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#577 - Why Your AI Cold Emails Are Failing (And How to Fix Them) | Jason Bay

46m 30s

#577 - Why Your AI Cold Emails Are Failing (And How to Fix Them) | Jason Bay

Jason Bay, CEO of Outbound Squad, shares a data-driven, actionable framework for modern outbound sales that counters the oversaturation of volume-based AI tools. He emphasizes moving beyond generic cold outreach by prioritizing quality over quantity. The core methodology is built on three pillars: first, disqualifying 80–90% of contacts to focus effort on high-potential accounts; second, using a tailored offer—like a personalized client success story—to increase reply rates by up to 28%; and third, structuring messaging around the "Triple T" framework: a trigger (a relevant business signal), a tension (a specific problem or pain point), and trust (social proof from a similar-sized, relevant client). This storytelling approach builds emotional engagement and credibility. Bay stresses that triggers must be meaningful, not generic (e.g., "hiring internationally" is better than "raised funding"), and tensions must be tailored to the persona—surface-level for operational staff and strategic for executives. He advocates for reverse-engineering tension from real deal outcomes and using AI to identify triggers efficiently, while maintaining human judgment. His framework is rooted in real-world data from over 85 million cold emails and 300 million cold calls. To implement this, sales reps should start with three core tension scenarios, identify three triggers per scenario, and create two tension variations (surface and strategic) for different personas. Each tension is paired with a concise, believable trust statement. The result is a compelling, emotionally resonant narrative that drives action and leads to higher conversion rates. Jason offers a free outbound masterclass and interactive workbook to help reps apply these principles, emphasizing that true outbound mastery comes from pattern recognition, emotional intelligence, and strategic storytelling—not just volume.

