October 1, 2025 • 26 mins
Most sellers say they “use AI,” but the real question is: is AI actually running your sales workflow? We pull back the curtain on what true AI proficiency looks like, why dabbling won’t keep you competitive, and how to jump from basic prompts to digital teammates that own the work. This isn’t a tool tour—it’s a working blueprint for transforming prospecting, research, coaching, and follow-through so you win more deals with less manual drag.
We map the five levels of AI proficiency, from ad hoc user to multiplier, with crisp examples you can copy today. You’ll hear how a “New Account Research” teammate can scrape signals and context before you even open your CRM, how a pricing-objection specialist can produce competitor-aware responses in seconds, and how manager-trained GPTs can review call transcripts and give targeted coaching using your actual playbook. Then we zoom out and show what happens at the agent level: calendar-triggered prep, Slack clarifications, automated recaps, and draft SOWs that land in your docs without you lifting a finger. The numbers are real—a 47% productivity lift, roughly 12 hours a week back—translating into more selling time, better personalization, and cleaner pipelines.
If you’re at level one, we lay out a fast track to level three: convert your best prompts into assistants, feed them product and persona context, and standardize outputs so quality is consistent. Leaders get a roadmap to become multipliers by setting a GenAI backlog, prioritizing high-impact workflows, and rolling out shared assistants across the team. Hiring is already shifting; candidates who can show live AI workflows will outrun those who “know ChatGPT.”
If this guide helps, subscribe, share it with a teammate, and leave a review so more sellers find it. Want to level up faster? Explore the AI certification for sellers and frontline leaders, and test-drive the MeetJourney assistants tailored for sales teams.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_00 (00:00):
A lot of people, when they think about AI
permission, they're like, oh, Iuse it to like help me do some
research and write an email.
And my friends, that's the lazyversion of AI.
That's the beginning of thebeginning of the beginning.
Building a system in place iswhere sales represent is it's
prioritizing the call list, it'sallowing you to compete with
(00:22):
insights.
It's pulling out, let's say yousell something that helps a
company with their website loadspeed.
It's scraping the site for youin advance, it's putting
together white papers and casestudies even before you even log
into Salesforce for you.
AI Powered Seller.
All right, what's going on,everyone?
Welcome to another episode ofthe AI Powered Seller.
(00:44):
I am your host, Jake Dunlap.
Uh, hopefully, if you're joiningus on YouTube, welcome to the
channel.
If you are listening uh onSpotify or your favorite
podcast, welcome as well.
This is the show where everysingle week I break down the
latest and greatest uh detailsthat every single seller needs
to know around AI and sales andhow to supercharge your career
(01:08):
in 2025, 26, and beyond.
So today's episode should be anamazing one.
I think I hear this all thetime.
We need to be AI proficient.
We've got to be more AI forward.
And I think the interesting partis what does that mean?
Like, what does it mean if I'm asales rep and my boss is asking
(01:30):
me, you know, Jake, you need tobe AI proficient, or if you're a
CEO and you're bored saying youguys need to be AI proficient.
What does that mean?
And really the uncomfortabletruth in 25 is if you aren't
proficient, you are going tofall behind.
And yes, most sellers today areusing AI.
(01:51):
I think it's like 80% is a statthat I've seen, but they're just
dabbling with it, just barely,barely scratching the surface.
Only, I think less than 13%actually know how to build
assistants or agents, et cetera.
And so in today's episode, I'mgonna break down for you a few
key areas.
(02:11):
One, what the heck is AIproficiency and what does that
mean for you as a seller?
Uh, two, what are the fivelevels of AI proficiency that
we've developed that we haveseen lead teams from just
walking around the gym, youknow, uh wearing their Lululemon
to actually like hitting theweights and seeing the outcomes?
(02:32):
And then I'm gonna talk aboutwhy leveling up isn't some type
of productivity hat, it is acomplete change in the way that
you work.
And so without further ado,let's jump into what proficiency
actually means.
Oh, and a quick heads up forthose of you, make sure to check
out the show links.
Uh, we have built the first AIcertification for sellers and a
(02:57):
whole separate track forfrontline leaders.
So those are live.
They are gonna kick off here inthe next three weeks.
There's no theory, no fluff.
If you are serious about gettingyou know ahead and not being
left behind, this is your 2025checkbox.
So make sure to go sign up forthat as well, too.
So, first, uh I'm gonna talk youthrough the definition of
(03:19):
proficiency, right?
And and I think where I amqualified to talk about this is
over the last year, I haveeasily talked to hundreds of VPs
of sales, CEOs, CIOs aroundthis.
And I have seen the completegamut, right?
I would say most people aregonna be in some of the earlier
(03:41):
stages.
So I'll talk about whatnon-proficient looks like.
But I have also seenorganizations out there that are
literally like little humancyborgs where all their people
have digital teammates, they'recranking, et cetera.
So let me try to make this verytactical, right?
So to me, AI isn't about havingtools, it's about transforming
(04:04):
the way you work.
So think about it that way.
If you want to be proficient,it's not I know this technology.
It's oh, I work completelydifferent now.
That's how you know it'sintegrated.
It's a part of every singlething that you do.
So for example, try to give youa very real world one.
Let's say you're prospecting.
I think a lot of people, whenthey think about AI proficient,
(04:26):
they're like, oh, I use it tolike help me do some research
and write an email.
And my friends, that is that'sthe lazy version of AI.
That's the beginning of thebeginning of the beginning,
right?
Building a system in place iswhere sales reps and teams is
it's prioritizing the call list,it's allowing you to compete
(04:48):
with insights, it's pulling out,let's say you sell something
that helps a company with theirwebsite load speed, it's
scraping the site for you inadvance, it's putting together
white papers and case studies,even before you even log into
Salesforce for you.
And so if you think aboutwriting an email as step zero,
the future for Outbound isinsight-driven one-to-one
(05:11):
communication.
