November 19, 2025 • 28 mins
🔥 Why Most AI Deployments Fail (And How Real Sellers Win With It) 🤖
Is AI actually helping sales teams — or just creating more noise? Why are so many companies struggling to get ROI from their AI investments? The brutal truth: it's often caused by broken processes, bad expectations, and outdated leadership. 😬
In this episode, Jake is joined by Ryan Cahill, a veteran GTM architect and operator who has helped scale revenue teams across SaaS. Ryan breaks down exactly why AI fails in most organizations — and what high-performing teams do differently to turn AI into a true competitive advantage.
He reveals the tactical playbook that top teams use to improve outbound, accelerate deal cycles, and make reps instantly smarter using AI.
🔥 What you'll learn in this episode (Don't miss the real truth behind AI!):
✨ The Core Problem: Why companies expect AI to be a magic wand — and why that mindset guarantees failure.
🧠 The Setup Mistake: The missing pre-work every team skips that destroys ROI before AI ever launches.
⚙️ Human-in-the-Loop: How elite teams combine rep judgment + AI to outperform both humans and automation alone.
📈 Outbound Breakthroughs: Why AI now outperforms template-based SDR outreach — and how reps can stay relevant.
🔍 Instant Expertise: How reps can now learn any industry in 10 minutes and run world-class discovery.
🏆 The GTM Advantage: How AI lets leaders analyze their business, pivot faster, and double down on what actually works.
This isn’t about more tools — it’s about better strategy, better execution, and smarter humans using AI the right way.
👉 Tune in and learn how to become a modern, AI-powered, outcome-driven seller!
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_00 (00:00):
When it comes to outbound, that's what I'm seeing
is AI will if we keep going downthe path, AI will replace a lot
of SDRs.
And it's only the ones that knowhow to call and have a
conversation and who know how tocustomize better than AI that
are gonna win.
That's my hot take.
My hot take on top of funnel.
What about you?
SPEAKER_01 (00:19):
No, I I 100% agree.
It will outscale you, it'llout-execute you, it'll
out-template you, it'llout-generic you every day of the
week and twice on Sunday.
Where I think the the gap forpeople that go, okay, but how do
I do it better?
I think again, it's that cuminin the loop.
It's like, well, are youexpecting AI to create the
(00:42):
cadence?
SPEAKER_00 (00:43):
Then you're making a mistake.
Welcome everybody to anotherepisode of the AI Powered
Seller.
Today's episode is AI is only assmart as your go to market
strategy.
Today's episode is going to be avery interesting one for my
leaders out there, for my repswho are trying to think more
strategically about how to runtheir business.
(01:06):
What I'm really excited about istoday's guest, Mr.
Ryan Cahill.
Ryan's been an SVP of enterprisesales, done a ton of
go-to-market consulting.
He's a CRO of GTM Advisors.
He's helped more than a hundredSaaS companies, including
LinkedIn, Cowanly, Dropbox,build scalable, data-driven GTM
(01:26):
systems.
And what you're going to reallyget out of today's episode is
where to think about the keyareas to get started around
what's going to actually movethe needle for my business right
now.
In a lot of the other episodes,we'll talk tactically about
different agents and differentassistants.
But today's episode, we're goingto help you to understand, you
know, what is a healthyAI-powered GTM system look like?
(01:49):
What does a RevOps leader looklike in today's day and age?
And exactly where should I bethinking about getting started
if I'm in kind of both like therep, the leader, or the
operational role.
So really excited to jump in.
And thank you, Ryan, for joiningme.
Pumped to have you on the show.
AI-powered seller.
Hey, Ryan, thank you so much forjoining me.
(02:10):
Looking forward to theconversation.
Yeah, pleasure to be here.
You've had a chance, you know,in your current role and other
roles to see AI or tools thatlook or feel or say they're AI,
right?
Which is a whole otherMythbuster show we could do.
Shout out to Mythbusters if youknow that show.
Yeah.
So why do you thinkorganizations, I've got my take,
but why do you think individualsand organizations are struggling
(02:34):
to get the ROI in particularfrom various AI deployments?
And then maybe false fast followis like, are there any culprits
you see as like the typicalpitfall?
It's usually we do this thingfirst.
SPEAKER_01 (02:49):
Yeah.
Yeah, I think it's a goodquestion.
I think I think from myexperience, what I've seen is I
I think maybe even the the setupis where things start to go
wrong.
I think the setup being thatthere is the assumption that AI
is this magic wand and go tomarket.
And that somehow when I wave mymagic wand, it will solve all my
(03:12):
problems, right?
And and I think that's part ofjust a misunderstanding of what
AI really is.
And I think the function that AIpractically plays, for at least
my point of view, for many yearsto come.
AI, in my opinion, is a tool.
A tool requires a user, and auser has to leverage said tool
(03:33):
to deliver an outcome, right?
And so I think the theperspective that AI on its own
can solve a problem is one ofthe gotchas where it's like, we
don't need a human or we don'tneed data infrastructure, or we
don't need a process.
We can just add AI and AI willkind of autonomously solve
problems.
It's like that doesn't existtoday and may not exist in my
(03:55):
lifetime.
I don't know.
We'll see.
So I think that's one thing isjust the expectation of what
you're gonna get out of it.
I think the other thing is theexpectation that somehow you can
adopt a new tool, technology,capability, and not do any
pre-work whatsoever.
That's just silly.
You don't implement a newproduct without doing some
pre-work, you don't roll out newmethodology without doing
(04:16):
pre-work, you don't train peoplelike you need to get some
structure in place.
So if you want AI to, in mostcases, increase capacity,
increase speed, and deliver anenhanced set of execution, well,
then you need to have at least alaunching point of what do you
want it to do?
And what does good look like?
(04:36):
How do I know if the thing isperforming the way I want it to
perform?
And I think where I've seenpeople go wrong is, and it's I
don't think it's necessarily thetool or the technology's fault,
is they're like, oh, we turnedit on and now it writes our
emails for us.
And it's like, well, maybe,maybe it could, or maybe it can
get you to 80%, or maybe it canget you from 80% to 90%, but
(04:58):
like it isn't gonna just do itfor you.
And I think that's where I thinkI've seen a lot of people go,
like, well, I tried it and itdidn't work.
And it's like, well, maybe, butmaybe it was set up to fail from
the beginning that you didn'tthoughtfully consider what this
thing would do.
SPEAKER_00 (05:12):
Yeah, I think for what I see is some type of
in-between there, where a lot ofwhat I talk to clients about in
our and our current customers islook, AI, and again, I'm talking
specifically like Gen AI, right?
And we'll and we can let's we'llget into the nuances too around,
you know, like I'm implementingGong versus, you know, I'm
implementing Chat GPT as aninfrastructure.
(05:33):
Right.
Is that I think what companiesneed to realize is Gen AI is
changing the way that people dotheir jobs.
It's not I like where I would, Idon't know if it's disagree, is
I don't think it's a tool.
I think it is a foundationalshift in how we solve problems
as humans and therefore isactually more similar to like
the internet and like how peopleshould deploy it, that it's
(05:54):
gonna completely rewrite the waythat we work.
And and I and what I see is thatsometimes when people think of
it as like, and again, differentlike rev tech, different than
Gen AI, maybe like caveat,right?