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Guys, I used to sing cold emails before there were sequinsers and it would queue up a task for the follow-up email It wouldn't send it for you. So once you made that available to everyone now It's like a button like I can send as many emails as I want and make as many bone calls as I want to like the volume It's just gotten out of control the way that people are using AI is the same way that we use sequinsers and dialers It's just to increase volume the quality hasn't really gone up really at all But we're in an age right now where you as a rep have to be too good to ignore and how you show up and Order to stand out all of the AI stuff like you can't just use that as a ball name tool to send more and more and more and more You have to think about how you're using it to be more precise Good morning everybody and welcome to another episode of 30 minutes to presidents club I'm your host Nixie Gelski joined with my co-host today Alex Murphy and today we've got I think he's the most frequent 30 NPC guests we've ever had and the person that I've learned the most about outbound from ever and that is Jason Bay he is the CEO of outbound squad Alex. Why should people listen if your job relies on you talking to strangers and getting them leaning in and saying I'd like to know more about your business You'd be a fool not so listen to this. I just learned like so much about each step of Outbound messaging and it applies to cold email cold calling social selling like all of the above and Jason's got a really elegant Framework that is easy to hold in your head while you're doing this which is so valuable. Yes 99% of the outbound advice that I see is like very very simplistic use a permission based opener or it's way too complex a 47 step AI workflow and like it's really tough to action on what we cover today It's easy to action on and also effective so action on continuing to listen to this episode. Let's roll all right Jason welcome back to the show. I hope that you remember we start every single episode with your top three actionable takeaways So let's get your three of course. Let's go. I'm happy to be here. Number one is disqualify So the number one mistake that you can make is treating your sales funnel like a funnel instead of a Martini glass So the goal is to go deep on fewer opportunities You should be disqualifying 80 to 90% of the accounts and contacts within those accounts that you could be reaching out to and putting all of your effort We are most likely to get a response Great. What's number two? Number two is offer. We studied 85 million cold emails with Gong With the presence of an offer the reply rate will go up by as much as 28% So your job when you're doing outbound is to put an offer in front of the buyer That they would feel irresponsible for saying no to an example would be one selling the blind date Which is anyone listening to this can immediately do if you're an SDR setting a meeting for an account executive I want you to hype them up talk about their experience the companies They're working with what they could expect in that meeting if you're an account executive You should be talking about a recent company you just worked with the transformation and the insight that you can share The second thing that you can do is also give them some sort of tailored Offer that's a little bit more personalized. So one of our clients sells an e-com solution They'll go through and buy something off of the website and do a card on it And that's what they offer to walk the buyer through amazing Well, I've got an offer for you listener. It's Jason Bay's action. It will take away number three number three is provoked So the provoked piece is hey, I've disqualified if offered I have to have provocative messaging in order for them to take action And what we're going to talk about today is what we call the triple T It's trigger tension trust. I need to use a framework that triggers So one talks to them about why now a conversation is relevant tension that is a problem statement why change? Why should I do anything different? And then the trust piece is why us so I need to have a one-liner around a similar customer that we've worked with or some sort of social proof And social proof especially in email will increase the reply rates by as much as 35 40 plus percent if you do it properly Jason, we've been running the 30 NPC podcast now for over six years and I have learned more about outbound from you Than anybody else that we have interviewed and you and I were having a phone call the other day And you were talking about some of the pretty material changes to the out-out environment that have been going on and how You are seeing some of the clients that you work with which are some of the most cutting-edge tech companies Adapt to those changes and that's informed some of the best practices and advice we're going to talk about today I'm wondering if you can speak to you first some of the changes you're seeing in outbound and then the strategy that you have Been building to help folks adapt to that and then we'll get into the actual what to do piece So where it kind of starts is from 2011 to 2018. We had the predictable revenue era Right you guys remember that book Aaron Rossis and they're not gonna air and Ross in predictable revenue But that was like the playbook the outbound playbook for a long time The first up on that I ever read was predictable revenue. Yes, I think B2 actually Great book now what spawned from that is what I call these sales engagement gold brush and that was Outreach sales loft and now it's like everyone's got a sequencing tool There were multi-billion dollar valuations built off of that playbook and the technology that enabled it Well, we got a shot ourselves in the foot because Once we've made accessible you guys I used to sing cold emails before the resequences And it would queue up a task for the follow up email It wouldn't send it for you It would queue up a task for you to do it and you couldn't do phone stuff in there either So once you made that available to everyone now it's like Click of a button and Some of these tools are free like Google Chrome extensions like I can send as many emails as I wanted to my team And make as many phone calls as I want to like the volume is just gotten out of control and AI the AI era the one that we're in right now The the way that people are using Ai is the same way that we use sequencers and dialers is just to increase volume the quality hasn't really gone up Really at all the the floor is a little higher where you're not seeing stuff that is like so bad It's got a little bit of like a relevance and like that kind of stuff in it But we're in an age right now where we call it too good to ignore like you as a rep have to be too good to ignore and how you show up In order to stand out and it's human-led AI assisted all of the AI stuff like you can't just use it as a volume tool to send more and more and more You have to think about how you're using it to be more precise And that's how we came up with that three-part methodology of disqualify Offer and provoke these are the things that you need to do radically different without bound in order to stand out right now Yeah, it's funny the that journey that you just laid out is pretty much the one that I personally have gone on with my outbound So I started red predicting a predictable revenue first BDR job I ever had I had a sequencer and it was just like cool Let me just like the number one guy on the leaderboard was just cranking emails same email to everybody just volume And I was like well, okay, I want to be that so I did that. I was number two guy on the leaderboard for most of the time because I could just mash that and Then pivoting to AI once that became available. I think my first use of it was just taking you just like write an email for me And I'll just send it send it send it send it and the problem is that just Increases further increases like worst messaging And so I feel like that now the usage of AI Cripping from wrong on this but it's a lot less about writing the message and a lot more about what is informing me as I as a human like create a message