For managers, if you're saying,hey, am I proficient?
It isn't about asking Chat GPT,you know, how do I be a better
coach?
It's really creating a GPTtrained on your specific
playbook.
I think everyone, you know, I'vegot a little Jake version of a
playbook that can review thecall transcript, surface
(05:32):
insights, and automatically givethat rep feedback and insights.
And that's really the differencebetween the people I see that
are that are dabbling and thepeople that are proficient.
The dabblers are the people thatare saying, Oh, yeah, I do some
prompting every day.
I do like some basic prompting.
It's very, you know, high level,you know, one or two sentences,
etc., for the people that areactually building systems for
(05:56):
themselves.
So if you want to think aboutwhere you are on the spectrum,
take a second.
Am I somebody who has built outmultiple systems for myself, for
my team, that is running behindthe scenes or that we interact
with every day, or am I stilldabbling?
And let me just tell you thereality of the art of possible
(06:16):
here.
The last stat that I saw is a47% increase in productivity
when sales teams actually haveAI into all their workflows.
That is almost 12 hours perweek.
Let's be honest, selling time.
(06:36):
Maybe you're doing six hours aweek.
That's two days a week, right?
This is not incremental.
It is literally career altering.
And that's what gets me soexcited about a lot of this is
this is the future.
This is where I see, you know,this ability for you as an
(06:57):
individual, whether you'relistening to this and you're on
the front lines, whether you'relistening to this and you're in
the frontline leadership, ormaybe you're an executive or you
know, private equity.
Um this is the opportunity.
And I think what we have torealize is we've all been
programmed to solve differentproblems or to do our jobs a
(07:18):
very, very certain way.
And so we've become proficientin the old way of doing it,
right?
We've come proficient, right, inum, you know, how I use Google
and how I use LinkedIn and how Iuse a sales engagement tool and
how I use CRM.
But there is a new proficiencygame in town.
(07:39):
And I'm gonna break down thevery tactical five ways.
I'm really gonna spend my timein today's episode.
Maybe in a few months, I'llspend more time on number four
and five.
I'm gonna spend most of today'sepisode talking about one, two,
and three.
Because I think most of you areprobably in one, two land.
And I wanna try to get reallytactical over the next 10, 15
(08:02):
minutes and really help you toget into, you know, kind of two,
three, maybe, maybe like peak,peak at four land.
Um, so before we dive in, I wantto make sure, make sure to hit
the subscribe button.
Uh, make sure you you sign upfor downloads if this is your
favorite uh podcast platform.
Make sure to hit the like buttonfor this video.
Uh share this video with yourteammates.
(08:24):
You know, again, I thinkeverybody's trying to figure out
this AI proficiency piece.
Uh, and definitely check outmeetjourney.ai.
Meetjourney.ai is literally theonly set of assistants built
only for sales teams.
There are workspaces in therefor all of your accounts.
There's a whole bunch ofassistance that will help you do
(08:44):
research, uh book meetings,scenario plan, role play, et
cetera.
So make sure as you're startingto think about your proficiency
journey, if you want to skipahead to step two or three, just
sign up for Meet Journey.
They've already done a lot ofthe work for you.
They built out the assistance.
You can program it with yourorg, uh, et cetera, and it's
free.
So make sure to go check thatout.
(09:05):
So, my friends, let's get intothe five levels of AI
proficiency.
Uh, as a part of this, I want usto think what we call level one
is well, let me just clean thatup a little bit.
Let's get into the five levelsof AI proficiency.
I'm gonna spend about the nextseven, eight, nine minutes just
(09:28):
talking about these five levelsand really, really honing in on
the ones where I feel like mostpeople are, you know, today,
which is one, two, and three.
So let's talk first about levelone as the ad hoc user, the
basic experimenter.
This is where, again, I want youto look yourself in the mirror.
There's no shame.
(09:48):
We're still early, so don'tworry about it.
If you are here, don't feel, youknow, like you're uh like you're
you're too late to the game orstill very early in the game.
The mindset, I think, is whatcan be your litmus test, which
is AI feels optional.
I want you to think about that.
Does AI feel optional?
Does it feel like, yeah, Ishould be, uh, yeah, I'm
(10:11):
dabbling, I'm using it a littlebit here.
Um, it's, you know, relativelygeneric ways that we're using
it, inconsistent outcomes.
We're constantly like not happywith the outcomes, heavy editing
required.
You know, we're saying, hey,help me write a prospecting
email for here's my company, andyou know, here's the company
that I'm trying to book ameeting with.
(10:32):
And I'd call this still like AIis a novelty, it's another tech
stack.
It's not something that I reallyview as has to be infused in
everything that I do.
Right.
And to me, if you stay here, youare going to be dead weight to
companies compared to your peersin six to 12 months.
(10:53):
The good news is I don't havethe actual like specific stats.
My gut tells me 70 to 80 percentof people are right here.
From working with thousands ofreps over the last year, I'm
gonna say a vast majority, youknow, call it three
three-fourths, are in this adhoc user, basic experimenter
(11:14):
level one.
Okay.
Where again, we're there's acouple of key factors I think
about when I think about thislevel.
Number one is we don't talk toit like a person, we still talk
to it like Google.
We can't fathom that we shouldbe giving it everything and more
context and more context andmore context.
(11:35):
Number two is we have veryspecific use cases like
research, like messaging thatwe've latched onto, and that's
how we that that's how we do it.
So if you want to know if you'rein level one, those are my two
key criteria.
You know, think about again, areyou using it in just a couple of
(11:55):
you know key use cases, right?
Are you also you know thinkingabout it again, giving it very
basic prompting, one or twowords or sentences, and that is
how you know if you're in levelone.
Okay.
Number two, now I'm gonna callthis the skilled prompter.
