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 incidence of the group before don'tline up with what the customer needs for the next group. Want to createdelightful 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 abouttheir craft. Trust me, you want to stick around. Here's your host, Eric Crane. Hey, I'm Eric Crane, CEO and Co founder offlat file, and I'm here today with Jake Dunlap, CEO. It's scaled. Hey, jake, hey, what's going on? Man, how areyou? I'm doing all right. Thanks. It's one of those another muggy dayshere 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 vicepresident of old like back when it was like its own thing. So Idon't know if you know any of your textas history and can remember. isnow 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 atthe 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 fromNew York. We were there for six years and then I grew up inKansas 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 therefor Dad. Dude, I look. I'm a barbecue fiend. So anyonewho's coming to Austin, let me know. I'll take care of you. Loveit. Thank you for taking the time with me today. I'd loveto talk a little bit more about what you do at scaled, like whatwas the idea for a scaled? Why did you get it started? Tellme a bit more about the the origins there. Yeah, sure, so. I mean my background, I've been in sales and sales leadership frolmost seventeenyears and then it just makes you feel old just saying it, but youknow, it is what it is at this point. So I you know, was a VP of sales at a few different startups, glass door inSan Francisco and then a started called chart beat New York, and through thoseexperiences what I saw was there's a real gap in the market for tactical needsas companies were scaling and I worked with consultants at both companies at every timeI 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 scaledwith 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 talkingabout this a little bit before that. You know a lot of times asa start up you don't need one person full time, you need itfor five or ten hours. and nothing like that ever existed for sales.You know, it was from marketing. They have PR agencies and digital andpaid and I really saw like sales needs the same thing. Sale need someonewho can come in and maybe we had to let go over first VP andsomeone who can be a three to four day a week VP and helped tobridge that gap through next full time or they needed help around operations or ourcontent, but not maybe full time. And so fast forward to today.You know, we spent the first really for five years only working with kindof the start up and Roath from one 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. And because we've workedwith hundreds and hundreds of hundreds of companies, you know, we've had a chanceto really hone and see. Even if you're a big company, thesethings applied. They're just on a different change management scale. And so reallythose are you cover two different customer types. Now it's that kind of still workingwith the growth stage companies, but more and more we're seeing big youknow, Linkedin is one of our largest clients. For example. It isbig orgs wanting to be nimble and work with a more boutique firm as opposedthat, you know, spend two hundred and Fiftyzero dollars on an assessment.So yeah, that's or up to. That's really cool. So we mighttalk a little bit more after I stopped the recording here, learn a littlebit more about you, off or, because I feel like we could usesome of that. I flaugh file. For sure, we go. Ilike it all right. So we're on a customer success podcast. You justtalked about how the sales team really needs ways to extend or scale what they'redoing more rapidly. So what gets you excited about getting on this podcast andtalking about customer success? Well, I think it's important for me as asale when I was a sales leader, I would never be a sales leaderwithout also owning success. I just would never do it because for me Iwant to make sure I can control the entire customer experience and I feel liketoo many organizations we've now we've segmented all of these roles so much that theincentives of the group before don't line up with what the customer needs for thenext group, and then the incentence of that groups don't line up with thecustomer needs for the next groups. Right, you got a sale development team that'strying to jam in meetings. You've got a sales team that's trying tojam in deals and none of those are. That's not what's best for the customerright. That's best for the customer is, you know, is gettingto power usage. And so whenever we work with organizations, what we tryto do is just re architect at times, you know, the thinking of noryour job isn't to create deals, it's to create power users. Andso for me, my entire career. Again, when I say sales,I almost use default to thinking about, you know, the customer Experience PostSale, because it's all a part of that customers life cycle. And soa customer success account management are are literally, I think, just as important asthe net new but you know, organizations like shiny new things, sothat 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'mnot going to prefer I mean I would cuy. I think I'd call myselfan 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'vedone this enough now and we do a lot of work organizations other customer successprocess too, because again, we just see it as an extension of thecustomer experience. You're an awesome Texas, Not San Francisco. You can't sayyou're a you gotta go. All right, that sounds good. Well, solet's I mean as an expert in customer success, how would you sortof formally define what customer success and I was like, I wonder if he'sgonna 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 Ithink 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 levelor 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 xRoi, 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 wedid at chart beat, that I think could be a cool wrinkle to justtoss out there for people, customer success is focused on power usage I meancan't lay at the end of the day, their job is to make everyone belowthat happy and using the product and making sure that they are getting theutility that they need. And so when you have these two groups, andsometimes it's the same person. Right, this depends on how big your orbis, and that's fine, but when you think about it, it's whenthese 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 theseconversations about tactical execution and utility and value. That is how you create a winningcustomer experience. And what we did it it chart be that, whichI think could be kind of cool for people at least, like maybe thinkabout 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 intoproduct 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 stickyand useful, etc. And so imagine tying your success seem. And youcould 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 istalking 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 havethat 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 