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Season 4, Episode 7

Perfecting Your Sales Process

With CEO of Skaled Consulting, Jake Dunlap

About the Episode

In this episode, we’re talking with Jake Dunlap, the CEO of Skaled Consulting. Skaled helps executives around the world accelerate their business growth with data-backed sales solutions. Before building Skaled, he held the roles of VP of Sales at Nowait (acquired by Yelp), Head of Sales + Customer Success at Chartbeat, and VP of Sales at Glassdoor (acquired by Recruit Holdings for $1.2B in 2018). Hear directly from Jake how to build out your sales department, mistakes small businesses often make, how to structure commissions, and much more!

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Full Transcript

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26:16

Chris:
Let’s do it. So if anyone doesn’t already follow your daily LinkedIn videos and all the awesome content that you put out, can you give them a quick intro of what scaled is, what you guys do just high level, how long have you been around what’s the team like

Jake:
Yeah, happy to do it. So, yeah, I’m looking forward to the conversation, like I said, so we are a sales consulting company and I know a lot of people like, Ugh, right. Consulting, um, you know, my background, like I was a VP of sales at Glassdoor, VP of sales at a few startups. And, um, you know, really what I saw is that as companies are growing and scaling sales is it’s kind of left in the coal that’s like marketing gets all this help, but finance does. But you know, it’s like hiring people full time and, you know, churn and burn. And, and I realized that sales really needed tactical support and that consultants were focused on strategy, which is great. And obviously, a lot of our work is strategy work, but really the difference between us and your typical consulting firm is it tactical execution and our knowledge of sales tech, you know, we’ve done hundreds and hundreds of sales, tech implementations. And so really when it comes to building, you know, a modern sales org, a modern demand gen org, I really think that we’re, you know, one of, if not the best in the world at modern best practices,

Chris:
I think people don’t realize how important sales operations or sales tech is to power and scale your Salesforce. Right? Because you can think of scales as just a sales is just a conversation, but you really can’t do that repeatably without putting that infrastructure in place. So is that really what you guys focus on?

Jake:
Yeah, I mean, think about our work as a mix of strategy work at the highest level, right? Hey, here are the corners we’re growing, we’re scaling, we’ve got to see around the corner. And instead of just hiring one VP, who’s done it once our team, you know, we’ve got the sales consultants who have done this 10, 15, 20 times, and then on the tactical side, think operations and enablement, right? Like think of, you know, right now, I mean, we’re really positioning ourselves as like the first operations and enablement agency. You know, we are the SWAT team that you bring in to either manage that for you. Um, just like you would a performance agency or a web agency for your marketing team. We’re really coming in and doing a mix of both. What’s the content that we need, the playbooks, and also then the tech stack to make the team successful. So it’s really, you know, candidly, it’s a mix of the process and the technology that really creates a winning formula for scaling

Chris:
Sales, SWAT team. I love that before training, you will, I did consulting as well. And some people perceive consulting as like unemployment and others actually get stuff done. So I totally get what you do and value it now, uh, this year obviously has been crazy for a lot of people. How, how did the pandemic, the world, how did this hit you guys this year? Was there a fear of shrinking? Were you in a contraction kind of zone or was it all about expansion?

Jake:
I think he looked for that for Q2. Q2 is rough. I mean, Q2 for us. And a lot of people was like a lot of people in wait and see, and then Q3 has kind of come around and Q4 has just exploded where people are like, look, I think we’re going to be okay. Like, I think we’re going to need to figure this stuff out. That Paul passed that we got, you know, for the last six months because the economy is about to run out and, you know, we still have got to go raise that series C or B or whatever you’re at. Right. So I think a lot of companies now are kind of at that stage of like, Hey, you know what, w we weathered the storm and now we’re trying to figure out how to really scale in a smart way. So I think we, like a lot of people, had a slower Q2, and then just, you know, gradually through Q3 things started to pick up and in the last month, I mean, they’ve exploded.

