August 18, 2025 • 45 mins
Chris Orlob, Founder and CEO of pclub.io, shares his journey from product marketing to sales leadership and discusses how to effectively develop sales teams in today's challenging environment. He offers a practical framework for setting clear expectations and explains why systematic skill development is now a strategic necessity rather than just a nice-to-have.
• Chris developed his "three pillars" framework for sales leadership: managing people, managing pipeline, and managing the business
• The most effective leaders make "the enemy the bar, not you" when coaching underperformers
• Creating a detailed "WGLL" (What Good Looks Like) document transforms how you set expectations and evaluate performance
• We're facing a "go-to-market skills crisis" driven by economic shifts, workforce changes, and increasingly sophisticated buyers
• Revenue per rep has replaced headcount as the critical metric for go-to-market excellence
• Skill capacity should be treated as a board-level metric rather than an afterthought
• Many high-performing leaders struggle with coaching B-players because they lack patience and clear frameworks
• Assessing whether underperformers have both the potential and desire to improve should guide your coaching approach
Connect with Chris on LinkedIn or visit pclub.io to learn more about systematically developing sales skills.
Music by Ben Cina & Ayler Young
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
It's time to say something real.
Speaker 2 (00:04):
I've been waiting on you to tell me how you really
feel.
Just be honest.
Words in me Like the joke.
I can't shake.
Speaker 1 (00:13):
I can't quit.
It's never really what you say.
Hello everyone, and welcome toanother episode of Pillar Talk,
where we build the foundationsof sales leadership success and
attempt to create clarity interms of what good looks like
for current and aspiring salesleaders.
Before we jump in with today'sguests, let's review the six
(00:34):
pillars of successful salesleadership.
It starts with talent,identification and attraction.
Obviously, both are verydifficult.
It's also the operating rhythm,the environment that fosters
the balance between motivation,engagement and accountability.
Business planning, which isaround the cross functional
dynamics, so that the companycan play offense instead of
(00:54):
reacting and playing defense tothings that happen around us.
Mastering the craft, which isall about helping the team win,
communication and ownership.
Today we are lucky to have as aguest Chris Orlob, the founder
and CEO of pclubio.
That's a platform designed tohelp enterprise sellers
(01:20):
consistently break intoPresident's Club by mastering
winning sales strategies.
Now I know Chris as a thoughtleader focused on sales
performance and analytics.
He previously was an earlyemployee and senior leader at
Gong, where he helped shape,from my perspective, the
company's narrative onconversation intelligence, which
created a category Beforefounding P-Club.
(01:43):
Chris built a career at theintersection, really
interestingly, of marketing andsales, leadership and technology
, sharing his learnings publicly, and I was one of the
beneficiaries of that before itreally became the norm to do so
on platforms like LinkedIn.
So, chris, thank you for beinghere today.
On Pillar Talk.
Speaker 2 (02:03):
Yeah, thanks for having me, Rick, excited to be
here.
Speaker 1 (02:06):
Yeah, excited to learn from you.
I've been learning from you foryears.
I recall back in like 2017, youwere probably the only marketer
in my inbox that had a voice.
Like you were the projection ofannouncements of what was
happening.
Projection of announcements ofwhat was happening, you were,
(02:27):
you know, sharing all kinds ofstuff around your you know,
around the company's positioning, and then it moved to your own
sort of leadership journey andthat was all kind of public.
What made you decide to liketake that approach back then,
before it was the cool thing todo or a trend?
Speaker 2 (02:43):
It just seemed obvious to me.
I don't think there was anylike sophisticated insight that
went behind it.
It was just we were anonymousat Gong right, like we were a
tiny little company.
Nobody knew who we were.
Most of our market spent timeon LinkedIn.
I had happened to spend a fewyears before that crafting my
(03:07):
chops when it came to writingand public speaking and all that
kind of stuff and then we weresitting on top of this data at
gong right, like we're analyzingthousands and eventually
millions of sales calls, and wewere able to extrapolate what's
working according to data.
And so it was kind of like thisperfect storm of like this is
the ultimate thought leadershipplay and it would have been a
(03:30):
complete waste if we weren'tbeating that drum loud and
consistently.
And I also think like I can'ttake all the credit for that,
because a lot of senior leadersand CEOs will not be on board
for something so polarizing.
And it was polarizing.
We were very polarizing whereyou know, even today, I mean
(03:54):
like 90% of the people who wouldengage with our content loved
it, and 10% of them I mean ourfaces were on like a dartboard
that they would throw darts at,like it was very polarizing in
that way, and Amit and Udi rightCEO and VP of marketing at the
time were very on board withthat kind of narrative approach.
(04:15):
Right, let's be edgy, let's putsome polarizing messages into
the market that are going to beboth good for them and good for
our business.
And if that generates some youknow trolls online, that's the
price we pay.
So that's how it started.
Speaker 1 (04:31):
Yeah, I mean I remember they were insightful.
It was I wouldn't saycontroversial, but it zagged a
little bit from maybeconventional thought.
It must've gotten wonderfulengagement and certainly helped
with the brand as well as theswag, and I think it was a dog
associated in there at somepoint.
