Customer Success Leader
Customer Success Leader

Episode · 2 years ago

How Sales & Customer Success Make Power Users w/ Jake Dunlap


We’ve all heard about sales and marketing alignment. But, to enable your customers to reach their full potential, it takes alignment between sales and customer success, starting at leadership.


In this episode, I caught up with Skaled Consulting CEO, Jake Dunlap. Jake shared how leadership can help customer success and sales teams cultivate power users.


Plus, we covered… 


- How focusing on power users instead of new deals benefits sales orgs


- How to align your customer success team w/ the business objectives of customers


- Why a growth mindset outperforms a service-only mindset


- Tools to help your customer success team be more proactive


Resources mentioned:




- LinkedIn Sales Navigator


For more info, check out or send a message to

Too many organizations. We've now we've segmented all of these roles so much that the incidence of the group before don't line up with what the customer needs for the next group. Want to create delightful customer experiences, you're in the right place. Welcome to customer success leader, where you'll learn about the successes and struggles of leaders who are passionate about their craft. Trust me, you want to stick around. Here's your host, Eric Crane. Hey, I'm Eric Crane, CEO and Co founder of flat file, and I'm here today with Jake Dunlap, CEO. It's scaled. Hey, jake, hey, what's going on? Man, how are you? I'm doing all right. Thanks. It's one of those another muggy days here in Atlanta, Georgia. Where are you calling in from? Austin? Austin, Texas. Oh Voice. So I got fun story for you. My multiple times great grandfather was the vice president of Texas, the vice president of old like back when it was like its own thing. So I don't know if you know any of your textas history and can remember. is now the only vice president ever in Texas as. Pretty cool man. Yeah, well, he's got that way because he pieced out on Davey Crockett at the Alama decided didn't want to stick around there too long. Oh No, Oh mad yeah, no, I we moved here a couple years ago from New York. We were there for six years and then I grew up in Kansas City. So but I'm enjoying Texas. It's been good, Austin in particular. Yasin's a great city and we weren't in the middle of tandemic. I'd love to do this in person so I get some great barbecue out there for Dad. Dude, I look. I'm a barbecue fiend. So anyone who's coming to Austin, let me know. I'll take care of you. Love it. Thank you for taking the time with me today. I'd love to talk a little bit more about what you do at scaled, like what was the idea for a scaled? Why did you get it started? Tell me a bit more about the the origins there. Yeah, sure, so. I mean my background, I've been in sales and sales leadership frolmost seventeen years and then it just makes you feel old just saying it, but you know, it is what it is at this point. So I you know, was a VP of sales at a few different startups, glass door in San Francisco and then a started called chart beat New York, and through those experiences what I saw was there's a real gap in the market for tactical needs as companies were scaling and I worked with consultants at both companies at every time I worked at a consulting firm or a trainer and it's always felt like okay, like now what that cool? Thanks for telling me about all this stuff, like I need tactical help to pull it through. So I started scaled with this idea that we could bring in expert sales leadership if they needed that, expert sales enablement if they needed that, or expert sales operations, you know, to bring in levels of expertise. And you know, we were talking about this a little bit before that. You know a lot of times as a start up you don't need one person full time, you need it for five or ten hours. and nothing like that ever existed for sales. You know, it was from marketing. They have PR agencies and digital and paid and I really saw like sales needs the same thing. Sale need someone who can come in and maybe we had to let go over first VP and someone who can be a three to four day a week VP and helped to bridge that gap through next full time or they needed help around operations or our content, but not maybe full time. And so fast forward to today. You know, we spent the first really for five years only working with kind of the start up and Roath from one to fifteen million, fifteen to fifty million like that sector. And now we... with a lot of much bigger companies that are trying to basically modernize their sales approach. And because we've worked with hundreds and hundreds of hundreds of companies, you know, we've had a chance to really hone and see. Even if you're a big company, these things applied. They're just on a different change management scale. And so really those are you cover two different customer types. Now it's that kind of still working with the growth stage companies, but more and more we're seeing big you know, Linkedin is one of our largest clients. For example. It is big orgs wanting to be nimble and work with a more boutique firm as opposed that, you know, spend two hundred and Fiftyzero dollars on an assessment. So yeah, that's or up to. That's really cool. So we might talk a little bit more after I stopped the recording here, learn a little bit more about you, off or, because I feel like we could use some of that. I flaugh file. For sure, we go. I like it all right. So we're on a customer success podcast. You just talked about how the sales team really needs ways to extend or scale what they're doing more rapidly. So what gets you excited about getting on this podcast and talking about customer success? Well, I think it's important for me as a sale when I was a sales leader, I would never be a sales leader without also owning success. I just would never do it because for me I want to make sure I can control the entire customer experience and I feel like too many organizations we've now we've segmented all of these roles so much that the incentives of the group before don't line up with what the customer needs for the next group, and then the incentence of that groups don't line up with the customer needs for the next groups. Right, you got a sale development team that's trying to jam in meetings. You've got a sales team that's trying to jam in deals and none of those are. That's not what's best for the customer right. That's best for the customer is, you know, is getting to power usage. And so whenever we work with organizations, what we try to do is just re architect at times, you know, the thinking of nor your job isn't to create deals, it's to create power users. And so for me, my entire career. Again, when I say sales, I almost use default to thinking about, you know, the customer Experience Post Sale, because it's all a part of that customers life cycle. And so a customer success account management are are literally, I think, just as important as the net new but you know, organizations like shiny new things, so that tends to get all the up. So I'm a massive, you know, account manager, customer success advocate. I don't know. I mean I'm not going to prefer I mean I would cuy. I think I'd call myself an expert at it. You know, I think I feel comfortable with that. I was going to say Guru and I'm like wow, that's maybe, that's maybe too far, but I'll go with expert. You know, I've done this enough now and we do a lot of work organizations other customer success process too, because again, we just see it as an extension of the customer experience. You're an awesome Texas, Not San Francisco. You can't say you're a you gotta go. All right, that sounds good. Well, so let's I mean as an expert in customer success, how would you sort of formally define what customer success and I was like, I wonder if he's gonna ask me this. So I think that there's two components and again, different companies call it different things, right. So there's account management, which I think typically we refer to as owning, like the business level relationship, right, what's happening in the macro? What's happening with the exactly cutive level or other individuals that are involved, and they're making sure that, you know, if we signed up or an organization signed up to try to achieve x Roi, that company is then seeing the...

