November 25, 2025 • 39 mins
In this episode of The AI-Powered Seller, Jake Dunlap sits down with Ryan Staley (Founder & CEO of Whale Boss) to break down the 2026 AI mindset shift every CRO, VP Sales, and frontline rep needs right now.
If you’re being asked to do more with less, increase personalization, and keep pipeline moving in a noisy market, this is your tactical playbook. Ryan and Jake go beyond basic “prompting tips” and show how to train AI like a digital teammate — not a tool you poke for answers — so it can take on multi-step work across research, deal strategy, enablement, and leadership workflows.
In this conversation, you’ll learn:
✅ The difference between a prompted assistant vs. a true digital teammate
✅ The top AI teammates to build first (account research, next-best-action, deal strategy)
✅ Why AI “liberates intelligence” and how to avoid the AI pit of despair
✅ What’s really holding sales orgs back from adoption (overwhelm + no top-down sponsorship)
✅ How to talk ROI in a way CFOs actually buy
✅ What’s coming next: agent orchestration, Cursor 2–style multi-agent management, and everyone becoming an “AI manager”
Whether you’re a rep trying to level up fast or a leader redesigning roles for the AI era, this episode will help you move from AI curiosity to AI execution.
👉 Subscribe for weekly episodes with real GenAI sales use cases.
⭐ If you got value, drop a comment: what digital teammate would save you the most time this week?
📩 Share this with one sales leader or rep who needs a 2-year edge.
Connect with us:
Jake Dunlap on LinkedIn: https://www.linkedin.com/in/jakedunlap/
Ryan Staley on LinkedIn: https://www.linkedin.com/in/ryan-staley/
Skaled: https://skaled.com/
Whale Boss: https://ryanstaley.io/
#AIPoweredSeller #SalesAI #GenerativeAI #SalesLeadership #DigitalTeammates
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 2 (00:00):
I think what we're seeing is digital teammates can
kind of step in and take overfour or five different things
and really sit as like a partlike a little sidekick, a little
buddies.
A lot of reps are kind ofsitting there and just saying,
like, uh, isn't my boss supposedto build this shit for me?
Or like it, like, who's gonnahelp save me and implement Gen
(00:21):
AI for me?
Because the my boss isn't doingit and I'm just still
prompting.
Speaker (00:24):
Like, it's funny, I had an invest a group of investors
tell a C-suite that like ROIwith AI is really, really hard
and like it's it's not easy atall.
And you you, you know, like,okay, you've probably never
tried to implement anything withAI in your life, investor.
Speaker 2 (00:37):
We are in an era right now where it is our job to
completely rework the way thatour people work.
And if you as a leader are notstaying on top of this, your
ability to continue to earnhundreds of thousands of dollars
is gonna quickly diminish.
Welcome to another episode ofthe AI Powered Seller.
If you are a CRO or a salesleader who's like, hey, you just
got to figure this out and domore with less.
(00:58):
Your quota is getting ready togo up, et cetera.
You know, you're grinding 60hours a week, and now it's, you
know, more pipeline, morepersonalization, or more, more,
more than ever before, morevolume, et cetera.
I'm telling you right now,today's episode's for you.
We're gonna talk through somevery, very, very tactical ways
that sales reps and salesleaders are leveraging Gen AI to
(01:20):
cut through the noise.
Not just your prompting, notjust, oh, here's a quick tip,
but some tactical assistance,some tactical ways that you'll
be able to deploy it, whetherit's from prep, whether setting
more meetings, closing moredeals, et cetera.
And I'm super pumped fortoday's guest, Ryan Staley.
Ryan is the founder and CEO ofWhale Boss.
I've known Ryan for, I don'tknow, 10 plus years probably.
(01:42):
He's helped 2,500 go-to-marketleaders multiply output without
adding headcount.
He's taken divisions ofcompanies from zero to 30
million with just four reps, noSDRs, no marketing.
That's what I'm talking about.
And what's this guy's secret?
Why did I think he would be agood person for you to hear
from?
Is it's not treating AI like ahelper that you prompt, it's
(02:07):
training it like a teammate.
And so if you're somebodythat's stuck in prompt mode, or
maybe you're trying to figureout why AI, this episode, the
2026 AI Mindset Shift episode,is for you.
Speaker 1 (02:20):
AI-powered seller.
Speaker 2 (02:22):
All right, Ryan, excited for today's
conversation.
As usual, we're gonna talk alittle bit about AI and about
its impact.
You know, today's episode's allabout mindset in 2026.
So help me to understand foryou.
When did you realize that AIwas not another technology?
Like, where was there a momentwhere you started to realize
(02:44):
yeah, this is like different,different?
Speaker (02:46):
Yeah.
Uh great question, Matt.
So I think like, and by theway, thanks for having me on.
Love, love being on the showand everything like that.
So I'm excited.
I guess like to answer thatquestion, there's kind of two
really core things, or maybethree things that happen.
One was like I had a guest onmy podcast called the Scale Up
Show, where about three yearsago, uh Chris Savage, who is the
(03:07):
founder and CEO of Wistia, hadme on.
And afterwards, he's like, HeyRyan, he's like, Have you heard
of the tool Dolly?
And I'm like, What the hell isDolly?
This is like like the imagegeneration version one, where it
was like, it was terrible, man.
It was absolutely brutal.
But because of that, I got onearly access to ChatGPT.
So that was like kind of myepiphany moment, right?
When I started using it, Iguess what really internalized
(03:29):
it for me was that remember whenthey had on LinkedIn, like,
hey, let's see if AI couldreplace me with my job.
And there was like peopletesting it out.
This was like GPT 3.5, and itwas like all over the place.
And people are like, Yeah, meh,it only does like 60% of what I
could do.
I'm fine, right?
Like, that was people'sattitude, right?
Well, what I saw there waslike, I'm like, I'm gonna stress
(03:49):
test this against like whattook me, something that took me
10 years to learn in enterprisesales.
And that was really how buyerswere like evaluated and stated,
what was specific to theirvertical niche.
Um, and then what really drovethe business all the way from
like an executive perspectivedown to like an individual
department, all the way up tothe board and investors, right?
And it got 95% of the way therein three questions.
(04:11):
And so that was one of thethings that, like, absolutely
I'm like, holy shit, this isgonna be completely different
than everything else I've everseen.
So I would say those were kindof like the key moments in time.
Speaker 2 (04:20):
Yeah, I had one very similar.
I remember afterwards, and nowI've I've kind of coined this, I
call it like the AI pit ofdespair, where you're like,
you're really excited about itand you're like, wow, we can do
this and this and this, and thenyou test it and it does things.
You go, oh my gosh, like whatdoes this mean?
And then you fall into the pit,and then you kind of come out
the other side where it was likeit was it was actually, I
think, maybe the exact same,like a deal evaluation thing
(04:40):
where it's like, all right,well, can AI actually break down
and help to give advice withreally no context on like what
are the steps in a good likemid-market enterprise deal?
And it gives the advice.
I'm like, pretty good.
Like, that's like 80, 90%there, like and it has always
like one or two good ideas.
You're like, oh yeah, that'sprobably smart.
Right.
And then it goes and finds thestakeholders in real time for
(05:02):
you and everything.
So I think a lot of people havehad that moment.
And and for those of youlistening, don't be scared of
that moment.
Like, it is what it is.
That's what I try to tell a lotof sales leaders, Ryan, is
like, look, you have to knowwhat this thing is capable of so
you can harness it, right?
And and I think that kind ofsegues into this next uh
question I've got.
One of the things you said isAI isn't just about
(05:23):
productivity, it's aboutliberating intelligence.
So if I'm not answering dealquestions, what can I do?
How is this liberating myintelligence if my job isn't as
a sales leader to answer theexact same question 500 times in
a year?
Speaker (05:36):
Good question, man.
Okay.
So we could hit this on a lotof different areas.
I think like I've seen it witha wide range and I've used it,
and I'm gonna use some likenon-work examples and then lead
into work examples, if thatmakes sense.
So I think, you know, one ofthem actually was a guest I had
on my show.
He he basically journaledelectronically, put all his
journals into general entriesinto a GPT, and he had lots of
(05:59):
stuff about how he worked withhis son.
And his son, I think, had likeextreme ADHD and some other like
challenges that made it hardfrom a parenting perspective to
really like understand like howto work.
And so he would actually relyon and kept updating the
instructions on how to work, andit helped him like kind of
co-parent in like anon-objective way.
(06:19):
And he said it's worked outreally, really well for his and
his son's relationship.
So, like that's one examplewhere it's like you're tapping
into a mind of someone else todo that um from a health
perspective.
So that's like yeah, parenting,right?
From a health perspective, oneof the things I did is um
basically I have um I had like achronic condition um that was
(06:40):
happening.
I'm not gonna really get intoit, but it was something that I
went to multiple doctors on andI asked them, you know,
questions.
They're like, try this, Ryan,try that.
Um didn't work.
Nobody could uh diagnose whatit was.
I took all my blood hormonetests, created a really killer
like prompt around being like apattern recognition expert in
terms of like health and chronicillnesses, and it basically
(07:03):
identified it for me in a snap,and it's pretty much gone now.
So, like that's on the healthside, right?
So I'm not a doctor by anymeans, and I'm I'm you know,
don't have that skill set.
And then last but not least islike I've seen executive teams
do top-down and bottom-upplanning for the entire year and
with like KPIs and veryspecific, like 45 minutes,
(07:24):
right?
That process used to take days.
So those are three like coreexamples that come to mind.
Speaker 2 (07:28):
Yeah, and I think the key is like what you're getting
at.
I mean, it it was able to siftthrough like data.
It wasn't and it was able tokind of pull through and pull
out it to get to like firstversion of insights quickly.
And I think for a lot ofpeople, that's how we have to
think about this because thenyou still had to turn your brain
on, right?
Then you still have to say,hey, as an exec team, how can we
(07:49):
actually manage this?
Is this possible?
You know, even going back tolike your health piece.
It's like, okay, this hasgotten me to hear.
Now let's go validate.
Let me go inspect, and it's alittle bit more of this or a
little bit more of that.
That's whenever I hear, youknow, what you said around call
it creating, you know, space formore, you know, uh, I call it
like creativity, you know,resourcefulness, et cetera.
(08:11):
That's what I love about it,right?
Is like I can get now to V inthe same amount of time it took
me to get to a rough draft.
And that to me is where I feellike the unlock is I'll I'll
give you a really practicalexample.
