Too Good To Ignore

Speaker A: Too good to ignore. That's, that's what it takes to make outbound work right now. Whether it's, hey, I'm an SDR and I'm trying to get a hold of a cold account, I'm an AE that's maybe trying to self source a bit. Uh, maybe I'm a rep that's trying to get some expansion business within a customer account. There's so much freaking noise in the digital inboxes of buyers. Whether that's LinkedIn, email, their phones, all of the sequencing tools, all of this stuff that was just the holy grail nearly a decade ago has really come back to bite the sales profession in the ass. The stuff that made it easier, ironically has made it insanely harder to get a hold of folks. And what we're going to talk about in this episode is what it takes in 2026 to make outbound work. Uh, we've worked with about 250 plus sales teams in the last five or six years. Folks like Shopify, Zoom, Rippling, Gong, some of the most successful SaaS, orgs in the entire world. And the best reps, they really show up in a different way and the best orgs do as well. And that's what we're going to talk about in this episode. So thanks for joining me. My name's Jason, I'm CEO at Outbound Squad. We are a firm that specializes in outbound pipeline generation. It's the only thing that we help with. I mentioned that we've worked with some pretty cool companies, but if you're a sales leader listening to this and you want your team to do more pipegen, to be more efficient at pipegen, and maybe you're trying to move up market, be more enterprise, maybe the meetings that you need to land need to be with more senior stakeholders so that those deals move faster, you're definitely in the right place. So this is a guest episode I did on another podcast called Revenue Insiders. I uh, met these folks here in Seattle actually through Pavilion, and they were nice enough to invite me on the pod. I had a really great time and we really just talked about the current state of Outbound, uh, where it's going and I gave a lot of very tactical, uh, things that you as either a rep or a leader can take away to really make Outbound pipegen work for you. We talk about everything from the current state of AI, um, the types of offers that we need to make to entice buyers to take meetings, we talk messaging, I give a ton of examples. So, uh, do me a favor. If you like this episode, you'll really like our Outbound Masterclass. It's a free course. It's on our website, outbound squad.commasterclass. it's nearly three hours of our very best stuff. I went in studio to record it and you really like it. So if you're a leader, send it over to your reps. If you're a rep, you're going to get a ton of value added. It's very tactical. It's outbound squad.com masterclass. And if you listen to this episode and you're like, you know what? I think that these guys could really help us implement this. Feel free to email me directly. Jasonutboundsquad.com would love to chat with you. Um, our clients, typically within a 90 day period of working with us, increase qualified opportunities created and pipeline by 20% or more. And we've done this for some very cool companies like Shopify, Rippling, Zoom, Gong, and work with a ton of smaller startups as well. So, so reach out to me. Jasonoutboundsquad.com let's get to the episode.

Speaker B: We are, uh, your revenue insiders. Today. We are sitting down with Jason Bay, founder and CEO of, uh, Outbound Squad. If you spent any time in Outbound sales over the last five years, you probably listened to his podcast or read some of his LinkedIn posts. He's got some of the biggest customers out there with strong B2B teams like Gong, um, Zoom, Shopify, Monday.com, the list goes on and on. So Jason is actually based in Seattle like Tiffany and I, which is how I met Jason. We were both part of Pavilion here in Seattle and he reached out looking to get connected in the Seattle area and I found what he offers to be fascinating. And I know our audience will be very interested as well. So, Jason, thank you for joining. Really excited to have you here.

Speaker A: Yeah, I'm excited too. You two definitely understand what it's like to be in Seattle right now, where it's like, we're right on the cusp of spring and the sun is almost about to come out and all that stuff. So I'm new here, I'm from the Pacific Northwest, but I'm relatively new to Seattle, but, uh, always good to jam with other folks in the area too.

Speaker C: We've had some nice sunny days and it is just gross out today.

Speaker B: Today is so gross. I don't want to leave my house, but I'm going to force myself to. Well, we're going to jump right in Jason. And one thing that I am super excited to talk to you about and learn more about is you are launching the first and you claim only I want to hear more about this Outbound framework and methodology. Can you tell us a little bit more about that?

Speaker A: Yeah. So the kind of lead in and build up for this I think is important. Outbound is arguably the hardest that it's ever been since we had to, you know, back in the day, open up the phone book and go like either door to door or just manually dial off the phone. Right. So since we've had like email sequences and access to phone numbers and all of that kind of good stuff, it's been very hard. I mean, the data shows that the average reply rate to an email is less than 1%. I mean, do you two pick up your phone when unknown numbers call you?

Speaker C: If never out the calls?

Speaker B: I do too.