Where because I think I thinkRevTe, I a hundred, you know, a
hundred percent, you know, theythey treat it like a tool.
And I think for most people, youhave to realize don't deploy it
(06:17):
if you're not gonna make peoplechange behavior.
If it's not about like we'regonna do something different, as
opposed to your point, like,well, we deployed it.
It's like I think it's thechange, but I think we're saying
the same thing around changemanagement lift.
If you're not ready for thechange management lift that's
gonna happen, then you're doomedfrom the start.
That that's kind of how I seeit.
It's like you gotta be able toappreciate that if you're going
to deploy this against X, you'reyou're changing the way that
(06:39):
someone has done X for a verylong time.
SPEAKER_01 (06:43):
Yeah, no, I think I think you make a good point.
So I think the the thing that Isee too is, you know, when you
look at, you know, SaaS as anindustry, both of us have a ton
of experience in.
And so like I think you lookacross SaaS, I think one of the
mistakes that I see repeatedlyis there is no definition of
good.
And so they they conclude thatactivity equals success.
(07:07):
It's wrong.
You can write the bad email amillion times and be
unsuccessful.
And so I think the key thing isif you're using this capability,
there needs to be anunderstanding or expectation of
a check and balance of like,well, what is good out of it?
So can AI write emails?
Absolutely, can write them atscale that humans can't ever
(07:29):
keep up with.
Does it mean they're good?
Absolutely not.
And so, like, there has to be acheck and balance to say, okay,
what is kind of like anoperational QA of like, is this
hitting the standard that wewant our business and our brand
and our team and our customer tointeract with?
And someone's got to define thatbecause otherwise anything is
good.
And so I think that's wherethere's there's a missing kind
(07:51):
of check and balance there tosay, like, there should be a
human in the loop to say, that'sright, okay, let's double check
this first and from QAstandpoint.
And then secondarily to yourpoint on the check and balance
of the outcome is like, are wedriving open rates?
Are we driving conversions?
Are we driving funnel?
Are we driving dollars?
If the outcome isn't there, thenyou need to start back at the
(08:12):
beginning and go, well, maybethe things we're doing, albeit
faster and more efficient,aren't any good.
SPEAKER_00 (08:17):
Yeah, let's go down.
I want to go, let's go down thisrabbit hole a little bit and
we'll focus on top of funnelbecause I I do think that this
is a good one for a lot ofpeople, because I think for a
lot of clients and what you seetoo, probably Ryan, a lot of the
first applications people arethinking about it.
And I put gong in a differentbucket.
Well, unless you're teaming likeGong Engage, is is top of
(08:37):
funnel.
And it's it, I I did a post onMonday, people were got really
upset when I talked about AIreplacing SDRs.
And the point that I was makingwas this most companies, to your
point, are focused on activitiesfirst and outcomes second.
And if you are asking your teamto send a bunch of templates
that are not customized to thesub-industry, customized to the
(09:00):
individual, and pulling inspecific insights, AI is better
than you.
AI can out-template you becauseit can pull in real-time
insights on, hey, what aretrends for a VP of operations in
Marquette, Michigan, aroundairplane aviation manufacturing
parts, right?
Where a rep is never going totake the time.
(09:21):
AI can at least pull insomething that's going to be
quasi-relevant and thereforebetter than your shitty template
that says, I help operationsleaders achieve this outcome.
And so that is what I actuallythink is the issue, Ryan, is
that I think this is actuallynot an there's an AI component
to this that using AI on baddoes not equal good.
(09:45):
But AI in place of statictemplates will win.
And if your teams are sendingstatic templates and you're not
asking, you you hit this on thehead, the human in the loop, the
only teams we see that arewinning at outbound.
AI or and my knowledge gets me80 to 90 percent.
And then I put my I put my sauceon it, right?
(10:06):
I put my like what I know islike, oh, it's not that value
prop, it's actually this statthat's gonna resonate with the
ops manager in Marquette,Michigan.
And so when it comes tooutbound, that's what I'm seeing
is AI will if we keep going downthe path, AI will replace a lot
of SDRs.
And it's only the ones that knowhow to call and have a
(10:26):
conversation and who know how tocustomize better than AI that
are gonna win.
That's my hot take.
My hot take on top of funnel.
What about you?
No, I I 100% agree.
SPEAKER_01 (10:36):
And I well, I think where people get maybe emotional
about it is that there's athere's a disconnect in that
ecosystem.
I think it's unfair tocharacterize all SDRs the same.
There are some very strategic,very thoughtful, very high EQ
SDRs, and there are people wholiterally cut and paste all day.
(10:59):
And they have the same title.
They are not the samecapability, the same person.
And so I think when you groupthem all together, I think
that's where you get kind of thefriction.
But I 100% agree, it willoutscale you, it'll out-execute
you, it'll out-template you,it'll out-generic you every day
of the week and twice on Sunday.
Where I think that the gap forpeople that go, okay, but how do
(11:22):
I do it better?
I think again, it's that humanin the loop.
Is like, well, are you expectingAI to create the cadence?
Then you're making a mistake.
AI is not smart enough to knowyou shouldn't be emailing people
Sunday morning.
AI is not smart enough to knowthose things out of the box.
Like AI is not smart enough toknow that the day after
Thanksgiving, you probablyshouldn't be hitting people up
(11:43):
with a, you know what I mean?
Like there's there's gotta besome human check and balance to
be like, okay, well, this personjust came to our event last
night, so we probably shouldtake them out of the cadence.
Like, there's gotta be somechecks and balance of like human
logic.
AI is not gonna replace that.
The ability to personalize amessage and tailor it to nuances
and things, it is better thanhumans, almost across the board.
(12:05):
I think there's some that arebetter than others that I've
seen and some of the tools, butlike it is just the ability to
tailor speech in an effectiveway, it is unrivaled in.
I've never seen anything likeit.
Now, to your point though, Ithink it will absolutely replace
the capacity constraint thathumans place on outreach today.
SPEAKER_00 (12:26):
Yeah, that's a good way to put it.
SPEAKER_01 (12:28):
But I I do think that the combination of
thoughtful strategic guidancefor outreach with however many
appropriate for your scale,humans leveraging AI will
outperform AI on its own andwill absolutely outperform
humans on its own.
SPEAKER_00 (12:45):
All right.
As usual, if you're gettingvalue out of the episode, thank
you so much for tuning in andlistening.
I really, really appreciate you.
Make sure to subscribe to thechannel.
Uh, make sure to to bookmarkthis if you're listening on the
podcast as well, too.
And make sure that you sharewith one friend.
That's what I've been trying toask people.
Share with one friend.
Everyone's trying to figure itout, this AI thing.
(13:07):
I am as well too.
I know I appreciate it whenpeople share something with me
that helps me to get smarter.
So make sure, share, subscribeto the episode, and help to make
somebody else smarter as well.
For a lot of leaders, you know,they'll come to us and they'll
say, you know, Ryan, look, youknow, our top of funnel is is
struggling, etc.
And then you go and you have theconversations.
And I think this is the scarypart.
(13:27):
This is leadership, this issenior leadership.
Most of the feedback is, butyeah, this will slow them down
and they won't be able to sendas many emails.