One of our clients, they'regetting ready to plan for SKO.
And she surveyed the entireorg, 50 plus people responded.
And then she's like, okay,let's summarize this and put it
in.
I was like, okay, there's twodifferent ways I could say
(08:33):
they're summarized.
You can go read every singleone.
And look, let's be honest.
Some AI, if it's reading 50different rows and nine and 80
columns, it's gonna mess up.
Like it's still not perfect interms of those sense.
Or I could just summarize itwith Chat GPT Pro and it'll take
10, 15 minutes and it'll bepretty good.
And it's like, it's that's thatto me is a good example.
(08:54):
It's like, I probably don'tneed to pour over all of this.
I now can actually trust butverify, I can get a really good
like outcome, spend another hourjust kind of combing through
for the nuances instead oftaking five hours.
And I think that's where when Ithink about liberating
intelligence, it just allows youto save time and also do a more
thorough job, you know?
Yeah.
When people are already, youknow.
(09:15):
Okay, look, if you are somebodywho can feel what we're talking
about, these different AI usecases, you're like, Jake, how do
I possibly make the time?
We have got you covered.
Okay.
So if you're getting value fromthis episode, make sure to
subscribe to the AI PoweredSeller Podcast.
We do episodes every week whereI'm interviewing somebody or
talking about what I'm seeing inthe market.
(09:36):
And make sure to pick up a copyof the innovative seller, USA
Today bestseller that I wrotearound what you need to know
about sales in the future andthe sales around AI, sales with
technology, the humaninteraction, etc.
Subscribe to the podcast andmake sure to go to Amazon, pick
up your copy of the book aswell.
Speaker (09:54):
I was kind of like you where I was naturally born
through the the uh the the thechild raising of sales, right?
Like there's a lot of othergo-to-market activities, and
like I didn't grow up being amarketer.
I didn't grow up being in abunch of different areas.
Now, granted, I touched allthem with the roles I did, but
like if I just apply certainconcepts and frameworks, I could
operate at a level of a peerthat's been doing the job for 25
(10:16):
years.
So, like that's anotherexample, man, where it's just
like like ancillary skill setsthat are close but not dead on
with what your experience levelis.
That's where there's hugeopportunity.
Speaker 2 (10:26):
I think that that's the that where a lot of,
especially if you're a youngerseller and you're listening,
that it can just help you get upto speed.
You know, for example, youknow, when I was getting up to
speed at a company, I got abinder that had a bunch of
industry insights in it.
And it was like, you know,here's what's going on in
manufacturing and this and thisand this and and all these
things.
And so I, you know, it took me,you know, nine to 12 months
(10:48):
worth of con.
And I was a good, I was reallygood.
It took me nine to 12 months toget up to the speed where I
could have an intelligentconversation with a business
owner in manufacturing and thenswitch gears and talk to someone
in pest control and then switchgears and talk to someone in
tech sale.
It took a long time.
Whereas now I can get theinsights.
And I think one of the thingsI'm curious to hear your thought
on a lot of what we're talkingto our clients about right now
(11:09):
is there's two different levelsto think about AI productivity.
There's one, which is gettingthem access to information and
insights faster.
But number two is retention,retaining the information.
And so, how do you think aboutthese two?
Because a lot of like, I'llgive you a good example.
We built an account researchassistant for one of our
clients, and she goes, I wantyou to at the end of every
single one of these as promptthem with a five question trivia
(11:32):
game to make sure they actuallyremember.
And I was like, that's a reallygood idea.
Like, we need because then theyactually remember it.
So, how do you think about youknow I've seen conflicting
studies?
MIT says it's making us youknow dumber.
Other people have said actuallyit's gonna unlock the
intelligence.
How do you think about thebalance of like speed to getting
the information and parrotingit versus actually retaining it
(11:53):
so you actually can become atrue professional?
Speaker (11:54):
It's a really good question, man.
I think I don't say it's makingus dumber.
I think it makes us smarter anddifferent.
Or right, it can make youdumber if you if you go down
that path, just like any socialmedia tool can make you dumber,
right?
Just by by using it.
So, in terms of like retention,I think like, and this is what
I see with my clients too, withlike large-scale AI rollouts, is
(12:17):
like the only path toretention, in terms of my
opinion, is like doing right,like because like you could have
a deep research before it spit50 pages out, but you're not
gonna remember all that shit,right?
So if you however, if you startto implement it, and that's
where it gets it gets reallyexciting.
I'll give you an example.
This is like another kind oflike apple flying on my head.
I was like, I remember onemorning and it was right after
(12:39):
voice came out, and this waslike GPT 4, not even 4.0.
And I'm like, I was shaving,I'm like, hey, you know what?
Like, there's this book I'vealways wanted to read, but I
don't have time to.
And so I'm just like, screw it,I'm gonna put on voice.
So I threw it on voice.
I'm like, apply, you know, the8020 principle and deconstruct
this book into two pages, giveme all the high points and
quotes with exact examples,right?
(13:00):
Something along those lines.
And boom, it busted it out, butit verbally talked to me while
I was shaving.
I was like, all right, that'scool.
I'm like, this is my business,this is what I'm doing, this is
what I'm focused on.
Customize this book so I canimplement this tomorrow, right?
And it gave me an exact likeimplementation plan.
I go now make checklists andsheets in a daily routine that I
could use to do that, right?
So, like, that's a quick pathbecause it goes all the way from
(13:20):
like idea to execution in likeminutes.
So that's what I think helpswith retention as well.
Speaker 2 (13:24):
Yeah, okay.
And I think this is a goodtransition.
So a lot of what we're talkingabout is using AI to do stuff we
already know, right?
Or or some some flavor of that,right?
It's like, hey, I've got anassistant.
Hey, AI, can you do ABC?
I want to talk about theconcept of a teammate.
And we're talking a lot aboutthis.
We're kind of coining thisterm, this idea of like a
digital teammate, right?
(13:45):
Which is somebody who has, youknow, it really is just a series
of automations that are justkind of orchestrated together.
I mean, at the end, if you kindof look at its insides, like
its skeleton and its its organs,maybe just explain what that
means to you.
Like, what's the differencebetween an assistant and a
digital teammate?
And and where do you see theimpact?
Let's start with like for salesreps, and then also let's go
(14:08):
for for leaders as well.
Speaker (14:09):
Yeah, I think um like everybody kind of like defines
it differently, right?
So I think like the bestprobably, and this is a great
question, Jake.
You're asking me.
So, like if I was if I were touse a teammate, it's usually
like like a like a co-pilotcould just be for like a single
function, right?
Like, like you're talking aboutthat research assistant, like
(14:30):
boom, bust out enterpriseaccount research, do this,
customize it to my company, allthat stuff, right?
Spits it out.
A teammate, I think, would besomething that could do a string
of different activities whenyou either link them together,
right?
So you have multiple kind ofassistants linked together to do
that, or you have someone thatthat does autonomous or
semi-autonomous work for you.
So, for example, if I'm using atool called GenSpark, right?
(14:52):
I could take a recording likethis that I'm doing with an
explainer and then infuse thetranscription and then have it
totally put together my entirenewsletter as well as thumbnails
for the YouTube design, and itdoes all that in like a couple
minutes, right?
That's like a multi-stepprocess.
And then if we're looking at itfrom a leadership perspective,
and I think there's still a lotof work to be done, and that
that's why I would say more froman individual contributor,
(15:14):
right?
We're talking from a leadershipperspective, it's the same
thing.
It's like, all right, I'm aboutto have a deal review with my
rep, a deal strategy.
Here's the transcripts, analyzeall these, give me ideal nest
best actions and holes, right?
That's an example.
Or if I was like a leader whereit would be a little bit
different, I would look at moreof like an orchestrated teammate
structure.
That would be like where you'retaking like transcripts, you're
(15:37):
taking support calls, you'retaking um, you know, details
from your chat bot, integratingall those together, creating a
customer brain, and thenspitting that out, right?
Speaker 2 (15:45):
Okay, if you are somebody who just heard what
Ryan laid down and you aresaying, My gosh, where am I
gonna find the time for this?
The AI certification course isit, right?
Shout out.
We are wrapping up our veryfirst cohort, which is really
exciting.
We've we've got the rep track,we've got the manager track,
you'll see the AI certificationbadges all over LinkedIn.
(16:05):
And DM me, shoot me a note onLinkedIn, we'll put a link there
if you're interested in signingup for the next cohort, or
check out the link, the pagesthat I'll link to below for the
landing pages, you could justsign up yourself.
But DM me, happy to give youmore insight into what other
people are doing to carve outthat so, so precious time and
get up to speed in just 12 to 24hours on what's the latest and
(16:29):
greatest with AI.
I'll tell you how we'rethinking about this is that when
you go to a client or anorganization and you're like,
okay, so here's how this works.
We take the Zoom API, we pullit in, we run it to three or
four assistants.
That's like your call grading'sgreat, you know, framework,
skills, whatever.
Then we're gonna, you know,ship that to Slack, ask for a
little bit of feedback, and thenput the output into a Google
Doc for the rep to be able toreview.
(16:50):
I'm just making something up,or push it to Salesforce or push
it to, you know, whatevertemplate.
We find that that's difficultfor people to comprehend.
If instead, and and notcomprehend, but more of just
like really get a picture of,instead, if you say, hey, Ava,
Ava is our digital teammate thatdoes your call scoring.
And what Ava does is Ava takesyour call, runs it through our
(17:11):
four or five step rubrics, andthen comes back to you with a
personal development plan thatfeeds off of the previous
conversations.
We find that that is morepalatable, you know, and it's
like, oh, cool.
Like, and it's also like, Ithink, less threatening, maybe,
and understanding of like, hey,what is an agent, what is an
assistant do, et cetera.
So for us, the concept ofdigital teammates, and even for
us, we're we're thinking nowabout like we're adding digital
(17:34):
teammates into ouraccountability chart.
Like we're building in like aconsulting ops digital teammate.
And what they do is they, youknow, running a consulting
business, they analyze hours,they analyze project milestones,
and on a daily, weekly basis,they're like, hey, what's going
on?
Like this one's behind.
Do you need a new template?
All those types of thingsthey're able to do.
And so I think I think of adigital teammate as something
(17:55):
that is orchestrating, usuallyI'm gonna call it more
operational or or consistenttasks, because even call
scoring, right?
Like if you go to a leader, heor she, you know, if you put the
same call in front of them,different reps, they're gonna
give probably similar advice.
