#577 - Why Your AI Cold Emails Are Failing (And How to Fix Them) | Jason Bay
46m 30s
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.
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
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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,
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Podcast Summary
Key Points:
Disqualify 80–90% of contacts by focusing on a small number of high-potential accounts to increase response rates and improve efficiency.
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%.
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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