is going to be compelling to the person sitting across the virtual table from me What's going into that messaging? That's where AI is hitting is that kind of how you think about it? Yeah, it's the inputs. How can I increase the quality of the input? Volume of the output itself is also helpful but the Increase in the level of the quality of the input, right? How can I like be smarter or find the information faster? Yeah, like that's what AI is all about and really a lot of this should be done at the org level in my opinion I don't think a rep should have to do all this stuff like think about a future in a year or two where you're using clawed to auto-populate all of the account Research messaging triggers potential use cases into the account into Salesforce for the rep so that when they're dialing They're looking at something that's like 80% of the way there and they can use like what really needs to be done by a human Is the soft skills dude. It's the ability to create a a creative email the ability to execute a cold call and be funny or have my Personality really pops through like that's what we're going to be able to spend more time on that's what we should be using AI for I want to talk about the provoked piece and you were sharing with me the three pieces that go into provoking which is yeah trigger tension Trust and those are the pieces of need be weaved into any effective outbound message could you give me the one sentence on each and maybe What that might actually sound like then in a let's say cold call for example Sure, so we developed this because I Found it really frustrating. I know if Alex your journey was like this I learned a different framework for email than I do cold calling then I do LinkedIn messages and everything's got its own unique way of saying things That doesn't really work when you're trying to scale a process across an org, which is oftentimes what we get brought in to do So this was really developed as a universal outbound messaging framework. So trigger answers to why now question It is though. What is unique to this individual or their company that says now is the time that we should be talking So if I sell an HR solution and I sell it to small business owners Let's say that might be I saw that you're doing hiring internationally right now in France and Italy This answers the Y-Change question. is like the golden question and sales, right? Everyone wants to know out of all of the things that I could be spending my effort on right now, why is this something I should care about right now? Why change? And this is typically done through a problem statement. So that problem statement might sound like this. I'll stack the trigger and the tension together. Alex, I saw that you're hiring internationally in France and Italy right now. And this is maybe my permission based opener. So I say, um, it's Jason with XYZ company and you got a minute for me to share the reason why I'm calling you specifically. Alex is either going to tell me to f off or he's going to be like, yeah, cool, you know, and then I know it's you calling Jason. That'll that'll change. I'll respond. Right. So then for the next part of my call, I'm going to do the triple T. So I can either restate again. If it's an enterprise account, I might need to restate that trigger again in more detail. Hey, again, I saw that you're hiring internationally, it looks like you guys have 150 open rex and from what I can see, it's the first time you've done this internationally before. And tension, not sure if you're running into this, but a lot of the HR orgs that we work with tend to run into a lot of compliance issues that keep them from hiring at the rate that they need to support the business growth. That's my tension statement, my problem statement, right? Next is trust. Trust is typically conveyed through social proof. Every single study you'll see on email or cold calling, whatever might be a social proof when used effectively will substantially increase your reply rates, your positive response rates, your success rate on the phone, et cetera. So what I might say after that is we recently helped XYZ through a transition like this. And it really opened up time for their HR team to focus more on recruiting and hitting their hiring targets instead of getting bogged down with legal compliance. So that is literally like the email. It would need to be a little tighter if it was an email, but that's the first line of my email, the tension statement, the problem that's the next line, the third line, that trust statement. And if it's an email, the call to action might be an offer. Can I put you in touch with Nick, who recently helped XYZ company with his transition? If it's a cold call, I might say, how does that compare to what you're seeing right now at your company? Today's show is brought to you by Unify. Top SDRs don't work every account the same. They tear by intent and then they work the hottest signals first. So Unify actually builds that list for you. If you just describe who you're targeting in plain English or connect your serum, it will literally search over 40 different sources to surface the tier one accounts automatically and then draft the outreach in your voice. So it's basically like clawed for outbound sellers. Grab our guide on how top SDRs hit quota every year in the show notes or sign up for free at unifygtm.com. The worst discovery advice is just be curious and ask lots of questions. Look, our prospects are not showing up to sales calls to answer our questions. They're showing up to get their questions answered and to figure out how we can solve their problem. And this is what PyTrak does. If you want to get clear, complete sales visibility, you can use PyTrak's easy to use and customizable CRM that is designed to be simple from day one and stay easy to use as your team grows. We actually put together an entire resource hub with PyTrak to help you get to president's club and you can get them for free in the 30 NPC PyTrak Closers hub. The link is in the show notes. Today's show was brought to you by outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale. And one thing that's worked well for me is assigning red line deadlines to my prospects when we kick off vendor review. Even artificial micro deadlines for things like first cut of red lines and security review helps my prospects get their internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at outreach. Get it free in the show notes. I want to go deeper on each of these. So I'm wondering if we can talk about dues and don'ts for trigger tension and trust. So could you give me some examples of maybe good triggers versus bad triggers to folks and start to orient themselves around what they should be calling out when they reach out to somebody. Yeah, what we talked about in our reply method course that we created together was soft triggers versus our triggers. I really like that framework. So if you can imagine a hard trigger is something that it reveals the pain that they are experiencing. So if I sell that econ solution and I see that they don't have a way to do upsells in the cart, that is a problem that I can see. That is a hard trigger. I don't need to confirm that with them. That's a problem that's happened. The soft trigger is something that is like 10 gentle to the problem and might lead you like give you the cookie crumbs or the bread crumbs towards the problem, but isn't the problem itself. So the one that I did earlier and most triggers are going to be soft triggers where I said, hey, I saw that you're hiring internationally. I don't know if that's actually a problem that they're going to have because I don't know what solution they're using right now. I just know based on the patterns of talking to a lot of them that that might be a problem that they experience. So with the triggers, the other layer behind this is in that research we did on cold emails, we found that company level triggers perform 50% better than individual and industry baseline triggers for director plus specifically. So what does that mean? That means that if there's a director VP or C suite, I don't need to point out where they went to college or something that I saw them post about