This is somebody who's startingto get, I'd call it, a little
(12:17):
bit consistent around some ofthese things.
So, what are the behaviors ofsomebody who's in my level two,
the skilled prompter bucket?
Uh, these are the types ofpeople that are doing some next
level.
They have saved prompts.
They've realized, like, why do Ikeep typing in this exact same
thing over and over again?
And I use it for multiple usecases.
(12:37):
That kind of is a very clear wayfor you to say, hey, Jake, I
think I'm here.
I've got some go-to prompts.
I've got two or three areas inthe sales process that I use it.
And I'll toss in a third here.
I I'm starting to get good atadding context.
I'm saying, hey, oh, I'm feelinga little bit like this.
(12:57):
Um, you know, my role is alittle this, or this industry is
nuanced this way.
So again, they're starting tomake the shift from like, okay,
I can feed it a couple ofthings, it'll give me some
answers to say, okay, Idefinitely see value in in more
than just one or two areas here.
I'm saving the prompts becausethat saves me, you know, time as
a part of it.
(13:18):
And I'm starting to be able tounderstand, I need to give it
more.
I need to give it more context.
My answers are more rich,they're better.
Right.
So again, it's like it's notwriting an email to this.
It's saying, hey, I need to do athree-line opener to this
director of marketing.
Here's what happened on thefirst call.
I'm a little nervous about this.
(13:39):
They work at this type ofindustry where we do okay here,
and I want to focus on this usecase around time savings and
their recent funding around andABC, insert something else,
right?
So you're just getting good atgiving it context, right?
At this layer, I'm telling you,if you when you move from layer
(13:59):
one, level one to level two, youmove from the ad hoc to the
skilled consistent, at least a2x game.
You're not having to writethings out anymore.
You're starting to see thosegains in productivity.
Um, you're faster than themanual drafters, but my friends,
you're still tactical.
You're still stuck a little bit,a little bit in prompting land.
(14:22):
That is level two.
Okay, and I would say my top 10,15 percenters in AI for
frontline leaders, most execs,honestly, I would say most execs
I talk to, maybe 10 to 20percent are in level two.
I think most leader executiveleaders I talk to are pretty
(14:44):
level one.
Um, sales reps, I'd say maybe20% or so are kind of in this.
They're starting to flirt withthis level, right?
15, you know, 20 or percent.
Whereas I think it's a very lowpercent of execs uh that get
there.
Um, again, if this is helpingyou, make sure to like the
video.
Uh, if you're listening on yourpodcast, make sure to sign up to
(15:07):
get the latest.
Uh, and I'm gonna walk throughthe next three.
But again, my goal here with AIPowered Seller is to always
bring you the tactical advice.
How do I get better at this?
How do I get better at this?
How do I get better at this?
So appreciate you tuning in.
And let's jump into the lastcouple here.
Number three is the assistantbuilder, the task specialists.
(15:30):
These are my friends who arestarting to create either gyms
and Gemini, agents and co-pilot.
Uh, in Meet Journey, they'reusing the Meet Journey agents,
their uh custom GPTs.
They have realized why do I haveto copy and paste when I can
just take some time, put my bestprompt into this, and now it's
(15:54):
my competitive deal winner,digital teammate.
And that's a new word I'mstarting to use more and more,
and even instead of the wordassistant, because it truly is
that powerful.
I think Journey now is up tolike nine digital teammates.
You can build, you know, moreand Chat GPT, you know, you can
build obviously as many as youneed to.
But think of these things, youknow, like competitive deal
winner.
(16:14):
This is like a digital teammate.
This is like a person that Ihave on call 24-7, ready to help
me win every single deal.
It knows all my products.
It knows, you know, what what myindustry is that I sell into in
the sub-industry.
It knows my personas, it knowswho we compete against.
And therefore, I'm not having togive it all the context all the
(16:38):
time because I've taken the timeto put the context behind the
scenes.
So these are my my level threesare the assistant builders, the
digital teammate builders,right?
They're training um assistantson playbooks, battle cards.
They use these things for theyhelp them to do.
I have, you know, my favoriteone that I use probably three
times a day.
I is called new accountresearch.
(16:59):
It says, I say, I'm ready to go.
It says, give me a link to thecompany, and it goes.
It's that you know, I can godeeper if I want to say, oh, you
know, help me to understand afew nuances, but it's gonna pull
mission values, it's gonna pull,you know, uh how they make
money, who the exec team is, youknow, found rounds of funding,
uh, competitive landscape, whothey sell to.
(17:20):
I mean, it can pull everythingfor me.
And I don't have to prompt it,you know, et cetera.
So, you know, this is somebodywho's, you know, maybe runs into
pricing objections.
So they've created a pricingobjective GPT, right?
That outputs kind of a companyaligned, competitor aware, and
immediately usable, you know,proposal battle card uh to be
able to help them to win more,you know, deals.
(17:43):
So again, you know, I I thinkthat the mindset here, oh, this
is a really good, this is a Idon't know if I've put it this
way before.
The mindset is a shift from AIhelps me to AI owns this task.
Think about that mindset shift.
AI is a helper, yeah, it'shelpful.
Oh no, no, no.
(18:04):
My digital teammates got this.
I don't do that anymore.
My competitive deal intelligenceteammate does it.
And that to me is a big, bigshift.
And so that's why I wanted tospend time on these first three.
I'm gonna talk you throughreally quick level four and
level five, but I want you tothink, just hit a quick pause
(18:25):
right now for yourself.
Where am I if I'm being honestwith myself?
Am I level one?
I'm in the ad hoc world.
Am I kind of making that move tolevel two?
And a lot of you could just gofrom one to three, right?
You could just say, hey, insteadof me writing these prompts and
copying and pasting them, let mejust write these prompts inside
of a digital teammate or anassistant, and it'll do it for
(18:48):
me.