Speaker A: Yeah. Yeah. And, um, the irony is that, you know, I teach cold calling. Our firm teaches cold calling to all of, you know, thousands of sales reps. Yet you ain't going to get me on the phone unless I'm answer it unexpectedly on accident.

Speaker C: If I'm, if I am looking at your website and I get a call, I might answer that. That's like the one exception that comes through.

Speaker A: So the predictable revenue era of outbound, like officially ended like five or six years ago. There was a. For those listening, I would assume that most of you know who what predictable revenue is, but Aaron Ross came out with a book in 2011, didn't pioneer this idea, but really popularized this idea of, hey, we're going to break apart the sales function into three roles. We're going to have people that do outbound and pipe gen. We're going to have people that close our account executives and then we're going to have account managers or folks that, you know, do the farming, so to speak. And that was like really great. But what it created was an entire generation of salespeople that, for lack of a better way of saying it, feel like they're above doing outbound pipe channel, like they're above having to build pipeline. So I can't tell you how many companies we get brought into where they're. They call it an outbound pivot. Right. They want to pivot the organization to be more outbound. I'm sure you two have seen this a lot, but you have a culture shift really that needs to happen because you have account executives that were hired with the expectation that they, they were literally told they wouldn't have to outbound yeah. And it's treated as this, like, junior activity when it's one of the hardest things to do in the job. Like, building pipeline is really, really hard. So we got to where we are today because the predictable revenue era really spawned this. I'm, um, call it the sales engagement gold rush, where we had outreach local to Seattle, right. Sales loft. Like, these were companies that were valued at multiple billions of dollars to support the workflow and process of this predictable revenue model. And then we sort of shot ourselves in the foot, right? I mean, 2024 rolls around in gong zoominfo clary. I mean, all of these companies now have, like, you can't find a sales tool without a sequencing functionality in it. So it's like really desensitized people to, like, the emails. It's desensitized people to the calls. Um, LinkedIn is starting to become a mess, and now there's all of this AI stuff, right? And last but not least, I'll kind of pause because I know I've been monologuing quite a bit. Is like, right now we're in the AI era, right? And this era is a lot about displacement. So we're looking at all of these activities. SDR teams are being replaced by AI. It's happening a lot. I don't think that it's necessarily the right move at a lot of companies, but I have a client that sells an enterprise database solution. That said, we're not going to let sales reps touch any of our inbound leads. So all of the stuff between a demo request and a pure cold outbound lead. So webinar signups, case studies, like, people that are signing up for their free version of their product, they are only letting AI agents interact. I think that's a terrible move. And we could talk about why that is, but that's like, what these companies are doing right now. So it's kind of a scary time. And the reason why we came up with a methodology, it's called too good to ignore. We're in an era right now where, as a sales rep, you have to be too good to ignore in order to stand out. We can talk about the pillars of that and what that means, but we're in an era where you cannot be average and succeed at building pipeline anymore. Average emails, like, that's average is just the floor Now. AI can send better than most average reps can. So it's your ability to differentiate yourself, which is. Which is really big.

Speaker C: And I've been circling this topic for, like, a few of the last, like, Episodes that we've talked through, I feel like around this concept of what's going on with pipe gen building and outbounding and communications and where does AI, uh fit in versus where do people fit into it? And at the end of the day, at least right now, people are still the buyers and so people have to fit in somewhere. I agree with you. Like an all AI SDR team is not the um, is not the move or an agent that touches everything before it gets to a certain point. It just feels as a buyer, as someone who has bought a lot of things or researched a lot of things. Like I can tell and I'm annoyed like when I'm at the point where I want to engage with someone, I want to engage and I can tell when it's an AI sequence. But AI has a place in all of this. I'm curious if this is part of your methodology around like where you should be leveraging, Whether it's like tools. I saw one of your LinkedIn posts around like evolving from chats to agents, or like being left behind. Like where does that fit into your overall methodology that you're rolling out?

