Customer Success Leader
Customer Success Leader

Episode · 1 year 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'vesegmented, all of these roles, so much that the incentives of the group beforedon't line up with what the customer needs for the next group want to createdelightful customer experiences. You are in the right place, welcome tocustomer success leader where you'll learn about the successes and strugglesof leaders who are passionate about their craft. Trust me. You want tostick around here's your host, Eric Crane, Heyo, I'm Erick, Crame Seo and Cofounder, a flat file, and I'm here today with Jake Dumlatt CEO, it skaled,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 youcalling in from Austin Austin Texas? Oh boy, so I got a fun story for you. Mymultiple times great grandfather was the vice president of Texas, the vicepresident of to like back when it was like its own thing. So I don't know ifyou know any of your textas history an remember now, the only vice president ever in Texas,AD's, pretty cool man yeah. Well, he shot that way because he pieced out onDavy crocket at the almo decided e didn't want to stick around there toolong, Oh, no, mad yeah. No, 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'menjoying Texas, it's been good ofeten in particular Yeahston's a great cityand 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 sadide. I look and I'm a barbecuefend, so anyone wis coming to Austin, let me know I'll, take care of you loveit. Well. Thank you for taking the time with me today. I love to talk a littlebit more about what you do at scaled, like what was the idea for scaled? Whydid you get it started? Tell me a bit more about the origins there yeah sure.So I mean my background. I've been in sales and sales leadership for almostseventeen years. Man. It just makes you feel old, just saying it, but you knowit is what it is at this point. So I you know was a vpfsales at a fewdifferent startups glass dor in San Francisco and then a started calledchart beat New York and through those experiences, what I saw was there'sreal gap in the market for tactical needs, as companies were scaling, and Iworked with consultants at both companies and every time I work withthe consulting firm or a trainer, and it's always felt like okay, like nowwhat Tlik cool thanks for tling me about all this stuff like I needtactical help to pull it through. So I started scaled with this idea that wecould bring in expert sales leadership if they needed that expert salesenablement if they needed that or expert sales operations. You know tobring in leuvels of expertise, and you know we were talking about this alittle bit before that. You know a lot of times as a startup. You don't needone person full time, you deed them for five or ten hours and notthing likethat ever existed for sales. You know it was for marketing, they have PRagencseason, digital and PAIVD, and I really saw like sales needs. The samething sale need someone who can come in and maybe we had to let go o er firstDPP and someone who can be a three to four day week, DP and help to bridgethat Gat through next full time more. They needed help around operations oror content, but not maybe full time and so fat forward to today. You know wespent the first really four or five years, only working of kind of oStartup and growth from you, Kno Onde to fifteen million fifteen to fiftymillion like that sector, and now we... with a lot of much biggercompanies that are trying to basically modernize their sales approach andbecause we've worked with hundreds and hundreds on hundreds of companies, youknow we've had a chance to really home and see, even if you're big company,these things apply, they just on a different change management, scaled andso really. Those are. You know, kind of two different customer types. Now it'sthat kind of still working with the growth stage, companies, but more andmore we're seeing big. You know: Linkon is one of our largest clients, forexample, theres big orgs, wanting to be nimble and work with a Mor Putique firm,as opposed to you know, spend two hundred and fifty hosand dolars on anassessment. So yeah that's Wowe're up to that's really cool, so we might talka little bit more after I stopped the recording here. It' learned a littlebit more about what you offer, because I feel like we could uase some of that.I flatfile for there we go. I like it all right, so we're on a customersuccess podcast! You just talked about how the sales team really needs ways toextend or scale what they're doing more rapidly. So what get you excited aboutgetting on this podcast and talking about customer success? Well, I think,what's important for me as a sale when I was a sales leader, I would never beassales leader without also owning success. I just would never do itbecause for me, I want to make sure I can control the entire customerexperience and I feel like too many organizamations we've. Now, we'vesegmented all of these roles, so much that the incentives of the group beforedon't line up with what the customer needs for the next group and then theinsid as that groups don't line up with the customer needs for the next groupsright, you got a sale development team, that's trying to do jam in meetings.You've got a sales team that trying to cham in deals, and none of those arethat's not what's best for the customer right, but's, tbet's