Again, like I said, that's why,you know, obviously I'm a big
fan of, you know, Meet Journeyhere because, you know, it
already has the assistance builtout.
But you can do this in any tool,okay?
Uh level four and level five,I'm gonna talk about this very
briefly.
Level four is when people, youstart to learn how to build
agents.
And this is another reason why Itruly believe everyone should
(19:10):
sign up for our AI certificationprogram.
It's literally a few hundreddollars, and you are going to
learn everything.
You're gonna learn how to buildassistance.
You're gonna be, we're gonnatake you all the way up to like
the beginning of level four.
That you're actually going tobuild an agent in like an hour,
and you're gonna start to seehow easy this stuff is.
So, agent builder, I'm gonnacall it process engineer, is
(19:33):
someone who doesn't just say AIdoes this task for me.
It's I've got AI teammatesworking together and they're
doing much more complex thingsfor me.
Right.
So this could be things like youknow, you leveraging the Zoom
API, you know, in and pullingthat into innate in or make or
zapier or agent force or youknow, insert uh you know, layer.
(19:56):
And then it automatically, youknow, creates a Slack that asks
clarifying questions.
And then once you integrateSlack and answer the questions,
it automatically spits out astatement of work at a Google
Doc.
This is here today.
My friends, we're doing thisright now.
This is how we do statements ofwork at my company.
And so this is where, again, youknow, it pulls from a Calendly,
(20:18):
it pulls the data from the CRMwho you're meeting with, it
automatically runs the accountresearch and auto slacks it to
the AAE.
So by the time that thing hitsyour calendar, the prep is done.
The automatic email is sent tothe prospect that says, hey, I'm
looking forward to aconversation.
Here's the basics around us,here's what you know, and it
automates it out.
(20:40):
At this level, AI starts tobecome invisible because it's
running your systems while yousell.
I truly believe if you are notthinking like this as a seller,
by the end of next year, you'regonna be surpassed.
Right?
I think again, if you can't getto that assistant builder, that
(21:00):
teammate, digital teammatepartner in the next six months,
man, people are gonna be runninglaps around you.
Um, last but not least, I'mgonna call this like force
multiplier, right?
AI multiplier, fluent acrosspomp uh prompting, fluent across
building teammates andlibraries, coaches, peers, says,
how do I raise the bar for myteam?
(21:22):
Right.
It takes it from personalproductivity to organizational
or department uplift, right?
So this is where you know aleader or a group of people are
working together on a true GenAI roadmap for their department,
right?
And this is a lot of work we dowith our clients as we're kind
of going out, we're havingdifferent conversations, we're
helping them to put togetherkind of their Kanban boards, and
(21:44):
then we're kind of building outthese different work streams on
a consistent basis, whether it'sa new digital teammate for this,
whether it's a new, you know,behind the scenes for this, a
workflow.
You are a leader when it comesto AI proficiency, right?
Multipliers, you know, thepeople in this group, the AI
multipliers, they don't just windeals, they change the way their
(22:06):
organization sells.
And so for a lot of you, onethrough three, okay.
One through three is where Iwant you to focus.
Okay, right.
And again, like I mentionedbefore, if you want to make that
move from kind of a skilledprompter to teammate, go to
check out meetjourneydata.ai,and that's a good starting
(22:27):
place.
If you're leading a team oryou're a frontline piece, that's
why I keep pushing thesecertifications, get involved
there as well.
So to wrap things up, I want youto think about this journey.
And we're all on this journeytogether, right?
Myself included.
Somebody asked me.
I was at a workshop with one ofour clients in the NBA.
Shout out to the PortlandTrailblazers.
(22:48):
Um, and uh one of the women inthe uh the the session, she
said, Jake, how long did it takeyou to get to uh you know the
level of proficiency you're at?
And I go, you know what?
I don't even think I'm there.
I'm like, I think I'm like afour, like three, four, maybe
somewhere in there.
(23:08):
And you know, my organization, Ithink we're a four.
I think we're a solid fourmoving to five.
Um, but you know, the theability to be proficient, it
might not be a skill that yourcompany is gonna teach you
because they don't know.
They're still at step one in thematurity curve, they're still at
wild, wild west, right?
And again, I want you to thinkof the the future here is you
(23:31):
know, the reps that are aregonna win in the future, you
know, they're gonna spend moretime selling, less time doing
the BS work.
They prep faster, they coachbetter, they ramp faster, right?
Uh hiring managers are gonna bescreening for this, right?
And I'm telling, I was talkingto somebody, he's like, um, how
do I screen for AI?
Like, if in the future will beif they can't show me their AI
(23:52):
workflows, they don't make thecut.
What am I gonna work withsomebody who's like asking me
these dumb manual questions?
Like, absolutely not, right?
So, again, I want you to thinkabout this.
In two years from now, if youare still level one, I really
maybe there's certain industriesI think it's gonna be tough to
compete.
Because somebody, you know, youmight think I've got all this
(24:12):
years of industry experience.
But again, if I know how tobuild an assistant and a
teammate that has all thoseyears of experience already,
well, that person can help methere.
And then I'm gonna be spendingmore time with customers than
you can possibly do.
Right.
And I think this isn't aboutmore efficiency, it's about
becoming more effective andsurviving.
Right.
So for everyone out there, youknow, this episode, you know,
(24:35):
for me is hopefully a little bitof a wake-up call and also maybe
a little bit of a tactical, youknow, okay, cool.
All right, I got me a littleroadmap here.
What we will do for you to makethis even better, I'm gonna put
a link in the show notes that'sgot like a little AI
proficiency, a little roadmapfor you.
So do not worry.
I got you covered.
Make sure if you have notalready signed up for Journey,
(24:57):
do it.
Um, it's assistance out of thebox.
It gets you literally to almosta level three, like out of the
gate.
Um, and for sure, make sure ifyou're somebody who wants to get
serious about this, sign up forthe certifications.
