How PClub.io Teaches Sales Teams to Close More Deals with Discovery Frameworks (Interview with CEO Chris Orlob)

Opening and Audience Warm-Up

Chris Orlob

00:02Alright. What's good? How is everybody? I wasn't here yesterday, so I didn't get the benefit of all the takeaways, but I feel like I just got the rundown. So thanks for the intro.

00:16Alright. Raise your hand. Actually, let's do this. Stand up if you get on at least one sales call per week. Come on. It's it's early, and I know it. You got come on. You Anthony, I know you get on a sales call every week.

00:34Stay standing if you get on five.

00:38Oh my god. Super sellers. 10? 20?

The Shift from Growth-at-All-Costs to Efficient Growth

Chris Orlob

00:44How many do you guys get on every week? Yeah. It sounds like it. Okay. So we have reason to be in this room then. That's what I hear. Yes. Okay. None of this is news, but we have transitioned from an era that has gone from growth at all costs, where we're hyper focused on growing the type top line no matter how much it costs, to an era we where we are hyper focused on efficient growth. We

01:16still wanna grow our businesses, but the unit economics need to make sense.

01:24Right? We need to do so efficiently.

01:28But we're struggling to. Who knows what this number represents? Any wild guesses? Oh my god. This is a really good room. This is the number of b to b tech salespeople who hit their number last year. That actually seems high to me. Does it seem high to you guys? Seems high to me. Every time I talk to somebody, it seems like it's more than we must be counting salesforce.com here. That's the only explanation. It's like some

01:55of these big companies were counted. Because every time I talk to somebody, it feels like it's more like 25, 30, maybe 35%. But the short version is even though we're all trying to grow our businesses more efficiently by the way, I hope you guys are okay with me, like, awkwardly pacing. I'm gonna do that this entire time. We're struggling to grow our businesses more efficiently. This is one indicator, not the only, of inefficiency in growing SaaS

Sales Rep Quota Attainment and the Efficiency Problem

Chris Orlob

02:18businesses. So the question is where did you end up last year? There's nothing right here, so I have to keep looking back at this. Welcome to the most awkward presenter of SaaS Open. And where will you end up this year? And what's the delta between those two? And what actions are you going to take to make your new trajectory? Alright. What's that Einstein quote? I'm about to butcher it, but if you did the same thing last

02:49year, I'm sure he was referring to sales. That's the definition of insanity if you're expecting new results, something like that. Einstein was clearly more eloquent than me. Is my mic coming through okay to you guys? Okay. Cool. So I have one goal in the short amount of time we have to do together today, and it's to give you a raise. If you're an individual seller, it's to give you a raise. If you run a business, it's

Chris's Goal: Give the Audience a Raise

Chris Orlob

03:17to give your business a raise through some of the techniques that you're going to learn. And I've helped many people, salespeople, entrepreneurs, etcetera, achieve exactly that with some of the techniques that you're going to learn in the next eighteen minutes or so.

03:35So here's a few things I have for you today. We're going to learn a couple of discovery questions that get to the heart of the deal fast, and we'll talk about why that matters. We'll talk about a simple discovery question to find business pain that money follows, a bulletproof question to quantify pain, which builds urgency and what to ask to drive timeline and close your deals on time so that you're not slipping deals quarter over quarter

04:00over quarter, and you get them in to the financial period that matters to you.

Chris's Background: Gong and Call Analysis

Chris Orlob

04:08A little bit about me, I'm not going to spend too much time on here because I'm sure you want the techniques. Probably what I'm best known for is playing a role in helping grow a company called Gong from a little under $200,000 in ARR at the time that I joined to a little over $200,000,000 in ARR by the time that I left. I primarily did that in a sales leadership capacity, building one of the most successful

04:37teams there. And there was a time during my tenure where I worked closely with our data science team to analyze several million discovery calls to figure out what works and what doesn't work. And so this presentation, I'm drawing on my personal experience. I'm drawing on the fact that I've reviewed about 2,500 discovery calls manually, and I'm going to be drawing on my experience working with our data science team, my previous data science team, analyzing millions more

05:08with some of their techniques. So what you're going to learn comes from these three. That's what they're rooted in. And here's the first one. Are you ready to not be blown away by this first one? You guys are gonna be like, wow, Chris. You flew all the way to New York City to tell me this? It'll get better as we go, but fundamentals are never sexy. Right? The first of the four is to ask a question

05:36that gets to the heart of the deal fast.

Question One: Get to the Heart of the Deal Fast

Chris Orlob

05:40Ask a question that gets to the heart of the deal fast. And here's why. Money follows pain. It's probably worth writing down and reflecting on every quarter or so as long as you find yourself selling stuff to other people. Money follows pain, follows other things too, follows benefits. Sometimes people buy for strange reasons. But the dominant reason people buy things is to alleviate pain. And so particularly in this economy, you have got to anchor your deals

06:15to business pain that money follows. Business pain that senior executives, especially the CFO these days, will fund and spend money on. And most sellers, entrepreneurs included, SaaS founders included, salespeople included, don't do that because they just take so long to even surface the surface level of the pain. Right? If you look at a typical discovery call, like thirty minutes, they start to understand the pain at minute twenty five or so. This is an observation of mine.