Chris:
Yeah. That seems to be the theme. And that’s what we heard a lot at the playbook event was we’re turning this corner and now everybody is starting to think of, okay, I, you know, I can’t rest anymore. What’s done is done now, how do we move ahead? So I always wonder with, with people that start consulting firms, you know, your experience at your few sales, you mentioned VP of sales at Glassdoor and some others. What was the commonality that you thought I want to fix this? This is why I’m going to start this business.

Jake:
I mean, look for me, I’m a really bad employee. You know, like that was my revelation. Like I’m extremely good at the work, you know, growing and scaling. I took Glassdoor from zero to a million MRR in about a year and we closed 24 of the fortune 100 my first year. And, but man, I sucked as a member of the exec team, you know, like I didn’t understand how to play nice, et cetera. And then I went to Chartbeat and me, you know, and I was like, the same story. Like I’m really good at the work and building and scaling and all these things. And I just realized, you know what, maybe this is my path. You know, I never thought I’d be an entrepreneur. You know, look, we’ve got 35 people now. Right. I didn’t start this, you know, this to be a lifestyle business. Right. I never was like, I want to be a solo.

Jake:
Like that was never in the cards. And look, we’ve had lots of ups, ups, and downs over the last seven years. Um, but I, you know, for me it was the need in the market that I just saw. Sales are really in sales, leadership and sales departments are really left on an Island to hire these people. Full-time who aren’t really experts and to really just fend for themselves. And I think a lot of it comes down to the attitude that these people make a lot of money. So why does the sales leader need help? He’s making more than everybody else. And, and I think that that’s one of the issues that we’re, that we’re, you know, sales leaders I think are starting to be more and more open. And I think executive and VC firms are starting to be more open to like, well, Hey, why don’t we give these guys support the same way we do other, other parts of the business.

Chris:
Yeah. When you think traditionally about sales support, I personally, I think of like, you know, the old sales guy in the neighborhood that passes out business cards and tells everybody’s like the sales coach and, and like, it’s so refreshing to see a brand like yours. That’s actually growing and, and, you know, implementing tech that these companies need.

Jake:
Yeah, it’s a must.

Chris:
So when small businesses go from hiring their maybe first couple salespeople and they’re still figuring it out, where do you see them going wrong? Most often,

Jake:
I think there’s a few things. One is we don’t treat sales. Like we do other parts of a company. And then the example that I always give, especially in that example, when you’re going from like two to 10. Okay. So how many developers do you have? Well, we’ve got a handful. Would you ever just turn your code base over to a developer and say, you’ve coded before, just go write some code, but for some reason in sales, that’s what we think it is. It’s like, Oh yeah, you’ve been in sales and tech before. Like, you know, go listen to John, do it, like, imagine if that’s how you wrote code, go shadow, XYZ person, writing code, and then just go do it yourself. It’s insane. Right? You’re like Jake, you couldn’t possibly do it. But that is exactly how we treat sales. Sales is just as much science as it is art.

Jake:
There’s a right and a wrong process. So the most important things you can do is document, right? Document version one. This is our pro, this is our ideal customer journey. And that’s what a lot of our work with early-stage let’s reverse engineer, the ideal customer experience and how we can shorten that, you know, to get them the information they need at the right time, accelerate the deal cycle, increase our average sales price. But I think you’ve got to document everything. Um, as you’re going along in the journey, the teams that we see when that’s what they do, they document, document. I talked, we talked a little bit about tech right now. There are well over 1500 sales technologies. So if you are doing something manually, there’s an app for that, right? Like you’re doing research, you’re doing this, you’re doing training for example, right?

Jake:
Like there’s, there is a much smarter way to do it. Chances are then what you’re doing. And then the last part is people that we, we don’t hire for the role that we need. Now we try to hire these jacks of all trades. And then we wonder why tenure so short at the VP of sales, our first few salespeople leave. We don’t think about what’s the right team for today. And then how’s that going to morph over the next 12, 24, 36 months? And are we prepared with the right people at the right stage? Because the needs of the sales organization changed so quickly. Um, but I think the teams that when they do, they do those three things, they invest in the documentation and, and really narrowing in a process that they can train people on, whether it’s good or bad, it’s at least it’s something to, they use technology to augment the team. So instead of throwing more bodies at it, they actually have a process and system, and three, they are very smart about the people and making sure they have the right people at the right stage. And I think if you do that, you’re gonna have a much higher likelihood to scale, uh, with less, you know, scrapes and bruises.