They're kind of a no-brainer.
I really feel like this issomething that everybody should
do who's trying to get really,really serious about their AI
game.
And so that's what I've got fortoday's episode.
(25:18):
Again, if this helped you, I'mI'm so glad to hear that.
I love to hear it.
Make sure to like and subscribeto the channel if you're
watching on YouTube or if you'relistening on the podcast, make
sure to sign up to get thedownload every time I've got a
new episode dropping.
And that's what I got for you,folks.
That's my AI proficiencyroadmap.
(25:40):
That if you follow it, I promiseyou will be from, you know, what
do they say, zero to hero inliterally no time.
So thanks again for tuning in,everyone.
Thank you so much for you knowtaking the time to invest in
yourself to realize howimportant this is.
And we will see you next week onthe next episode of the AI
Powered Seller.
A lot of people, when they think about AI
permission, they're like, oh, Iuse it to like help me do some
research and write an email.
And my friends, that's the lazyversion of AI.
That's the beginning of thebeginning of the beginning.
Building a system in place iswhere sales represent is it's
prioritizing the call list, it'sallowing you to compete with
(00:22):
insights.
It's pulling out, let's say yousell something that helps a
company with their website loadspeed.
It's scraping the site for youin advance, it's putting
together white papers and casestudies even before you even log
into Salesforce for you.
AI Powered Seller.
All right, what's going on,everyone?
Welcome to another episode ofthe AI Powered Seller.
(00:44):
I am your host, Jake Dunlap.
Uh, hopefully, if you're joiningus on YouTube, welcome to the
channel.
If you are listening uh onSpotify or your favorite
podcast, welcome as well.
This is the show where everysingle week I break down the
latest and greatest uh detailsthat every single seller needs
to know around AI and sales andhow to supercharge your career
(01:08):
in 2025, 26, and beyond.
So today's episode should be anamazing one.
I think I hear this all thetime.
We need to be AI proficient.
We've got to be more AI forward.
And I think the interesting partis what does that mean?
Like, what does it mean if I'm asales rep and my boss is asking
(01:30):
me, you know, Jake, you need tobe AI proficient, or if you're a
CEO and you're bored saying youguys need to be AI proficient.
What does that mean?
And really the uncomfortabletruth in 25 is if you aren't
proficient, you are going tofall behind.
And yes, most sellers today areusing AI.
(01:51):
I think it's like 80% is a statthat I've seen, but they're just
dabbling with it, just barely,barely scratching the surface.
Only, I think less than 13%actually know how to build
assistants or agents, et cetera.
And so in today's episode, I'mgonna break down for you a few
key areas.
(02:11):
One, what the heck is AIproficiency and what does that
mean for you as a seller?
Uh, two, what are the fivelevels of AI proficiency that
we've developed that we haveseen lead teams from just
walking around the gym, youknow, uh wearing their Lululemon
to actually like hitting theweights and seeing the outcomes?
(02:32):
And then I'm gonna talk aboutwhy leveling up isn't some type
of productivity hat, it is acomplete change in the way that
you work.
And so without further ado,let's jump into what proficiency
actually means.
Oh, and a quick heads up forthose of you, make sure to check
out the show links.
Uh, we have built the first AIcertification for sellers and a
(02:57):
whole separate track forfrontline leaders.
So those are live.
They are gonna kick off here inthe next three weeks.
There's no theory, no fluff.
If you are serious about gettingyou know ahead and not being
left behind, this is your 2025checkbox.
So make sure to go sign up forthat as well, too.
So, first, uh I'm gonna talk youthrough the definition of
(03:19):
proficiency, right?
And and I think where I amqualified to talk about this is
over the last year, I haveeasily talked to hundreds of VPs
of sales, CEOs, CIOs aroundthis.
And I have seen the completegamut, right?
I would say most people aregonna be in some of the earlier
(03:41):
stages.
So I'll talk about whatnon-proficient looks like.
But I have also seenorganizations out there that are
literally like little humancyborgs where all their people
have digital teammates, they'recranking, et cetera.
So let me try to make this verytactical, right?
So to me, AI isn't about havingtools, it's about transforming
(04:04):
the way you work.
So think about it that way.
If you want to be proficient,it's not I know this technology.
It's oh, I work completelydifferent now.
That's how you know it'sintegrated.
It's a part of every singlething that you do.
So for example, try to give youa very real world one.
Let's say you're prospecting.
I think a lot of people, whenthey think about AI proficient,
(04:26):
they're like, oh, I use it tolike help me do some research
and write an email.
And my friends, that is that'sthe lazy version of AI.
That's the beginning of thebeginning of the beginning,
right?
Building a system in place iswhere sales reps and teams is
it's prioritizing the call list,it's allowing you to compete
(04:48):
with insights, it's pulling out,let's say you sell something
that helps a company with theirwebsite load speed, it's
scraping the site for you inadvance, it's putting together
white papers and case studies,even before you even log into
Salesforce for you.
And so if you think aboutwriting an email as step zero,
the future for Outbound isinsight-driven one-to-one
(05:11):
communication.
For managers, if you're saying,hey, am I proficient?
It isn't about asking Chat GPT,you know, how do I be a better
coach?
It's really creating a GPTtrained on your specific
playbook.
I think everyone, you know, I'vegot a little Jake version of a
playbook that can review thecall transcript, surface
(05:32):
insights, and automatically givethat rep feedback and insights.
And that's really the differencebetween the people I see that
are that are dabbling and thepeople that are proficient.
The dabblers are the people thatare saying, Oh, yeah, I do some
prompting every day.
I do like some basic prompting.
It's very, you know, high level,you know, one or two sentences,
etc., for the people that areactually building systems for
(05:56):
themselves.
So if you want to think aboutwhere you are on the spectrum,
take a second.