WFOR, the customeris, you know, is getting to power usage and so what? Whenever we work withorganizations, what we try to do is just rearchitect. At times you know thethinking of Norg, your job isn't to creat deals it's to create power users,and so for me, my entire career. Again, when I say sales I almost is default tothinking about. You know the customer experience postsal because it's all apart of that customers, life cycle and so customer success account. Mangmenare literally, I think, just as important as the net knew, but you knoworganizations like Shinyn new things, so that tends to get all the love. SoI'm a massive you know account manager at Customer Success Advocate, I don'tknow I mean I'm not goingto prefer to I mean I would, I think, I'd call myselfan expert at it. You know, I think I feel comfortable with that. I was goingto say Guru and I'm like wow. That's, maybe that's maybe too far, but I'll gowith expert. You know I've done this enough Han. We do a lot of work withorganizations othe customer success process to because again we just see itas an extension of the customer experience, Yeah you're in Austin,Texas, Not San Francisco, you can't say Gura, 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 formallydefine what customer success yeah and I was like? I wonder if he's Gonta ask methis, so I think that there's two components and again differentcompanies- call it different things right, so there's account management,which I think, typically we refer to as owning like the business levelrelationship right, what's happening in the macro, what's happening if theexecutive level or other individuals that are involved and they're, makingsure that you know if we signed up or an organizzation signed up to try toachieve Xroi. That company is then...

...seeing the results from that rycustomer success on the other hand, and I'll give you a story about what we didat chart, bea that I think could be cool wrinkle to just toss out there forpeople. Customer success is focused on power usage. I mean can't be at the endof the day. Their job is to make everyone below that happy and using theproduct and making sure that they are getting the utility that they need, andso, when you have these two groups- and sometimes it's the same person right,this depends on how big your org is and that's fine. But when you think aboutit and it's when these two are working together, we've got one person oragainit's the same person you're focused on I'm having theseconversations about business impact mabing these conversations abouttactical execution and utility and value. That is how you create a winningcustomer experience and what we did it it chart me that, which I think couldbe kind of cool for people at at least is like maybe think about is again likeI said, I've always controlled like all of this, but whet we actually did atChartbe. Was the customer success the people again who are like in theproduct talking the frontline users? We actually ended up having them dottedline into me, because you know I ran the account management component and weactually had tam report into product and we were very intentional aboutthatit's like well. You know whose job is it to make sure that people use itWellell, that's actually products job right, like products responsible formaking the product, sticky and useful, etc, and so imagine tying your successteam and you could do it the opposite way: have them dotedline in the producttoo. You know we could have done it one one way or the other, but we actuallythought it would be better because then the success team is talking to theproduct team in real time every day, because they're working with them theirreport to them, and so I think again an when you have that mindset that thatsuccess in product are kind of married at the hip. I think that that that ishow you create a recipe for building sticky products and so often as well.There are Berors of each other's roles to as a product manager, former productmantor, aniformer CSM. There was so much that was similar between thedifferent roles where one was largely internal facing one was largetheexcernal facing, but you still have to interface with basically every othergroup within the company. That's right! So, when you're working with yourcustomers, what are the biggest flockers to them? Sort of removing thisbarrier that oftentimes exist between a sales and a successo work? Well, someof it comes from incentives, candidly meaning. If you have a salesorganization, that's only compensated on sign contract and there's nocomponent, that's tied to usage. It can create some, not great behavior oragain. 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 theyh topromise the moon, and we all want to sit here and say everyone's a greathuman and whatever. But that's you know, people are going to try to do what theyneed to do to make money as well to, and so I feel like. I starts withincentives and how do you make sure that the incentives are lined to dowhit's best for the business, which is create users, so I'm a actually bigproponent of tying part of the sales commission to some usage metric, whichis somewhat revolutionary. I think, but I really believe every salesorganization should have a a small percent of their comp tie to did theyactually use the product, and I think that that distance cinivizes, thatsales person is make sure that they're...