And so I think what we'reseeing is digital teammates can
kind of step in and take overfour or five different things
(18:17):
and really sit as like a part,like a little sidekick, a little
buddy, right?
Ryan, that's like sitting therehelping you to do things
throughout the day.
So those are just like a coupleof examples.
Speaker (18:28):
Yeah, I mean, everybody gets freaked out about getting
replaced to some aspect of it,right?
Or these AI tools becomingSkynet, taking over everything.
So the other thing, too, andI'm sure you've seen this, is
like the branding of what anagent can do versus the actual
execution of what an agent cando is massively different for a
lot of companies, right?
It's like night and daydifference.
(18:48):
Um, that's something always toconsider too, right?
If you're looking through it.
So I do like the teammatesconcept and I use that as well
on a continuous basis.
Speaker 2 (18:55):
Well, what do you okay?
So what I mean, for you, Imean, you've it says, you know,
you've run 500 plus AI usecases.
Like, what would you say ifsomebody's out there, whether
it's a digital teammate orseries of assistants, do you
have, I don't know, maybe liketop few where you're like, hey,
if you're a and let's start withthe rep, right?
Because I think here's whathappens.
A lot of reps are kind ofsitting there and just saying,
(19:16):
like, uh, isn't my boss supposedto build this shit for me?
Or like, it, like, who's gonnahelp save me and implement Gen
AI for me?
Because the my boss isn't doingit and I'm just still
prompting.
If if I was a rep today, okay,and let's say I had I had the
ability to build out anassistant, my team had paid for
ChatGPT, my team had paid forMicrosoft Copilot, my team had
(19:36):
paid for Jim and I can build agym.
What would you what would bethe top one or two things you
would tell them to build in youknow the first you know month or
two?
Speaker (19:45):
I would say, like, I don't think it's the same across
the board because you have likehigh velocity SMB reps that are
churning and going throughdemos left and right versus
mid-market versus enterprise,like on the sales side, right?
And then you know, existingaccounts.
So the way I kind of look at itis like either there's kind of
like three ways to attack it.
One is like, what's the numberone blocker to you hitting your
(20:08):
KPI or goal, right?
So that's more like outcomedriven.
Two is like, what do you wastea ton of time on as a rep?
And then three is like, what doyou hate doing?
Right.
Like you could look at itthrough any lens just to start
to facilitate adoption and do itthat way.
And so, for example, let's sayyou're you're on the enterprise
side and you're doing massiveaccount research, then like map
(20:30):
out all your ideas and whatyou're doing, and then create it
once and ask for like, youknow, open AI to create, or I'm
sure to say Chat GPT to createcustom GPT instructions for that
exact process.
And then what it'll do is it'lltake that process that took 45
minutes to do and turn it intolike a 30-second process, and
then you just kind of iterate onit, right?
Like the time that that itwould take you to do one
(20:51):
research process with that wouldbasically it would finance from
a time perspective the cost tomake one to infinitely get you
know 35 minutes every timemoving forward.
So I think that's super easy.
Speaker 2 (21:03):
Research would be research would be one that you
would peg then, like again, likebasically building something
out.
Speaker (21:08):
Yeah, and that's like I hate saying that because that's
that's common, right?
But like another one is nextbest action.
Like, I think next best actionwith like integrating your sales
methodologies into that withtranscripts is so freaking easy.
It used to take me 45 minutesor an hour to do that.
Now I could do it in 30seconds, and it's probably
better than what I would do if Idid it all manually looking
(21:30):
through my notes.
So that's another example, iswhat I would say.
How about you, man?
What do you think are your toptop couple that come to mind?
Speaker 2 (21:36):
I think look, to me, research is a no-brainer that
and again to because to yourpoint, you're like, yeah,
everybody says it, but mostpeople are just prompting.
And by the way, prompting islike not bad, right?
If you're like, hey, I'm doingresearch, blah, blah, blah.
The problem is most reps arestill, and most people I think
are still using very basicprompting.
They're not layering things in.
So it's like, I want to do thisand this and this and this and
(21:57):
this and this.
And that's where, you know, youdon't want necessarily copy and
paste anymore.
It would be easier for anassistant to just ask you those
questions.
And so I think there's like,you know, if you're somebody
who's consistently doingenterprise deal, what is your
enterprise research process?
Well, great.
Just put that all into custominstructions inside of a gym or
an agent or a custom GPT.
And then it says, great, what'sthe account we're working on
(22:19):
today, Jake?
And it's like, uh, we'reworking on this one.
And you could even upload adocument of like three or four
of your best account, you know,research plans you've ever done.
So I think research is anabsolute no-brainer.
The other big one, with more,again, maybe not less on the rep
side, but I think digital C Sslash digital S E, like, I don't
need any more.
Like, I'd say those areprobably some of the more common
(22:39):
ones, Ryan, that we're buildingout out of the gate.
Is I don't need to loop in ahuman to say, does this
integrate with Azure or not?
Or what are the five thingsthat I need to think about
around A, B, C, or D?
And so for me, I think I'mlooking at these use cases where
where is there information thatisn't really value add in the
(23:00):
customer lifecycle and reallyisn't even value add between the
two people that areinteracting, right?
Like product data.
Hey, I'm a customer, I have aquestion, hey, I'm an inbound
lead, I want to book a meeting.
Like, I think that there arecertain use cases at the exec
level, customer success, digitalSE, inbound, that are kind of
those to me for the theexecutive level are no-brainer.
And then I'll call it likeresearch and prospect insights.
(23:22):
We've got kind of a uh amessage framework we call the
triangle, which is it basicallysays, okay, for this persona in
this sub-industry, what are thetrends that that that persona is
facing in that sub-industrythat we actually help to solve
for?
And that's where Gen AI isreally good.
It's like trends for industrialmanufacturing, especially it's
like specifically heavyequipment machine manufacturing
(23:44):
for a VP of operations, here arethe top three headwinds this
person's facing.
And you you have a product thatdoes X, here are the three
things you should talk to themabout.
And that's where you know thatused to take someone 15 years in
an industry.
So I think building anassistant that knows, you know,
your version of good messaging,an assistant that knows your
version of great research,that's going to get you a long
way.
And then I like the one yousaid, that's probably the other,
(24:06):
if I had to pick a third, whichwe'd call that deal strategy
evaluation, where it knows, andwhat we have it do is it looks
at competitive threats, it looksat stakeholder map threats,
right?
Hey, you're only talking tothese two people.
Typically, your deal has a CFO.
I by the way, I found it.
It's Lisa Henderson.
Here's her LinkedIn, here'sfive things that she just talked
about.
(24:26):
So being able to build anassistant that can, I don't need
to go ask my boss.
I call it 100% deal coverage.
Yeah, I'm gonna talk to my bossabout the top 15%, 20% of
deals, but I can actually run100% of my deals through some
type of evaluation frameworkthat should help to increase my
close rate by five, 10%.
You know, so those are yeah,those are some of my, I don't
(24:47):
know, like go-to go-to's as apart of it.
Tell me a little bit right now,what's holding people back?
So we're talking about theseuse cases, right?
Of like implementing thesetools, the time savings is very
obvious.
What do you feel like isholding people back right now?
Why do you feel like morepeople aren't leaning in?
I know, look, we're all busy,everyone's busy, but why do you
feel like more most peoplearen't leaning in further?
Speaker (25:09):
So, and it's a great question, man.
I think like there's there itlike I think there's naturally
people who are hungry to learnand others that aren't.
And like, you know, obviouslyyour brain rationalizes to save
energy and avoid pain, right?
So, like those are the two corethings it tries to do every
day.
And so, like, there's a couplethings that it influence.
I think what's holding peopleback is like things are moving
(25:32):
faster and faster every day interms of the number of releases,
the quantity of releases, thenumber of SaaS tools that are
released.
And so it's just sooverwhelming that people decide
to do nothing, right?
Like, I think that's numberone.
Number two is I would say, andlike, it's why your business is
doing well and my business doingwell right now, is like um if
(25:52):
companies aren't like sponsoringthis and saying this is a
priority, then most people don'tcome to that conclusion on
their own.
There's a fraction of powerusers that do, right?
And those are the power users.
And then if that doesn't happenthough, innovation happens in
the dark and you lose all thatinsane tribal knowledge
integrated with AI for thosepower users.
If you if you like bring it alltogether through like a
(26:15):
corporate-led approach with atop-down and bottom-up, then
that's when you start to reallysee things take off.
So that's what I would say,man.
Top of brain.
What do you feel like?
Speaker 2 (26:24):
What do you feel like at the top?
What's stopping people at thetop from diving in?
Why do you feel like leadersare, and again, maybe they're
not reticent, but they're notdoing it.
Why do you feel like from thetop down there's struggle points
to kind of really get startedon this AI journey?
Speaker (26:39):
Yeah, I think a couple points.
I think, you know, one is a lotof it's fear-driven, to be
honest with you.
And so now that we're reachingmore of a level of maturity,
like it's funny.
I had an invest a group ofinvestors tell a C-suite that
like ROI with AI is really,really hard and like it's it's
not easy at all.
And you you, you know, like,okay, you've probably never
(27:00):
tried to implement anything withAI in your life, investor.
Um so that's one aspect of it.
I think the other thing at thetop of like why someone wouldn't
is like the median tenure of aCRO is 15 months, right?
So it's like their their timeto execute is so freaking tight.
Um if they don't do that andthey just look at this as like
another barrier sometimes ofjust focusing on just doing the
(27:23):
work of like hitting the number,right?
So I think that's the otherthing, man.
That's super, super critical.
What do you think on that side?
Speaker 2 (27:29):
Are you saying the same thing?
I mean, time is certainly apart of it.
ROI, here's what I would tellyou.
Just in general, and all mysellers know this time savings
is the worst sales argument.
We as humans struggle strugglestruggle to properly credit
certain initiatives as like thecorrelation or direct impact on
a productivity gain metric,right?
(27:50):
We love revenue gains.
We love uh, you know, whetherthat's you know dollars or
whether that's volume um base,but I'll just in general,
productivity gains aredifficult.
Now, the good news is how youknow how we're doing it with AI
is we're mapping how long a jobtakes to be done today.
Okay, this is what ishappening.
We're gonna build an assistantaround X.
And here is the actual impact.
(28:11):
Here are the user logs.
The user logs say this job usedto take 19 minutes.
They're now doing it in five.
And let's say I only get creditfor 40% of that gain, another
40%, they're just using it tomess around and not to sell.
That's real money.