Am I somebody who has built outmultiple systems for myself, for
my team, that is running behindthe scenes or that we interact
with every day, or am I stilldabbling?
And let me just tell you thereality of the art of possible
(06:16):
here.
The last stat that I saw is a47% increase in productivity
when sales teams actually haveAI into all their workflows.
That is almost 12 hours perweek.
Let's be honest, selling time.
(06:36):
Maybe you're doing six hours aweek.
That's two days a week, right?
This is not incremental.
It is literally career altering.
And that's what gets me soexcited about a lot of this is
this is the future.
This is where I see, you know,this ability for you as an
(06:57):
individual, whether you'relistening to this and you're on
the front lines, whether you'relistening to this and you're in
the frontline leadership, ormaybe you're an executive or you
know, private equity.
Um this is the opportunity.
And I think what we have torealize is we've all been
programmed to solve differentproblems or to do our jobs a
(07:18):
very, very certain way.
And so we've become proficientin the old way of doing it,
right?
We've come proficient, right, inum, you know, how I use Google
and how I use LinkedIn and how Iuse a sales engagement tool and
how I use CRM.
But there is a new proficiencygame in town.
(07:39):
And I'm gonna break down thevery tactical five ways.
I'm really gonna spend my timein today's episode.
Maybe in a few months, I'llspend more time on number four
and five.
I'm gonna spend most of today'sepisode talking about one, two,
and three.
Because I think most of you areprobably in one, two land.
And I wanna try to get reallytactical over the next 10, 15
(08:02):
minutes and really help you toget into, you know, kind of two,
three, maybe, maybe like peak,peak at four land.
Um, so before we dive in, I wantto make sure, make sure to hit
the subscribe button.
Uh, make sure you you sign upfor downloads if this is your
favorite uh podcast platform.
Make sure to hit the like buttonfor this video.
Uh share this video with yourteammates.
(08:24):
You know, again, I thinkeverybody's trying to figure out
this AI proficiency piece.
Uh, and definitely check outmeetjourney.ai.
Meetjourney.ai is literally theonly set of assistants built
only for sales teams.
There are workspaces in therefor all of your accounts.
There's a whole bunch ofassistance that will help you do
(08:44):
research, uh book meetings,scenario plan, role play, et
cetera.
So make sure as you're startingto think about your proficiency
journey, if you want to skipahead to step two or three, just
sign up for Meet Journey.
They've already done a lot ofthe work for you.
They built out the assistance.
You can program it with yourorg, uh, et cetera, and it's
free.
So make sure to go check thatout.
(09:05):
So, my friends, let's get intothe five levels of AI
proficiency.
Uh, as a part of this, I want usto think what we call level one
is well, let me just clean thatup a little bit.
Let's get into the five levelsof AI proficiency.
I'm gonna spend about the nextseven, eight, nine minutes just
(09:28):
talking about these five levelsand really, really honing in on
the ones where I feel like mostpeople are, you know, today,
which is one, two, and three.
So let's talk first about levelone as the ad hoc user, the
basic experimenter.
This is where, again, I want youto look yourself in the mirror.
There's no shame.
(09:48):
We're still early, so don'tworry about it.
If you are here, don't feel, youknow, like you're uh like you're
you're too late to the game orstill very early in the game.
The mindset, I think, is whatcan be your litmus test, which
is AI feels optional.
I want you to think about that.
Does AI feel optional?
Does it feel like, yeah, Ishould be, uh, yeah, I'm
(10:11):
dabbling, I'm using it a littlebit here.
Um, it's, you know, relativelygeneric ways that we're using
it, inconsistent outcomes.
We're constantly like not happywith the outcomes, heavy editing
required.
You know, we're saying, hey,help me write a prospecting
email for here's my company, andyou know, here's the company
that I'm trying to book ameeting with.
(10:32):
And I'd call this still like AIis a novelty, it's another tech
stack.
It's not something that I reallyview as has to be infused in
everything that I do.
Right.
And to me, if you stay here, youare going to be dead weight to
companies compared to your peersin six to 12 months.
(10:53):
The good news is I don't havethe actual like specific stats.
My gut tells me 70 to 80 percentof people are right here.
From working with thousands ofreps over the last year, I'm
gonna say a vast majority, youknow, call it three
three-fourths, are in this adhoc user, basic experimenter
(11:14):
level one.
Okay.
Where again, we're there's acouple of key factors I think
about when I think about thislevel.
Number one is we don't talk toit like a person, we still talk
to it like Google.
We can't fathom that we shouldbe giving it everything and more
context and more context andmore context.
(11:35):
Number two is we have veryspecific use cases like
research, like messaging thatwe've latched onto, and that's
how we that that's how we do it.
So if you want to know if you'rein level one, those are my two
key criteria.
You know, think about again, areyou using it in just a couple of
(11:55):
you know key use cases, right?
Are you also you know thinkingabout it again, giving it very
basic prompting, one or twowords or sentences, and that is
how you know if you're in levelone.
Okay.
Number two, now I'm gonna callthis the skilled prompter.
This is somebody who's startingto get, I'd call it, a little
(12:17):
bit consistent around some ofthese things.
So, what are the behaviors ofsomebody who's in my level two,
the skilled prompter bucket?
Uh, these are the types ofpeople that are doing some next
level.
They have saved prompts.
They've realized, like, why do Ikeep typing in this exact same
thing over and over again?
And I use it for multiple usecases.
(12:37):
That kind of is a very clear wayfor you to say, hey, Jake, I
think I'm here.
I've got some go-to prompts.
I've got two or three areas inthe sales process that I use it.
And I'll toss in a third here.
I I'm starting to get good atadding context.
I'm saying, hey, oh, I'm feelinga little bit like this.
(12:57):
Um, you know, my role is alittle this, or this industry is
nuanced this way.