...results from that. Roy Customer success. On the other hand, and I'll give you a story about what we did at chart beat, that I think could be a cool wrinkle to just toss out there for people, customer success is focused on power usage I mean can't lay at the end of the day, their job is to make everyone below that happy and using the product and making sure that they are getting the utility that they need. And so when you have these two groups, and sometimes it's the same person. Right, this depends on how big your orb is, and that's fine, but when you think about it, it's when these two are working together we've got one person or again it's the same person. Your focus on. I'm having these conversations about business impact, maybe these conversations about tactical execution and utility and value. That is how you create a winning customer experience. And what we did it it chart be that, which I think could be kind of cool for people at least, like maybe think about is again. Like I said, I've always controlled like all of this, but will we actually did it? Chart be was the customer success, the people again, who are like in the product, talking the frontline users. We actually ended up having them dotted line into me, because you know, I ran the account management component, and we actually had a report into product and we were very intentional about that. It's like, well, you know, whose job is it to make sure that people use it? Well, that's actually products job right, like products responsible for making the product sticky and useful, etc. And so imagine tying your success seem. And you could do it the opposite way. Have them dotted line in the product too. You know, we could have done it one way or the other, but we actually thought it would be better because then the SUC cess team is talking to the product team in real time every day because they're working with them, the report to them, and so I think again, when you have that mindset, that that success and product are kind of married at the hip. I think that that that is how you create a recipe for building sticky products. And so often as well, there are mirrors of each other's roles too. Is a product manager, former product manager and a farmer CSM. There was so much that was similar between the different roles. Where one was largely internal facing, one was largely external facing, but you still have to interface with basically every other group within the company. That's right. So when you're working with your customers, what are the biggest blockers to them, sort of removing this barrier that oftentimes exists between a sales and a success org. Well, in some of it comes from incentives, candidly, meaning if you have a sales organization that's only compensated on sign contract and there's no component that's tied to usage, it can create some not great behavior. Or again, if you have a sales leader who's not also, you know, kind of responsible, then you know there's absolutely I mean this is might sound crazy, there's really no incentive or disincentive for them to not just sell anything and to promise the moon. And we all want to sit here and say everyone's a great human and whatever, but that's you know, people are going to try to do what they need to do to make money as well too, and so I feel like it starts with incentives and how do you make sure that the incentives are aligned to do it's best for the business, which is create users? So I'm an actually a big proponent of tying part of a sales commission to some usage metric, which is somewhat revolutionary, I think. But I really believe every sales organization should have a small percent of their comp tied to do they actually use the product, and I think that that Distinceeadi. EIZES that salesperson is make sure that they're...