And you go, oh my God.
Again, are we talking aboutoutcomes?
Like, do you care more about andit's like, how did you pick the
(13:48):
activity metric in in the firstplace?
I guarantee it was like, or likethis is what I did at my
previous job, or it's based onthe mean.
And the reality is, this isanother place I think AI crushes
it, which is look, Jake'snumbers are this, Ryan's numbers
are this.
Let me manage to the individual,right?
And I think that we're just so alot of sales leadership manages
(14:08):
to the mean.
And and and that top performerscan't stand it.
Bottom performers are like,yeah, whatever, I'll do what you
tell me to do.
SPEAKER_01 (14:15):
And and what doesn't make any sense about that is
like, and I'm sure you're nodifferent than I am, I get
prospected a dozen to two dozentimes a day.
LinkedIn, email, text,unfortunately, elsewhere.
With all the technology, it's nobetter than it was five to ten
years ago.
SPEAKER_00 (14:32):
It's worse, outrageous worse durable.
It's getting worse.
I actually think it's easier tocut through the noise today than
it ever has been.
Like if you literally show thatyou've done this much research,
you're top one percenter.
And and this is what I think itgo go back to like early 2010s,
or let's even go back, likesales loft outreach 2015.
(14:53):
So let's go back literally just10 years ago.
I would argue the outreach in2013 is way better than the
outreach in 2025.
SPEAKER_01 (15:02):
But but let's dig into that though.
So, what's different?
One, I think during that period,because I managed North America
for Celogen at that time, and Ihad two people running my
business development teams.
Weekly coaching.
How often does that happenanymore?
None.
Yeah.
unknown (15:19):
Yeah.
SPEAKER_01 (15:20):
They good luck.
They they reviewed weekly thetop performing email.
When does that happen?
They optimized subject lineamongst the team weekly.
Like they were doing the work,the real work, which is what
works, what's driving outcomes.
They weren't just going, well,let's everyone get X number of
messages out.
I didn't care.
I never set, my manager did, butI never personally said as an
(15:43):
organization running revenue, Inever set an outreach volume
goal.
I set an outcome goal.
I want you to book X number ofmeetings.
If you have to send two messagesor two million, I don't care.
You have to get the outcomebecause the outcome is the only
way that we progress as abusiness.
That's how people should bemanaging.
The fact they send 20 emails or30 emails or a million emails
(16:04):
doesn't make any difference ifthey don't convert to dollars at
some point.
SPEAKER_00 (16:06):
That's right.
And also to do in managing fromthat, like what we'll do is a
lot of our clients is like makewhat we call it meaningful
conversations is the firstpiece, which is like, look,
you've got to connect with threepeople.
So they say, hey, I'm not theright person.
I'm gonna connect you with John,or yeah, timing's interesting,
but maybe not like now, let'swork on booking time.
And it, but that's also anoutcome, right?
And again, to your point, if youif if and then and then with a
(16:29):
rep, it's like, look, you're nothitting the outcomes.
So now what we need to work itback, right?
Now we need to start to workbackward on look, it's 20 calls
or or whatever.
So so let me ask you this.
So we're talking about a lotwhat doesn't work.
So what does a healthyAI-powered go-to-market system
look like?
What are people doing?
What works, what doesn't work.
SPEAKER_01 (16:48):
I I think from what I've seen, it's it's very
dependent on leadership, on whattheir understanding and
capability is.
I have not seen AI besuccessfully adopted without
pretty experienced leadership.
And I think it takes someonethat understands how the
ecosystem works, thatunderstands the funnel at a deep
(17:12):
level, that really understandsthe components of how you're
driving success to optimize andimprove the machine.
I I think I kind of go back tomy like go-to-market
architecture like experience.
If you don't understand thenuances of that, you'll just
keep getting it wrong.
And you'll just be you'll justbe more efficiently wrong.
(17:33):
And so, like a couple examplesthat I've seen that I think are
just best practice.
So one is sales reps using ahopefully constrained private
GPT for an account, no-brainer.
Everyone should be able to queryall the data, all the calls, all
the transcripts, and go, whatdid they say about this?
What is this?
So an executive comes into ameeting and goes, hey, prep me,
(17:54):
I gotta go talk to this VP intwo minutes.
I want to know what I need totalk about and what their hot
buttons are.
You should be able to just querythat and get those answers.
That's an easy one, it's ano-brainer, but I don't see it
used that often.
I think it's pretty rare that'snot a good idea.
SPEAKER_00 (18:07):
Because leaders don't know how.
Most leaders know how rightthey're not investing.
And I think this is a reallygood point.
If you are in revenue, you know,we just launched our AI
certification program.
And um, you know, depending onwhen you're listening, we you
might have to sign up for thenext one.
But you know, we have 20 plus Vfrom VP to frontline managers in
the leadership track, and it'sgreat to see.
But I think what happens inleadership is you were
(18:28):
successful doing it this way,and and you all and we need to
wake up that the way that youdid account review in 2020, you
know, back when I had theaccount planning and account
strategy, and it's justcompletely changed.
And there's no there is nobenefit for you to make people
pay the dues because that's howyou did it.
And I feel like sales is verymuch a pay your dues culture,
(18:50):
and I feel like that is wherelike leaders are just not taking
the time that they need to learnthe Gen AI.
And like, and then I thinkthere's also a little bit of ego
or like what got me here, let'sjust keep running back the good
old times.
Yeah.
That I feel like it's it'shurting them.
Because what you just said ispossible today.
A lot of you leaders might belistening and go, Wait, you can
(19:12):
do that?
It's like you could do thatabout nine months ago.
SPEAKER_01 (19:16):
Yeah, you know, and I'll give you another example
that I've seen that I think isis also kind of low-hanging
fruit.
Is account research anddiscovery prep is the most
underutilized thing in sales.
Discovery is the most importantskill, and prep for discovery is
the most missed opportunityacross the board.
The ability with AI to soundlike an expert or maybe even be
(19:40):
an expert is unparalleled at anypoint in my career.
I remember preparing formeetings, like when I was back
selling like responses for likemarketers, like, I didn't know
shit about the travel industry.
I would kind of like, well, Itravel too.
Like you try to make somethinganecdotal.
You can be an expert on travelin maybe 10 minutes.
(20:01):
And an expert in nothing.
You could know industry trends.
Like, if you actually know whatto ask, you can sound like an
MBA in any industry with 10 to15 minutes of preparation.
SPEAKER_00 (20:12):
We just did this, so you'll you'll appreciate this.
So we work with a lot ofprofessional sports teams.
So we did a uh uh workshop withshout out to the Pittsburgh
Penguins last week, and we hadtheir reps do this.
And hey, I'm reaching out tothis business, you know, this
26-year-old rep, they don't knowwhat an HVAC company is.
So it's like, hey, what are thetrends?
Here's the company.
What are trends for HVACcompanies in the greater
(20:34):
Pittsburgh area?
What's a typical, most likelyaverage customer acquisition
cost?
What are some potential waysthat we might be able to help
them grow their business andcompare that?
And then, and you know, theydidn't have it hooked into their
CRM, but if you had it hooked inyour CRM, compare that to other
people that we have.
So again, it's a hundred percentspot on that like this.