Speaker A: Yeah. So the three part framework is disqualify, offer and provoke. So We've worked with 250 sales teams in the last six or seven years and it's about 20,000 sales reps. And there are very prominent patterns in the teams that do really well at pipegen, especially the reps that do well at pipegen. The archetype that I would describe that does well is I would call them an owner. Every sales leader wants their reps to own their book of business, right? To be an operator, an owner. It's not the grinders and the people that are really good at hammering out the activity. And in our clients it's not really, I call them, uh, the cyborgs. It's not the people that are really great at leveraging AI either. It's the people that really own, just like a business owner, their time. So I'll kind of weave in how AI fits into this here. Uh, Tiffany. So disqualify. What the best sales organizations do is they set up a system that allows the rep to say no to a lot of accounts and opportunities that they could be reaching out to. So I am a really big fan. I was taught the martini glass shaped pipeline. So we don't want our pipeline to look like a funnel, we want it to look like a martini glass. We're going to shrink the top of funnel and it's about going really deep on fewer opportunities that have a higher propensity to buy, you couldn't ask for a better use case of AI. So I'll give you an example. We worked with a client that sells cybersecurity solutions. And like, their clients are like Pepsi, Costco, like those types of businesses. And it's specifically cybersecurity in the manufacturing plant. Right. So it's not it. It is ot operational technology. So, for example, in a warehouse on Pepsi, someone might be using their cell phone to hotspot a machine because the Internet's down and they're that you could get hacked or whatever. Right. Long story short, what we found through a lot of the AI analysis was, hey, there's 10 industry verticals you reach out to, but there's really two where you guys are winning the most right now. You win almost all of the competitive deals, you win faster, the are larger, etc. So we said outbound team, we're going to say no to six out of those eight industry verticals, and we're only going to go in on these two. And oh, by the way, there's five Personas. We're not going to focus on five Personas because two of them are really important to show up to the first meeting. Could you do this without AI? Yes. You could work with an ops person like Tiffany, someone like yourself and like your team, let's say. And you could do all of this, like, analysis and spend hours and try to sell people on it, or you could just open up Claude and do it in like five minutes, you know, um, so from a disqualified standpoint, it's where am I pointing my effort? Where am I asking the team to point their efforts? And how can I do that in a way where the propensity to buy from these folks or to engage is very high? And I'm stacking the odds in our favor. So I'll pause there. That's the first pillars disqualify. What are we going to say no to? That's the first decision that we have to make.

Speaker B: You're so right. This is where so many organizations really struggle. I'm finding because pipeline is hard to find, there's a fear of saying no. And just when you're a seller, you always learn, like, first to know, like, say no. But in reality, when your pipeline's really low and someone's inspecting your pipeline, people are more likely to say yes when they shouldn't. So I'm curious, before we go into the other two parts of it, how do you help someone understand why it's so important. How do you get them, um, to flip that mindset? Because I just think as people, they want to fill their pipeline even though we know and the numbers show they're not going to turn that pipeline into closed deals.

Speaker A: Yeah. So I think it's the old people buy based on emotion but justify with logic. For some reason when we get into sales leadership, especially at the executive level, like we go super logical and we forget to actually sell. Like you have to sell. Like when we get hired by an organization to come in, I always joke with them like the sale hasn't ended. Like we still have to sell your reps at every single enablement session that we do with them. When we build out your playbook and the messaging, we have to sell you on this and get you excited about it. So we can bring all the data that we want with it. But I think one of the biggest things, Ryan Longfield is probably one of the most talented sales leaders that I've worked with. He was the previous CRO at Gong. He brought us into Shopify and the dude is just a masterful storyteller. Like there was a whole narrative around why Shopify has to do outbound and how it's such an essential part for the company's future and how you as an individual, here's how you win doing that. And I think with this, Kelly, to answer your question around the qualification, it's hey, do we have internal champions at our company reps that are already doing this and can we spread those stories internally and as a enablement professional or as a, a director of sales that has managers reporting to them. You should be facilitating these stories and giving them to your managers to share. That was one of the things I learned as a first time sales manager at 19 when I was managing college students running house painting businesses, going door to door, that was my first sales job was going door to door selling house painting services. And VP of sales. Dan was so brilliant at that. He was like, hey, on um, Barry's team over there, this rep, Eric, he's doing this thing. I want you to tell Susie on your team about this and like get her really excited about it. And like, honestly we didn't have great data at that point so I didn't even need the data to back it up. I just said this is working for so and so and I think we forget to do that sometimes, that we can build the best programs ever and like have all the IT operationalized and all of the steps and like all of this kind of stuff. But what about the stories? Like that's, that's a huge part of

Speaker C: tangent off your methodology. But I totally agree and I think it's really important for people in like the ops role to hear that you often have to go through a sales process internally for change management. You have to do this every. You have to understand the solutions that like all the. You do the negotiations with internal resources to make things happen. And I find that people are so much more successful at change management when they take that approach that you're describing. And like people who can storytell on top of that are just like immensely success and driving projects forward. I do agree because I, similar to Kelly, I've seen a lot of stance to pulling people pipeline away from people. Even if you can show them with data, it's not good pipeline. Like, well, I can. Let me have it, let me do something with it. I can nurture it. I can, I can make some connections. And it's never the right use of time though.