on LinkedIn unless it's relevant to the business. What I really need to do, they're closer to the business problem. I need to talk about stuff going on in their business. So what you need to think about beforehand is so if you could imagine like almost like a mind map with the trigger attention trust, you would have like two or three tension buckets in the middle. These are the two or three problems that I solve leading up to that would be like the triggers that funnel down into each of those tension buckets. And then I would have trust statements that align with those specific problems. If you sell an enterprise solution, this is going to be kind of big because you might have two or three problems that you solve across four or five different solutions. For a lot of you listening to this, I imagine you're probably selling like a bid market solution. Something that's like pretty straightforward that might have like three use cases, let's say. But if you can map that out, it's like an exercise more and like where do they fit in here versus guessing every single time what they're having challenges with. So I think just to recap what I've heard from you, what I should be doing as a wrap is I should be identifying what are the big three tension statements or tensions that I might be able to lean on. And then for let's say I pick my three, then I'm going upstream and I'm identifying for each tension statement or tension scenario, what are the three most relevant triggers that would cause that tension to be a reality. Now I have a list across my three tension buckets of nine trigger triggers three times three is nine. Then what I'm doing is I'm associating it trust. Hey, you know what? I got eggs your first seconds. It was like, is it? Hey, listen, I'm only laughing because at this stage of my life, I have to ask clog what three times three is. At this point, man, I don't even know. I'll stop my head. But so now what I've identified is I have a list of nine triggers that I can look for and I can use my LLM of choice to go identify for any of my accounts, which trigger is going to be most relevant, which then attaches to what I pitch when I call them. My question for you, Jason, is how attached does the trigger need to be to the tension statement? What's coming up for me is Alex in theory could find a trigger of company raised around a funding. That must mean they want to grow, so they probably want some sales enablement support. Is that too generic of an attachment or should be he be looking for things more specific? Because in theory, pretty much any solution could be attached to the trigger of they just raised money. So they just raised money is not really a trigger as much of it is like if I had to use that as a way to point my efforts in the right direction across my account base, that might be a good place to start. Honestly, I haven't seen a lot of correlation and all of the work that we do with like whether a company just raised around or not. So it sounds like what I should be doing if I'm a rep in that scenario is if I see that Acne Co raises money, what I actually want to do is say, Oh, I might actually put a little more effort into finding a trigger. The raising money is actually just a trigger for it might make more sense to look at what are they doing with that money to then attach to a tension statement. That's a trigger for you to reach out. That's not a trigger for them to take action though. So yeah, maybe that's a better way to think about the trigger is like what would they acknowledge is a reason for them to take action on a problem. Okay, great. Can I ask one more thing? Actually like another way to find triggers is through the sales process. So like when you get a sales call set up and you're doing research, like you're finding the triggers that are making that conversation relevant, like reverse engineer why people hop on sales calls with you, right? Ask them these questions. If you're an SDR, listen to those call recordings with your account executive, like you can reverse engineer those triggers. That's part of that disqualify bucket too. Like the first thing you want to do is like a closed one and closed last analysis and look at your last 10 or 12 deals or if you're a sales leader, look at your last six months of deals and look at all the deals that you win and reverse engineer like what's going on at those companies that we can connect back to our solution. Yeah, it was just about to ask you how do you choose the triggers you're looking for and then like prioritize them across the account. So clearly like our own first party data of what we know is happening in our actual sales like it was a huge piece of it. What's your process? Is that where you start when you're working with a new company and then what is your process from that kind of research all the way through to okay team? Here's what we're looking for when we go and we we figure out which accounts we're gonna reach out to this week. - Yeah, you're gonna reverse engineer, that's the start. The second thing is there's kind of like really common go-to buckets for stuff that you're selling, right? I mean, there's like expansion and contraction is a really big bucket. Like is there evidence of a company growing or like shrinking in size, right? There's hiring as a really common bucket or they're hiring for roles whose jobs are to help fix the problems that our solution solves for? There's mergers and acquisitions, there's the social proof that you see them displaying, like the stuff that they brag about. So brag about, educate their customer base about, like these are all kind of areas that you can dig into and there's a big list of them in that course, too. But yeah, it's, I think the biggest mistake you can make is starting with the triggers versus starting with the tension. Think about the problems and the tension first and then you wanna reverse engineer that. - So let's move now to the tension piece because you gave one example of company was hiring in France and Italy and they were running into compliance problems, hiring internationally because they were doing it for the first time. Can you talk to me about what goes into crafting a good tension statement or a good tension scenario? - Yeah, so you could think of tension in two buckets. There's like surface level tension. So this is skip miller selling above and below the line. This would be the equivalent of BTL or below the line problems. So a surface tension is like if we're using the HR example, it would be takes so long to process payroll. That is not really strategic tension, like a business problem. And the most common mistake here you can make is using the wrong type of tension statements with the wrong type of persona mismatching those. Oftentimes what I'll see is we're talking about payroll to a CHRO at a 1000 person org who gives zero shits about payroll and how it's done. They just wanna know that it's done on time and that we're compensating people properly, that we're retaining them, like that's what they wanna know. Cyber security, the CSO doesn't really care about, okay cool, some people like to use their hotspot when the internet goes down inside the factory. And that's unsecure. What they care about is like how many alerts that their team is getting and are they able to pinpoint and find the right ones 'cause they get thousands of them. What's their exposure? What's the remediation time? How quickly do they fix it when something happens? So you kind of need a combination of the two for each account that you're reaching out to because it depends on who you're reaching out to. Yeah, right, but that strategic tension, you wanna make sure that like you really understand like the core business stuff is stuff that affects revenue profit and introduces some sort of risk into the business. Like it needs to connect to one of those three things if it's a business thing that you're talking about. Can we go back to that compliance example? Because I'm thinking about the mental map that we've been crafting here, which is I'm starting with my three different tension statements. I'm identifying the three triggers for each. So now I have my nine triggers by three tension statements. That