That's that's a lot of money.
And so that's how we're tryingto quantify it.
And then the other thing that Itry to uh this is my favorite
one for a CFO when they askthat.
(28:32):
I go, okay, what's the ROI onNet Suite?
And they go, What do you mean?
I go, what's the ROI on NetSuite?
How did you quantify the ROI?
Well, it's obviously betterthan the way that we Exactly.
What's the what's the ROI ofGoogle search?
Well, it's better than going tothe library.
There are what's the ROI ofSalesforce?
All of these are about makingour people more effective and
more efficient.
(28:52):
And so I think you really haveto think of AI in that bucket.
That AI CFO is net suite.
It is obviously better thanExcel docs and version control
and people not adhering toprocesses, as opposed to, you
know, yeah, I'm gonna manuallygo to Google search and LinkedIn
and do this and go to a websiteand think and blah, blah, blah.
(29:13):
Like it's obviously better andfaster.
But I think, look, if you cantell the ROI story, all the
better.
But I feel like there's athere's a gap at the the CFO
level.
I agree with you 100% on thetime at the leadership level.
And I think the reps are just,I think reps actually are just
way outpacing leaders.
I think reps are coming to yourpoint, the bottoms up play.
(29:34):
I think reps are coming up withall kinds of smart, innovative
ways to do things.
And if they even had theopportunity to learn how to
build assistants or agents, itwould be even more effective as
a part of it.
Speaker (29:45):
So there's definitely something that gravitates
towards a I think yeah, I Ithink there's definitely
elements of truth to that withat the rep level.
I have seen though, I will tellyou this I've seen a ton of
reps just using basically theseAI tools.
Get an enhanced version ofGoogle and that's it, right?
Like, that's the other thingthat I think a lot of people are
lying to themselves or abouttheir AI competency because it's
(30:08):
like I use AI every daymultiple times a day.
It's like, how do you do it?
I use it to look up stuff, likelike Google.
I'm like, well, that's that'syou're missing you're getting
like one percent of it, right?
So it's like that's anopportunity too.
Speaker 2 (30:19):
I think, but that goes back to, I mean, it it's
changed a little bit, but youknow, we'll go and we'll we'll
meet with a client and we'll bedoing something with their
revenue org.
And you say, How many of youuse Genai every day?
Probably 90% or more hands goup.
How many of you have had anytraining from your organization
on how to use it other thancompliance training?
All the hands go down, right?
(30:40):
And and I think it, but this iswe're kind of in a cycle where
sales leaders, you cannot affordto not master this.
It is our job as leaders overthe next two to three years to
completely rework the way thatpeople do their job.
Like that, this is not a newtechnology.
I'm shifting.
Hey, you used to do this thisway, now you do it this way.
You used to do it this way, nowyou do it this way.
And and that's the journey thatwe're all signing up for if
(31:01):
you're gonna be in leadershipover the next two to three
years, is you are signing up toit's the same way, like, look,
we didn't get a pick this pointin time, right?
It's like if you were a salesleader, I wasn't, or a revenue
leader or CEO back in 1995 orsix, you didn't get a pick that
the internet happened.
Somebody had instead, someonehad to retrain Brenda on how to
send an email.
Hey, Brenda, we're not doingthat anymore.
(31:21):
Hey, and uh, we're not gonnaprint our emails out anymore,
Rachel.
We're gonna do this.
Like, hey, Frank, we're notgonna send the facts anymore.
Remember the email thing.
Like, that's a real thing thathappened.
And and I think we have torealize that that's where we're
at right now.
That we are in an era right nowwhere it is our job to
completely rework the way thatour people work.
And if you as a leader are notstaying on top of this, your
(31:42):
ability to continue to earnhundreds of thousands of dollars
is gonna quickly diminishbecause I'm gonna be able to
bring someone much smarter, moreeffective, and more efficient,
and where you're just used tobeing the deals guy who just
comes, the parachutes in, givesdeal advice, parachutes out.
Guess what?
Like to your point, how howRyan and I both found out about
the power of AI was seeing howgood it is at deal evaluation.
(32:04):
And if you think you're betterthan me and Ryan, maybe you are,
but I want you to go and runyour deal evaluation criteria
through it too.
And it will be definitely a uhan awakening for you,
potentially.
Yeah.
Speaker (32:14):
I don't know.
I mean, dude, I don't know.
I I agree with you, like interms of reimagining what's
possible with work because likethere's a couple things you got
to look at is like, all right,how are roles gonna change or
how how do they need to change?
Not just like um how they'regonna organically change, but if
you're intentional about it andthen you're aligned with like
updates as they happen, that'swhen you can get like a two-year
(32:36):
head start on your competition.
And that's something that youknow I'm starting to work with
is like with clients on is likeredesigning roles and and
creating outcome charts more asopposed to you know org charts,
right?
And um, it's really pushingpeople forward.
And even if they're not at thebleeding edge of like executing
that, the fact that they'realready starting to do it now,
they're ahead of 99.9% ofpeople, is what I would say.
Speaker 2 (32:58):
All right.
So what's next?
All right.
So as we start to kind of likewind down, wrap things up here,
great conversation.
I hope everybody out there hada ton of tactical takeaways in
terms of, ooh, I like that thingRyan said.
Like, I think I can do that.
And again, the funniest part isI was at a conference last
week, Ryan.
Um, content marketing person,she was doing a presentation and
she was talking about this cuthow they turned this kind of
(33:20):
product-based asset into acustom GBT and it took off an
adoption.
And somebody, you know, anolder gentleman asked her a
question and said, you know, howlong did that take you to
build?
She has a few hours.
And it's just like, that'sthat's all it takes.
It's a few hours, and like it'syeah, if she spent another few
hours, it'd probably be like,you know, even better.
But but where do you think thisthing's going, man?
If you had to predict in maybenext six to twelve months, you
(33:43):
know, what are some of theexciting use cases?
And what are some things thatpeople need to be thinking about
today?
Speaker (33:49):
Well, that's a great question, man.
I think everybody is gonna getpromoted to be a manager, and
what I mean by that is likeyou're gonna have the capability
for folks to take advantage.
Actually, have you used likecursor two at all?
Have you looked at that or usedthat at all?
Speaker 2 (34:02):
Yeah, yeah, yeah.
Cursor lovable.
Speaker (34:06):
But no, have you seen Cursor Two, like the newest
version they just released weeksago?
Okay.
So basically, they almost havelike an agent interface window,
so you could have multipleagents running at the same time,
and you could see what they'reall doing.
So, what I think is like, andI'll do that sometimes with
Claude Code or other areas, I'llfire up one on the side and
(34:26):
have it do law inform while I'mdoing other more tactical
things, and then every now andthen I'll need to respond.
But basically, I'll kind ofhybrid and use those like
law-inform agents to do thatwhile I'm doing my main job, and
I think that's gonna be a bigchange because the reasoning
models are getting so freakinggood.
With, I mean, I don't know ifyou saw Humanity's last exam.
(34:48):
I think GPT-5 is now at 47%,which is better than most
world-class humans.
So the intelligence layer isgetting so freaking smart, and
it grew 8x in seven months interms of like from the the
quality.
So that's the other thing.
Outside of that, man, I thinklike so.
Everybody is now gonna have thecapability, especially over the
next 12 months, to have theseagents almost like sitting in a
(35:08):
window that you could manage andorchestrate that aren't like
these complex like N8N diagramsthat you see from like the
automation bros on X orLinkedIn, right?
So that's what I think is gonnacontinue to go down and they're
gonna make it easier and easierfor normal Joe's and Bob's and
Susie's and whatever and Ryan'sto use it.
And so that's what I think isgonna change over the next 12
(35:29):
months.
Speaker 2 (35:29):
I love that.
Yeah, I I agree.
I think the and and the otherthing that I'll say is that you
have to start to take time tolearn this.
And the other thing that Iagain for a lot of you, um I
really want a lot of you tothink about is this is that you
have to invest in yourself,which which by the way, it might
mean that you got to do thisstuff after hours.
(35:50):
You might need to take fivehours, 10 hours on a weekend to
learn this stuff because thealternative is what Ryan said.
I want you to picture, picturethis world, Ryan said.
You got, you know, Jenny overhere, and Ginny has four or five
automation.
She's figured this out.
She took the extra 60 hoursover the last three months to go
and mess around with Cursor 2,etc., to go build her own
(36:12):
assistant.
And you're over here beinglike, but yeah, I had to go to
Costa Rica for a two weeks.
And I had like, my friend,like, this is happening.
And I'm not that, you know, I'mnot trying to, you know, don't
get me started with like thehustle culture and all this.
This is not about hustle hard,out work, kill your quota.
This is about being super,super employable in three to
(36:35):
five years because this is avery real use case that Ryan
just gave.
He is doing this right now.
Ryan, are you a programmer?
Are you like a a never salesguy?
I mean, like, and again, likeyou know, we're we're a couple
of you know, sales leaders, youknow, who have who have kind of
(36:55):
woken up and realized that thisis where we're at.
So I just really hope everyone,again, you really start to
think about your ownprofessional development.
I don't care what level, ifyou're 25 or 55, unless you're
planning to retire in a fewyears, then maybe you're good.
But but we are entering a worldwhere not understanding what is
possible today will put youbehind the eight ball
(37:16):
significantly in, I don't know,two years, three years.
Speaker (37:20):
I mean, I think it's gonna be shorter than that, man,
with how faster things moving.
I think it's gonna be a year.
And yeah, it's crazy, it'sgoing fast, amazing
opportunities.
And like on a parting note,man, because I know we're just
about up on time, like the onething, and you were talking
about work on the weekends.
Like, if I want to use clawedcode and understand it, I might
watch like a half hour YouTubevideo, and I might only get 15
(37:42):
minutes of the way through itbecause I'm pausing and
implementing it, and it mighttake me two two hours or three
hours to do, right?
But the next time I do it, it's10 times easier.
So, like, here's the way that Iapproach it, and I was funny,
I've gotten asked this questiona lot is like, Ryan, do you
approach it where like you havevery specific outcomes you want,
or do you just free flow it?
(38:02):
And the answer is both.
There's some times where I'mlike, I gotta get this shit
done, I got a super tight timeframe, just go, go, go, go, and
I'm laser focused.
And then I have other more likeexploratory time where I'm
like, all right, this is what Ithink.
Let's see where this takes me.
And that's where I see likehelping me really advance
development in terms of uh AIusage.