Speaker A: Yes. And the story is always more interesting than the data anyways. Like, think about, um, like multi threading is a common thing that an ops team would like look at really detailed analysis around. Right. One of my clients also sells a cybersecurity solution. Found that, hey, the win rate's a little higher when we bring in our technical. Our SE in the first call. So then they started looking at like all of the calls didn't have the SEs and they started rolling out like, hey, it's required and we're doing this. And it's like, what was much more powerful is when they kind of stepped back and they were like, hey, you guys, let's think about the buyer for a second. Right. You have a cybersecurity buyer. Someone that's very technical coming onto that first call. And when we listen to a lot of those calls. Here's a lot of what they said in those calls. Hey, can I speak to one of your experts? Can we get a custom demo to show us how this would work in our specific. And they were asking all of these things and the story was just like, hey, we're. We're offering a better buying experience for them by bringing in this individual. Well, by the way, the data supports that too. It's like you, you need both. And I think that we can just get so fixated on data sometimes.

Speaker B: I would agree with you. Okay, so we've disqualified. What are we doing next?

Speaker C: Yep.

Speaker A: Let me give like a second, like action. Like, here's what you could do. So if you're if you're in ops or enablement and, or you're a sales leader, look at the last six weeks of our six months rather of closed one and closed loss data and just look at patterns in like the industries and niches on the account level. Look at like what moves fast, uh, through the sales pipeline. Look where the deals are the largest, like all of that kind of stuff and you can get some really good criteria to filter on. So the second pillar is offer. There's some really interesting data around the buyer's experience right now that I think is really important to start with. And most buyers are pretty sick of hopping on sales calls. I mean all of the Gartner data would show you that three quarters of them preferred not to interact with the sales rep. Right? Which is kind of sad being honest. But I think the more compelling piece is Rain Group did a big study of B2B buyers and they said that 58% of the meetings that they spend, uh, time with sales reps is a complete waste of time. So over half of the time they regret spending time with a salesperson. And the Gartner's got more data that over half of the purchases they make they experience buyer's regret. So think about how jaded the buyer is hopping on sales calls. So the offer, the idea behind this is like, I gotta give them a compelling reason to spend time with me. And it can't just be take a look at our solution because around 3% of your market at any given time is actively buying. So how do we entice that other 97% and it's through compelling offers. Um, the data on Gong, like We just studied 85 million cold emails, uh, last year with them, um, cold, uh, emails with the presence of an offer will have a reply rate that is 28% higher than just simply asking them for time. So let's talk about what an offer is. I worked with a company that sells an automated welding solution. So think about really large RVs and trailers. A lot of that has to be manually welded by a human. And guess what? Most people right now like the trades. Blue collar jobs are having a heck of a time getting people to want to do those types of jobs. So there's a huge shortage of welders. Okay? So the first type of offer that anyone here can do and take back to their team is what I call selling the blind date. So if I'm talking to you, Kelly and Tiffany, you're my account executive, I would say, hey Kelly, by the way, I want to set you up With Tiffany because she's got about a decade of experience working with companies like Caterpillar and they're automating traditionally really hard to automate parts like what you have over at XYZ company And she'll also tell you a little bit more about how they're handling the welder shortage. If nothing else, you'll get some really good ideas you can take back to your team. So that's selling the blind date. It's if I have an sdr, sell the expertise of the account executive. If I'm an account executive, bring in an SE. Sell the expertise of my SE. If I sell EdTech and I used to be a teacher and I'm talking to educators, tell them that I used to be a teacher and I can share what that experience is like. And I think this is something that is often overlooked.

Speaker B: Easy and so simple.

Speaker A: It's so easy.

Speaker B: But this is like people are not doing that. I don't know. I do that in my inbox.