Used to take me, the you'llyou'll love this, one of my
(20:55):
first jobs.
We had an industry trendsbinder.
Like it was literally a binderthis thick, and it was like
manufacturing, transportation,and and that's how I had to
learn to get up to speed.
And it took me a year to get upto speed on again.
I think you can ramp a rep andlike one.
SPEAKER_01 (21:13):
A testboard to like not that long ago, uh, because
I'm guilty of this.
I built playbooks as part ofwinning by design.
I did hundreds of them.
How many of those had that onescreen battle card that somehow
was going to summarize likemanufacturing?
It was like that's right, acouple of data points, whatever.
Like, you can't understandmanagement.
(21:33):
And manufacturing isn'tmanufacturing.
It's like, well, do you do pressmanufacturing?
Is it plastic injectionbuilding?
Package good, industrialmanufacturing, heavy equipment.
But but I think to your point,like back to like kind of this
stuck in the past kind ofmentality.
When you think about likeaccount research in the past,
you truncated it out ofnecessity because you just
(21:56):
couldn't go down the rabbit toget the information.
You can now summarize, I don'tknow, a million pages of
information in 30 seconds.
You can scan through it, you cando a couple deep dives as you
go, maybe refine a couple thingsin a way that just was not
possible without AGI.
And if you're not thinking thatway, you're not to your point
(22:19):
customer centric.
SPEAKER_00 (22:21):
Yeah, you're you're I just think don't think at this
point you're being customercentric.
Like, guys, if AI can automate alot of the research and prep for
your clients, when they talk toa human, if you can't add value,
they're not gonna want to keeptalking to you.
You know, again, I'm talking tosales teams.
I go, guys, the future is gonnabe if on the front end of the
sale, if you can't addincremental value and show that
(22:42):
you get it and you know, I justwant to go talk to customer
success.
Like, let me just talk to thesolutions engineer and customer
success, because that's who Iactually need to know.
Because I've already done mydiligence.
Or the scary thing is you justtalk to Chat GPT, and if those
answers are better than talkingto the direct company, you don't
ever talk to the company.
That's my point.
That's why self-service, likeevery SaaS company, I believe
(23:02):
this should have a self-serviceoption for that exact reason.
And then I've got a killeronboarding program, but that's a
whole other part two here.
So so we're almost at time here,and this has been, you know, I
think we're definitely gonnahave to do a part two because
this is this is the like thetype of energy that I enjoy.
What are you excited about overthe next six to 12 months?
If you said, Jake, AI-poweredseller folks, what is the thing?
(23:25):
And I love the two tacticalpieces of advice.
I think everyone can go run withthose two use cases.
They're no-brainer use cases,they won't move the needle.
Account research, account-basedyou know, GPTs or projects, if
you use you can use projects tooin a similar capacity.
Yeah.
What is the other thing that yousay in the next six months, this
is what gets me excited?
SPEAKER_01 (23:42):
I I hope it can get there.
I think it's gonna take a bit ofprompting, but I think the
opportunity to learn about yourown business is a missing one.
So this is kind of likemarketing ops, RevOps, sales
ops, like that kind ofecosystem.
I think really understanding thenuance of like who are we doing
business with and is thatdifferent than what's happened
(24:03):
in the past?
There's a lot of dependencies.
One, you gotta have some gooddata, you got some good data
architecture, et cetera.
But I think one of the missedopportunities for a lot of
organizations is they don'tlisten enough to what's
happening.
And so we're still chasing likethe enterprise customer, and we
don't realize that we haven'tsold an enterprise customer in
three quarters and we're sellingmid-market.
Or, like, you know, that's asilly example, but that kind of
(24:26):
idea is like, okay, well, thisvertical's hot for whatever
reason.
Let's take care of it back.
Let's learn about that, let'smarket to them.
Like, let's double down.
And that's one of the feedbackthat I've been giving over the
last, you know, handful ofquarters, because it's been a
tough time in SaaS, right?
Is you need to be double andtripling down on your success.
You should be amplifyingsuccess.
(24:47):
Who's winning in every aspect?
How are they winning?
Who are they winning with?
And let's go do more of that.
Don't go into new markets, don'ttry new things, go find where
success is happening and just domore of it.
I think that's a missedopportunity.
And but I think a lot oforganizations need a little bit
of hand holding to help themfigure that out, especially when
(25:08):
you have any scale.
You know, that that's a harderanswer to get to.
If we can do some of that dataanalysis and kind of summarize
it and go, okay, these are yourthree best verticals.
This is what that profile lookslike.
This is the persona thatgenerally engages with us.
I think bubbling that up to thesurface would empower revenue
leaders in a very tangible waythat I think is difficult today.
SPEAKER_00 (25:29):
Yeah, I love that one.
I think like that ability toreally learn your business and
then, you know, just imagine howmuch smarter we're gonna be to
make quick pivots.
Do boom, boom.
Okay, yeah.
Oh, was this a good idea?
Nope, not a good idea.
Like so much of revenueleadership is gut and just the
ability to move toward moredatabase so you can spend more
time talking to customers, theright people.
Like it's all the things thatwe, you know, we should want to
(25:50):
do.
So I think that's a good thing.
SPEAKER_01 (25:57):
If you do three tests a year, you might do 40.
And and across and across therevenue spectrum, that's the
other thing is I think missingacross every organization I work
with is any effective closedloop feedback between different
departments.
Why are we churning out?
Does that go back to sales?
Almost never.
No.
Sale doesn't go back to BD, BDdoesn't go back to marketing.
(26:17):
It's like, guys, this is a teamsport.
If people played team sportslike this, they would lose every
game.
You have to talk, likecommunicate.
But I think creating easy waysto bubble up those insights to
be able to share.
I mean, you could optimizemarketing, business development
sales in like a quarter, not ayear.
SPEAKER_00 (26:36):
Okay, that might, yeah, that might be the quote of
the episode.
If people play team sports likethis, they would lose every
single time.
So that's it.
I I love that quote.
I'm gonna I'm definitely gonnasteal that.
So, hey man, I I love theconversation.
This is a great conversation.
Oh, I appreciate it.
It was great.
A lot of tactical advice.
And where can people find you?
What's the best place to get ahold of you?
SPEAKER_01 (26:55):
Uh, LinkedIn normally, I I try to communicate
pretty efficiently there.
I get bombarded by messages, butI'm always open to talk to
people.
I mean, I love this stuff.
Like I'm a fixer by nature, so Ilike wrestling with this stuff.
It's fun.
And uh yeah, hopefully uh we'llsee a lot of cool things.
I'm excited to try out you know,some of the stuff that you've
launched as well.
And um, you know, really I thinkthere's a huge opportunity to
(27:19):
apply this stuff in real life.
I just think it's gonna beharder than people want it to
be, but it's no lesstransformational.
It just means you gotta get yourhands dirty a little bit.
And so that's right.
You just gotta go into it withthat point of view.
SPEAKER_00 (27:30):
Stop thinking.
Yeah, for a lot of some ofthese, it's like you gotta just
pick the one use case and justgo and stop thinking about what
85 steps down the road lookslike.
So yeah, just go win one battlefor sure.
Where yeah, fix one bottleneck.
That's what I say.
It's like, let's just we can doall this cool stuff later.