Chris:
I love that. Obviously, we love documentation and training over here. So I’m going to ask you a question. A lot of people ask me, which is when do you start to write things down? So what is the early success indicator you’re looking for from your first person or a couple of people? When do you encourage them to start documenting versus it’s just a waste of time because they haven’t figured it out yet?

Jake:
Well, it’s a good call out because like, you know, sometimes companies come to us and it’s like, dude, just figure it out. Like I, you know, like sure we can develop a playbook and this, but you’ve got one or two people you’re not looking to really grow. But, but here’s the thing. If it’s not documented, how can you improve it? Like the whole thing is like, you know, I would say, once you get somewhere in there, but even if you’re a founder-led sales team, you should be documenting. So when you hire the people, they can get up to speed faster. So, you know, candidly, you should start documenting on day one. Now, when do you really need to tighten it up? You know, it’s usually after you’ve gone through that scrappy, like, Hey, we’re, you know, 50, 30,000, 50,000 MRR, uh, we’re going to try to scale now.

Jake:
Like it’s, it’s about time for us to get our act together. And then, and then the important stuff is, as you moved to 5 million, 20 million, 50, a hundred million, it never stops. You’re always optimizing that. We’ve got this very sloppy, like mentality in sales. These companies look at their sales process, every, you know, 16, 18, 24 months. I’m like, what are you doing if you’re pumping data through it? Why aren’t you optimize, optimize, optimize top of the funnel, optimize middle funnel optimize? So I think you also have to just realize that a high-performing sales team is always optimizing. That’s why sales ops are so important. I can’t tell you how many times I’ve come into orgs and you know, well, Jake, you know, we, we’ve under-invested in sales ops, you know, we’ve got 30 salespeople and we’ve got two people in ops. One of them was definitely an ex SDR, the other one’s a sales developer, a Salesforce admin. And then you introduce them to what a VP of sales ops looks like. And they’re like, wait, people do this and this recording and this and this, like yeah, your manager just spending 20% of their time in BS. And I think there’s so much sunk cost time that people don’t realize when they’re scaling because they’re too scared to hire non-revenue producing roles in sales orgs. And that’s another big no-no,

Chris:
What’s the right ratio. You said if 30 to two is a, is no good. Okay.

Jake:
Is not, it’s not good. I think once you get up to eight to 10 is when you need to hire your first person, right. Eight to 10 is probably right. Stop promoting SDRs and salespeople to be your first sales ops hire. You have no clue how much you are shooting yourself in the foot versus someone who has been there and done it two to three times, right? Like the learnings that that person has already incurred. So that’s like rule one, I think for every like 10 to, you know, eight to 10, every eight to 10, I think you should think about ops or enablement person. You just, depending on what you need. Cause just think about it. But you know, look, and it could be, if you’ve got a certain type of, it could be a little bit more, but again, it’s all about, it’s like if I hire this one person and my, we did a survey, we surveyed 167 senior salespeople and sales leaders.

Jake:
And over 50, almost 50% of them said they’re spending over 15% of their time between 15 and 30% of their time, every single week in operations activities. And just go ask your team. And if your team says that you just go do the math. If your sales team’s quota is $30,000 and they’re wasting 20% of their time, you do the math that you only need to have about five people, and this role more than pays for itself. So I just feel like sometimes we’re hesitant to hire those non-revenue producing roles early on. And instead, we just need to do some basic math and you’ll see what comes out on the other side. And this role

Chris:
It’d be new for people. So if they haven’t heard about this before, are they searching scouring, LinkedIn for people with sales, operations, titles, or people with certain background experience, who’s the person to hire for this. Yeah.