Speaker 2 (38:21):
Yeah, I love that.
Again, it's it's not aboutbeing perfect, right?
It's in and it's about findinga system that works for you.
So, Ryan, I appreciate you,man.
It was good to good to chat,man.
It's been too long.
We got to set us some timeseparately to just kind of go
deep and kind of find out whatthe latest and greatest is.
So thank you so much.
I really appreciate you joiningin.
Yeah, man, it was awesome.
Thanks for having me on theshow.
That is another episode,everybody.
(38:42):
Thank you so much.
Make sure to hit that subscribebutton.
Make sure to share this withone person, one person, one
peer, one leader, somebody who'slike, man, I've talked to this
person about AI all the time.
I know they will, they'll getsomething out of this.
And make sure to leave a reviewif you enjoyed the episode on
your favorite podcast, Apple,Spotify, et cetera.
(39:03):
I always really appreciate thereviews and I take the time to
read those as well.
So until next time, everyone,go build these AI teammates we
were talking about.
I think what we're seeing is digital teammates can
kind of step in and take overfour or five different things
and really sit as like a partlike a little sidekick, a little
buddies.
A lot of reps are kind ofsitting there and just saying,
like, uh, isn't my boss supposedto build this shit for me?
Or like it, like, who's gonnahelp save me and implement Gen
(00:21):
AI for me?
Because the my boss isn't doingit and I'm just still
prompting.
Speaker (00:24):
Like, it's funny, I had an invest a group of investors
tell a C-suite that like ROIwith AI is really, really hard
and like it's it's not easy atall.
And you you, you know, like,okay, you've probably never
tried to implement anything withAI in your life, investor.
Speaker 2 (00:37):
We are in an era right now where it is our job to
completely rework the way thatour people work.
And if you as a leader are notstaying on top of this, your
ability to continue to earnhundreds of thousands of dollars
is gonna quickly diminish.
Welcome to another episode ofthe AI Powered Seller.
If you are a CRO or a salesleader who's like, hey, you just
got to figure this out and domore with less.
(00:58):
Your quota is getting ready togo up, et cetera.
You know, you're grinding 60hours a week, and now it's, you
know, more pipeline, morepersonalization, or more, more,
more than ever before, morevolume, et cetera.
I'm telling you right now,today's episode's for you.
We're gonna talk through somevery, very, very tactical ways
that sales reps and salesleaders are leveraging Gen AI to
(01:20):
cut through the noise.
Not just your prompting, notjust, oh, here's a quick tip,
but some tactical assistance,some tactical ways that you'll
be able to deploy it, whetherit's from prep, whether setting
more meetings, closing moredeals, et cetera.
And I'm super pumped fortoday's guest, Ryan Staley.
Ryan is the founder and CEO ofWhale Boss.
I've known Ryan for, I don'tknow, 10 plus years probably.
(01:42):
He's helped 2,500 go-to-marketleaders multiply output without
adding headcount.
He's taken divisions ofcompanies from zero to 30
million with just four reps, noSDRs, no marketing.
That's what I'm talking about.
And what's this guy's secret?
Why did I think he would be agood person for you to hear
from?
Is it's not treating AI like ahelper that you prompt, it's
(02:07):
training it like a teammate.
And so if you're somebodythat's stuck in prompt mode, or
maybe you're trying to figureout why AI, this episode, the
2026 AI Mindset Shift episode,is for you.
Speaker 1 (02:20):
AI-powered seller.
Speaker 2 (02:22):
All right, Ryan, excited for today's
conversation.
As usual, we're gonna talk alittle bit about AI and about
its impact.
You know, today's episode's allabout mindset in 2026.
So help me to understand foryou.
When did you realize that AIwas not another technology?
Like, where was there a momentwhere you started to realize
(02:44):
yeah, this is like different,different?
Speaker (02:46):
Yeah.
Uh great question, Matt.
So I think like, and by theway, thanks for having me on.
Love, love being on the showand everything like that.
So I'm excited.
I guess like to answer thatquestion, there's kind of two
really core things, or maybethree things that happen.
One was like I had a guest onmy podcast called the Scale Up
Show, where about three yearsago, uh Chris Savage, who is the
(03:07):
founder and CEO of Wistia, hadme on.
And afterwards, he's like, HeyRyan, he's like, Have you heard
of the tool Dolly?
And I'm like, What the hell isDolly?
This is like like the imagegeneration version one, where it
was like, it was terrible, man.
It was absolutely brutal.
But because of that, I got onearly access to ChatGPT.
So that was like kind of myepiphany moment, right?
When I started using it, Iguess what really internalized
(03:29):
it for me was that remember whenthey had on LinkedIn, like,
hey, let's see if AI couldreplace me with my job.
And there was like peopletesting it out.
This was like GPT 3.5, and itwas like all over the place.
And people are like, Yeah, meh,it only does like 60% of what I
could do.
I'm fine, right?
Like, that was people'sattitude, right?
Well, what I saw there waslike, I'm like, I'm gonna stress
(03:49):
test this against like whattook me, something that took me
10 years to learn in enterprisesales.
And that was really how buyerswere like evaluated and stated,
what was specific to theirvertical niche.
Um, and then what really drovethe business all the way from
like an executive perspectivedown to like an individual
department, all the way up tothe board and investors, right?
And it got 95% of the way therein three questions.
(04:11):
And so that was one of thethings that, like, absolutely
I'm like, holy shit, this isgonna be completely different
than everything else I've everseen.
So I would say those were kindof like the key moments in time.
Speaker 2 (04:20):
Yeah, I had one very similar.
I remember afterwards, and nowI've I've kind of coined this, I
call it like the AI pit ofdespair, where you're like,
you're really excited about itand you're like, wow, we can do
this and this and this, and thenyou test it and it does things.
You go, oh my gosh, like whatdoes this mean?
And then you fall into the pit,and then you kind of come out
the other side where it was likeit was it was actually, I
think, maybe the exact same,like a deal evaluation thing
(04:40):
where it's like, all right,well, can AI actually break down
and help to give advice withreally no context on like what
are the steps in a good likemid-market enterprise deal?
And it gives the advice.
I'm like, pretty good.
Like, that's like 80, 90%there, like and it has always
like one or two good ideas.
You're like, oh yeah, that'sprobably smart.
Right.
And then it goes and finds thestakeholders in real time for
(05:02):
you and everything.
So I think a lot of people havehad that moment.
And and for those of youlistening, don't be scared of
that moment.
Like, it is what it is.
That's what I try to tell a lotof sales leaders, Ryan, is
like, look, you have to knowwhat this thing is capable of so
you can harness it, right?
And and I think that kind ofsegues into this next uh
question I've got.
One of the things you said isAI isn't just about
(05:23):
productivity, it's aboutliberating intelligence.
So if I'm not answering dealquestions, what can I do?
How is this liberating myintelligence if my job isn't as
a sales leader to answer theexact same question 500 times in
a year?
Speaker (05:36):
Good question, man.
Okay.
So we could hit this on a lotof different areas.
I think like I've seen it witha wide range and I've used it,
and I'm gonna use some likenon-work examples and then lead
into work examples, if thatmakes sense.
So I think, you know, one ofthem actually was a guest I had
on my show.
He he basically journaledelectronically, put all his
journals into general entriesinto a GPT, and he had lots of
(05:59):
stuff about how he worked withhis son.
And his son, I think, had likeextreme ADHD and some other like
challenges that made it hardfrom a parenting perspective to
really like understand like howto work.
And so he would actually relyon and kept updating the
instructions on how to work, andit helped him like kind of
co-parent in like anon-objective way.
(06:19):
And he said it's worked outreally, really well for his and
his son's relationship.
So, like that's one examplewhere it's like you're tapping
into a mind of someone else todo that um from a health
perspective.
So that's like yeah, parenting,right?
From a health perspective, oneof the things I did is um
basically I have um I had like achronic condition um that was
(06:40):
happening.
I'm not gonna really get intoit, but it was something that I
went to multiple doctors on andI asked them, you know,
questions.
They're like, try this, Ryan,try that.
Um didn't work.
Nobody could uh diagnose whatit was.
I took all my blood hormonetests, created a really killer
like prompt around being like apattern recognition expert in
terms of like health and chronicillnesses, and it basically
(07:03):
identified it for me in a snap,and it's pretty much gone now.
So, like that's on the healthside, right?
So I'm not a doctor by anymeans, and I'm I'm you know,
don't have that skill set.
And then last but not least islike I've seen executive teams
do top-down and bottom-upplanning for the entire year and
with like KPIs and veryspecific, like 45 minutes,
(07:24):
right?
That process used to take days.
So those are three like coreexamples that come to mind.
Speaker 2 (07:28):
Yeah, and I think the key is like what you're getting
at.
I mean, it it was able to siftthrough like data.
It wasn't and it was able tokind of pull through and pull
out it to get to like firstversion of insights quickly.
And I think for a lot ofpeople, that's how we have to
think about this because thenyou still had to turn your brain
on, right?
Then you still have to say,hey, as an exec team, how can we
(07:49):
actually manage this?
Is this possible?
You know, even going back tolike your health piece.
It's like, okay, this hasgotten me to hear.
Now let's go validate.
Let me go inspect, and it's alittle bit more of this or a
little bit more of that.
That's whenever I hear, youknow, what you said around call
it creating, you know, space formore, you know, uh, I call it
like creativity, you know,resourcefulness, et cetera.
(08:11):
That's what I love about it,right?
Is like I can get now to V inthe same amount of time it took
me to get to a rough draft.
And that to me is where I feellike the unlock is I'll I'll
give you a really practicalexample.
One of our clients, they'regetting ready to plan for SKO.
And she surveyed the entireorg, 50 plus people responded.
And then she's like, okay,let's summarize this and put it
in.
I was like, okay, there's twodifferent ways I could say
(08:33):
they're summarized.
You can go read every singleone.
And look, let's be honest.
Some AI, if it's reading 50different rows and nine and 80
columns, it's gonna mess up.
Like it's still not perfect interms of those sense.
Or I could just summarize itwith Chat GPT Pro and it'll take
10, 15 minutes and it'll bepretty good.
And it's like, it's that's thatto me is a good example.
(08:54):
It's like, I probably don'tneed to pour over all of this.
I now can actually trust butverify, I can get a really good
like outcome, spend another hourjust kind of combing through
for the nuances instead oftaking five hours.
And I think that's where when Ithink about liberating
intelligence, it just allows youto save time and also do a more
thorough job, you know?