actually sounds like each tension statement I need to have two versions of it. One that is a surface level tension for someone who's below the line and one that is a strategic level tension for someone that is above the line. Could you, and I know I'm asking you to do this on the fly, Jason, could you let's say that I identify someone's hiring in France and Italy? And I know that that causes compliance problems hiring internationally for the first time. What would an example of a surface problem statement sound like or surface tension statement sound like? And what would an example of a strategic tension statement sound like for that same trigger and then problem? I want people to hear the difference in the language. - So the way that I would organize this is around the persona. - Okay. - So the most common mistake is that teams build things around their products instead of around their personas. So I would have a separate set up because the tension statements Nick actually might be different. They might be completely different for a CHRO versus an HR manager at the same company. So I want to separate those. But the triggers could be the same. So let's use the CHRO example. I see that you're hiring in France and Italy. We talk with a lot of HR leaders whose hiring plans get bogged down and they fall behind when all of the compliance issues are introduced when hiring internationally. Something like that. That's my Asian statement. Now for that HR manager might be like, hey, I saw your hiring in France and Italy right now. I imagine you got to be bogged down with hours of compliance work and working back and forth with legal. You got to be frustrating. - Yeah, dude, it sucks. It's what I do all day long. Do you have a fix for that? Yeah, it's like that's a very different talk track for both of those. But I would think about separating, you need tension buckets for each persona. That's where we start. We're the core personas and then let's create the tension buckets there first. And then we reverse into the triggers. Then we pull the customer's stories for the trust. - Could I ask you for some free coaching in the moment, live? - This whole podcast was just an excuse. - This is my favorite thing to do. - Free coaching for the smart people. We have been workshopping this actively, like two day on my team. It's like how are we bringing this? So we work, you know, I sell our team enable program part of which is your course. And then we help train people on it. And like we're reaching out to enablement folks is a primary persona for us. And we've been workshopping it. What's the, what are we using as a trigger? And then how are we describing that tension? I'd love to tell you what we came up with and you tell me what you think of it. - Basically what in terms of tension that we are seeing. So we backwards engineered the tension from what we're hearing in deal cycles, which I think lines up with you. And the big thing that we are hearing from enablement leaders is I'm being asked to address nine different priorities all at the same time. And everybody's mad that I'm putting time on their calendar. All the sales people, they just want to be in, they just want to go sell. And I have to like do all this training and stuff. And so what we look for is kind of two pieces. One is specific members of their team who are downloading assets from us. So that gives us a little lead. I'm like, all right, there's a warmth there of like, you've got some fans of 30 minutes to presence coming to your org already. And they're downloading content on these couple of topics. And that also the next thing we're looking for is that company level signal of you, something has changed is the way I'm thinking of it. So you got a couple of folks downloading stuff on these topics. And also you just launched this new product to try to go up market. I read your announcement about that. That makes me think oftentimes like what that leads me to believe is, this is kind of your bread crumbs example is that you've got a ton of different demands on your time right now as an enablement team. And like training folks on like, how do I right kick ass cold emails? You just don't have time for that. And then I would go into an explanation of like, why us like, well, how do we help address that and offer a value? But we haven't gotten quite into that yet. Like what's your take on how we're thinking about that? - Yeah, I think that your current messaging allows you to connect on an emotional level with that enablement leader and how they feel. But it's surface tension. You're talking about features and functions really. Is like, you can't do this thing, right? - Yeah. - For an enablement leader, it's like, you got to chunk up a little bit, right? And if you chunk up to the business outcome, let's talk about launching a new product. Like enablement is the arm that upskills the team and builds the process in the program around how they're going to accomplish this huge revenue goal that they have. So you got to think about like, what's getting in the way of them accomplishing the things that the business needs? And I could tell you some of those. Front-line managers aren't bought into the program. So there's no reinforcement. It doesn't stick. It's a flavor of the quarter type of thing. - Mm-hmm. - The second thing is the partnership with sales, right? So it's being a strategic partner to the sales team. This is what's enablement leader. The best ones talk about all the time. You know, Jonas, Masters, head of VP of sales enablement at Ripley and the way that they work with the sales team is like they bring insights to the sales leaders around what's working and what isn't. Like that's your offer. Like if I'm trying to get in contact with an enablement person, I'm trying to help them be a better partner in the organization by arming them with like things that they can go look for and find that the sales team would find value out of. Like, that's a heck of an offer, right? But it's like enablement is being sort of unfairly, I would say measured on the results that the sales team gets. So whether they get the results, whether it sticks, the retention, what the frontline managers think about it, like those are the, that's the tension that an enablement leader feels. - That's the strategic tension of like, this is like why this whole initiative that you're getting measured on, hey, we're rolling out this new product. Everyone needs to be able to sell this thing. If they don't, that's on you enablement leader. That's the big tension. - Speed is also a really big one. Dude, this is like our value prop, man. The fact that we increased qualified pipeline by 20 or more percent within 90 days, it's quicker than it would take for them to even build the program. - Uh-huh, uh-huh. - So, dude, that's a really big one. It's the time to value. It's having an outside trusted voice. It's being able to quickly spin up a program that they don't have content for. - So those are some of the big pillars. But that's an example of like you got a chunk up. and then really think about like the business outcomes that they are aligned to and measured on are did the sales team accomplish what they needed to with these big strategic moves that we're making. You got to align the tension to those things, not the day-to-day pain, for a leader at least, for a VP of sales enablement. And this is what PypeDrive does. If you want to get clear complete sales visibility, you can use PypeDrive's easy to use and customizable CRM that is designed to be simple from day one and stay easy to use as your team grows. We actually put together an entire resource hub with PypeDrive to help you get to President's Club and you can get them for free in the 30 MPC PypeDrive Closers hub. We built a guide on how to help you drive six and seven figure deals with our friends and outreach. Yeah. So just to recap, this chunking up approach that you're talking about is our ability to say great. I know the trigger. I know the surface tension that it creates. And I know how to chunk that surface tension up to a strategic tension that happens. The example that you gave for the compliance one was hiring in France and Italy. Makes