you have one power-user tip that you would share? That you'd say, oh, man, this is the thing that is my favorite thing. Besides scheduling meetings, we'll say we gave that one away. Maybe what's your second tip, or what's one you would share with the audience that it's really your go to?

      Dave Derington 33:49

      I like to have my back pocket the ability to use templates or snippets really quickly. I mean, we've already talked about sequence that's kind of like the table stakes. That's the bread and butter of the product.

      Dave Derington 33:57

      But imagine, you're going to go and talk to several prospects, and some new feature has rolled out rather than me having to type up that email. What is it? Okay, I've got a good deal on my research now, oh, gosh, instead of me having to craft that email every time, you can quite easily go to our template library, find the appropriate template, and you've got a starter scaffold for that messaging.

      Dave Derington 34:21

      And what's even better is that, in many cases, if you have an organization that has enough, I think diversity in a big enough bench, you may have somebody that's a content creator. They're the ones that are actually building these snippets and templates.

      Dave Derington 34:34

      I'll tell you, as a matter of fact, we use these and I'm not a day to day user about reaching like, I'm not a salesperson, but I support sales people. I use templates, I use snippets, all the time in my emails, because somebody will say, Hey, did you get that information? I'm trying to learn about this new feature. We know we have a library of all this content.

      Dave Derington 34:53

      So maintaining that library of really juicy really helpful, impactful content that I know is going to save our customers a lot have a headache and save me trouble because I don't have to copy it. That's a lifesaver all the time.

      Sarah E. Brown 35:05

      Well, Dave, thanks for sharing that tip and sharing your expertise on the show. For folks who want to learn more about you and your work. Where should we direct them t

      Dave Derington 35:13

      For us? Outreach.io. That's the website. If you want to go to our university, you could check us out at university.outreach.io it's all the same area. You can also find me on Twitter and LinkedIn @DaveDerington on Twitter, I don't post there as much. But you can find me on LinkedIn if you want to talk more.

      Michael Pollack 35:32

      Great. Well, thanks so much for joining us.

      Dave Derington 35:34

      Thanks a lot. I appreciate you having me on the show. Good talking with you, Mike and Sarah.

      Michael Pollack 35:39

      That's it for us. And this episode may be over but we can continue the conversation on Twitter with the hashtag #sellinginthe cloud. On Twitter, I'm at @MRPollack,

      Sarah E. Brown 35:47

      And I'm @SEBMarketing.

      Michael Pollack 35:50

      Thanks to everyone for joining us for this episode of selling in the Cloud brought to you by Intricately, the authoritative source of digital product adoption, usage, and spend data for cloud sales and marketing teams.

      If you like the show, head on over to iTunes or wherever you listen to podcasts. And please give us a review. We appreciate it. Until next time,


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