...not overpromising, make sure that they're delivering on the value that was promised in the beginning. And then, I think on the success side, to me it's I think more success people need to also make sure that they are aligned to the business needs of the clients. Sometimes, whenever I see success teams, it's almost a service only mindset and verse a growth mindset at times of like, look your job, at the end of the day, a all a tool or piece of software does is to provide some business utility, some impact on the business, and I think a lot of the Times cs people are almost overly focused on just the usage of their one thing for trying to understand that the cut the companies, you know, real objectives, and what happens then is like, you know, even though some people are using it, it actually is less of a priority now, and so that accounts actually at risk because you know, in your mind you think a people are using this or they're not using it, and it's because you don't understand the bigger picture. So I feel like on the CSID, you know, CS individuals need to do a better job of staying up to speed on, you know, what the customer is trying to accomplish, not just are they using. So for a CSM or a lot of times you're not necessarily directly exposed to that executive level decision making at your customers organization. So how do you go about uncovering that information about what is most important to my customers business? Well, obviously, if it's just you, I mean you got to work with your account manager to have a joint plan. You know, we call it a joint success plan, Mutual Action Plan. That you know, account management and see us or quarterbacking these plays together. The other thing I would say is why? Why don't you know? They're a subjectives. Just go sit in on the call. Just this goes right, right along with your acount manager, to go understand the business objectives. You know, and so I would say, you know, work with your am but you know, you need to understand that. You need not do I'm not it would be nice to. You need to understand that. So if you need the information, go get the information, don't just sit there. Well, my account managers now just go say how I want to be on the next call so I understand when I'm working with the team to make sure they're actually doing what the decision makers need. Got It. So if I'm reading this the right way, you're basically saying, hey, that'll usually come up in a sales process anyways. So get integrated into part of that sales process where it's most relevant to understand what the customers objectives are. Is Business Right? Because, okay, and then let me just let me try to make this very practical for everyone to so very tactical and practical. Imagine an account where, at the executive level, they're making a shift toward channel partner sales. You sell a product that is built for direct sales. Right, of just making up a scenario here, you can insert whatever it is you are focused on the front lines is to see us of making they're using it, it's going well, things are happening and and three months later they make this decision. They have you peggued incorrectly as a direct sales tool and reality you actually could do channel and then that you they don't renew. If instead, I know where the...