So, all right, man.
Appreciate you, Ryan.
Thanks for joining andappreciate everybody for tuning
in to this episode of the AIPowered Seller.
(27:52):
We'll see you on the next one.
Cheers.
If you are somebody who isgetting serious about this, now
is the time.
Sign up for our AI certificationprogram that is going live,
cohort number two in January.
Uh, we're about halfway throughcohort one.
Uh, we've got a rep track, aleader track.
If you don't have the time,you're busy, but you go, Jake, I
need to make time.
I need like two hours a weekwhere I'm getting up to speed on
(28:14):
this.
It's six weeks.
Sign up for the certification.
I promise you, I've got a moneyback guarantee.
If you don't get value out ofit, I will more than refund you
your money because I'm thatconfident that this is going to
change the way you sell and theway that you lead sales teams.
When it comes to outbound, that's what I'm seeing
is AI will if we keep going downthe path, AI will replace a lot
of SDRs.
And it's only the ones that knowhow to call and have a
conversation and who know how tocustomize better than AI that
are gonna win.
That's my hot take.
My hot take on top of funnel.
What about you?
SPEAKER_01 (00:19):
No, I I 100% agree.
It will outscale you, it'llout-execute you, it'll
out-template you, it'llout-generic you every day of the
week and twice on Sunday.
Where I think the the gap forpeople that go, okay, but how do
I do it better?
I think again, it's that cuminin the loop.
It's like, well, are youexpecting AI to create the
(00:42):
cadence?
SPEAKER_00 (00:43):
Then you're making a mistake.
Welcome everybody to anotherepisode of the AI Powered
Seller.
Today's episode is AI is only assmart as your go to market
strategy.
Today's episode is going to be avery interesting one for my
leaders out there, for my repswho are trying to think more
strategically about how to runtheir business.
(01:06):
What I'm really excited about istoday's guest, Mr.
Ryan Cahill.
Ryan's been an SVP of enterprisesales, done a ton of
go-to-market consulting.
He's a CRO of GTM Advisors.
He's helped more than a hundredSaaS companies, including
LinkedIn, Cowanly, Dropbox,build scalable, data-driven GTM
(01:26):
systems.
And what you're going to reallyget out of today's episode is
where to think about the keyareas to get started around
what's going to actually movethe needle for my business right
now.
In a lot of the other episodes,we'll talk tactically about
different agents and differentassistants.
But today's episode, we're goingto help you to understand, you
know, what is a healthyAI-powered GTM system look like?
(01:49):
What does a RevOps leader looklike in today's day and age?
And exactly where should I bethinking about getting started
if I'm in kind of both like therep, the leader, or the
operational role.
So really excited to jump in.
And thank you, Ryan, for joiningme.
Pumped to have you on the show.
AI-powered seller.
Hey, Ryan, thank you so much forjoining me.
(02:10):
Looking forward to theconversation.
Yeah, pleasure to be here.
You've had a chance, you know,in your current role and other
roles to see AI or tools thatlook or feel or say they're AI,
right?
Which is a whole otherMythbuster show we could do.
Shout out to Mythbusters if youknow that show.
Yeah.
So why do you thinkorganizations, I've got my take,
but why do you think individualsand organizations are struggling
(02:34):
to get the ROI in particularfrom various AI deployments?
And then maybe false fast followis like, are there any culprits
you see as like the typicalpitfall?
It's usually we do this thingfirst.
SPEAKER_01 (02:49):
Yeah.
Yeah, I think it's a goodquestion.
I think I think from myexperience, what I've seen is I
I think maybe even the the setupis where things start to go
wrong.
I think the setup being thatthere is the assumption that AI
is this magic wand and go tomarket.
And that somehow when I wave mymagic wand, it will solve all my
(03:12):
problems, right?
And and I think that's part ofjust a misunderstanding of what
AI really is.
And I think the function that AIpractically plays, for at least
my point of view, for many yearsto come.
AI, in my opinion, is a tool.
A tool requires a user, and auser has to leverage said tool
(03:33):
to deliver an outcome, right?
And so I think the theperspective that AI on its own
can solve a problem is one ofthe gotchas where it's like, we
don't need a human or we don'tneed data infrastructure, or we
don't need a process.
We can just add AI and AI willkind of autonomously solve
problems.
It's like that doesn't existtoday and may not exist in my
(03:55):
lifetime.
I don't know.
We'll see.
So I think that's one thing isjust the expectation of what
you're gonna get out of it.
I think the other thing is theexpectation that somehow you can
adopt a new tool, technology,capability, and not do any
pre-work whatsoever.
That's just silly.
You don't implement a newproduct without doing some
pre-work, you don't roll out newmethodology without doing
(04:16):
pre-work, you don't train peoplelike you need to get some
structure in place.
So if you want AI to, in mostcases, increase capacity,
increase speed, and deliver anenhanced set of execution, well,
then you need to have at least alaunching point of what do you
want it to do?
And what does good look like?
(04:36):
How do I know if the thing isperforming the way I want it to
perform?
And I think where I've seenpeople go wrong is, and it's I
don't think it's necessarily thetool or the technology's fault,
is they're like, oh, we turnedit on and now it writes our
emails for us.
And it's like, well, maybe,maybe it could, or maybe it can
get you to 80%, or maybe it canget you from 80% to 90%, but
(04:58):
like it isn't gonna just do itfor you.
And I think that's where I thinkI've seen a lot of people go,
like, well, I tried it and itdidn't work.
And it's like, well, maybe, butmaybe it was set up to fail from
the beginning that you didn'tthoughtfully consider what this
thing would do.
SPEAKER_00 (05:12):
Yeah, I think for what I see is some type of
in-between there, where a lot ofwhat I talk to clients about in
our and our current customers islook, AI, and again, I'm talking
specifically like Gen AI, right?
And we'll and we can let's we'llget into the nuances too around,
you know, like I'm implementingGong versus, you know, I'm
implementing Chat GPT as aninfrastructure.
(05:33):
Right.
Is that I think what companiesneed to realize is Gen AI is
changing the way that people dotheir jobs.
It's not I like where I would, Idon't know if it's disagree, is
I don't think it's a tool.
I think it is a foundationalshift in how we solve problems
as humans and therefore isactually more similar to like
the internet and like how peopleshould deploy it, that it's
(05:54):
gonna completely rewrite the waythat we work.
And and I and what I see is thatsometimes when people think of
it as like, and again, differentlike rev tech, different than
Gen AI, maybe like caveat,right?
Where because I think I thinkRevTe, I a hundred, you know, a
hundred percent, you know, theythey treat it like a tool.
And I think for most people, youhave to realize don't deploy it
(06:17):
if you're not gonna make peoplechange behavior.
If it's not about like we'regonna do something different, as
opposed to your point, like,well, we deployed it.
It's like I think it's thechange, but I think we're saying
the same thing around changemanagement lift.
If you're not ready for thechange management lift that's
gonna happen, then you're doomedfrom the start.
That that's kind of how I seeit.
It's like you gotta be able toappreciate that if you're going
to deploy this against X, you'reyou're changing the way that
(06:39):
someone has done X for a verylong time.
SPEAKER_01 (06:43):
Yeah, no, I think I think you make a good point.