it hard to navigate compliance complexity in those new regions, which this is the chunking up part makes you fall behind on your hiring plan. A CHRO does not care about nitpick issues with navigating compliance. They do care about missing their hiring plan. Jason, do you have any guidance for folks who are like, okay, I need to start chunking up. Are there other common examples you seen of taking a surface tension up to a strategic tension that might help folks who are trying to build this for themselves? We could use another example of contact centers is another kind of like very common persona that that of clients that we work with. Yeah. So if you think about like when you have an issue with something, let's say you bought something at Nordstrom and you have an issue with it. Nordstrom does not want you to talk to people in their call center. Yes. Like that's the irony of all this. People want to deliver good service, but they do not want to talk to you. So they'll do everything that they can to make sure that you can't like call or that you get routed somewhere or that AI fixes it for you. So if I'm a rep and I'm dialing in and I'm looking for instances of how they're trying to get the customer to self serve and I say, hey, I noticed that you had the phone number on and you guys are probably getting a lot of dials in there. And you know, one thing that we can help you do is you know, make sure that more of that gets routed to do AI and like your chat bot and all that kind of stuff. That's like surface tension. I'm just talking about like surface level features and functions versus, hey, I'm not sure if you're focused on this or not, but a lot of companies that were working with like Nordstrom, they they have the chat bots and the AI stuff that you have on the website. And they're trying to reduce the cost to serve the customer. And they put millions of dollars in like ways to do that. But when it doesn't fix or resolve the issue, they end up calling in any ways. It costs money and they have an unhappy customer. And I'm curious like, how does that compare to what what you're seeing right now in your contact center? Like I'm just thinking about like metrics. It's the first M and med pick. You know what I mean? Like, would you sell to people, you should know what metrics they care about and are measured on. It's like a really simple question to ask. Right. Hey, what KPR metric is relevant to our conversations today that would be good for me to know. Like, where would you be trying to get movement if we if we worked on something together? This is a great example of your point about simplicity versus complexity. We're like, it is so easy to get overly complicated. And then you forget the basic stuff, which is that the end of every month or week or day executives are looking at some dashboard to figure out if they're succeeding or not. And it's probably the same dashboard that their boss or board or whoever is also looking at. If I can like accurately understand and picture that dashboard, that gives me my sort of where can I positively influence. There's my attention bucket. Like those are my buckets of tension. Which of those things on that dashboard can we help with? And then let's go find them. It's really cool. As most buyers, at least within the same industry and like organization size, they're going to have the same things that they're measured on. It's not like you have to guess every single time you reach out to a new CFO. Or a new VP of sales or marketing or contact center. Like this is where true outbound mastery and sales mastery is attained is when you can start to really pick up on patterns. They don't have to do so much customization all the time. You can be like, okay, cool. They're hiring internationally. Awesome. I know like the story that I'm going to tell around that. And that's what I love about trigger tension trust is it's a storytelling framework. Like you need to grip them emotionally with the story. What am I doing now for this last piece, which is building my trust statement? What goes into it? And how can I build one for myself? So this is essentially your social proof. And there's a couple things that are really important here. In terms of what not to do, you want to avoid shearing the name of a company that is very unrelated to what the buyer does, but has a lot of notoriety. People tell me when they reach out. Yeah, we work with Walmart and Google and Amazon. That's really great. But I don't have a lot in common with those companies. So the company needs to be similar in size, similar industry, if possible. And you need to have some sort of story around it and it could be a sentence or two. And it could sound as simple as, hey, XYZ company was running into something similar doing a lot of international hiring. And we cut down the time it took for them to do this type of hiring and about half. So instead of taking six months to work through all the compliance, it took about three or bonus points. If you can throw a person's name in there, if it's a prominent industry, like, well, I would say, hey, we work with Shabon over there at Shopify who who heads up enablement. And one thing that we rolled out was an outbound program across the entire org. They didn't have to do it themselves. And most importantly, it made a really quick impact within 90 days that the mid-market team saw 40% left in ops created. That's your trust statements. So I need to have something that aligns with those tension buckets. You mentioned that really what we are doing is telling a story. It's interesting because I'm over here writing. I'm looking for a character, their conflict, the change, and then some climactic solution, which is a story arc. That is literally what I'm doing. And it's almost like, I've got a social proof story where I've got a character over here who's similar to you who also could be the hero of this story. It's not me that's the hero of the seller. It's you buyer who's the hero. And you've got this conflict. I can be your sage in the heroes journey and help you figure out the way to get past. Because I helped that other customer over there who was dealing with the same thing and they're in a relevant. And I think I'm curious about how specific you get. I think one of the risks of social proofing is it starts to feel like almost like overhyped. We help so-and-so 10X their revenue and it gets really like bombastic and people don't trust that. It almost feels like it's doing the opposite of what it's intended to do. So how do you think about what to include and what to exclude, especially in email where you really only get one line for this? I think if your case studies are so good that they're unbelievable, I would maybe leave out the result. So that's like a good rule of thumb to follow. Other than that, I've found that there's a pattern in the more senior a person is the more they care about the numbers. So like if I was doing some sort of pipeline metric, it might be instead of increasing, you know, pipeline by 25% I might give, hey, they increased pipeline by 120 million dollars across their SDR team. They had their best quarter ever, right? Something like that. I think that facts and figures and like numbers, I think people talk a lot of shit about case studies and results and like, dude, executives want to see that. It's called a proof point. It's like literally the first thing I need to do when a CRO or VP of sales gets introduced is they want to know proof points. Who have you worked with and what results did they get? So you need both. I think we tend to overindex maybe on the proof point, but you have to have, you know, people buy based off of motion and justify with logic. Well, I think that's why the sequencing here really matters Jason. So what you're doing is to Alex's point, you are telling a story and the story gets them emotionally bought in and then you finish the story. You've got them bought and emotionally by helping them justify with logic. And that's why that's why this works is you go story, get them bought and emotionally, hit them with the proof point and the reason that it's believable is because because your tension statement is so specific that they're like, ah, this