Jake:
Yeah. I mean, hire someone with sales operations do not hire a Salesforce admin, your problems usually don’t think of sales. Chels ops are not just tech sales ops it’s systems and systems are also processes. It’s how you forecast. It’s having clean opportunity stages. It’s it is, you know, how you set up Salesforce, but more importantly, a good sales ops resource partners with the sales leader seat and says, look okay, what’s the challenge. Okay. W our forecasting sucks. Okay, well, let’s go fix it. We need clear opportunity, stage definitions. We need Gates between each stage. We need better reporting and dashboards. I got you. It’s not just the Salesforce piece, it’s all this other stuff. And you’ve got to have an appreciation for sales too. So I would certainly recommend for your first hire, hiring someone with a few years of experience. I think that it’s one of those investments, or, you know, you might pay 15 to 20 K more, but I think that because I’ve seen it so many times to CEOs, there’s a CEO of a company that comes to mind a company who is doing twenty-five million. These guys were a rocket ship. And they had like, you know, some part-time people I’m like, dude, it is time, man. Like, you need to hire this. And then, sure enough, they did. I had drinks with them like, you know, two months after I was like, I don’t know what we did before. And so I just encourage you to go talk to some sales ops people and see if you feel the same.

Chris:
Now, another problem I hear people make is they promote someone from being a salesperson to a sales leader, a sales manager, something like that. Sure. When’s the right time to bring in a leader to the number of reps.

Jake:
Yeah. Oh, man. That’s a really tough one. I mean, obviously, look, we do a lot of interim work, so I’m biased, right? I think you should hire us for it until you get to five to 10, let us build out the process, and then hire someone because that person, then, you know what you actually need. But if not, I mean, I think the key is, look, don’t promote someone to the manager who hasn’t been in a managerial position before. Just the learning that you’ve got a new team. I made this mistake at Glassdoor, for example, you know, as we scaled really quickly, we went from literally almost zero people in the sales org to 40 and 16 months. And so I made that mistake of promoting junior leaders to manage junior people. And it was, or miss some stepped up some didn’t, but you know, I think some reps didn’t ever make it because I had a junior leader who was learning how to be a leader.

Jake:
So my advice is just to know what you need at each stage. You know, you need someone, who’s a manager who can get you to five, to 10 to 15 people. Maybe that person can stretch into director and manage two or three. Um, but, but don’t, you know, I think sometimes we feel like we need to over reward people that have been there. And instead, it’s like, you got to put the right person in, who knows how to build a scaffolding that gets you to the next stage. So I think for each organization it’s different, but you know, once you get to five to 10 people, you need someone in there to really help to manage those people because you’re, you’re losing a lot, whether you realize it or not.

Chris:
Right. Okay. Good advice. So let’s talk about the life cycle of customers. It’s often that, you know, marketing conditions, people to buy and then sales closes them and support, or success is fulfilling or something like that. Right. What’s the best way to keep all these different departments in sync.

Jake:
Oh man, this is such a good question. Yeah. It’s messed up right now. I’ll have to tell you that it is messed up. Um, you gotta, you gotta start with your comp plans, meaning I’ll tell you one of the radical ideas that we are. We are pushing our in our clients is that sales commission, a percent of commission should be paid upon usage. Once a company hits a certain usage threshold, then the salesperson gets the other 20% of the commission. Well, why is that? Well right now, because we’ve created all these segmented roles. If I’m an SDR, I have no. And a lot of SDRs have no incentive to make sure deal closes done. So I’m, again, I’m a big fan of, they get part of their comp is tied to a percentage of the deal, right? Incentivizes them to do that. And the same thing with the Salesforce salespeople right now have no incentive other than to jam deals through.

Jake:
And you wonder why your customer success team is overwhelmed with bad deals or broken promises because your sales incentive is there. So I candidly think that if your executive team’s incentive plans aren’t aligned and your frontline teams, there is no process change that I can make or that anyone can make or best practices that will change people’s behavior. Because if I am only incentivized to jam deals through and culturally that’s aligned at the top, why would I ever stop? And so I think it starts at comp plans and then it’s an incentive. And thinking about that customer journey, what’s the best experience and how do I align my organization to create that experience for that? Because, and that’s why I liked the idea of a salesperson, making sure they use it, let’s get the, you know, I’m just, I’m not spending really a lot of time there, but I’m going to make sure I don’t over-promise. I’m going to make sure that these people get set up for success. They get through onboarding and then I get paid by another part of my commission. So I just think you have to, you, we have to be a little bit smarter than we have been because we’re actually, self-inflicting a lot of these wounds because we’ve over-specialized and not corrected the compensation to take into account how that’s affected the customer journey. And that’s really what this is all about is the customer.