...not overpromising make sure thatthey're delivering on the value that was promised in the beginning, and thenI think, on the success side to me. It's I think more success. People needto also make sure that they are aligned the business needs of the clients.Sometimes, whenever I see success teams, it's almost a service only mindset aversus growth mindset at times of like look your job at the end of the day. Aall a tool or piece of software does is to provide some business utility, someimpact on the business, and I think, a lot of the Times CS. People are almostoverly focused on just the usage of their one thing. First, trying tounderstand that the the COMPANI's, you know real objectives and what happensthen is lit. You know, even though some people are using it, it actually isless of a priority now and so that accounts actually at risk, because youknow in your mind you think: Hey 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 onthe CSI. You know: CS individuals need to do a better job of staying up tospeed on you know what the customer is trying to accomplish. Not just are theyusing so for a CSM A a lot of times, you're not necessarily directly exposedto that executive level decision making at your customers organization. So howdo you go about uncovering that information about what is mostimportant to my customers? Business? Well, obviously, if it's just you, Imean you got to work with your account manager to have a joint plan. You knowwe called it joint success plan, meutural action plan that you knowacount management and Cs ar quarterbacking these plays together.The other thing I would say is why why don't you know theyre be subjective.Just couse sit in on the call us g hust goes right right, along with your count,Manjer to go understand the business objectives you know, and so I would sayyou know work with your am, but you know you need to understand. Thet t youneed not the not. It would be nice to. You need to understand that. So, if youneed the information, go, get the information, don't just sit there. Well,my account Mane Truh, no just go, say Hoy. I want to be on the next call. SoI understand when I'm working with the team to make sure they're actuallydoing what the decision makers need got it. So if I'm reading this the rightway, you're, basically saying hey that'll, usually come up in a salesprocess anyway, so get integrated into part of that sales process, where it'smost relevant to understand what the customer ubjectives are as a businessright because, okay and then let me Tusi'me- try to make this verypractical for everyone to so very tactical and practical imagina accountwhere, at the executive level they're making a shift toward channel partnersales, you sell a product that is built for direct sales right of this, makingup a the scenario here, you can insert whateever it is. You are focused on thefront lines as the CS of making they're using it. It's going. Well, things arehappening and three months later they make this decision. They have youpagged incorrectly as a direct sales to an reality actually could do channeland then they 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 startto retrain an maybe rebuild different ways that they can use the platform forchannel sales, that it's really that and those types of examples you knoware all over the place. You know, and so I think a lot of people just have todo a better job of not overssuming. You know you always assume that thebusiness quarities are changing. You know, there's different actors orplayers involved for sure that makes sense so to flip that last question onits head. What information could customer success be giving the salesteam in order to improve the overall customer experience as well? Well, Ithink CS teams need to do a better job of trying to educate the sales team. Iwhat actually goes into on boarding and goes into being successful as acustomer, I think a lot of times. You know sales, only exposure o this iswhat their sales manager told them, which is like it's easy. Our CS team isreally really good, and so then sales just goes and tells that to customersthiy don't want to mislead customers, they just don't know. So. If I was a CSleader, I would spend all of my time educating the sales leadership team onwhat actually goes into onboarding and being successful, making it making surethey have a slide or slide at the end of a presentation. They can talk aboutit because it've actually helped them to close more deals. It's a big reasonwhy a lot of people deals go long and they don't actually understand whathappens next, and so they make no decision instead. So that's what Iwould do if I was going to see US leadership or pries o CSM, I wouldspend a good amount of o time focusing on education of the sales, ord andthat'll help to make them more successful and let's have substantiallyless customerturn yeah. That makes a lot of sense. It's got to be a to Aycommunication for sure, but doing that at scale probably requires a lot oftechnology right, so whether it's figuring out activation based COPstructures for your sales team or whether it's you know communicatingrequirements back and forth, or business objectives between the salesand the CS side of the