Speaker A: Yeah, you have to standardize. This is like, you know, this is what you have to do in enablement. Right? I mean, you have to standardize these two and three liners. So it's like, it's pitching. It's. You do that in a cold call, you can do that in a cold email. I mean, and it's, it's great. So that's like one type of offer. The, the other one, I'll give you a couple of other types. One is, I call it one to many. You can take a marketing asset and you can use that, the insights from that as a reason to meet too. The marketing asset has to be really good though. So it can't be like an 80 page white paper. That sucks. Okay, so it's gotta be one of my clients. They sell a customer like outsourced customer support. So I think you two would get a kick out of this. Because we're in the Pacific Northwest, they sell to a lot of outdoor brands like Patagonia, North Face, Columbia. They worked with a third party to mystery shop 300e.com businesses. And what they would do is they would figure out like response time via chat. Do they have chat? What hours is chat available? All these stuff that affects the conversion rate into a sale. So the way that they would open the cold calls is they would say, you know, Tiffany, this is Jason. I was calling you, I'm not sure if you're aware, but your response time via chat is three times longer than the North Face in Columbia. And I wanted to talk to you about that because we mystery shopped you and a few other competing brands. Do you got a minute? For me to share more? Every time when I would listen to the call recordings, it was like an emotional, visceral response. The prospect honestly was kind of pissed off. They're like, what, what are you talking about? You know, and it immediately got their attention and like think about that insight. People talk about Challenger sale and like all of this other kind of stuff and we can talk about the misconceptions with Challenger, but the teach tailor, take control teach, that is a teaching moment right there. It doesn't get any better than that. Like that's, that's a type of offer too. And it's also a really good example of the marketing team and the sales team working together where marketing is like really creating this like pillar piece of content that like every buyer would love to get their hands on. So you gotta create that type of stuff to really make the outbound stick out so to kind of backtrack a bit. The thing that really makes outbound emails and phone calls and all of that stuff really blend in is when there's just nothing to give. There's no give.

Speaker C: That's totally true.

Speaker A: No give at all.

Speaker C: I see a lot of like very highly personalized, clearly AI driven outbound emails that are like, they'll pull like where I went to school, they'll pull something personal. Like they find all this like rant, they'll pull the revenue insiders, they pull all this information and it's great, like it's very personalized but like I have no, like there's nothing about what they're selling. Like it's just like you want to grab time, like that's, that's the end result. And like I get the same email with the same five basic clips or reference to two LinkedIn posts on the regular basis. And so like you can only go so far with that personalization before like you're drowning in a sea of everyone doing the same thing. I'm curious Jason, is, is there like a, uh, way to think about the right offer to put together based on like either the data you have available or the type of maybe role that you're in that works best that you've seen?

Speaker A: Yeah, the blind data is a great place for anyone to start. Like anyone can start doing that immediately after this. Rep, leader, et cetera. I gave you an example of like a one to many offer, a marketing asset that you can leverage. The other type of offer is more one to one. So if you sell enterprise or strategic, like think about what you could offer and do for them to give them a taste of what it's like to like meet with you. It really depends on like so examples of that would be like if you sell an E comm solution, going onto the website and checking out something through the cart and creating like a 60 second video or a Google Doc or something that's got that summarized, um, you could offer workshops. There's all kinds of stuff that you could offer. I think that the first question I would ask is can you visually show someone something? Not all solutions are going to be like that, right? Is it something visible I can see on the web about their website? Can I do a store visit? Can I do something like that? And then I think the second thing is the insights insight. Is there something that I can share with them that's insightful? I mean like now you have Claude and we use perplexity, but whatever you use, you can build some of those insights, right? You can do some of that deep research and build some of those insights to share. So I would be thinking about how technical is it that what you sell and can you show them their actual problem? If you can show them their problem, you should do that. If you cannot show them their problem, the insight driven way is a great way to do it. And then last but not least again for enterprise and Strat, if there's something that you can do, you know, ground, swelling, motion, if you can talk to people on their team that is also a form of an offer. Hey Kelly, I talked to Tiffany and so and so on your team about some of the enablement that hasn't been sticking, you know, with your reps specifically around cold calling. Uh, I would love to share with you how we guided Shopify through that.

Speaker B: I would get any enabler on the phone in two seconds because they're going to be like who'd you talk to? And what they say? I want to know.

Speaker A: Yeah, yeah.

Speaker B: So um, you have to be careful with that obviously. But I do think there's something there and I loved your example that around the we went to your competitor's website and their response rate because that the part of your brain that that debates is so powerful in a conversation.

Speaker C: It essentially puts you in a fight or flight mode as like an executor. It's like I have to like I'm either going to hear about this from someone else that I need to deal with or like I need to go deal with this problem to myself.

Speaker A: Yep, the acid test. I always say with the offer is what could you offer that the buyer would feel irresponsible for saying no to? It would be irresponsible for the buyer to say no to. Getting an insight from 300 other E comm businesses that they mystery shop that stack ranks your customer support abilities.

Speaker B: Oh, uh, that's like. So at the end of our episodes, we always ask a point of view question, and I feel like that has to be our point of view question. We'll let you do another one, but I'm like, oh, I gotta come.

Speaker A: I was like, I was stressing out about that question too. I was writing stuff down when I said that.

Speaker C: You already got it right now.

Speaker B: I know. I'm, uh, learning so much. And I love this. This is an area. It's funny, one of the first roles I had in leadership was running a BDR team, but it was in 2017. And so the way you run to your point, a BDR team now is very different. Wildly different. Okay, so we've done the first two. Is there anything else you wanted to cover on the second part of your method?