So I think the the thing that Isee too is, you know, when you
look at, you know, SaaS as anindustry, both of us have a ton
of experience in.
And so like I think you lookacross SaaS, I think one of the
mistakes that I see repeatedlyis there is no definition of
good.
And so they they conclude thatactivity equals success.
(07:07):
It's wrong.
You can write the bad email amillion times and be
unsuccessful.
And so I think the key thing isif you're using this capability,
there needs to be anunderstanding or expectation of
a check and balance of like,well, what is good out of it?
So can AI write emails?
Absolutely, can write them atscale that humans can't ever
(07:29):
keep up with.
Does it mean they're good?
Absolutely not.
And so, like, there has to be acheck and balance to say, okay,
what is kind of like anoperational QA of like, is this
hitting the standard that wewant our business and our brand
and our team and our customer tointeract with?
And someone's got to define thatbecause otherwise anything is
good.
And so I think that's wherethere's there's a missing kind
(07:51):
of check and balance there tosay, like, there should be a
human in the loop to say, that'sright, okay, let's double check
this first and from QAstandpoint.
And then secondarily to yourpoint on the check and balance
of the outcome is like, are wedriving open rates?
Are we driving conversions?
Are we driving funnel?
Are we driving dollars?
If the outcome isn't there, thenyou need to start back at the
(08:12):
beginning and go, well, maybethe things we're doing, albeit
faster and more efficient,aren't any good.
SPEAKER_00 (08:17):
Yeah, let's go down.
I want to go, let's go down thisrabbit hole a little bit and
we'll focus on top of funnelbecause I I do think that this
is a good one for a lot ofpeople, because I think for a
lot of clients and what you seetoo, probably Ryan, a lot of the
first applications people arethinking about it.
And I put gong in a differentbucket.
Well, unless you're teaming likeGong Engage, is is top of
(08:37):
funnel.
And it's it, I I did a post onMonday, people were got really
upset when I talked about AIreplacing SDRs.
And the point that I was makingwas this most companies, to your
point, are focused on activitiesfirst and outcomes second.
And if you are asking your teamto send a bunch of templates
that are not customized to thesub-industry, customized to the
(09:00):
individual, and pulling inspecific insights, AI is better
than you.
AI can out-template you becauseit can pull in real-time
insights on, hey, what aretrends for a VP of operations in
Marquette, Michigan, aroundairplane aviation manufacturing
parts, right?
Where a rep is never going totake the time.
(09:21):
AI can at least pull insomething that's going to be
quasi-relevant and thereforebetter than your shitty template
that says, I help operationsleaders achieve this outcome.
And so that is what I actuallythink is the issue, Ryan, is
that I think this is actuallynot an there's an AI component
to this that using AI on baddoes not equal good.
(09:45):
But AI in place of statictemplates will win.
And if your teams are sendingstatic templates and you're not
asking, you you hit this on thehead, the human in the loop, the
only teams we see that arewinning at outbound.
AI or and my knowledge gets me80 to 90 percent.
And then I put my I put my sauceon it, right?
(10:06):
I put my like what I know islike, oh, it's not that value
prop, it's actually this statthat's gonna resonate with the
ops manager in Marquette,Michigan.
And so when it comes tooutbound, that's what I'm seeing
is AI will if we keep going downthe path, AI will replace a lot
of SDRs.
And it's only the ones that knowhow to call and have a
(10:26):
conversation and who know how tocustomize better than AI that
are gonna win.
That's my hot take.
My hot take on top of funnel.
What about you?
No, I I 100% agree.
SPEAKER_01 (10:36):
And I well, I think where people get maybe emotional
about it is that there's athere's a disconnect in that
ecosystem.
I think it's unfair tocharacterize all SDRs the same.
There are some very strategic,very thoughtful, very high EQ
SDRs, and there are people wholiterally cut and paste all day.
(10:59):
And they have the same title.
They are not the samecapability, the same person.
And so I think when you groupthem all together, I think
that's where you get kind of thefriction.
But I 100% agree, it willoutscale you, it'll out-execute
you, it'll out-template you,it'll out-generic you every day
of the week and twice on Sunday.
Where I think that the gap forpeople that go, okay, but how do
(11:22):
I do it better?
I think again, it's that humanin the loop.
Is like, well, are you expectingAI to create the cadence?
Then you're making a mistake.
AI is not smart enough to knowyou shouldn't be emailing people
Sunday morning.
AI is not smart enough to knowthose things out of the box.
Like AI is not smart enough toknow that the day after
Thanksgiving, you probablyshouldn't be hitting people up
(11:43):
with a, you know what I mean?
Like there's there's gotta besome human check and balance to
be like, okay, well, this personjust came to our event last
night, so we probably shouldtake them out of the cadence.
Like, there's gotta be somechecks and balance of like human
logic.
AI is not gonna replace that.
The ability to personalize amessage and tailor it to nuances
and things, it is better thanhumans, almost across the board.
(12:05):
I think there's some that arebetter than others that I've
seen and some of the tools, butlike it is just the ability to
tailor speech in an effectiveway, it is unrivaled in.
I've never seen anything likeit.
Now, to your point though, Ithink it will absolutely replace
the capacity constraint thathumans place on outreach today.
SPEAKER_00 (12:26):
Yeah, that's a good way to put it.
SPEAKER_01 (12:28):
But I I do think that the combination of
thoughtful strategic guidancefor outreach with however many
appropriate for your scale,humans leveraging AI will
outperform AI on its own andwill absolutely outperform
humans on its own.
SPEAKER_00 (12:45):
All right.
As usual, if you're gettingvalue out of the episode, thank
you so much for tuning in andlistening.
I really, really appreciate you.
Make sure to subscribe to thechannel.
Uh, make sure to to bookmarkthis if you're listening on the
podcast as well, too.
And make sure that you sharewith one friend.
That's what I've been trying toask people.
Share with one friend.
Everyone's trying to figure itout, this AI thing.
(13:07):
I am as well too.
I know I appreciate it whenpeople share something with me
that helps me to get smarter.
So make sure, share, subscribeto the episode, and help to make
somebody else smarter as well.
For a lot of leaders, you know,they'll come to us and they'll
say, you know, Ryan, look, youknow, our top of funnel is is
struggling, etc.
And then you go and you have theconversations.
And I think this is the scarypart.
(13:27):
This is leadership, this issenior leadership.
Most of the feedback is, butyeah, this will slow them down
and they won't be able to sendas many emails.
And you go, oh my God.
Again, are we talking aboutoutcomes?
Like, do you care more about andit's like, how did you pick the
(13:48):
activity metric in in the firstplace?
I guarantee it was like, or likethis is what I did at my
previous job, or it's based onthe mean.
And the reality is, this isanother place I think AI crushes
it, which is look, Jake'snumbers are this, Ryan's numbers
are this.
Let me manage to the individual,right?
And I think that we're just so alot of sales leadership manages
(14:08):
to the mean.
And and and that top performerscan't stand it.
Bottom performers are like,yeah, whatever, I'll do what you
tell me to do.
SPEAKER_01 (14:15):
And and what doesn't make any sense about that is
like, and I'm sure you're nodifferent than I am, I get
prospected a dozen to two dozentimes a day.
LinkedIn, email, text,unfortunately, elsewhere.