business. So what are some of your favorite toolsand systems that you've set up in order to let help organizations do that moreefficiently? Far, I mean I think, th, there's a you know. It's a sales,engaging platform called outre out reached OIO that if I was starting tosee s team right now, it would be my every first purchase a lot of people.Think of it as like a legue generation tool, but all it is is a sequence ofthat activities with different workclotes in it. So imagine you knowwh n an account comes in. Hopefully your organization is to kind of tearedout of accounts right of like Ererow. We treat our tear ones, t or tos Icould say hey. This is tear want to count. I know I want to talk to them atleast every three weeks: Cool I'll put them on my every three week: sequenceTehese people tear to account. I need to talk to them every forty five daysboom y tier two secret puts theese, I needd to talk to once a quarter boomevery ninety days and then, of course, you have conversations before you knowore. You have conversations with your customers as a part of this, but Ithink a lot of companies are not interacting as much as they want toproactively with clients, because I feel like we're overloading a lot of cspeople and then therefore, the only way that you're going to be able to managethis is with technology, and I think outreach is probably the best tool todo that. Then the other would be linked an sales navigator, meaning what Iwould be doing again. If I was a CSRAP and I started tomorrow, S is, I wouldget us sales navigator, bicense and I would make sure I'm connected to all ofthe people that are in my like spir of...

...influence at these accounts. Why?Because then, when I post a piece of content on Linton guess who sees it mycustomers right, and so I feel like there's some sales tactics that CSpeople should be deplaying to help them to manage more accounts and add morevalue to their accounts on a consistent basis. When I think Linkdon is to dothat, and then I think you know managing the email and call componentof that, I mean you can even Bak in the linkd ink opponent to out reach to, butI think those are two tools that I think we're sleeping on as opposed to,like you know, gainsider Totango, or what you know like some of these toolsthat are more about like raising flags like that's cool, that's important, butmore so if I can get in a regular rhythm with my customers and I can addvalue to them on a consistent basis. Maybe I you know, maybe I trioge someof these issues from happening understand their business objectives. Imean, I don't think were indexing enough time there of just like if I canget all of our meeting set up for the next year. On Day, one I'm good rightas opposed to again in's that changing from a a reactive to a proactivemindset from a account management and success factor yeah. I hear that allthe time from different guests on the podcast is like sort of strivingtowards that proactivity and what I find a lot of times is that there'sstill a lot of manual work that has to go into that. So what are some of thethings that you feel like are being done manually today? That machineshould really be doing instead. Well, we'll talk about today, vers, maybetomorrow, right because think we can talk about like dynamic account,hearing bassed on Prepap, like look alike models right like there's somecool stuff, that people are doing with artificial intelligence hat, helps youto really understand who your best customers are there's, so many micronewvances. You know to like you know right now, we kind of do it SOM, prettybasic demographic and psychographic. You know term of how we tear ouraccounts, so I'm excited for that. I think that will just continue toprovide better customer experience. Itwill continue to allow people to youknow, spend more of their time with the right types of custsomers. First Ho,you think, is the right type of customer, so that's exciting, but inthe short term, again Asu. You can tell I like to plan right, Abuti like toplan, and I like to get things done, so I don't have to think about them again.I would just re. I would create a para process in t e onboarding that everycustomer went through and it's like a four point: checkless, where weschedule all of your monthlior quarterly business reviews up front. Weschedule all the trainings and details ind the one on one ha, two oone, thewhatever upfront that you know we schedule a you know by Ol, something orother, and then we even get like you know. We start to have conversationsaround the renewal. We call e hundred and Twenty Day renewal process thatmost renewal process US start a hundred and twenty days from the contract. Andso I don't know if you need to get the renewal contract books, but I woulddefinitely have it in my own tast management that I needed to do it andthen guess what I don't need to think about that account ever again and whatI mean by that is like well Jake. What do you mean? Well, all the mile stonesare already built. Now I just go execute and then al. My proactivetouchpoints are already there and I think, we're. Instead, we take theopposite, which is: Let's do nothing and just react all day that sucks. Thatsounds horrible. You know, like just...