Speaker A: Nope. Yeah, so disqualify offer. The last one's provoke. So provoke is Tiffany, you mentioned. Hey, like, yeah, you can know everything about me and where I went to school and all about my favorite color and, like, books to read, but, like, why should I take action? There's. There's three fundamental questions that we have to answer. It's, you know, why change? Why now? Why you? Right. These are very fundamental sales questions. So, uh, we do that through the three T's. It's triggering tension, trust. So every message. I think YouTube will appreciate this being an ops and enablement. What we struggled with when we're teaching this was, okay, we have, like, a, uh, way that we message over the email. We have a different framework that we teach the message over the phone. And then when we go to talk about social, it's another framework. We're like, this is too many frameworks. It's too many things to remember. A reverse pitch via phone reply method via cold email. I'm like, it's just too much. So he said, there is a universal framework at play here, and it's trigger tension, trust. The trigger is. That's. That's the why now? Why am I reaching out to you? That is the if I sell an HR solution that helps with international hiring and compliance, it's. I saw you're hiring in Italy and France.

Speaker C: Right?

Speaker A: The tension is the problem. That's the why change. So what I recommend is that we Think of tension in buckets. There's typically depending on how complex the solution is that you sell. Of course, there's typically like two or three buckets, tension buckets, problem buckets, if you will, that you solve. So the tension bucket right there is around compliance. There's all kinds of stuff that fit into that bucket. But international hiring is a really big compliance piece that requires a ton of manual work for a small business to be able to pull off. So it's saw that you're hiring in France and Italy. Not sure if you come across this, but a lot of HR leaders that we speak with share that it's tough to stay compliant without eating up your entire week. And you'd rather spend that time on, you know, capturing top talent or hiring top talent. Some sort of problem statement like that. The trust piece is social proof. It's why you. That's the question that we're answering. And we need a one sentence like customer snippet. We recently helped XYZ company with this. So that framework can apply in a cold call. Where in the cold call. I like permission based openers. Hello? Yep, this is Jason. I was calling because I saw that you guys are doing some international hiring right now. Do you got a minute for me to share a little bit more about why I called you specifically? Yes. Cool. Trigger Tension Trust. Again, saw you were doing international hiring. Here's the problem that we usually hear with that. Here's how we help. Is this something that's remotely close to what you're working on right now? Boom. And then I have a cold call, right Cold, uh, email, same framework. Hi Tiffany. Boom. Trigger saw this thing. Tension. Not sure if you're running across this, but this might be a problem you're having trust. Here's another company that we helped and then our CTA. And the CTA ideally is an offer based CTA. Maybe instead of asking for 30 minutes of their time, which the stats from Gong show that that decreases your reply rate by 44% if you ask for time directly versus asking for interest. Interested in chatting further versus making an offer? I'd like to put you in touch with Kelly. She recently helped XYZ company with this transition. If nothing else, you'll get some really good tips on how to handle the compliance piece. So Trigger Tension Trust is the messaging framework we have to provoke action. It's not enough to just share a vanilla message of I saw you're doing this and it looks like, uh, you're really awesome. Here's what we sell. Do you want to Chat about it. We have to provoke action.

Speaker B: I like it. Okay, I have a question for you. Uh, so because you mentioned it up a little, you mentioned it a little bit earlier when I hear why now, why you? I think corporate visions like uh, that's some of the methodology based there. But then you also mess talked about Challenger and you talked about the misconceptions there. I would love to understand what are those misconceptions that maybe we're missing.

Speaker A: I think that like, I think with Challenger the biggest misconception is that people feel like they have to be assholes to their buyers in like challenge them. So

Speaker B: I feel that way with Sandler too.

Speaker A: Yeah, I. With Sandler I'm just like this sales methodology was created in the 60s. So I just. Yeah. And I'm saying that on a recorded call. So I think that something like that similar. So I think with Challenger. I love Challenger. Big fan of Challenger. I think that the commercial insight and the perspective that you are challenging and the way that folks approach things like that's really Challenger. Challenger would be you hopping on a sales call with me for the first time. And I say, hey, I want to talk about something that is a really big challenge. And I would show a Gartner stat that says, you know, reps forget 92% of what they learn within 30 days of learning it. We have a perspective on this around why that's happening. And like what I would point to is it's not because they don't get taught great tips and tricks and tactics and strategies and all that kind of stuff. It's that typically when this stuff is rolled out, one, there isn't buy in. There's no tailoring or collaboration with the managers to make sure that they had input. The manager reinforcement plan is not even a part of the game plan. Um, they don't look at the tools and workflow that enable them to do this and they don't think about like how are we making this really simple for them to take action. Like that's that. That would be the conversation. That's. That's me challenging a common way that people approach things and then our perspective on it. That's. That's what Challenger is. I think in a nutshell it's educating.