Yeah.
When people are already, youknow.
(09:15):
Okay, look, if you are somebodywho can feel what we're talking
about, these different AI usecases, you're like, Jake, how do
I possibly make the time?
We have got you covered.
Okay.
So if you're getting value fromthis episode, make sure to
subscribe to the AI PoweredSeller Podcast.
We do episodes every week whereI'm interviewing somebody or
talking about what I'm seeing inthe market.
(09:36):
And make sure to pick up a copyof the innovative seller, USA
Today bestseller that I wrotearound what you need to know
about sales in the future andthe sales around AI, sales with
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Subscribe to the podcast andmake sure to go to Amazon, pick
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Speaker (09:54):
I was kind of like you where I was naturally born
through the the uh the the thechild raising of sales, right?
Like there's a lot of othergo-to-market activities, and
like I didn't grow up being amarketer.
I didn't grow up being in abunch of different areas.
Now, granted, I touched allthem with the roles I did, but
like if I just apply certainconcepts and frameworks, I could
operate at a level of a peerthat's been doing the job for 25
(10:16):
years.
So, like that's anotherexample, man, where it's just
like like ancillary skill setsthat are close but not dead on
with what your experience levelis.
That's where there's hugeopportunity.
Speaker 2 (10:26):
I think that that's the that where a lot of,
especially if you're a youngerseller and you're listening,
that it can just help you get upto speed.
You know, for example, youknow, when I was getting up to
speed at a company, I got abinder that had a bunch of
industry insights in it.
And it was like, you know,here's what's going on in
manufacturing and this and thisand this and and all these
things.
And so I, you know, it took me,you know, nine to 12 months
(10:48):
worth of con.
And I was a good, I was reallygood.
It took me nine to 12 months toget up to the speed where I
could have an intelligentconversation with a business
owner in manufacturing and thenswitch gears and talk to someone
in pest control and then switchgears and talk to someone in
tech sale.
It took a long time.
Whereas now I can get theinsights.
And I think one of the thingsI'm curious to hear your thought
on a lot of what we're talkingto our clients about right now
(11:09):
is there's two different levelsto think about AI productivity.
There's one, which is gettingthem access to information and
insights faster.
But number two is retention,retaining the information.
And so, how do you think aboutthese two?
Because a lot of like, I'llgive you a good example.
We built an account researchassistant for one of our
clients, and she goes, I wantyou to at the end of every
single one of these as promptthem with a five question trivia
(11:32):
game to make sure they actuallyremember.
And I was like, that's a reallygood idea.
Like, we need because then theyactually remember it.
So, how do you think about youknow I've seen conflicting
studies?
MIT says it's making us youknow dumber.
Other people have said actuallyit's gonna unlock the
intelligence.
How do you think about thebalance of like speed to getting
the information and parrotingit versus actually retaining it
(11:53):
so you actually can become atrue professional?
Speaker (11:54):
It's a really good question, man.
I think I don't say it's makingus dumber.
I think it makes us smarter anddifferent.
Or right, it can make youdumber if you if you go down
that path, just like any socialmedia tool can make you dumber,
right?
Just by by using it.
So, in terms of like retention,I think like, and this is what
I see with my clients too, withlike large-scale AI rollouts, is
(12:17):
like the only path toretention, in terms of my
opinion, is like doing right,like because like you could have
a deep research before it spit50 pages out, but you're not
gonna remember all that shit,right?
So if you however, if you startto implement it, and that's
where it gets it gets reallyexciting.
I'll give you an example.
This is like another kind oflike apple flying on my head.
I was like, I remember onemorning and it was right after
(12:39):
voice came out, and this waslike GPT 4, not even 4.0.
And I'm like, I was shaving,I'm like, hey, you know what?
Like, there's this book I'vealways wanted to read, but I
don't have time to.
And so I'm just like, screw it,I'm gonna put on voice.
So I threw it on voice.
I'm like, apply, you know, the8020 principle and deconstruct
this book into two pages, giveme all the high points and
quotes with exact examples,right?
(13:00):
Something along those lines.
And boom, it busted it out, butit verbally talked to me while
I was shaving.
I was like, all right, that'scool.
I'm like, this is my business,this is what I'm doing, this is
what I'm focused on.
Customize this book so I canimplement this tomorrow, right?
And it gave me an exact likeimplementation plan.
I go now make checklists andsheets in a daily routine that I
could use to do that, right?
So, like, that's a quick pathbecause it goes all the way from
(13:20):
like idea to execution in likeminutes.
So that's what I think helpswith retention as well.
Speaker 2 (13:24):
Yeah, okay.
And I think this is a goodtransition.
So a lot of what we're talkingabout is using AI to do stuff we
already know, right?
Or or some some flavor of that,right?
It's like, hey, I've got anassistant.
Hey, AI, can you do ABC?
I want to talk about theconcept of a teammate.
And we're talking a lot aboutthis.
We're kind of coining thisterm, this idea of like a
digital teammate, right?
(13:45):
Which is somebody who has, youknow, it really is just a series
of automations that are justkind of orchestrated together.
I mean, at the end, if you kindof look at its insides, like
its skeleton and its its organs,maybe just explain what that
means to you.
Like, what's the differencebetween an assistant and a
digital teammate?
And and where do you see theimpact?
Let's start with like for salesreps, and then also let's go
(14:08):
for for leaders as well.
Speaker (14:09):
Yeah, I think um like everybody kind of like defines
it differently, right?
So I think like the bestprobably, and this is a great
question, Jake.
You're asking me.
So, like if I was if I were touse a teammate, it's usually
like like a like a co-pilotcould just be for like a single
function, right?
Like, like you're talking aboutthat research assistant, like
(14:30):
boom, bust out enterpriseaccount research, do this,
customize it to my company, allthat stuff, right?
Spits it out.
A teammate, I think, would besomething that could do a string
of different activities whenyou either link them together,
right?
So you have multiple kind ofassistants linked together to do
that, or you have someone thatthat does autonomous or
semi-autonomous work for you.
So, for example, if I'm using atool called GenSpark, right?
(14:52):
I could take a recording likethis that I'm doing with an
explainer and then infuse thetranscription and then have it
totally put together my entirenewsletter as well as thumbnails
for the YouTube design, and itdoes all that in like a couple
minutes, right?
That's like a multi-stepprocess.
And then if we're looking at itfrom a leadership perspective,
and I think there's still a lotof work to be done, and that
that's why I would say more froman individual contributor,
(15:14):
right?
We're talking from a leadershipperspective, it's the same
thing.
It's like, all right, I'm aboutto have a deal review with my
rep, a deal strategy.
Here's the transcripts, analyzeall these, give me ideal nest
best actions and holes, right?
That's an example.
Or if I was like a leader whereit would be a little bit
different, I would look at moreof like an orchestrated teammate
structure.
That would be like where you'retaking like transcripts, you're
(15:37):
taking support calls, you'retaking um, you know, details
from your chat bot, integratingall those together, creating a
customer brain, and thenspitting that out, right?
Speaker 2 (15:45):
Okay, if you are somebody who just heard what
Ryan laid down and you aresaying, My gosh, where am I
gonna find the time for this?
The AI certification course isit, right?
Shout out.
We are wrapping up our veryfirst cohort, which is really
exciting.
We've we've got the rep track,we've got the manager track,
you'll see the AI certificationbadges all over LinkedIn.
(16:05):
And DM me, shoot me a note onLinkedIn, we'll put a link there
if you're interested in signingup for the next cohort, or
check out the link, the pagesthat I'll link to below for the
landing pages, you could justsign up yourself.
But DM me, happy to give youmore insight into what other
people are doing to carve outthat so, so precious time and
get up to speed in just 12 to 24hours on what's the latest and
(16:29):
greatest with AI.
I'll tell you how we'rethinking about this is that when
you go to a client or anorganization and you're like,
okay, so here's how this works.
We take the Zoom API, we pullit in, we run it to three or
four assistants.
That's like your call grading'sgreat, you know, framework,
skills, whatever.
Then we're gonna, you know,ship that to Slack, ask for a
little bit of feedback, and thenput the output into a Google
Doc for the rep to be able toreview.
(16:50):
I'm just making something up,or push it to Salesforce or push
it to, you know, whatevertemplate.
We find that that's difficultfor people to comprehend.
If instead, and and notcomprehend, but more of just
like really get a picture of,instead, if you say, hey, Ava,
Ava is our digital teammate thatdoes your call scoring.
And what Ava does is Ava takesyour call, runs it through our
(17:11):
four or five step rubrics, andthen comes back to you with a
personal development plan thatfeeds off of the previous
conversations.
We find that that is morepalatable, you know, and it's
like, oh, cool.
Like, and it's also like, Ithink, less threatening, maybe,
and understanding of like, hey,what is an agent, what is an
assistant do, et cetera.
So for us, the concept ofdigital teammates, and even for
us, we're we're thinking nowabout like we're adding digital
(17:34):
teammates into ouraccountability chart.
Like we're building in like aconsulting ops digital teammate.
And what they do is they, youknow, running a consulting
business, they analyze hours,they analyze project milestones,
and on a daily, weekly basis,they're like, hey, what's going
on?
Like this one's behind.
Do you need a new template?
All those types of thingsthey're able to do.
And so I think I think of adigital teammate as something
(17:55):
that is orchestrating, usuallyI'm gonna call it more
operational or or consistenttasks, because even call
scoring, right?
Like if you go to a leader, heor she, you know, if you put the
same call in front of them,different reps, they're gonna
give probably similar advice.
And so I think what we'reseeing is digital teammates can
kind of step in and take overfour or five different things
(18:17):
and really sit as like a part,like a little sidekick, a little
buddy, right?
Ryan, that's like sitting therehelping you to do things
throughout the day.
So those are just like a coupleof examples.
Speaker (18:28):
Yeah, I mean, everybody gets freaked out about getting
replaced to some aspect of it,right?
Or these AI tools becomingSkynet, taking over everything.
So the other thing, too, andI'm sure you've seen this, is
like the branding of what anagent can do versus the actual
execution of what an agent cando is massively different for a
lot of companies, right?
It's like night and daydifference.
(18:48):
Um, that's something always toconsider too, right?
If you're looking through it.
So I do like the teammatesconcept and I use that as well
on a continuous basis.
Speaker 2 (18:55):
Well, what do you okay?
So what I mean, for you, Imean, you've it says, you know,
you've run 500 plus AI usecases.