...pucks headed. I know that because I was in a meeting three or four months ago. I can start to retrain and maybe rebuild different ways that they can use the platform for channel sales. That's it's really that in those types of examples. You know, are all over the place, you know, and so I think a lot of people just have to do a better job of not over assuming. You know, you always assume that the business priorities are changing. You know there's different actors or players involved. For sure, that makes sense. So to flip that last question on ased, what information could customer success be giving the sales team in order to improve the overall customer experience as well? Well? I think see US teams need to do a better job of trying to educate the sales team on what actually goes into on boarding and goes into being successful as a customer. I think a lot of times, you know, sales only exposure to this is whe their sales manager told them, which is like it's easy, our CS team is really, really good, and so then sales just goes and tells that to customers. They don't want to miss lead customers. They just don't know. So if I was a CS leader, I would spend all of my time educating the sales leadership team on what actually goes into on boarding and being successful making it, making sure they have a slide or slides at the end of a presentation. They can talk about it because I've actually helped them to close more deals. It's a big reason why a lot of people deals go along as they don't should understand what happens next and so they make no decision instead. So that's what I would do if I was in to see US leadership or pris the CSM. I would spend a good amount of my time focusing on education of the sales org and that will help to make them more successful and less have substantially less customer turn yeah, that makes a lot of sense. It's got to be a two way communication, for sure, but doing that its scale probably requires a lot of technology. Right. So, whether it's figuring out activation based COMP structures for your sales team or whether it's, you know, communicating requirements back and forth or business objectives between the sales and the CEE US side of the business. So what are some of your favorite tools and systems that you've set up in order to let help organizations do that more efficiently? There? I mean I think there's a you know, it's a sales engagement platform called outread outreached ioh that if I was starting a see US team right now, it would be my very first purchase. A lot of people think of it as like a lead generation tool, but all it is is a sequence of activities with different workflows in it. So imagine, you know what an account comes in. Hopefully organization is to kind of tiered out accounts right of like here's how we treat our tier ones tier two. So I get to Hey, this is tier one account. I know I want to talk to them at least every three weeks. Cool, I'll put them on my every three week sequence. These people tier to account. I need to talk to them every forty five days. Boom. By Tier Two secrets, these I need to talk to once a quarter. Boom, every ninety days. And then, of course you have conversations before you know are you have conversations with your customers as a part of this, but I think a lot of companies are not interacting as much as they want to proactively with clients, because I feel like we're overloading a lot of cus people. And then, therefore, the only way that you're going to be able to manage this is with technology, and I think outreach is probably the best tool to do that. Then the other would be linkedin sales navigator, meaning what I would be doing again if I was a CS wrap and I started tomorrow, there's I would get us sales navigator license and I would makeke sure I'm connected to all...