With all the technology, it's nobetter than it was five to ten
years ago.
SPEAKER_00 (14:32):
It's worse, outrageous worse durable.
It's getting worse.
I actually think it's easier tocut through the noise today than
it ever has been.
Like if you literally show thatyou've done this much research,
you're top one percenter.
And and this is what I think itgo go back to like early 2010s,
or let's even go back, likesales loft outreach 2015.
(14:53):
So let's go back literally just10 years ago.
I would argue the outreach in2013 is way better than the
outreach in 2025.
SPEAKER_01 (15:02):
But but let's dig into that though.
So, what's different?
One, I think during that period,because I managed North America
for Celogen at that time, and Ihad two people running my
business development teams.
Weekly coaching.
How often does that happenanymore?
None.
Yeah.
unknown (15:19):
Yeah.
SPEAKER_01 (15:20):
They good luck.
They they reviewed weekly thetop performing email.
When does that happen?
They optimized subject lineamongst the team weekly.
Like they were doing the work,the real work, which is what
works, what's driving outcomes.
They weren't just going, well,let's everyone get X number of
messages out.
I didn't care.
I never set, my manager did, butI never personally said as an
(15:43):
organization running revenue, Inever set an outreach volume
goal.
I set an outcome goal.
I want you to book X number ofmeetings.
If you have to send two messagesor two million, I don't care.
You have to get the outcomebecause the outcome is the only
way that we progress as abusiness.
That's how people should bemanaging.
The fact they send 20 emails or30 emails or a million emails
(16:04):
doesn't make any difference ifthey don't convert to dollars at
some point.
SPEAKER_00 (16:06):
That's right.
And also to do in managing fromthat, like what we'll do is a
lot of our clients is like makewhat we call it meaningful
conversations is the firstpiece, which is like, look,
you've got to connect with threepeople.
So they say, hey, I'm not theright person.
I'm gonna connect you with John,or yeah, timing's interesting,
but maybe not like now, let'swork on booking time.
And it, but that's also anoutcome, right?
And again, to your point, if youif if and then and then with a
(16:29):
rep, it's like, look, you're nothitting the outcomes.
So now what we need to work itback, right?
Now we need to start to workbackward on look, it's 20 calls
or or whatever.
So so let me ask you this.
So we're talking about a lotwhat doesn't work.
So what does a healthyAI-powered go-to-market system
look like?
What are people doing?
What works, what doesn't work.
SPEAKER_01 (16:48):
I I think from what I've seen, it's it's very
dependent on leadership, on whattheir understanding and
capability is.
I have not seen AI besuccessfully adopted without
pretty experienced leadership.
And I think it takes someonethat understands how the
ecosystem works, thatunderstands the funnel at a deep
(17:12):
level, that really understandsthe components of how you're
driving success to optimize andimprove the machine.
I I think I kind of go back tomy like go-to-market
architecture like experience.
If you don't understand thenuances of that, you'll just
keep getting it wrong.
And you'll just be you'll justbe more efficiently wrong.
(17:33):
And so, like a couple examplesthat I've seen that I think are
just best practice.
So one is sales reps using ahopefully constrained private
GPT for an account, no-brainer.
Everyone should be able to queryall the data, all the calls, all
the transcripts, and go, whatdid they say about this?
What is this?
So an executive comes into ameeting and goes, hey, prep me,
(17:54):
I gotta go talk to this VP intwo minutes.
I want to know what I need totalk about and what their hot
buttons are.
You should be able to just querythat and get those answers.
That's an easy one, it's ano-brainer, but I don't see it
used that often.
I think it's pretty rare that'snot a good idea.
SPEAKER_00 (18:07):
Because leaders don't know how.
Most leaders know how rightthey're not investing.
And I think this is a reallygood point.
If you are in revenue, you know,we just launched our AI
certification program.
And um, you know, depending onwhen you're listening, we you
might have to sign up for thenext one.
But you know, we have 20 plus Vfrom VP to frontline managers in
the leadership track, and it'sgreat to see.
But I think what happens inleadership is you were
(18:28):
successful doing it this way,and and you all and we need to
wake up that the way that youdid account review in 2020, you
know, back when I had theaccount planning and account
strategy, and it's justcompletely changed.
And there's no there is nobenefit for you to make people
pay the dues because that's howyou did it.
And I feel like sales is verymuch a pay your dues culture,
(18:50):
and I feel like that is wherelike leaders are just not taking
the time that they need to learnthe Gen AI.
And like, and then I thinkthere's also a little bit of ego
or like what got me here, let'sjust keep running back the good
old times.
Yeah.
That I feel like it's it'shurting them.
Because what you just said ispossible today.
A lot of you leaders might belistening and go, Wait, you can
(19:12):
do that?
It's like you could do thatabout nine months ago.
SPEAKER_01 (19:16):
Yeah, you know, and I'll give you another example
that I've seen that I think isis also kind of low-hanging
fruit.
Is account research anddiscovery prep is the most
underutilized thing in sales.
Discovery is the most importantskill, and prep for discovery is
the most missed opportunityacross the board.
The ability with AI to soundlike an expert or maybe even be
(19:40):
an expert is unparalleled at anypoint in my career.
I remember preparing formeetings, like when I was back
selling like responses for likemarketers, like, I didn't know
shit about the travel industry.
I would kind of like, well, Itravel too.
Like you try to make somethinganecdotal.
You can be an expert on travelin maybe 10 minutes.
(20:01):
And an expert in nothing.
You could know industry trends.
Like, if you actually know whatto ask, you can sound like an
MBA in any industry with 10 to15 minutes of preparation.
SPEAKER_00 (20:12):
We just did this, so you'll you'll appreciate this.
So we work with a lot ofprofessional sports teams.
So we did a uh uh workshop withshout out to the Pittsburgh
Penguins last week, and we hadtheir reps do this.
And hey, I'm reaching out tothis business, you know, this
26-year-old rep, they don't knowwhat an HVAC company is.
So it's like, hey, what are thetrends?
Here's the company.
What are trends for HVACcompanies in the greater
(20:34):
Pittsburgh area?
What's a typical, most likelyaverage customer acquisition
cost?
What are some potential waysthat we might be able to help
them grow their business andcompare that?
And then, and you know, theydidn't have it hooked into their
CRM, but if you had it hooked inyour CRM, compare that to other
people that we have.
So again, it's a hundred percentspot on that like this.
Used to take me, the you'llyou'll love this, one of my
(20:55):
first jobs.
We had an industry trendsbinder.
Like it was literally a binderthis thick, and it was like
manufacturing, transportation,and and that's how I had to
learn to get up to speed.
And it took me a year to get upto speed on again.
I think you can ramp a rep andlike one.
SPEAKER_01 (21:13):
A testboard to like not that long ago, uh, because
I'm guilty of this.
I built playbooks as part ofwinning by design.
I did hundreds of them.
How many of those had that onescreen battle card that somehow
was going to summarize likemanufacturing?
It was like that's right, acouple of data points, whatever.
Like, you can't understandmanagement.
(21:33):
And manufacturing isn'tmanufacturing.
It's like, well, do you do pressmanufacturing?
Is it plastic injectionbuilding?
Package good, industrialmanufacturing, heavy equipment.