...surprise after surprise after surprise,like no. I want to get in front of that stuff. So that's what I would do. Iwould be more proactive and scheduling, and I would do it from day one. So howdo you get more ahead of the design of that process as well? So a lot of ourlisteners will probably be working at an early stage business. It doesn'tnecessarily know what the best steps are. So do you have any advice orrecommendations on how you could set that up and itorate on it effectively?If you don't know an ideal customer experience, stop selling you tink thecustomer knows you sell the product like if you don't know that you need togo take next week off and pause on. This podcast immediately go take nextweek off and figure it out. If you don't know the best pat and again, wekind of make it make atabout assumptions. Soi'll try to I'll try togive you some tactical frame step. One is developing intry and exit criteriafor the onboarding process. What s? What does somebody need to do inadvance to get into this process? whate are the things that need to happen tothen exit to what we would call initial usage initial uses is defined as Xyzfor your company. Then what is p somebody need to do to get to powerusage that is defined as this threshold go figure out. Those assumptions rightnow like if you got a you've, got to think about that. Your job in CS is tocreate power users. That is it, that is it. It is not to field inbound. CALS isto create power users. That is the job, and so, if you don't understand wbut,it takes for someone to get there take next week off and just guess: write setdown some assumptions because that's how you should be engineering yourprocess is to try to drive then keep people in that wheel. In that motion, II love it create powers or as hard stop and that's h what else? What else isthe 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 itand love it. You know that that's the that's the job. I would just love tosee that as a single senane job description out there somewhere yeahyour job is to create your, not n, accaunt manager. Your your job is topower users yeah. I believe it Kay well we're getting up on time here. So Iwanted to ask one last question. I asked t us of every single guest on thepodcast, which is just what is the best piece of advice related to customersuccess that you've ever gotten from someone else. Well, we've talked aboutit a little bit right. We've talked about that. If I was again, if I was inCS, it's kind of a culmination of thethings that we talked about, you know, which is you got to understand, howyour customers make money if, if I did ti still it down to one thing, if Iknow how you make money then helps me to understand how I can be better foryou. If I don't, I'm only focused on my product and its usage, first, theutility that you're going to gain because the utility is going to bedifferent, even if it's by a micro for each business and definitely by eachindustry. So if you don't know how your clients make money, you are never goingto be able to truly serve them. You're, never going to tru truly be able tohelp them as much as you could, because...'re not going to be you're not goingto have a global picture of what that main contact going through or theindusers are going through, because you don't understand it. So you have toknow how they make money and therefore you can. You can really start tocustomize their experience. I well thank you. So Much Jake appreciate yourtime today. Again Yoll that was Jake Dumblap, the CEO, it's scaled, I' aric,Crane, the Sio and cofounder your Blat file have a great one. You depend onthe fastest time to value for your customers. So why let data onboard andsell you down? Stop emailing spreadsheets, creating CSB templates,forsetting up ftq transfers, create collaborative secure workspaces withyour customers and their data saving you time, while providing a memorable,onboarding experience. Oh and there's no code required, you can go to flatfile, dot, IO, slash CS leader to learn more and get started for free. Thank you so much for joining us forthis episode. Customer Success leader is brought to you by flat file. Ifyou're a fan of the show and want to help us share these conversations withothers, 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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