...of the people that are in my like sphere of influence at these accounts. Why? Because then when I post a piece of content on Linkedin, guess who sees it? My customers, right. And so I feel like there's some sales tactics that see us people should be deploying to help them to manage more accounts and add more value to their accounts on a consistent basis. When I think linkedin is to do that. And then I think, you know, managing the email and call component of that. I mean, you can even bake in the linkedin component to outreach to but I think those are two tools that I think we're sleeping on as opposed to like, you know, gain cider to tango or what you know, like some of these tools that are more about like raising flags, like that's cool, that's important, but more so if I can get in a regular rhythm with my customers and I can add value to them on a consistent basis, maybe I, you know, maybe I triage some of these issues from happening and I understand their business objectives. I mean I don't think we're indexing enough time. They're. I'm just like, if I can get all of our meeting set up for the next year on Day One, I'm good right, as opposed to again, it's set changing from a reactive to a proactive mindset, from account management and success factor. Yeah, I hear that all the time from different guests on the PODCASTS, like sort of striving towards that proactivity. What I find a lot of times is that there's still a lot of manual work that has to go into that. So what are some of the things that you feel like you're being done manually today that machine should really be doing instead? Well, we'll talk about today verse, maybe tomorrow, Right, because I think we can talk about like dynamic account tearing based on prepere like look alike models. Right, like there's some cool stuff that people are doing with artificial intelligence that helps you to really understand who your best customers are. There's so many micronwuances, you know, to like you know right now, we kind of do it is, I we're pretty basic demographic and psychographic you in terms of how we tier our accounts. So I'm excited for that. I think that will just continue to provide better customer experience. It will continue to allow people to, you know, spend more of their time with the right types of customers. First few, you think, is the right type of customer. So that's exciting. But in the short term, again, as you can tell, I like to plan right about. I like to plan and I like to get things done so I don't have to think about them again. I would just really I would create a process and the onboarding that every customer went through, and it's like a four point checklist where we schedule all of your monthly or quarterly business reviews up front. We schedule all the trainings and details and the one hundred and one, T two, one, that whatever up front. Now, you know, we schedule a you know buyal something or other, and then we even get like, you know, we start to have conversations around the renewal. We called the hundred and Twenty Day renewal process. That most renewal process. You start a hundred and twenty days from the contract and so I don't know if you need to get the renewal contract books, but I would definitely have it in my own task management that I needed to do it and then, guess what, I don't need to think about that account ever again. And what I mean by that is like, well, take what do you mean? Well, all the milestones are already built. Now I just go execute and then I'll my proactive touch points are already there and I think we're instead we take the opposite, which is let's do nothing and just react all day. That sucks. That sounds horrible, you know, like just surprise after surprise after surprise. Like no, I want... get in front of that stuff. So that that's what I would do. That would be more proactive in scheduling and I would do it from day one. So how do you get more ahead of the design of that process as well? So a lot of our listeners will probably be working at an early sage business. It doesn't necessarily know what the best steps are. So do you have any advice or recommendations on how you could set that up and it errate on it effectively? If you don't know an ideal customer experience, stop selling. You think the customer knows you sell the product like. If you don't know that, you need to go take next week off and pause on this podcast immediately. Go take next week off and figure it out if you don't know the best path. And again we kind of make it make about assumptions. So I'll try to I'll try to give you some tactical frame. Step one is developing entry and exit criteria for the onboarding process. What is it? What does somebody need to do in advance to get into this process? One? Are the things that need to happen to then exit to what we would call initial usage? Initial uses is defined as x, Y Z for your company. Then what is somebody need to do to get to power usage that is defined as this threshold? Go figure out those assumptions right now, like if you do, you've got to think about that. Your job and CS is to create power users. That is it. That is it. It is not to field inbound calls. is to create power users. That is the job. And so if you don't understand what it takes for someone to get there, take next week off and just guess right, set down some assumptions, because that's how you should be engineering. Your process is to try to drive and then keep people in that wheel, in that motion. I love it create power user as hard stuff, and that's how what? What else? What else is the goal? Right, like what? If you're especially in CS, it's not. You know, it's like your goal is to make people love it. You know that people use it and love it. You know that. That's that's the job. I would just love to see that as a single sentence job description out there somewhere. Yeah, your job is to create your non account manager, your your job is power users. Yeah, I believe it. Okay. Well, we're getting up on time here, so I wanted to ask one last question. I asked this of every single guest on the podcast, which is just what is the best piece of advice related to customer success that you've ever gotten from someone else? Well, we've talked about it a little bit, right, we've talked about that. If I was again, if I was in CS, we it's kind of a culmination of the things that we talked about, you know, which is you got to understand how your customers make money. If I did distill it down to one thing, if I know how you make money, it then helps me to understand how I can be better for you. If I don't, I'm only focused on my product and its usage verse the utility that you're going to gain, because the utility is going to be different, even if it's by a micro for each business and definitely by each industry. So if you don't know how your clients make money, you are never going to be able to truly serve them. You're never going to truly be able to help them as much as you could, because you're not...

...going to be at you're not going to have a global picture of what that main contacts going through or the end users are going through, because you don't understand it. So you have to know how they make money and therefore you can you can really start to customize their experience. All right. Well, thank you so much, Jake. Appreciate your time today. Again, y'all, that was Jake Dunlap, the CEO. It's scaled. I'm Aericrane, the CEO and Co founder or flat file. Have a great one. You depend on the fastest time to value for your customers. So I let data on board and sell you down. Stop emailing spreadsheets, creating CSP templates or setting up FTP transfers. Create collaborative, secure workspaces with your customers and their data, saving you time while providing a memorable onboarding experience. Oh and there's no code required. You can go to flat file DOT IO CS leader to learn more and get started for free. Thank you so much for joining us for this episode. Customer Success leader is brought to you by flat file. If you're a fan of the show and want to help a share these conversations with others, leave us a rating on apple podcast. Just tap the number of stars you think the show deserves. That's it for today. Catch you in the next one.

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