Like, what would you say ifsomebody's out there, whether
it's a digital teammate orseries of assistants, do you
have, I don't know, maybe liketop few where you're like, hey,
if you're a and let's start withthe rep, right?
Because I think here's whathappens.
A lot of reps are kind ofsitting there and just saying,
(19:16):
like, uh, isn't my boss supposedto build this shit for me?
Or like, it, like, who's gonnahelp save me and implement Gen
AI for me?
Because the my boss isn't doingit and I'm just still
prompting.
If if I was a rep today, okay,and let's say I had I had the
ability to build out anassistant, my team had paid for
ChatGPT, my team had paid forMicrosoft Copilot, my team had
(19:36):
paid for Jim and I can build agym.
What would you what would bethe top one or two things you
would tell them to build in youknow the first you know month or
two?
Speaker (19:45):
I would say, like, I don't think it's the same across
the board because you have likehigh velocity SMB reps that are
churning and going throughdemos left and right versus
mid-market versus enterprise,like on the sales side, right?
And then you know, existingaccounts.
So the way I kind of look at itis like either there's kind of
like three ways to attack it.
One is like, what's the numberone blocker to you hitting your
(20:08):
KPI or goal, right?
So that's more like outcomedriven.
Two is like, what do you wastea ton of time on as a rep?
And then three is like, what doyou hate doing?
Right.
Like you could look at itthrough any lens just to start
to facilitate adoption and do itthat way.
And so, for example, let's sayyou're you're on the enterprise
side and you're doing massiveaccount research, then like map
(20:30):
out all your ideas and whatyou're doing, and then create it
once and ask for like, youknow, open AI to create, or I'm
sure to say Chat GPT to createcustom GPT instructions for that
exact process.
And then what it'll do is it'lltake that process that took 45
minutes to do and turn it intolike a 30-second process, and
then you just kind of iterate onit, right?
Like the time that that itwould take you to do one
(20:51):
research process with that wouldbasically it would finance from
a time perspective the cost tomake one to infinitely get you
know 35 minutes every timemoving forward.
So I think that's super easy.
Speaker 2 (21:03):
Research would be research would be one that you
would peg then, like again, likebasically building something
out.
Speaker (21:08):
Yeah, and that's like I hate saying that because that's
that's common, right?
But like another one is nextbest action.
Like, I think next best actionwith like integrating your sales
methodologies into that withtranscripts is so freaking easy.
It used to take me 45 minutesor an hour to do that.
Now I could do it in 30seconds, and it's probably
better than what I would do if Idid it all manually looking
(21:30):
through my notes.
So that's another example, iswhat I would say.
How about you, man?
What do you think are your toptop couple that come to mind?
Speaker 2 (21:36):
I think look, to me, research is a no-brainer that
and again to because to yourpoint, you're like, yeah,
everybody says it, but mostpeople are just prompting.
And by the way, prompting islike not bad, right?
If you're like, hey, I'm doingresearch, blah, blah, blah.
The problem is most reps arestill, and most people I think
are still using very basicprompting.
They're not layering things in.
So it's like, I want to do thisand this and this and this and
(21:57):
this and this.
And that's where, you know, youdon't want necessarily copy and
paste anymore.
It would be easier for anassistant to just ask you those
questions.
And so I think there's like,you know, if you're somebody
who's consistently doingenterprise deal, what is your
enterprise research process?
Well, great.
Just put that all into custominstructions inside of a gym or
an agent or a custom GPT.
And then it says, great, what'sthe account we're working on
(22:19):
today, Jake?
And it's like, uh, we'reworking on this one.
And you could even upload adocument of like three or four
of your best account, you know,research plans you've ever done.
So I think research is anabsolute no-brainer.
The other big one, with more,again, maybe not less on the rep
side, but I think digital C Sslash digital S E, like, I don't
need any more.
Like, I'd say those areprobably some of the more common
(22:39):
ones, Ryan, that we're buildingout out of the gate.
Is I don't need to loop in ahuman to say, does this
integrate with Azure or not?
Or what are the five thingsthat I need to think about
around A, B, C, or D?
And so for me, I think I'mlooking at these use cases where
where is there information thatisn't really value add in the
(23:00):
customer lifecycle and reallyisn't even value add between the
two people that areinteracting, right?
Like product data.
Hey, I'm a customer, I have aquestion, hey, I'm an inbound
lead, I want to book a meeting.
Like, I think that there arecertain use cases at the exec
level, customer success, digitalSE, inbound, that are kind of
those to me for the theexecutive level are no-brainer.
And then I'll call it likeresearch and prospect insights.
(23:22):
We've got kind of a uh amessage framework we call the
triangle, which is it basicallysays, okay, for this persona in
this sub-industry, what are thetrends that that that persona is
facing in that sub-industrythat we actually help to solve
for?
And that's where Gen AI isreally good.
It's like trends for industrialmanufacturing, especially it's
like specifically heavyequipment machine manufacturing
(23:44):
for a VP of operations, here arethe top three headwinds this
person's facing.
And you you have a product thatdoes X, here are the three
things you should talk to themabout.
And that's where you know thatused to take someone 15 years in
an industry.
So I think building anassistant that knows, you know,
your version of good messaging,an assistant that knows your
version of great research,that's going to get you a long
way.
And then I like the one yousaid, that's probably the other,
(24:06):
if I had to pick a third, whichwe'd call that deal strategy
evaluation, where it knows, andwhat we have it do is it looks
at competitive threats, it looksat stakeholder map threats,
right?
Hey, you're only talking tothese two people.
Typically, your deal has a CFO.
I by the way, I found it.
It's Lisa Henderson.
Here's her LinkedIn, here'sfive things that she just talked
about.
(24:26):
So being able to build anassistant that can, I don't need
to go ask my boss.
I call it 100% deal coverage.
Yeah, I'm gonna talk to my bossabout the top 15%, 20% of
deals, but I can actually run100% of my deals through some
type of evaluation frameworkthat should help to increase my
close rate by five, 10%.
You know, so those are yeah,those are some of my, I don't
(24:47):
know, like go-to go-to's as apart of it.
Tell me a little bit right now,what's holding people back?
So we're talking about theseuse cases, right?
Of like implementing thesetools, the time savings is very
obvious.
What do you feel like isholding people back right now?
Why do you feel like morepeople aren't leaning in?
I know, look, we're all busy,everyone's busy, but why do you
feel like more most peoplearen't leaning in further?
Speaker (25:09):
So, and it's a great question, man.
I think like there's there itlike I think there's naturally
people who are hungry to learnand others that aren't.
And like, you know, obviouslyyour brain rationalizes to save
energy and avoid pain, right?
So, like those are the two corethings it tries to do every
day.
And so, like, there's a couplethings that it influence.
I think what's holding peopleback is like things are moving
(25:32):
faster and faster every day interms of the number of releases,
the quantity of releases, thenumber of SaaS tools that are
released.
And so it's just sooverwhelming that people decide
to do nothing, right?
Like, I think that's numberone.
Number two is I would say, andlike, it's why your business is
doing well and my business doingwell right now, is like um if
(25:52):
companies aren't like sponsoringthis and saying this is a
priority, then most people don'tcome to that conclusion on
their own.
There's a fraction of powerusers that do, right?
And those are the power users.
And then if that doesn't happenthough, innovation happens in
the dark and you lose all thatinsane tribal knowledge
integrated with AI for thosepower users.
If you if you like bring it alltogether through like a
(26:15):
corporate-led approach with atop-down and bottom-up, then
that's when you start to reallysee things take off.
So that's what I would say,man.
Top of brain.
What do you feel like?
Speaker 2 (26:24):
What do you feel like at the top?
What's stopping people at thetop from diving in?
Why do you feel like leadersare, and again, maybe they're
not reticent, but they're notdoing it.
Why do you feel like from thetop down there's struggle points
to kind of really get startedon this AI journey?
Speaker (26:39):
Yeah, I think a couple points.
I think, you know, one is a lotof it's fear-driven, to be
honest with you.
And so now that we're reachingmore of a level of maturity,
like it's funny.
I had an invest a group ofinvestors tell a C-suite that
like ROI with AI is really,really hard and like it's it's
not easy at all.
And you you, you know, like,okay, you've probably never
(27:00):
tried to implement anything withAI in your life, investor.
Um so that's one aspect of it.
I think the other thing at thetop of like why someone wouldn't
is like the median tenure of aCRO is 15 months, right?
So it's like their their timeto execute is so freaking tight.
Um if they don't do that andthey just look at this as like
another barrier sometimes ofjust focusing on just doing the
(27:23):
work of like hitting the number,right?
So I think that's the otherthing, man.
That's super, super critical.
What do you think on that side?
Speaker 2 (27:29):
Are you saying the same thing?
I mean, time is certainly apart of it.
ROI, here's what I would tellyou.
Just in general, and all mysellers know this time savings
is the worst sales argument.
We as humans struggle strugglestruggle to properly credit
certain initiatives as like thecorrelation or direct impact on
a productivity gain metric,right?
(27:50):
We love revenue gains.
We love uh, you know, whetherthat's you know dollars or
whether that's volume um base,but I'll just in general,
productivity gains aredifficult.
Now, the good news is how youknow how we're doing it with AI
is we're mapping how long a jobtakes to be done today.
Okay, this is what ishappening.
We're gonna build an assistantaround X.
And here is the actual impact.
(28:11):
Here are the user logs.
The user logs say this job usedto take 19 minutes.
They're now doing it in five.
And let's say I only get creditfor 40% of that gain, another
40%, they're just using it tomess around and not to sell.
That's real money.
That's that's a lot of money.
And so that's how we're tryingto quantify it.
And then the other thing that Itry to uh this is my favorite
one for a CFO when they askthat.
(28:32):
I go, okay, what's the ROI onNet Suite?
And they go, What do you mean?
I go, what's the ROI on NetSuite?
How did you quantify the ROI?
Well, it's obviously betterthan the way that we Exactly.
What's the what's the ROI ofGoogle search?
Well, it's better than going tothe library.
There are what's the ROI ofSalesforce?
All of these are about makingour people more effective and
more efficient.
(28:52):
And so I think you really haveto think of AI in that bucket.
That AI CFO is net suite.
It is obviously better thanExcel docs and version control
and people not adhering toprocesses, as opposed to, you
know, yeah, I'm gonna manuallygo to Google search and LinkedIn
and do this and go to a websiteand think and blah, blah, blah.
(29:13):
Like it's obviously better andfaster.
But I think, look, if you cantell the ROI story, all the
better.