Speaker C: I. The challenge I have challenge that I have with a lot of the sales methodologies that I think is lacking in yours and I appreciate is that ah, most sales methodologies still assume the buyer is incompetent or they don't.

Speaker B: They.

Speaker C: They don't understand things. And right now in the world of AI, the buyer is even if they didn't know before you sent an email or the first conversation, by the time like you're on the phone with them, if they picked up the call, they have some idea of the problem they're talking about. They've used whatever LLM of choice. They Googled it. Like there's just so much information and so many of these sales methodologies assume so much education about the problem versus understanding what the problem is and where that like trigger point is from an emotional response perspective that in the body. And I like that you're. And it serves itself well in outbound that you don't have that perception anywhere embedded into the methodology. That this is truly like about finding the right point in that. In wherever you're selling to. That's most necessary to like really engage that fight or flight kind of perspective or that emotional like response and then uh, reinforce it with logic and an offer to help them. To help them fix it.

Speaker A: Yes, 100%. Like we went through this thing with the Internet in search. It was called zero moment of truth. Google coined this like Zmont is what they called it. And it was this idea that I don't need to talk to salespeople in order to get answers to my questions anymore. I don't need to talk to someone about what they think of that restaurant. I could look at review sites. We're going through that with B2B buyers right now too. I really don't think that. I don't believe that you can educate a buyer on a problem that they are not already aware of. I think you can educate them on the root cause of it. And I think that you can educate them and on a perspective maybe that you have about it. But I think of like what I sound like. Really? You don't think that like every revenue leader that I talk with knows that they need more pipeline? Come on. That's like the captain obvious moment for them, right? It's like, tell me why this is happening. Tell me why the way that we're fixing it right now is not going to stick or it might take longer than I want it to. So I think that you really have an opportunity to think about that stuff. And to your point about treating buyers like they're stupid. I mean, like, dude, I just would not want a process that speaks down to the people that I'm selling to. They're in the business doing the thing that I am not on a daily basis. And that's true for whatever you sell. Like they are in that business, like they are so much more nuanced and understanding of their business than you could ever be as a salesperson. And you have this very narrow window of expertise that you can bring in because you talk to probably dozens or hundreds of their peers and they don't. So I think that like wanting to help and that's more servant approach I, I really like while maintaining a position of like, I'm up here, I have

Speaker B: one more question for you. I know that we are about a time, but you at the beginning of this talked about the AE and the AE who thinks prospecting is too junior for them, that an SDR and a marketing team should be feeding them warton blades. I see this everywhere I go. And I also see the struggle because it's not just the AE that struggles with this concept, it's the AE frontline manager who also grew up in that world and doesn't know how to coach their teams on how to do this well and more importantly, doesn't know how to hold them accountable to doing that because in the back of their mind also doesn't think they should be doing this. So when you think, again, I'm an enablement person. So when you think about the behavior change, how are you doing that with teams to get the AE and the frontline M manager to understand, like, you gotta wake up. This is the new reality and if you want to hit your number, this is what you have to do. Like, how are you having those conversations?

Speaker A: Yeah, I think it starts at the story level in the C suite or SVP level of the Pushing the narrative down. Right on. Um, why we need to do this, why it's essential for our future, why it's essential for you as a rep to win. And the best thing that you can do is just a simple math exercise and look at what that person's pipeline looks like in the next 12 months.

Speaker C: Okay, we are at point in our. Go ahead, Jason. Sorry.

Speaker A: No, no, it's okay. It's like, I think that that like the story that their pipeline tells, like that's oftentimes the easiest thing to do. The other thing I've, uh, found with frontline managers and AES, a big reason why they are resistant to it is really rooted and based, I think in shame. And if I've been in an AE for 10 years and I haven't really outbounded in the last three or four years, I don't know what I'm doing. That's kind of not something I'm going to be really open and forthcoming about. And as a manager, if I never had to do it because I sold during the best economic time America has ever had in its history from 2009 to 2020. And then like a little blip there and then through 2022. Yeah. For my own job security. I'm probably not going to admit that I don't know how to do this. So I think that having a level of vulnerability there and just saying, like, hey, um, we haven't done this in a little while and we're going to like enable the. I don't know if we can use profanity in your podcast. So I want. We're going to definitely, you know. So, uh, we're going to enable the beep out of you. Um, and so that to teach you how to do this, I think that gold standard for what that looks like. We can't just ask people to pipe gen and not give them the strategy.