So again, they're starting tomake the shift from like, okay,
I can feed it a couple ofthings, it'll give me some
answers to say, okay, Idefinitely see value in in more
than just one or two areas here.
I'm saving the prompts becausethat saves me, you know, time as
a part of it.
(13:18):
And I'm starting to be able tounderstand, I need to give it
more.
I need to give it more context.
My answers are more rich,they're better.
Right.
So again, it's like it's notwriting an email to this.
It's saying, hey, I need to do athree-line opener to this
director of marketing.
Here's what happened on thefirst call.
I'm a little nervous about this.
(13:39):
They work at this type ofindustry where we do okay here,
and I want to focus on this usecase around time savings and
their recent funding around andABC, insert something else,
right?
So you're just getting good atgiving it context, right?
At this layer, I'm telling you,if you when you move from layer
(13:59):
one, level one to level two, youmove from the ad hoc to the
skilled consistent, at least a2x game.
You're not having to writethings out anymore.
You're starting to see thosegains in productivity.
Um, you're faster than themanual drafters, but my friends,
you're still tactical.
You're still stuck a little bit,a little bit in prompting land.
(14:22):
That is level two.
Okay, and I would say my top 10,15 percenters in AI for
frontline leaders, most execs,honestly, I would say most execs
I talk to, maybe 10 to 20percent are in level two.
I think most leader executiveleaders I talk to are pretty
(14:44):
level one.
Um, sales reps, I'd say maybe20% or so are kind of in this.
They're starting to flirt withthis level, right?
15, you know, 20 or percent.
Whereas I think it's a very lowpercent of execs uh that get
there.
Um, again, if this is helpingyou, make sure to like the
video.
Uh, if you're listening on yourpodcast, make sure to sign up to
(15:07):
get the latest.
Uh, and I'm gonna walk throughthe next three.
But again, my goal here with AIPowered Seller is to always
bring you the tactical advice.
How do I get better at this?
How do I get better at this?
How do I get better at this?
So appreciate you tuning in.
And let's jump into the lastcouple here.
Number three is the assistantbuilder, the task specialists.
(15:30):
These are my friends who arestarting to create either gyms
and Gemini, agents and co-pilot.
Uh, in Meet Journey, they'reusing the Meet Journey agents,
their uh custom GPTs.
They have realized why do I haveto copy and paste when I can
just take some time, put my bestprompt into this, and now it's
(15:54):
my competitive deal winner,digital teammate.
And that's a new word I'mstarting to use more and more,
and even instead of the wordassistant, because it truly is
that powerful.
I think Journey now is up tolike nine digital teammates.
You can build, you know, moreand Chat GPT, you know, you can
build obviously as many as youneed to.
But think of these things, youknow, like competitive deal
winner.
(16:14):
This is like a digital teammate.
This is like a person that Ihave on call 24-7, ready to help
me win every single deal.
It knows all my products.
It knows, you know, what what myindustry is that I sell into in
the sub-industry.
It knows my personas, it knowswho we compete against.
And therefore, I'm not having togive it all the context all the
(16:38):
time because I've taken the timeto put the context behind the
scenes.
So these are my my level threesare the assistant builders, the
digital teammate builders,right?
They're training um assistantson playbooks, battle cards.
They use these things for theyhelp them to do.
I have, you know, my favoriteone that I use probably three
times a day.
I is called new accountresearch.
(16:59):
It says, I say, I'm ready to go.
It says, give me a link to thecompany, and it goes.
It's that you know, I can godeeper if I want to say, oh, you
know, help me to understand afew nuances, but it's gonna pull
mission values, it's gonna pull,you know, uh how they make
money, who the exec team is, youknow, found rounds of funding,
uh, competitive landscape, whothey sell to.
(17:20):
I mean, it can pull everythingfor me.
And I don't have to prompt it,you know, et cetera.
So, you know, this is somebodywho's, you know, maybe runs into
pricing objections.
So they've created a pricingobjective GPT, right?
That outputs kind of a companyaligned, competitor aware, and
immediately usable, you know,proposal battle card uh to be
able to help them to win more,you know, deals.
(17:43):
So again, you know, I I thinkthat the mindset here, oh, this
is a really good, this is a Idon't know if I've put it this
way before.
The mindset is a shift from AIhelps me to AI owns this task.
Think about that mindset shift.
AI is a helper, yeah, it'shelpful.
Oh no, no, no.
(18:04):
My digital teammates got this.
I don't do that anymore.
My competitive deal intelligenceteammate does it.
And that to me is a big, bigshift.
And so that's why I wanted tospend time on these first three.
I'm gonna talk you throughreally quick level four and
level five, but I want you tothink, just hit a quick pause
(18:25):
right now for yourself.
Where am I if I'm being honestwith myself?
Am I level one?
I'm in the ad hoc world.
Am I kind of making that move tolevel two?
And a lot of you could just gofrom one to three, right?
You could just say, hey, insteadof me writing these prompts and
copying and pasting them, let mejust write these prompts inside
of a digital teammate or anassistant, and it'll do it for
(18:48):
me.
Again, like I said, that's why,you know, obviously I'm a big
fan of, you know, Meet Journeyhere because, you know, it
already has the assistance builtout.
But you can do this in any tool,okay?
Uh level four and level five,I'm gonna talk about this very
briefly.
Level four is when people, youstart to learn how to build
agents.
And this is another reason why Itruly believe everyone should
(19:10):
sign up for our AI certificationprogram.
It's literally a few hundreddollars, and you are going to
learn everything.
You're gonna learn how to buildassistance.
You're gonna be, we're gonnatake you all the way up to like
the beginning of level four.
That you're actually going tobuild an agent in like an hour,
and you're gonna start to seehow easy this stuff is.
So, agent builder, I'm gonnacall it process engineer, is
(19:33):
someone who doesn't just say AIdoes this task for me.
It's I've got AI teammatesworking together and they're
doing much more complex thingsfor me.