06:50This isn't like according to data or anything like that. But they get to the surface level, and then it's time to talk about next steps. And you have no urgency, no pain, no leverage.

Tactical Tips for High-Impact Discovery Questions

Chris Orlob

07:00Okay. So here are a couple questions that get you there faster. Now I'm not going to teach you how to set up a discovery call or set an agenda or anything like that. But once you've done those things, recognize where your deal is coming from. This is an outbound deal where you have to create demand or is it an inbound deal where you are fulfilling demand? If it's an outbound deal, as one of your kick start

07:22questions to get to the heart of the deal fast, ask this. Can you help me understand the biggest challenges you're experiencing in x area that would derail you if you didn't solve them? Right? That language matters because you're getting them to talk about things that are going to be urgent, what would derail you. And now if they came to you, which some of you apparently have very well refined inbound marketing engines, especially if you're a customer

07:52of Audience plus, Anthony. Can you help me understand what motivated you to talk to us today? Alright. What are the drivers? Like I said, I didn't fall fly all the way to New York City to just teach these. Many of you might be doing this. Many of you aren't though. There's a difference between knowledge and action. And so your call to action is to start asking these questions or one that feels very much like it earlier

08:21in your sales call so that you have the rest of the sales call to develop that pain with the following three questions that I'm going to teach you. Before we move on to those, a couple tactical tips for you to get more out of those questions. You want to phrase high impact questions in a way that signals to your buyer you want them to go in-depth. We're all familiar with who, what, when, where, why, and there's

08:46nothing wrong with those. But these phrases, when you tack them on front of those questions, signal to your buyer that you want them to go in-depth. Can you help me understand? Can you walk me through? Can you talk to me about? Those phrases get the desired effect.

09:08So that's how you start. And here's where we start to get more interesting.

Question Two: Peel Back the Onion to Find the Need Behind the Need

Chris Orlob

09:15Once you start talking with your customer about the challenge that they've just expressed, your next job is to peel back that onion and understand the need behind the need. K. Because as a rule, I don't know why this is, but it's true. The first answer a customer is going to give you to a discovery question is going to be surface level. If you stop there, what happens to your deal?

09:44They go dark on you. Apparently, they they ghost you. That's like the millennial thing to say. I don't spend much time on TikTok, but

09:54I'm told that's the language.

09:58You can tell this entire presentation deck was designed by a professional except for this slide. This is Chris Orlob, Design Studios Incorporated. We're going out of business fast if you can't tell. But I'm gonna walk you through a story. This is a discovery call I had with one of one of my reps at Gong a few years ago. And we started the question or the discovery call with the enablement manager taking the lead. He said, we

10:21need better visibility into our sales calls. Pretty surface level. Right? Is that pain?

10:29No. Of course not. And so we peeled back the onion a little bit, and we said, what's driving you to cry or crave that visibility? And we he said, we need to coach our reps on selling to power. Now here's a question for the group. We need to coach our reps on selling to power. Is that a problem or is that a solution? It's a solution. One of the best things you can do as somebody who

10:55sells software is understanding, is your customer using solution language when you ask about challenges, or are they using problem language? Many times they're going to be using solution language and you're gonna have to peel back the onion. So we did that here. And we said basically the same question he answered with selling too low has led to nine month sales cycles. Is that a problem?

11:20Yeah. We're starting to get somewhere. Now at the risk of sounding interrogative and almost redundant, we said, bear with us. We get why you would wanna reduce your sales cycle, but there's probably a lot going on in your business, and you could be prioritizing a lot of different things. So what's driving the focus there? And now notice power took over the conversation. She chimed in. She said she said nine months sales cycles are creating a cash

The PClub.io Customer Story: Quantifying Close Rate Pain

Chris Orlob

11:48flow issue with the company. We have a typical net 60 after this nine months. It takes us eleven months to collect cash from the start of a deal. Now we're getting somewhere. And, of course, we decided to peel the onion a little more with her. And she said if we don't solve this cash flow issue, we're essentially gonna have to sell some of our company in the form of raising another round. Now that's not always a

12:14bad thing raising another round, but if you have to do it to solve a cash crunch instead of accelerating the business, usually not a good spot to be in. So we've gone from a $0 problem to a $50,000 problem to a $500,000 problem, all using one question that we phrased in different ways, why? Now if you just say why 10 times to your customer, they're probably gonna curse you out of the room. And so here's the

12:47second question for you to swipe. I don't know why this works so much better than just asking why, but it does. When your customer starts talking about a surface level challenge, try asking them what challenge is going on in your business that's driving that to be a priority.