Chris:
And that kind of goes back to your last point, because if you don’t have the tech and the sales ops set up to be able to track that they close this deal and this customer is this active and that triggers this incentive or this, this commission, then the fee, it just doesn’t work. Right.

Jake:
They can’t do it well. And I’ll tell you, man, that the hot, the newest hot button is rev ops, right? Rev ops to me are the 2020 ABM. Everyone is like, ah, you know, what we need is rev ops to connect all these things. Let me tell you the problem with rev ops nine out of 10 rev ops teams that I talked to, and I’m sorry for all my rev ops, people have no authority to actually drive change. They present, they came from McKinsey. They came from other consulting firms like ours and they surface all these insights and then sales still do whatever the hell they want. And again, if the incentives aren’t aligned, if this, so to me, rev ops is the, was the dream is the dream. But I would say almost 90% of organizations are using rev ops, completely wrong.

Jake:
Rev ops have no authority. Relevance has no authority to drive change that can’t fix the things that I’m talking about. And if they can’t fix anything who cares, if they’re tracking it, who cares? Great more data who get, who cares, right. If they’re not actually doing anything about it. Right? And so that, that’s, that’s my issue right now with rev ops is we re rev ops is supposed to be the Messiah now, but the problem is it’s not going to materialize into the gains that you want because they’re hamstrung, they’re hamstrung to actually do anything about it. So, um, that would be the other answer to this, because again, I think that would be the popular answer. Right? Well, rev ops are supposed to do that. I’m telling you rev ops is not doing it. So shout out to my rev ops people, right. Get a voice at the table if you’re actually going to drive change.

Chris:
So, so you’re talking about data and tracking, how do you measure the department’s success? So the sales team success, you know, is it individual quotas? Is it team quotas? Is it their percentage contribution to the overall growth? How do you look at that?

Jake:
I’m, I’m totally fine with it being individual codas and maybe a team kicker, you know, team 10%, 15%. It’s all about, you know, that a lot, some of this is cultural, what are you, what are you comfortable with? Again, I think about, am I incentive in my incentivizing every person in my revenue or doing what’s right for the customer. Now my incentivizing them to drive because of the goal of a revenue organization, and I think this is where we’ve got it twisted. The whole goal of a revenue organization is to create power users. That’s the whole goal. And I’m talking about tech companies, right? In particular, the whole goal of a tech company’s revenue organization is to create power users. That’s it? That’s the only goal, right? Not a signed contract. Really. That isn’t what we’re trying to get to, that still leads to churn. And so if you get everyone aligned with this idea, look, we’re trying to create happy users and users as in they’re actually using it. And then we think about the processes and systems behind it and reverse engineer. I think that’s how you build a modern, um, you know, a modern sales organization that’s really grounded in best practices is you’re very customer-centric and always thinking about the end-user throughout.

Chris:
So do you think the rep should be bonus than on some kind of retention metric? Are they involved with upsells and retentions or does it not extend that far

Jake:
In the lifecycle pens? I mean, it depends on the sale. I’m fine with it. And certain sales, if it’s a transit, you know, if it’s not a transactional sale and you spend six months getting into an account and then you hand it off, it’s the stupidest thing I’ve ever heard in my life. Like some of the handoff processes we have, again, they’re very anti-customer. Okay. I’m a customer we’re in the middle. Like you sell me 25 seats out of a hundred. And then you trend, why would you transition the account? That’s stupid. Like you just spent this time to get them there. You’ve built up all this relationship capital internally, and then you hand it over. This is dumb. So I feel like we’ve got to add some common sense that there’s a time and a place for winning salespeople should stay with an account and the time and a place when they’ve it when a handoff makes sense. So to me, this is more about creating the right, the right, you know, uh, rules and processes internally. But Hey, if an account looks like this, the rep stays with it. If it looks like this, they don’t, but this, this, this clean break I’m telling you is costing companies a lot of money a lot, because they’re, they’re basically starting all over again after they spent six months getting to point a. So I think it’s, it’s, you’ve gotta have a smarter handoff process than just like one size fits. All