Right.
So this could be things like youknow, you leveraging the Zoom
API, you know, in and pullingthat into innate in or make or
zapier or agent force or youknow, insert uh you know, layer.
(19:56):
And then it automatically, youknow, creates a Slack that asks
clarifying questions.
And then once you integrateSlack and answer the questions,
it automatically spits out astatement of work at a Google
Doc.
This is here today.
My friends, we're doing thisright now.
This is how we do statements ofwork at my company.
And so this is where, again, youknow, it pulls from a Calendly,
(20:18):
it pulls the data from the CRMwho you're meeting with, it
automatically runs the accountresearch and auto slacks it to
the AAE.
So by the time that thing hitsyour calendar, the prep is done.
The automatic email is sent tothe prospect that says, hey, I'm
looking forward to aconversation.
Here's the basics around us,here's what you know, and it
automates it out.
(20:40):
At this level, AI starts tobecome invisible because it's
running your systems while yousell.
I truly believe if you are notthinking like this as a seller,
by the end of next year, you'regonna be surpassed.
Right?
I think again, if you can't getto that assistant builder, that
(21:00):
teammate, digital teammatepartner in the next six months,
man, people are gonna be runninglaps around you.
Um, last but not least, I'mgonna call this like force
multiplier, right?
AI multiplier, fluent acrosspomp uh prompting, fluent across
building teammates andlibraries, coaches, peers, says,
how do I raise the bar for myteam?
(21:22):
Right.
It takes it from personalproductivity to organizational
or department uplift, right?
So this is where you know aleader or a group of people are
working together on a true GenAI roadmap for their department,
right?
And this is a lot of work we dowith our clients as we're kind
of going out, we're havingdifferent conversations, we're
helping them to put togetherkind of their Kanban boards, and
(21:44):
then we're kind of building outthese different work streams on
a consistent basis, whether it'sa new digital teammate for this,
whether it's a new, you know,behind the scenes for this, a
workflow.
You are a leader when it comesto AI proficiency, right?
Multipliers, you know, thepeople in this group, the AI
multipliers, they don't just windeals, they change the way their
(22:06):
organization sells.
And so for a lot of you, onethrough three, okay.
One through three is where Iwant you to focus.
Okay, right.
And again, like I mentionedbefore, if you want to make that
move from kind of a skilledprompter to teammate, go to
check out meetjourneydata.ai,and that's a good starting
(22:27):
place.
If you're leading a team oryou're a frontline piece, that's
why I keep pushing thesecertifications, get involved
there as well.
So to wrap things up, I want youto think about this journey.
And we're all on this journeytogether, right?
Myself included.
Somebody asked me.
I was at a workshop with one ofour clients in the NBA.
Shout out to the PortlandTrailblazers.
(22:48):
Um, and uh one of the women inthe uh the the session, she
said, Jake, how long did it takeyou to get to uh you know the
level of proficiency you're at?
And I go, you know what?
I don't even think I'm there.
I'm like, I think I'm like afour, like three, four, maybe
somewhere in there.
(23:08):
And you know, my organization, Ithink we're a four.
I think we're a solid fourmoving to five.
Um, but you know, the theability to be proficient, it
might not be a skill that yourcompany is gonna teach you
because they don't know.
They're still at step one in thematurity curve, they're still at
wild, wild west, right?
And again, I want you to thinkof the the future here is you
(23:31):
know, the reps that are aregonna win in the future, you
know, they're gonna spend moretime selling, less time doing
the BS work.
They prep faster, they coachbetter, they ramp faster, right?
Uh hiring managers are gonna bescreening for this, right?
And I'm telling, I was talkingto somebody, he's like, um, how
do I screen for AI?
Like, if in the future will beif they can't show me their AI
(23:52):
workflows, they don't make thecut.
What am I gonna work withsomebody who's like asking me
these dumb manual questions?
Like, absolutely not, right?
So, again, I want you to thinkabout this.
In two years from now, if youare still level one, I really
maybe there's certain industriesI think it's gonna be tough to
compete.
Because somebody, you know, youmight think I've got all this
(24:12):
years of industry experience.
But again, if I know how tobuild an assistant and a
teammate that has all thoseyears of experience already,
well, that person can help methere.
And then I'm gonna be spendingmore time with customers than
you can possibly do.
Right.
And I think this isn't aboutmore efficiency, it's about
becoming more effective andsurviving.
Right.
So for everyone out there, youknow, this episode, you know,
(24:35):
for me is hopefully a little bitof a wake-up call and also maybe
a little bit of a tactical, youknow, okay, cool.
All right, I got me a littleroadmap here.
What we will do for you to makethis even better, I'm gonna put
a link in the show notes that'sgot like a little AI
proficiency, a little roadmapfor you.
So do not worry.
I got you covered.
Make sure if you have notalready signed up for Journey,
(24:57):
do it.
Um, it's assistance out of thebox.
It gets you literally to almosta level three, like out of the
gate.
Um, and for sure, make sure ifyou're somebody who wants to get
serious about this, sign up forthe certifications.
They're kind of a no-brainer.
I really feel like this issomething that everybody should
do who's trying to get really,really serious about their AI
game.
And so that's what I've got fortoday's episode.
(25:18):
Again, if this helped you, I'mI'm so glad to hear that.
I love to hear it.
Make sure to like and subscribeto the channel if you're
watching on YouTube or if you'relistening on the podcast, make
sure to sign up to get thedownload every time I've got a
new episode dropping.
And that's what I got for you,folks.
That's my AI proficiencyroadmap.
(25:40):
That if you follow it, I promiseyou will be from, you know, what
do they say, zero to hero inliterally no time.
So thanks again for tuning in,everyone.
Thank you so much for you knowtaking the time to invest in
yourself to realize howimportant this is.
And we will see you next week onthe next episode of the AI
Powered Seller.
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