But but I think to your point,like back to like kind of this
stuck in the past kind ofmentality.
When you think about likeaccount research in the past,
you truncated it out ofnecessity because you just
(21:56):
couldn't go down the rabbit toget the information.
You can now summarize, I don'tknow, a million pages of
information in 30 seconds.
You can scan through it, you cando a couple deep dives as you
go, maybe refine a couple thingsin a way that just was not
possible without AGI.
And if you're not thinking thatway, you're not to your point
(22:19):
customer centric.
SPEAKER_00 (22:21):
Yeah, you're you're I just think don't think at this
point you're being customercentric.
Like, guys, if AI can automate alot of the research and prep for
your clients, when they talk toa human, if you can't add value,
they're not gonna want to keeptalking to you.
You know, again, I'm talking tosales teams.
I go, guys, the future is gonnabe if on the front end of the
sale, if you can't addincremental value and show that
(22:42):
you get it and you know, I justwant to go talk to customer
success.
Like, let me just talk to thesolutions engineer and customer
success, because that's who Iactually need to know.
Because I've already done mydiligence.
Or the scary thing is you justtalk to Chat GPT, and if those
answers are better than talkingto the direct company, you don't
ever talk to the company.
That's my point.
That's why self-service, likeevery SaaS company, I believe
(23:02):
this should have a self-serviceoption for that exact reason.
And then I've got a killeronboarding program, but that's a
whole other part two here.
So so we're almost at time here,and this has been, you know, I
think we're definitely gonnahave to do a part two because
this is this is the like thetype of energy that I enjoy.
What are you excited about overthe next six to 12 months?
If you said, Jake, AI-poweredseller folks, what is the thing?
(23:25):
And I love the two tacticalpieces of advice.
I think everyone can go run withthose two use cases.
They're no-brainer use cases,they won't move the needle.
Account research, account-basedyou know, GPTs or projects, if
you use you can use projects tooin a similar capacity.
Yeah.
What is the other thing that yousay in the next six months, this
is what gets me excited?
SPEAKER_01 (23:42):
I I hope it can get there.
I think it's gonna take a bit ofprompting, but I think the
opportunity to learn about yourown business is a missing one.
So this is kind of likemarketing ops, RevOps, sales
ops, like that kind ofecosystem.
I think really understanding thenuance of like who are we doing
business with and is thatdifferent than what's happened
(24:03):
in the past?
There's a lot of dependencies.
One, you gotta have some gooddata, you got some good data
architecture, et cetera.
But I think one of the missedopportunities for a lot of
organizations is they don'tlisten enough to what's
happening.
And so we're still chasing likethe enterprise customer, and we
don't realize that we haven'tsold an enterprise customer in
three quarters and we're sellingmid-market.
Or, like, you know, that's asilly example, but that kind of
(24:26):
idea is like, okay, well, thisvertical's hot for whatever
reason.
Let's take care of it back.
Let's learn about that, let'smarket to them.
Like, let's double down.
And that's one of the feedbackthat I've been giving over the
last, you know, handful ofquarters, because it's been a
tough time in SaaS, right?
Is you need to be double andtripling down on your success.
You should be amplifyingsuccess.
(24:47):
Who's winning in every aspect?
How are they winning?
Who are they winning with?
And let's go do more of that.
Don't go into new markets, don'ttry new things, go find where
success is happening and just domore of it.
I think that's a missedopportunity.
And but I think a lot oforganizations need a little bit
of hand holding to help themfigure that out, especially when
(25:08):
you have any scale.
You know, that that's a harderanswer to get to.
If we can do some of that dataanalysis and kind of summarize
it and go, okay, these are yourthree best verticals.
This is what that profile lookslike.
This is the persona thatgenerally engages with us.
I think bubbling that up to thesurface would empower revenue
leaders in a very tangible waythat I think is difficult today.
SPEAKER_00 (25:29):
Yeah, I love that one.
I think like that ability toreally learn your business and
then, you know, just imagine howmuch smarter we're gonna be to
make quick pivots.
Do boom, boom.
Okay, yeah.
Oh, was this a good idea?
Nope, not a good idea.
Like so much of revenueleadership is gut and just the
ability to move toward moredatabase so you can spend more
time talking to customers, theright people.
Like it's all the things thatwe, you know, we should want to
(25:50):
do.
So I think that's a good thing.
SPEAKER_01 (25:57):
If you do three tests a year, you might do 40.
And and across and across therevenue spectrum, that's the
other thing is I think missingacross every organization I work
with is any effective closedloop feedback between different
departments.
Why are we churning out?
Does that go back to sales?
Almost never.
No.
Sale doesn't go back to BD, BDdoesn't go back to marketing.
(26:17):
It's like, guys, this is a teamsport.
If people played team sportslike this, they would lose every
game.
You have to talk, likecommunicate.
But I think creating easy waysto bubble up those insights to
be able to share.
I mean, you could optimizemarketing, business development
sales in like a quarter, not ayear.
SPEAKER_00 (26:36):
Okay, that might, yeah, that might be the quote of
the episode.
If people play team sports likethis, they would lose every
single time.
So that's it.
I I love that quote.
I'm gonna I'm definitely gonnasteal that.
So, hey man, I I love theconversation.
This is a great conversation.
Oh, I appreciate it.
It was great.
A lot of tactical advice.
And where can people find you?
What's the best place to get ahold of you?
SPEAKER_01 (26:55):
Uh, LinkedIn normally, I I try to communicate
pretty efficiently there.
I get bombarded by messages, butI'm always open to talk to
people.
I mean, I love this stuff.
Like I'm a fixer by nature, so Ilike wrestling with this stuff.
It's fun.
And uh yeah, hopefully uh we'llsee a lot of cool things.
I'm excited to try out you know,some of the stuff that you've
launched as well.
And um, you know, really I thinkthere's a huge opportunity to
(27:19):
apply this stuff in real life.
I just think it's gonna beharder than people want it to
be, but it's no lesstransformational.
It just means you gotta get yourhands dirty a little bit.
And so that's right.
You just gotta go into it withthat point of view.
SPEAKER_00 (27:30):
Stop thinking.
Yeah, for a lot of some ofthese, it's like you gotta just
pick the one use case and justgo and stop thinking about what
85 steps down the road lookslike.
So yeah, just go win one battlefor sure.
Where yeah, fix one bottleneck.
That's what I say.
It's like, let's just we can doall this cool stuff later.
So, all right, man.
Appreciate you, Ryan.
Thanks for joining andappreciate everybody for tuning
in to this episode of the AIPowered Seller.
(27:52):
We'll see you on the next one.
Cheers.
If you are somebody who isgetting serious about this, now
is the time.
Sign up for our AI certificationprogram that is going live,
cohort number two in January.
Uh, we're about halfway throughcohort one.
Uh, we've got a rep track, aleader track.
If you don't have the time,you're busy, but you go, Jake, I
need to make time.
I need like two hours a weekwhere I'm getting up to speed on
(28:14):
this.
It's six weeks.
Sign up for the certification.
I promise you, I've got a moneyback guarantee.
If you don't get value out ofit, I will more than refund you
your money because I'm thatconfident that this is going to
change the way you sell and theway that you lead sales teams.
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