13:07You are going to notice that about 50% of buyers chuckle when you ask that question Because they're thinking about the train wreck going on in their business. Train wrecks are usually things you can solve if it's the right train wreck.

13:24Hey.

13:27We've gotten the surface level. We've started to develop that and mold that and understand the need behind the need. Your next job is to start to quantify it.

13:40What do you think that is? Any professional salespeople in the room who have a crisp answer to this one? ROI. ROI? Outcomes. Outcomes?

13:51All true.

13:54I'll give you my answer in a second, but once you have pain, you need a metric associated with that pain. Okay. I'm gonna tell you a quick story as an example, then I'll give you the lesson, then I'll give you the question that you can start using. And don't get me wrong, you're gonna have to tweak some of these questions to form fit your business. But it's not very hard. These are fundamental and they work in

Question Three: Quantify the Metric Suffering Most

Chris Orlob

14:17most cases.

14:19So at pclub.io, we recently closed a deal with a customer whose first articulation of the business problem was my reps sound like donkeys during their demos.

14:36His words, not mine. I'm just here to solve that. Now we ended up quantifying that, and it showed up as close rates. Their close rates were suffering. They had an annual model that they had built that relied on their close rates being 33, right? We're all familiar with annual models here, at least a lot of them are. We've got all these inputs, close rates, sales cycle length, reps to be hired, ramp times, all that stuff. And

15:00if you screw up one of those too much, you're going to miss your annual number. This was one of them that was being screwed up as a result of apparently reps sounding like donkeys during their sales demos.

15:14So we quantified that with them. And they were like seed round startups. So this amount of money was significant for them. If they could move the needle by 300 basis points on their close rates, it amounted to £280,000. I don't know what that is in dollars. But it's not a bad chunk of change to start with. So quantifying the problem, now here's my answer. ROI outcomes, all those things that you guys mentioned, true.

15:45When you quantify a problem, it helps your customer appreciate the magnitude of that problem.

15:54Who are you serving most by answer or asking that kind of question?

16:01You or the buyer? The You're serving you too. There's nothing wrong with that. But you're actually providing a service to your buyer by helping them understand the scope of the problem.

16:16And so this is the question you can swipe. I can't tell you how to quantify your business or your customer's business. Every person in here is gonna have a unique ROI model, quantification model. But this will kick start it in pretty much every case because almost every metric has a financial value associated with it. So you kick start your discovery with the questions I shared with you. You understand the need behind the need. And now try

16:42asking what metric is suffering most as a result of those challenges if they haven't shared it already. In my business, that typically looks like close rates, deal size, sales cycle length, quota participation. Yours will look different, and I can't tell you what the answer is, but I can tell you how to start it, and it's this.

Question Four: Find the Compelling Event and Drive Timeline

Chris Orlob

17:07Now peel back the onion with the metric they gave you unique to your business. Alright. Number four. How are doing on time? Head of schedule? Right on time? Behind? Two Two minutes. Okay. We're I'll make it happen. The last one is find the compelling event and drive timeline against it. Now here's what you have to know about this next question I'm going to teach you. It is weak, generic, and doesn't get the effect you want if

17:35you don't ask it after all the questions I already taught you. It's powerful if you do the steps that I taught you. Okay? So here's the question, but I'm going to spend more time selling you on why it's powerful to ask this at the end. If you ask what's driving you to solve all of this now than rather than later at the beginning of a discovery conversation or just too early, you're gonna get a very unsatisfying

18:02answer. Well, you know, we're losing money every day that we don't solve this. Really generic sounding. When you ask this after going through those first three questions and where they are as a customer is understanding the full scope and magnitude of the problem, oh, boy. This starts to get more interesting now because they're answering the question with all the context front of mind.

Q&A: Which of the Four Questions Matters Most

Chris Orlob

18:34So the order of these questions matter, you start by kicking off with a question that gets you to the heart of the deal fast. You peel the onion back by asking what's going on in your business that's driving this to be a priority followed by a hearty chuckle from the customer, typically. You quantify it, what metric is suffering the most as a result of that, and then and only then do you drive timeline. That's all I

18:59got for you. Yep.

19:05Peeling back the onion. Peeling back. Is that the question you're answering or asking? Like, of these four?

19:15Mhmm.

19:19Fucking love quantification. Yeah.

19:26Peeling back the onion. Yeah. The best salespeople are insanely curious. They The whole thing. All four? Okay. Yeah. Yeah. If if you got nothing else right from these four, and don't do that. Get all four right. There's no reason you can't get all four of these right. Peeling back the onion is by far the most important. Getting to the center of the onion, the need behind the need. Because what people voice is the surface level need.

19:52You need to get to the center.

19:56Time.

19:59Alright. Thank you.