stickyproducts. And so often as well, there are mirrors of each other's rolestoo. Is a product manager, former product manager and a farmer CSM.There was so much that was similar between the different roles. Where one waslargely internal facing, one was largely external facing, but you still have tointerface with basically every other group within the company. That's right. So whenyou're working with your customers, what are the biggest blockers to them, sortof removing this barrier that oftentimes exists between a sales and a success org.Well, in some of it comes from incentives, candidly, meaning if youhave a sales organization that's only compensated on sign contract and there's no component that'stied to usage, it can create some not great behavior. Or again,if you have a sales leader who's not also, you know, kind ofresponsible, 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 topromise the moon. And we all want to sit here and say everyone's agreat human and whatever, but that's you know, people are going to tryto do what they need to do to make money as well too, andso I feel like it starts with incentives and how do you make sure thatthe incentives are aligned to do it's best for the business, which is createusers? So I'm an actually a big proponent of tying part of a salescommission to some usage metric, which is somewhat revolutionary, I think. ButI really believe every sales organization should have a small percent of their comp tiedto 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'redelivering on the value that was promised in the beginning. And then, Ithink on the success side, to me it's I think more success people needto 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 andverse a growth mindset at times of like, look your job, atthe end of the day, a all a tool or piece of software doesis to provide some business utility, some impact on the business, and Ithink a lot of the Times cs people are almost overly focused on just theusage 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 prioritynow, and so that accounts actually at risk because you know, inyour 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 onthe CSID, you know, CS individuals need to do a better job ofstaying up to speed on, you know, what the customer is trying to accomplish, not just are they using. So for a CSM or a lotof times you're not necessarily directly exposed to that executive level decision making at yourcustomers organization. So how do you go about uncovering that information about what ismost 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 jointplan. You know, we call it a joint success plan, Mutual ActionPlan. That you know, account management and see us or quarterbacking these playstogether. 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 thisgoes right, right along with your acount manager, to go understand the businessobjectives. You know, and so I would say, you know, workwith your am but you know, you need to understand that. You neednot 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 justsit there. Well, my account managers now just go say how I wantto be on the next call so I understand when I'm working with the teamto 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'llusually come up in a sales process anyways. So get integrated into partof 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 metry 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 shifttoward channel partner sales. You sell a product that is built for direct sales. Right, of just making up a scenario here, you can insert whateverit is you are focused on the front lines is to see us of makingthey're using it, it's going well, things are happening and and three monthslater they make this decision. They have you peggued incorrectly as a direct salestool 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 becauseI was in a meeting three or four months ago. I can start toretrain 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, areall over the place, you know, and so I think a lot ofpeople 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 differentactors or players involved. For sure, that makes sense. So to flipthat last question on ased, what information could customer success be giving the salesteam in order to improve the overall customer experience as well? Well? Ithink see US teams need to do a better job of trying to educate thesales team on what actually goes into on boarding and goes into being successful asa customer. I think a lot of times, you know, sales onlyexposure to this is whe their sales manager told them, which is like it'seasy, our CS team is really, really good, and so then salesjust 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, Iwould spend all of my time educating the sales leadership team on what actually goesinto on boarding and being successful making it, making sure they have a slide orslides at the end of a presentation. They can talk about it because I'veactually helped them to close more deals. It's a big reason why a lotof people deals go along as they don't should understand what happens next andso they make no decision instead. So that's what I would do if Iwas in to see US leadership or pris the CSM. I would spend agood amount of my time focusing on education of the sales org and that willhelp 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 yoursales team or whether it's, you know, communicating requirements back and forth or businessobjectives between the sales and the CEE US side of the business. Sowhat are some of your favorite tools and systems that you've set up in orderto let help organizations do that more efficiently? There? I mean I think there'sa you know, it's a sales engagement platform called outread outreached ioh thatif I was starting a see US team right now, it would be myvery first purchase. A lot of people think of it as like a leadgeneration tool, but all it is is a sequence of activities with different workflowsin it. So imagine, you know what an account comes in. Hopefullyorganization is to kind of tiered out accounts right of like here's how we treatour tier ones tier two. So I get to Hey, this is tierone account. I know I want to talk to them at least every threeweeks. Cool, I'll put them on my every three week sequence. Thesepeople tier to account. I need to talk to them every forty five days. Boom. By Tier Two secrets, these I need to talk to oncea quarter. Boom, every ninety days. And then, of course you haveconversations before you know are you have conversations with your customers as a partof this, but I think a lot of companies are not interacting as muchas they want to proactively with clients, because I feel like we're overloading alot of cus people. And then, therefore, the only way that you'regoing to be able to manage this is with technology, and I think outreachis probably the best tool to do that. Then the other would be linkedin salesnavigator, meaning what I would be doing again if I was a CSwrap and I started tomorrow, there's I would get us sales navigator license andI would makeke sure I'm connected to all...

