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

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

In this episode of *30 Minutes to Presidents Club*, host Nick Sigeleksi and co-host Alex Murphy interview Jason Bay, CEO of Outbound Squad, about transforming outbound sales in the age of AI. Jason argues that the era of predictable revenue (2011-2018) and the rise of sequencing tools and AI have led to a flood of low-quality, high-volume outreach, making it critical for reps to be "too good to ignore." He advocates a human-led, AI-assisted approach centered on three pillars: disqualify, offer, and provoke. The "disqualify" principle means treating the sales process like a martini glass—focusing deeply on fewer, high-potential accounts rather than a wide funnel. An effective "offer" (e.g., a "blind date" introduction to a top AE or a personalized product walkthrough) can increase reply rates by 28%. The "provoke" component uses the "Triple T" framework: Trigger (why now, e.g., "I see you're hiring internationally"), Tension (why change, e.g., compliance issues slowing hiring), and Trust (social proof, e.g., "We helped XYZ through this transition"). Jason emphasizes that triggers should be company-level and tied to specific problems, not generic events like funding rounds. AI should enhance precision—improving inputs like research and personalization—rather than just boosting volume, allowing reps to focus on creative, human skills like crafting compelling messages and executing calls with personality.

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Guys, I used to send cold emails before they were sequincers 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 sequincers 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 volume 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 Nick Sigeelski 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 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 to 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 Ot 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 Bayes action will take away number three number three is provoked So the provoked pieces hey, I've disqualified if offered I have to have provocative messaging in order for them to take action 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 an 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 of Ironman 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 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 watch 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 and 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 sink all the 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 keep 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 sequinsers 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 the number one guy on the leaderboard was just cranking emails same email to everybody just volume I was like well, okay, I want to be that so I did that I was number two guy on the leaderboard from us 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 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 Quad 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 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 provoke piece and you were sharing with me the three pieces that go into Voking 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 into do So this was really developed as a universal outbound messaging framework So trigger answers the 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 And Shin this answers the why change question This 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 to open her. So I say it's Jason with XYZ company. And he 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'm going to do-- - To be honest, I know it's you calling Jason. 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. Looks like you guys have 150 open rucksons. From what I can see, it's the first time you've done this internationally before. Hension. 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 Consensus which helps your demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learn in discovery. Number two, how we solve those problems. And number three, a, what does success look like today slide? You can steal that exact 30-MPC Demo Deck template powered by Consensus. Go check it out on the show notes. Today's show is brought to you by 11X. You're all in one digital GTM team handling, creating, qualifying and converting pipeline across every channel. If you are still using stale triggers like congrats on the funding, you're getting blended in with everybody else. The best use unique signals, exact LinkedIn posts, negative product reviews, podcast appearances and use those as their trigger. And we built a growth playbook with our friends at 11X breaking this stuff down. You can get it for free at 11X.ai/30MPC or grab it in the show notes. Today's show is brought to you by Responsive which helps sales teams respond to RFPs, security questionnaires and buyer requests faster so deals don't die at the last mile. One great way to drive your deals faster is to run parallel processes instead of linear processes. For example, in vendor review, work with your buyer to kick off legal security and procurement review simultaneously instead of doing them one by one sequentially. We built a playbook with our friends at Responsive on different proposal accelerators that you can use to close deals faster, grab it 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 hard 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 e-com 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. - Mm-hmm. - So what you need to think about beforehand is, so if you could imagine 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 gonna be kind of big 'cause 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 pretty straightforward that might have three use cases, let's say. But if you can map that out, it's like an exercise more in 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 triggers, three times three is nine. Then what I'm doing is I'm associating it, trust. Hey, you know what? I got an actual three seconds, it was like, is it? - Hey listen, I'm only laughing 'cause at this stage of my life I have to ask Claude what three times three is. At this point man, I don't even know off top of 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 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 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 Acme Co raises money, what I actually want to do is say, oh, I might actually put a little more effort in defining 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 state. - That's a trigger for you to reach out. That's not a trigger for them to take action though. So 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. They 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 figure out what your accounts are going to reach out to this week. - Yeah, you're going to reverse engineer. That's the start. The second thing is there's, 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. Yes, 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 want to 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 B T L 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 work who gives zero shits about like payroll and like how it's done. They just want to know that it's done on time and then we're compensating people properly that we're retaining them. Like that's what they want to know. Cyber security. That C So 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 unscrupulous. 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 because they get a 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 on to because it depends on who you're reaching out to. Yeah. Right. But that strategic tension, you want to 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. I think 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. 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 C H R O 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 C H R O example. I see that you're hiring in France and Italy. We talk with a lot of HR leaders who's 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, 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 force of legal. 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 in the engine of the triggers. Then we pulled a customer's choice for the trust. Could I ask you for some free coaching in the moment live? This whole podcast is just an excuse. This is my favorite thing to do. Coaching for this part of people. We have been workshopping this actively like 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. 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 of view. 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 leader like, all right, there's a warmth there of like you've got some fans of 30 minutes to president's coming to org already. 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 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 push don't have time for that. And then I would go into an explanation of like why us like why 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? I think that your current messaging allows you to connect on an emotional level with that in the implement 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. 