guy actually talks with and works with people like me. Or not calling him and saying, hi, how is your day going? Do you wanna know that we created $120 million of pipeline and we can do it for you too? They're like, fuck off, I don't wanna work with you. But when you use that trigger, oh, I actually know you, the problem statement, oh shit, this person actually understands my world. The social proof, oh, they name drop someone like me, not Walmart. And then the data, they're like, okay, cool. And then what I know you do really well, Jason, is you finish not with, do you wanna book a meeting to learn more, you're finishing with an offer of value where you're actually giving them something, offering them something, you talked about it and you're taking away in the beginning of selling the blind date or giving them some sort of tailored offer, which takes a little bit more work to deliver, but you get so many more meetings on the back end so you don't have to do as much crummy outbound work and you can do more meeting with and helping clients work. And I know we put together a lot of offer stuff and the clock's ticking, so we don't really have time to go deep on offers, but what you just talked to is extremely powerful and actionable for folks. I really appreciate you sharing your expertise. - Yeah, thank you for letting me join the 45 minutes to President's class. - I know, and I never let people do this. Could you give us the one line on, I know you wanna, I know you're doing some outbound master class stuff, Jason, could you give me one or two sentences on, folks wanna go deeper with you, other than buying the 30MPC outbound squad course that we built, how else can people go deeper with you, Jason? - Best way right now is a couple things. So we put together an outbound master class. I said in a studio for seven hours, walked away with around three hours of content, we created an interactive workbook that I freaking vibe coated myself, you guys. I vibe coated it. - I saw you talking about this. - So instead of being a Google doc, yeah, you can literally go into a thing and fill it out and it'll help you kind of find stuff. It's pretty badass. It's outboundsquad.com/masterclass. So it's completely free. Check it out. My hope and why we're giving it away for free is, you know, we don't have a business selling anything to individuals. So if you're a rep, an AESDR, et cetera, that's not our business. We want you using our stuff so that you talk about us and we get to work with your organization. That's what we really care about and what we do an excellent job at. So outboundsquad.com/masterclass and then outboundsquad.com, if you're a leader and you're like, hey, I'd love to implement a lot of the things that the guys talked about today. I would love to meet with you and we can help you benchmark against companies like Shopify, Gong, Zoom, Bripling, et cetera and talk about what's working right now for outbound. So go check us out. - And what an offer of value that was right at the end there. That is the, we didn't get to dig into all of it. You just did it. Hey, I can tell you what I learned from these AESD companies. You probably want to know how they're thinking about this. - These new practices, what do you preach? - Jason, thank you for joining us. I really appreciate it. Everybody speak around for a 60-second recap coming up soon. - All right, Alex, it's time for your two-by-two recap. What do you got for your two? - I think the two big things that stuck out to me really came from the feedback that I just got on my own, outbound messaging. One is the difference between a below the line above the line problem. I realized just now I have been pitching a sort of a features and functions like service level problem to everybody. Instead of looking at what metric is going to be most compelling, especially for senior leaders, what are they care most about that I can positively influence and anchoring to that. So that's one big takeaway. And I think the other is related, which is, I often think about boundists. Let me start with a trigger and then I'll figure out what my problem hypothesis is. And then I'll talk about what I saw. Jason recommended going the other direction. Let me figure out which problems I'm really, really good at solving. My business is good at solving. And then we can backwards engineer. What would have to be true at a business for it to make sense that they might be having that problem. And so you go backwards into the trigger. So those are both super valuable. Number one for me was the mental map of how to build your triple T story of trigger tension trust. So step one, start with your big three tension statements or tension scenarios. The big issues that your product or service solves. Then for each of those three, identify the top three triggers that would make that tension be true. You will now have a list of nine different triggers that you can go look for yourself or you can use your AI tool of choice to go identify anytime you choose to go after a new account. From there for your tension statements, you're going to need to come up with two variants. So you'll end up having a total of six tension statements a below the line surface level statement. And an above the line chunked up statement of, okay, if that surface level thing is happening, what's a metric that is being negatively impacted or hurt as a result of that? That will allow you to for the same trigger and same tension pitch to two different personas in a way that resonates with. And then for each of your tension statements come up with an associated trust statement. And what this allows you to do and get this brings me to the last takeaway folks can have from this is this allows me to tell an emotionally resonant story that gets them bought in on a motion and then sells them on logic with the metrics that we give them. I can't flip the order. I've got to tell the story and then touch it home with the metric that we impact. So that's what we covered, Alex. Do you have any questions from me? - I mean, the only question I have is how can folks help us out? - Oh, that's a great question. - I think you, I'm learning how to ask good questions. - We've got a ton of resources that we covered today. We talked about constructing great offers. We talked about finding hard versus soft triggers. We talked about the Jason Bay Outbound Squad and 30MPC cold email course. We talked about Jason Bay's Outbound Masterclass that he has built. We've got links to all of those in today's show notes. Go check them out. Most of those are free. Some you can buy for yourself. So if you are a rep listening and you're like, "Hey, I want to action on some of this." We've got some 30MPC resources in the course that we built with Jason that I promise will help you. It is backed by data from studying over 85 million cold emails and 300 million cold calls in partnership with GONGs data science teams. So you know, it's not just advice that sounds good. It is advice that is actually backed by data that works. So how's that for an emotionally resonant story backed by data, Alex? - I feel extremely emotional hearing you talk about that and honestly, I get that. - Okay, go make some cold calls. Thanks for listening folks, and we'll see you next week on the show. - The worst discovery advice is just be curious and ask lots of questions. And this is what PipeDrive does. If you want to get clear, complete sales visibility, you can use PipeDrive's easy to use and customizable CRM that is designed to be simple from day one and stay easy to use as your team grows. We actually put together an entire resource hub with PipeDrive to help you get to president's club and you can get them for free and the 30MPC PipeDrive Closers hub, the link is in the show notes. - Today's show is brought to you by Unify. If you just describe who you're targeting in plain English or connect your CRM, it will literally search over 40 different sources to surface the tier one accounts automatically and then draft the outreach in your voice. - Today's show was brought to you by Outreach, the Agentech AI platform for driving execution across every stage of your deal. Get it free in the show notes.