...of the people that are in mylike sphere of influence at these accounts. Why? Because then when I posta 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 peopleshould be deploying to help them to manage more accounts and add more value totheir 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 ofthat. I mean, you can even bake in the linkedin component tooutreach to but I think those are two tools that I think we're sleeping onas opposed to like, you know, gain cider to tango or what youknow, 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 ina regular rhythm with my customers and I can add value to them on aconsistent basis, maybe I, you know, maybe I triage some of these issuesfrom happening and I understand their business objectives. I mean I don't thinkwe're indexing enough time. They're. I'm just like, if I can getall of our meeting set up for the next year on Day One, I'mgood right, as opposed to again, it's set changing from a reactive toa proactive mindset, from account management and success factor. Yeah, I hearthat all the time from different guests on the PODCASTS, like sort of strivingtowards that proactivity. What I find a lot of times is that there's stilla lot of manual work that has to go into that. So what aresome of the things that you feel like you're being done manually today that machineshould really be doing instead? Well, we'll talk about today verse, maybetomorrow, Right, because I think we can talk about like dynamic account tearingbased on prepere like look alike models. Right, like there's some cool stuffthat people are doing with artificial intelligence that helps you to really understand who yourbest customers are. There's so many micronwuances, you know, to like you knowright now, we kind of do it is, I we're pretty basicdemographic and psychographic you in terms of how we tier our accounts. So I'mexcited 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 theirtime with the right types of customers. First few, you think, isthe right type of customer. So that's exciting. But in the shortterm, 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'thave to think about them again. I would just really I would create aprocess and the onboarding that every customer went through, and it's like a fourpoint 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 getlike, you know, we start to have conversations around the renewal. Wecalled the hundred and Twenty Day renewal process. That most renewal process. You starta hundred and twenty days from the contract and so I don't know ifyou need to get the renewal contract books, but I would definitely have it inmy own task management that I needed to do it and then, guesswhat, I don't need to think about that account ever again. And whatI mean by that is like, well, take what do you mean? Well, all the milestones are already built. Now I just go execute and thenI'll my proactive touch points are already there and I think we're instead wetake the opposite, which is let's do nothing and just react all day.That sucks. That sounds horrible, you know, like just surprise after surpriseafter 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 schedulingand I would do it from day one. So how do you getmore ahead of the design of that process as well? So a lot ofour listeners will probably be working at an early sage business. It doesn't necessarilyknow what the best steps are. So do you have any advice or recommendationson how you could set that up and it errate on it effectively? Ifyou don't know an ideal customer experience, stop selling. You think the customerknows you sell the product like. If you don't know that, you needto go take next week off and pause on this podcast immediately. Go takenext 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 toI'll try to give you some tactical frame. Step one is developing entry and exitcriteria for the onboarding process. What is it? What does somebody needto do in advance to get into this process? One? Are the thingsthat 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 whatis somebody need to do to get to power usage that is defined as thisthreshold? 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 powerusers. That is it. That is it. It is not to fieldinbound calls. is to create power users. That is the job. And soif you don't understand what it takes for someone to get there, takenext week off and just guess right, set down some assumptions, because that'show you should be engineering. Your process is to try to drive and thenkeep people in that wheel, in that motion. I love it create poweruser as hard stuff, and that's how what? What else? What elseis the goal? Right, like what? If you're especially in CS, it'snot. You know, it's like your goal is to make people loveit. 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 asingle sentence job description out there somewhere. Yeah, your job is to createyour non account manager, your your job is power users. Yeah, Ibelieve it. Okay. Well, we're getting up on time here, soI wanted to ask one last question. I asked this of every single gueston the podcast, which is just what is the best piece of advice relatedto customer success that you've ever gotten from someone else? Well, we've talkedabout it a little bit, right, we've talked about that. If Iwas again, if I was in CS, we it's kind of a culmination ofthe things that we talked about, you know, which is you gotto understand how your customers make money. If I did distill it down toone thing, if I know how you make money, it then helps meto understand how I can be better for you. If I don't, I'monly focused on my product and its usage verse the utility that you're going togain, because the utility is going to be different, even if it's bya micro for each business and definitely by each industry. So if you don'tknow how your clients make money, you are never going to be able totruly serve them. You're never going to truly be able to help them asmuch as you could, because you're not...

...going to be at you're not goingto have a global picture of what that main contacts going through or the endusers 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 to customizetheir 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 flatfile. Have a great one. You depend on the fastest time to valuefor 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 providinga memorable onboarding experience. Oh and there's no code required. You can goto 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 leaderis brought to you by flat file. If you're a fan of the showand want to help a share these conversations with others, leave us a ratingon apple podcast. Just tap the number of stars you think the show deserves. That's it for today. Catch you in the next one.

In-Stream Audio Search


Search across all episodes within this podcast

Episodes (28)