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 and 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 can tell you some of those front line managers are bought into the program. So there's no reinforcement. It doesn't stick. There's it's a flavor of the quarter type of thing. 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. The 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 a in contact with an enablement person and 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 front line 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 all not this new product. Everyone needs to be able to sell this thing if they don't that's on you enablement leader. Yeah. And speed is also a really big one. Dude, this is like our value prop me on the fact that the 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. Yeah. Yeah. 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 those are 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. on, or 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. Today's show is brought to you by Unify, which helps you prioritize the right accounts at the right time. Try this. Stack your tier one highest intent leads at the front of your morning dial block. So if someone signs up for a trial, visits your pricing page, dial them first before any other accounts before you open your Slack, your email, before anything. Unify makes it stupidly simple to surface those tier one accounts automatically. We built a guide with you to find on how to get 100% of BDR's to quota in 2026. Go check it out in the show notes. Today's show is brought to you by Insightly. The CRM helps you spot deal risk early. So pipe reviews actually drive your number. One question I ask in nearly every deal review is, what do we need to get in our next interaction with the customer? If my rep can't answer that question, the deal has risk, and I have something I can coach to. Now we built a guide with our friends at Insightly CRM on how to run pipe reviews that surface real risk and get deals moving again. And you can get it for free at the link in the show notes. Today's show is brought to you by Text Us, which helps you keep deal momentum moving at every stage of the sales cycle. Texting is one of my favorite ways to sell between meetings. I use it for post big team meeting debriefs and also for game planning with my champions about how to navigate the politics of their org. And I've found that when you move somebody off company email, it makes folks a lot more open and honest. Now we put together a guide with our friends at Text Us on how to revive ghosted deals and keep your deals moving at every stage of the funnel with texting that you can get for free in the show notes. 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 apart makes you fall behind on your hiring plan. Yeah. The 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 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 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 chatbot 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 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 you're seeing right now in your contact center? I'm just thinking about like metrics. It's the first M and MedPick. 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's KPI or 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 worked on something together? This is a great example of your point about simplicity versus complexity. Or 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. Idiots, 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 that 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 sharing the name of a company that is very unrelated to what the buyer does but has a lot of notoriety. People tell me all this time when they reach out. Yeah, we work with Walmart and Google and Amazon. Like, that's really great. But I don't have a lot in common with those companies. You know? So the company needs to be similar in size, similar industry, if possible. And you need to have like some sort of story around it and 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 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 worked with Shabban over there at Shopify 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% lift and 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 in some climactic solution, which is a story arc. Like, 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 in the 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. Like 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 the 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. Yeah. 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 a hey, they increased pipeline by $120 million 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. Yeah. 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 over index 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 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 them and saying hi how is your day going do you want to know that we created a hundred and twenty million dollars of pipeline and we can do it for you to they're like fuck off I don't want to 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 want to 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 in your takeaway in the beginning of selling the blind date or 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 ends 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 sticking so we don't really have time to go deep on offers but like 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 presidents I know and I never let you do this could you give us the one line on I know you want to I know you're doing some outbound masterclass stuff Jason could you give me one or two sentences on yeah folks want to go deeper with you other than buying the 30 NPC outbound squad course that we built yeah how else could people go deeper with you Jason best way right now is is a couple things so we put together an outbound masterclass 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've I saw you talk 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 it's pretty badass it's outbound squad comm slash masterclass so it's completely free check it out my 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 etc 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 that's what we really care about and what we do an excellent job at so outbound squad dot com slash masterclass and then outbound squad dot 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 and we can help you benchmark against companies like Shopify, Gong, Zoom, Bripling, etc 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 how you just did it hey I can tell you what I learned for these as companies you probably want to know how they're thinking about this. These practices what he preached is Jason thank you for joining us I really appreciate it everybody's around for a 60 second recap coming up soon. All right Alex 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 I outbound a messaging what 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 and 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 to make sense that they might be having that problem and so you go backwards into the triggers 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 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 I get this brings me to 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 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 thank 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 30 NPC 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 wrap listening and you're like hey I want to action on some of this we've got some 30 NPC resources and 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 GONG's data science teams you know it's not just advice that sounds good it is vice 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 honestly okay go make some cold calls thanks for listening folks and we'll see you next week on the show today's show was brought to you by outreach the agentic AI platform for driving execution across every stage of your deal great sellers dried 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 today shows brought to you by tight next which helps you connect with prospects instead of dialing into the void so you can make a hundred cold calls a day but if nobody picks up your burning time so tight next literally guarantees you will triple your cold call connect rate or they will pay you ten thousand dollars so the link in the show notes down below will show you that they match literally five thousand credits for every five thousand you buy go check it out I use it personally and it's a phenomenal way to get more conversations on the phone today's tactic is brought to you by attention which uses AI to capture all of your sales interactions automate sales busy work like CRM updates and flag hidden deal risk so if you want to avoid ghosted deals and every discovery call with these three questions number one do you want to buy a k validate if the deal is real number two when do you want to buy validate if it will close this year and then number three how do you buy validate that they will get you in front of power we put together a guide on how to unblock the three biggest deal blockers in your pipeline there's a link to get it down in the show notes