Podcast Summary

Key Points:

  1. Disqualify 80–90% of contacts by focusing on a small number of high-potential accounts to increase response rates and improve efficiency.
  2. Include a specific, tailored offer in every outreach—such as highlighting a recent client success or a personalized value proposition—to boost reply rates by up to 28%.
  3. Use the "Triple T" framework (Trigger, Tension, Trust) to create emotionally resonant messaging: identify relevant triggers, frame a problem-based tension statement tailored to the persona, and back it with credible social proof to drive action.

Summary:

Jason Bay, CEO of Outbound Squad, shares a data-driven, actionable framework for modern outbound sales that counters the oversaturation of volume-based AI tools. He emphasizes moving beyond generic cold outreach by prioritizing quality over quantity. The core methodology is built on three pillars: first, disqualifying 80–90% of contacts to focus effort on high-potential accounts; second, using a tailored offer—like a personalized client success story—to increase reply rates by up to 28%; and third, structuring messaging around the "Triple T" framework: a trigger (a relevant business signal), a tension (a specific problem or pain point), and trust (social proof from a similar-sized, relevant client).

This storytelling approach builds emotional engagement and credibility. , "hiring internationally" is better than "raised funding"), and tensions must be tailored to the persona—surface-level for operational staff and strategic for executives. He advocates for reverse-engineering tension from real deal outcomes and using AI to identify triggers efficiently, while maintaining human judgment.

His framework is rooted in real-world data from over 85 million cold emails and 300 million cold calls. To implement this, sales reps should start with three core tension scenarios, identify three triggers per scenario, and create two tension variations (surface and strategic) for different personas. Each tension is paired with a concise, believable trust statement.

The result is a compelling, emotionally resonant narrative that drives action and leads to higher conversion rates. Jason offers a free outbound masterclass and interactive workbook to help reps apply these principles, emphasizing that true outbound mastery comes from pattern recognition, emotional intelligence, and strategic storytelling—not just volume.

FAQs

A funnel implies narrowing down many leads, while a martini glass means focusing on fewer opportunities and disqualifying 80-90% of accounts to increase the quality and response rate of your outreach.

Including an offer increases reply rates by up to 28%. It creates a sense of responsibility for the prospect to say yes, such as offering a personalized walkthrough or a testimonial from a similar client.

The Triple T framework consists of Trigger, Tension, and Trust. Trigger identifies a relevant moment (e.g., hiring internationally), Tension presents a problem (e.g., compliance issues), and Trust adds social proof (e.g., a similar company’s success).

Triggers should be specific, business-relevant, and tied to real problems. Use company-level signals like hiring, M&A, or product launches, and avoid generic ones like raising capital unless they lead to a specific pain point.

Surface-level tension focuses on day-to-day pain (e.g., slow payroll), while strategic tension links to business outcomes (e.g., missed hiring targets or revenue loss), which resonates better with senior leaders.

Social proof increases reply rates by 35–40% when used effectively. It should feature a similar-sized, industry-matched client with a clear problem-solution story and measurable results, not just big names like Walmart or Amazon.

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