Speaker C: Yeah.

Speaker A: Like we have to be the personal trainer, give them the workout plan, give them the meal plan, hold them accountable, coach them through it, et cetera.

Speaker B: And from the OPS standpoint, I think it's so important to understand this isn't going to change overnight too. There's going to be a build up to what outbound, um, um, looks like on day one. And then after you hire Jason and his amazing team, like when do you start seeing changes in it? Because I think oftentimes when you're building your revenue models, you're like, this year we're switching to an outbound AE team and they expect to get those great numbers day one. And if you don't have enablement or anything ahead of time, you're falling short.

Speaker A: And a one, which is one, one last thing, sorry, is Gigi might not have the right team either.

Speaker B: Yes. Oh, you're so right.

Speaker C: No, I, sorry Tiffany. I was going to layer onto that though and say I, um, think that having uh, a methodology, like a blank slate starting point for everyone, helps people feel like they're on an even playing field and they're not. Like it's not a everyone go in prospect. That's now your job, like to go pipeline and do outbound. Then they're like, I don't have the tools. Like this person knows and I don't know, I'm just copying what they're doing on LinkedIn or reposting company marketing stuff. I'm just not sure what to do. But when you come in for the whole team with a methodology, you really do create that blank slate to see where people can Adopt and learn and where people are unwilling and maybe are not the right fit because they just were lucky during that economic boom and not actually have not built any skills and are not willing to build those skills at this point in their career. And I think that that's an important piece to figure out before you just start cutting people away because they're not generating pipe gen or they're not outbounding. Like there's a, there's a window there where you need to help them build the skills and see where they're at.

Speaker B: I think we definitely need a part two to this episode because this m. The fact that Tiffany and I have interrupted you maybe seven times, Jason, is because we're very excited about you're talking about and I think it's something that is a hot topic for every CRO that we're talking to these days. So thank you. We'll be inviting you back. But before we leave today, is there anything we didn't ask you today that you think's really important for everyone to know?

Speaker A: Uh, you had me think about the question before we started hitting recording, uh, hitting record. The other question that I think is really good is I can't remember if Tim Ferriss or someone like this I heard it from. You know, what does addition by subtraction look like? So I think like when we're building out process, they tend to get really bloated over time where you've like added so many things to it. And I'll ask the CROs and VPs of sales sometimes, like when's the last time you were a rep for a day? Like have you tried like adding an order form in Salesforce? It takes a like 90 minutes, dude, for an SMB sales cycle to do that. It's crazy. You know, um, so I think if you had to subtract in order to achieve the outcome, what does that look like? Like what could we take away that's oftentimes a better answer.

Speaker C: I think that there is so much more to unpack with process evolution that needs to happen right now at the speed that tools are moving. Um, and I think that that is, that is spot on. I think something even Kelly and I in our little two person shop can think of because we have over complicated a number of things in our first to you.

Speaker A: I hear you.

Speaker C: It's a great, it's a great

Speaker B: one. Does keep it simple. Stupid, right? Yep. Okay, well, where does everyone find you? Because I know people are going to be very hungry for more information on this.

Speaker A: Yeah. So there's Two places. One of them is free. Uh, I went in a studio here in Seattle for an entire day and recorded a three hour long masterclass and we're giving it away for free. So the idea here is with this methodology and approach, like we want every rep and manager to have free access to this and just we want you to get as much value as possible. So it's outboundsquad.com masterclass. It's got everything from the disqualification stuff that we talked about. We talked about how to leverage AI, how to control the phone conversation, how to own the email inbox, how to handle objections. Um, it's really built like for the rep and the execution, like those skills, like what's working right now. And then the other place would just be our website, outboundsquad.com so if you're, you know, running a big sales org and you're like, we need to like, do more of the stuff that, you know, Jason talked about today, uh, I would love to talk to you. Um, if you're a team that's just rolling out, maybe your first SDR team, we help a lot with that too. So outboundsquad.com is going to be the best place to, uh, get a hold of us. And outboundsquad.com masterclass is where you can check out the free course.

Speaker C: We are definitely going to have you back because we had a whole bunch of other questions we had talked about and we got nowhere near them. There's a lot more to discuss soon for sure. Yeah. Thanks so much, Jason.

Speaker A: Thank you.

Speaker B: Thanks everyone. And if you are not following us or subscribed, please make sure to hit the follow and subscribe button so that you can help others find this podcast. Thanks everyone.