Podcast Summary

Key Points:

  1. The overuse of sales engagement tools and AI has increased volume but not quality, making it harder for reps to stand out.
  2. The "Triple T" framework (Trigger, Tension, Trust) is a universal messaging approach for outbound across email, calls, and LinkedIn.
  3. "Disqualify" is key
  4. Including a clear "offer" in outbound can boost reply rates by up to 28%, e.g., a "blind date" introduction or a tailored walkthrough.
  5. "Hard triggers" (revealing pain) outperform "soft triggers" (leading to pain), and company-level triggers work 50% better for senior buyers.
  6. AI should be used for precision and input quality (e.g., research) rather than just scaling output, leaving human creativity for soft skills.

Summary:

In this episode of *30 Minutes to Presidents Club*, host Nick Sigeleksi and co-host Alex Murphy interview Jason Bay, CEO of Outbound Squad, about transforming outbound sales in the age of AI. Jason argues that the era of predictable revenue (2011-2018) and the rise of sequencing tools and AI have led to a flood of low-quality, high-volume outreach, making it critical for reps to be "too good to ignore." He advocates a human-led, AI-assisted approach centered on three pillars: disqualify, offer, and provoke.

The "disqualify" principle means treating the sales process like a martini glass—focusing deeply on fewer, high-potential accounts rather than a wide funnel. An effective "offer" (e.g., a "blind date" introduction to a top AE or a personalized product walkthrough) can increase reply rates by 28%. The "provoke" component uses the "Triple T" framework: Trigger (why now, e.g., "I see you're hiring internationally"), Tension (why change, e.g., compliance issues slowing hiring), and Trust (social proof, e.g., "We helped XYZ through this transition"). Jason emphasizes that triggers should be company-level and tied to specific problems, not generic events like funding rounds. AI should enhance precision—improving inputs like research and personalization—rather than just boosting volume, allowing reps to focus on creative, human skills like crafting compelling messages and executing calls with personality.

FAQs

The goal is to go deep on fewer opportunities instead of treating your sales funnel like a funnel. You should disqualify 80-90% of accounts and contacts to focus your effort where you are most likely to get a response.

Including an offer in your cold email can increase reply rates by up to 28%. An example is 'selling the blind date' by hyping up an account executive or offering a tailored, personalized proposal like walking a buyer through a card audit of their own website.

Provoke means using provocative messaging with three elements: trigger (why now), tension (why change), and trust (why us). This framework helps create compelling outbound messages that drive action.

A hard trigger reveals a direct pain point you can see, like a missing upsell feature. A soft trigger gives breadcrumbs toward a potential problem, like seeing a company hiring internationally. Company-level triggers perform 50% better for director-plus roles.

AI should be used to improve input quality—like auto-populating account research and messaging triggers—rather than just increasing volume. The human focus should be on soft skills like creativity, personality, and executing calls or emails effectively.

In the current AI era, reps must be too good to ignore by using human-led, AI-assisted approaches. Instead of relying on volume, focus on being precise and standing out with quality messaging and personalization.

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