But I feel like there's athere's a gap at the the CFO
level.
I agree with you 100% on thetime at the leadership level.
And I think the reps are just,I think reps actually are just
way outpacing leaders.
I think reps are coming to yourpoint, the bottoms up play.
(29:34):
I think reps are coming up withall kinds of smart, innovative
ways to do things.
And if they even had theopportunity to learn how to
build assistants or agents, itwould be even more effective as
a part of it.
Speaker (29:45):
So there's definitely something that gravitates
towards a I think yeah, I Ithink there's definitely
elements of truth to that withat the rep level.
I have seen though, I will tellyou this I've seen a ton of
reps just using basically theseAI tools.
Get an enhanced version ofGoogle and that's it, right?
Like, that's the other thingthat I think a lot of people are
lying to themselves or abouttheir AI competency because it's
(30:08):
like I use AI every daymultiple times a day.
It's like, how do you do it?
I use it to look up stuff, likelike Google.
I'm like, well, that's that'syou're missing you're getting
like one percent of it, right?
So it's like that's anopportunity too.
Speaker 2 (30:19):
I think, but that goes back to, I mean, it it's
changed a little bit, but youknow, we'll go and we'll we'll
meet with a client and we'll bedoing something with their
revenue org.
And you say, How many of youuse Genai every day?
Probably 90% or more hands goup.
How many of you have had anytraining from your organization
on how to use it other thancompliance training?
All the hands go down, right?
(30:40):
And and I think it, but this iswe're kind of in a cycle where
sales leaders, you cannot affordto not master this.
It is our job as leaders overthe next two to three years to
completely rework the way thatpeople do their job.
Like that, this is not a newtechnology.
I'm shifting.
Hey, you used to do this thisway, now you do it this way.
You used to do it this way, nowyou do it this way.
And and that's the journey thatwe're all signing up for if
(31:01):
you're gonna be in leadershipover the next two to three
years, is you are signing up toit's the same way, like, look,
we didn't get a pick this pointin time, right?
It's like if you were a salesleader, I wasn't, or a revenue
leader or CEO back in 1995 orsix, you didn't get a pick that
the internet happened.
Somebody had instead, someonehad to retrain Brenda on how to
send an email.
Hey, Brenda, we're not doingthat anymore.
(31:21):
Hey, and uh, we're not gonnaprint our emails out anymore,
Rachel.
We're gonna do this.
Like, hey, Frank, we're notgonna send the facts anymore.
Remember the email thing.
Like, that's a real thing thathappened.
And and I think we have torealize that that's where we're
at right now.
That we are in an era right nowwhere it is our job to
completely rework the way thatour people work.
And if you as a leader are notstaying on top of this, your
(31:42):
ability to continue to earnhundreds of thousands of dollars
is gonna quickly diminishbecause I'm gonna be able to
bring someone much smarter, moreeffective, and more efficient,
and where you're just used tobeing the deals guy who just
comes, the parachutes in, givesdeal advice, parachutes out.
Guess what?
Like to your point, how howRyan and I both found out about
the power of AI was seeing howgood it is at deal evaluation.
(32:04):
And if you think you're betterthan me and Ryan, maybe you are,
but I want you to go and runyour deal evaluation criteria
through it too.
And it will be definitely a uhan awakening for you,
potentially.
Yeah.
Speaker (32:14):
I don't know.
I mean, dude, I don't know.
I I agree with you, like interms of reimagining what's
possible with work because likethere's a couple things you got
to look at is like, all right,how are roles gonna change or
how how do they need to change?
Not just like um how they'regonna organically change, but if
you're intentional about it andthen you're aligned with like
updates as they happen, that'swhen you can get like a two-year
(32:36):
head start on your competition.
And that's something that youknow I'm starting to work with
is like with clients on is likeredesigning roles and and
creating outcome charts more asopposed to you know org charts,
right?
And um, it's really pushingpeople forward.
And even if they're not at thebleeding edge of like executing
that, the fact that they'realready starting to do it now,
they're ahead of 99.9% ofpeople, is what I would say.
Speaker 2 (32:58):
All right.
So what's next?
All right.
So as we start to kind of likewind down, wrap things up here,
great conversation.
I hope everybody out there hada ton of tactical takeaways in
terms of, ooh, I like that thingRyan said.
Like, I think I can do that.
And again, the funniest part isI was at a conference last
week, Ryan.
Um, content marketing person,she was doing a presentation and
she was talking about this cuthow they turned this kind of
(33:20):
product-based asset into acustom GBT and it took off an
adoption.
And somebody, you know, anolder gentleman asked her a
question and said, you know, howlong did that take you to
build?
She has a few hours.
And it's just like, that'sthat's all it takes.
It's a few hours, and like it'syeah, if she spent another few
hours, it'd probably be like,you know, even better.
But but where do you think thisthing's going, man?
If you had to predict in maybenext six to twelve months, you
(33:43):
know, what are some of theexciting use cases?
And what are some things thatpeople need to be thinking about
today?
Speaker (33:49):
Well, that's a great question, man.
I think everybody is gonna getpromoted to be a manager, and
what I mean by that is likeyou're gonna have the capability
for folks to take advantage.
Actually, have you used likecursor two at all?
Have you looked at that or usedthat at all?
Speaker 2 (34:02):
Yeah, yeah, yeah.
Cursor lovable.
Speaker (34:06):
But no, have you seen Cursor Two, like the newest
version they just released weeksago?
Okay.
So basically, they almost havelike an agent interface window,
so you could have multipleagents running at the same time,
and you could see what they'reall doing.
So, what I think is like, andI'll do that sometimes with
Claude Code or other areas, I'llfire up one on the side and
(34:26):
have it do law inform while I'mdoing other more tactical
things, and then every now andthen I'll need to respond.
But basically, I'll kind ofhybrid and use those like
law-inform agents to do thatwhile I'm doing my main job, and
I think that's gonna be a bigchange because the reasoning
models are getting so freakinggood.
With, I mean, I don't know ifyou saw Humanity's last exam.
(34:48):
I think GPT-5 is now at 47%,which is better than most
world-class humans.
So the intelligence layer isgetting so freaking smart, and
it grew 8x in seven months interms of like from the the
quality.
So that's the other thing.
Outside of that, man, I thinklike so.
Everybody is now gonna have thecapability, especially over the
next 12 months, to have theseagents almost like sitting in a
(35:08):
window that you could manage andorchestrate that aren't like
these complex like N8N diagramsthat you see from like the
automation bros on X orLinkedIn, right?
So that's what I think is gonnacontinue to go down and they're
gonna make it easier and easierfor normal Joe's and Bob's and
Susie's and whatever and Ryan'sto use it.
And so that's what I think isgonna change over the next 12
(35:29):
months.
Speaker 2 (35:29):
I love that.
Yeah, I I agree.
I think the and and the otherthing that I'll say is that you
have to start to take time tolearn this.
And the other thing that Iagain for a lot of you, um I
really want a lot of you tothink about is this is that you
have to invest in yourself,which which by the way, it might
mean that you got to do thisstuff after hours.
(35:50):
You might need to take fivehours, 10 hours on a weekend to
learn this stuff because thealternative is what Ryan said.
I want you to picture, picturethis world, Ryan said.
You got, you know, Jenny overhere, and Ginny has four or five
automation.
She's figured this out.
She took the extra 60 hoursover the last three months to go
and mess around with Cursor 2,etc., to go build her own
(36:12):
assistant.
And you're over here beinglike, but yeah, I had to go to
Costa Rica for a two weeks.
And I had like, my friend,like, this is happening.
And I'm not that, you know, I'mnot trying to, you know, don't
get me started with like thehustle culture and all this.
This is not about hustle hard,out work, kill your quota.
This is about being super,super employable in three to
(36:35):
five years because this is avery real use case that Ryan
just gave.
He is doing this right now.
Ryan, are you a programmer?
Are you like a a never salesguy?
I mean, like, and again, likeyou know, we're we're a couple
of you know, sales leaders, youknow, who have who have kind of
(36:55):
woken up and realized that thisis where we're at.
So I just really hope everyone,again, you really start to
think about your ownprofessional development.
I don't care what level, ifyou're 25 or 55, unless you're
planning to retire in a fewyears, then maybe you're good.
But but we are entering a worldwhere not understanding what is
possible today will put youbehind the eight ball
(37:16):
significantly in, I don't know,two years, three years.
Speaker (37:20):
I mean, I think it's gonna be shorter than that, man,
with how faster things moving.
I think it's gonna be a year.
And yeah, it's crazy, it'sgoing fast, amazing
opportunities.
And like on a parting note,man, because I know we're just
about up on time, like the onething, and you were talking
about work on the weekends.
Like, if I want to use clawedcode and understand it, I might
watch like a half hour YouTubevideo, and I might only get 15
(37:42):
minutes of the way through itbecause I'm pausing and
implementing it, and it mighttake me two two hours or three
hours to do, right?
But the next time I do it, it's10 times easier.
So, like, here's the way that Iapproach it, and I was funny,
I've gotten asked this questiona lot is like, Ryan, do you
approach it where like you havevery specific outcomes you want,
or do you just free flow it?
(38:02):
And the answer is both.
There's some times where I'mlike, I gotta get this shit
done, I got a super tight timeframe, just go, go, go, go, and
I'm laser focused.
And then I have other more likeexploratory time where I'm
like, all right, this is what Ithink.
Let's see where this takes me.
And that's where I see likehelping me really advance
development in terms of uh AIusage.
Speaker 2 (38:21):
Yeah, I love that.
Again, it's it's not aboutbeing perfect, right?
It's in and it's about findinga system that works for you.
So, Ryan, I appreciate you,man.
It was good to good to chat,man.
It's been too long.
We got to set us some timeseparately to just kind of go
deep and kind of find out whatthe latest and greatest is.
So thank you so much.
I really appreciate you joiningin.
Yeah, man, it was awesome.
Thanks for having me on theshow.
That is another episode,everybody.
(38:42):
Thank you so much.
Make sure to hit that subscribebutton.
Make sure to share this withone person, one person, one
peer, one leader, somebody who'slike, man, I've talked to this
person about AI all the time.
I know they will, they'll getsomething out of this.
And make sure to leave a reviewif you enjoyed the episode on
your favorite podcast, Apple,Spotify, et cetera.
(39:03):
I always really appreciate thereviews and I take the time to
read those as well.
So until next time, everyone,go build these AI teammates we
were talking about.
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