Chris:
Right. Okay. All right. Last couple of questions here. I know you are super creative and you’ve got some great tips I saw on your LinkedIn stories. Um, what’s the best way to get on a prospect’s radar these days, because I’m getting just blasted with cold emails and cold LinkedIn messages. So what are you recommending? Um,

Jake:
I do, I’m telling you if I was an SDR today, I think I could work five hours a week. I really think it’s that easy to cut through the noise right now. And let me tell you why. I think it’s so easy because everybody is hitting send all and sending customized, like non-customized email templates. We forgotten how to call, like in so many different sales organizations were just mailing. I mean, we were just mailing it in. So when you ask me, I think there’s a few keys like plays and different things. The first is video. I really believe that video is one of the more powerful ways to cut the noise. And now, now here’s what I will say about the video. If you are a younger or more junior person, maybe you want to go voicemail. You know, if you’re reaching out to somebody who’s 30 years, your senior, you know, again, unless your delivery is confident, you look confident, you look the part, you look smart, you look like, you know what you’re talking about, but, but I really feel like the video is a way to cut through the noise that, and if the video is smart and it, and again, it goes back to what it’s always been, which is like, you understand the buyer persona.

Jake:
Do you understand what they’re going through? I think video, LinkedIn voicemail if you’re a first-degree connection with someone, you can, you hit messages. There’s a little microphone. You can drop a voicemail straight to someone’s LinkedIn DMS that is killing it. And then we’re seeing some plays, that integrate a lot of this, right? So you’re doing a video or maybe, maybe you like, and comment someone’s post, and then you cold call. Right? So I just think right now, the amount, the amount of creativity you can have, and again, we’ve got some plays that are like video, video, email call, like, and then we’ve got some that are like LinkedIn connect, like a comment than wait four days, like a comment than a cold call. So I just feel like there are so many different ways to not do the basic stuff that it would be really easy. And I know reps, I mean, we’ve got, clients are reps, they’ve got SDRs that just sit there every day.

Jake:
They make 20 customized videos a day and they crushed their number. You know, this kid, Adam fees at six meetings in two, he ain’t got, he got two callbacks with this new sequence. He ran where he likes he views their LinkedIn profile, then sends an email about the insights he gained from their profile. Then does a double tap on day two with another email. So it’s like view profile connects day one email day two email. The guy said six meetings in two days when he first launched the sequence. So there’s just a lot of creativity that I think people need to start, to think about as opposed to just, you know, executing the whole call, email, call, call, call, email, email.

Chris:
I love it so much tech out there. No reason to not be creative. So for anyone that’s listening, go follow Jake. He’s got amazing tips. Where can people find you for more of this? Or what resources would you point them to?

Jake:
That’s right. Go, come check out. LinkedIn, obviously. Um, I’m very active there. I share a lot of, uh, what we’re up to also. I would go check out what, you know, look we’ve been, I’ve been putting a lot of work into YouTube as well, too. So if you’re in sales or you’re in sales leadership, I’ve gotten, I think over 300 plus videos on YouTube, just type Jake on that sales. And I’ll be the first result. And you know, I tell some people I’m like, you know, if you don’t want to hire us, you can just go watch the videos. Like pretty much you can get a lot of what we’ll do. So I’d say check out YouTube, check out LinkedIn. And you can always email me, Jake@skaled with a K. And I’ll, I’ll try to get back to you.

Chris:
Well, I think it’s the same for everyone. You know, if you’ve got the time to go watch 300 videos, go do that. If you want to cut to the chase, reach out to Jake and his team. And as long as you’re here listening, at least you’re getting some good tips to build some structure and some scale into your sales organization. So, Jake, thanks again for being here. This was fun.

Jake:
Awesome, man. Thanks. I appreciate you having me.

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