But then you know, you hadseemed to be a master of like
product marketing, messaging outto a large community, and then
(04:53):
all of a sudden I'm seeing thatyou're in sales leadership and
at the time I don't think thatwas a conventional move that
people made.
It's probably not aconventional move that people
make today.
Speaker 2 (05:11):
Love to hear, just like what drove that decision.
And you know what did you learnearly on that you didn't expect
?
Well, I think, even to this dayI'm I'm in a career where I
can't really explain to myparents what I want to be when I
grow up and and what I am,because my passion is not sales
or sales leadership or productmarketing, is not sales or sales
leadership or product marketing, it's all of it, it's business.
I like category definingbusiness and that if you're
(05:33):
going to do something like that,you need command over all of
those functions.
And so my background.
Funny enough, like a lot ofpeople in the world think like,
oh, chris was a product marketerwho went into sales leadership.
It's actually not true in theworld.
Think like, oh, chris was aproduct marketer who went into
sales leadership.
It's actually not true, it was.
Chris was a sales guy and thenhe tried his hand at product
marketing by joining Gong andthen went back into sales and
sales leadership.
My career before Gong was beside, you know, being an
(05:57):
entrepreneur was sales and Iwanted to try my hand at product
marketing because at the timemy goal was to be a CEO and one
of the patterns I identifiedamong many CEOs is they didn't
come from one function.
They had kind of like a windingcross-functional rise or ascent
(06:19):
up to the CEO position.
Many of them had salesbackgrounds, many of them had
product management backgrounds.
A CEO position Many of them hadsales backgrounds, many of them
had product managementbackgrounds and many, if not
most of them, spent some time ina couple different functions.
And so that's where that camefrom.
Right.
When Gong hired me, they weredoing about 200 grand in ARR and
Amit reaches out wanting totalk and he wanted me to be an
(06:41):
enterprise seller, right, thatwas like his first offer and at
the time I just wasn'tinterested.
I was like I, you know, I've,I've done this job.
It's not what excites me rightnow, at least at this point in
life.
And so he came back and he'slike look, I like how you
marketed your own business on ashoestring budget, how about you
lead product marketing?
I was like great, that's that.
And so I did product marketingfor a couple of years and I
(07:02):
still love product marketing,not necessarily as the job, but
like the craft right, narrativedesign and all that kind of
stuff.
Love that stuff.
I think about it all day, evenin my current role.
I didn't love the role as muchthough I liked being accountable
to a revenue number, I likedbeing well I'll put it the other
way and hopefully I'm notoffending any product marketers
(07:23):
out there I didn't like to besecond fiddle.
I wanted to be the sales leaderwho was, you know, your head's
on the chopping block.
But if your head's on thechopping block, that also means
you've got some authority,hopefully to call the shots, and
I was craving that kind ofdynamic again, and so I can't
even remember how all of thathappened.
I think I just started to talkto my boss about how I was
(07:46):
getting bored in the currentrole, but I didn't want to leave
the company, and so we lookedfor different roles.
Leading a segment of our salesorganization was the next one.
Speaker 1 (07:56):
I will say that that foresight that you had to take a
product marketing role in andof itself had to take a product
marketing role in and of itself,coming from a sales background.
And, truth be told, myknowledge of your background
starts with the productmarketing and gong.
So it's a lot of people fullyprevious.
(08:16):
It's just not conventionaleither.
So the storytelling and I getit.
I mean I just looked at a postyou put on today and look, I
scroll through LinkedIn, likemany people that listen to this
do.
It's a ton of amazing contenton there and you do just have
the knack for engrossing content.
I mean I'm immediately like,yeah, people do blow their shot
with the C-suite in the firstfive minutes.
(08:38):
Yeah, these are the reasons.
So you do have a natural knackfor an ability to do that and I
do like that.
In my career also, I didn't likehave purpose behind what I was
going to do.
I had the basis of like, okay,where can I make the biggest
impact in the organization?
And naturally, if I'm making abig impact in the organization,
they'll likely be a lot oflearning that is happening
(09:00):
associated with that.
So it's not like I want to getthe next role.
I just want to make sure that,as time passes, my impact is
growing in the org and then Iwill evolve to whatever that
ends up being.
Rather than having this likepurposeful journey of art.
I want to do this, spend thismuch time and then it's just you
can plan a pretty picnic, butlike life and the changing
dynamics of go-to-market aresuch that, like it's really hard
(09:22):
to follow a predeterminedtrajectory associated with it.
So it makes sense to me that itwasn't like purposeful, it was
like that's where you wereneeded and it made sense.
And then you started to talkabout what that was like.
And since this podcast is a lotabout the sales leadership
impact, I'd love to go back to,like when you moved into that
role, anything that stood outthat you didn't expect it.
(09:44):
When you had to like becomestoryteller to people manager,
quota carrying people manager.
Speaker 2 (09:51):
Yeah, I mean it's, it's just a totally different
job.
Now I will say, being a productmarketing leader made me a
better sales and salesleadership professional and, on
the other hand, being a salesand sales leadership
professional at the time made mehand.
Being a sales and salesleadership professional at the
time made me a better productmarketing leader, because these
aren't totally distinct skillsets.
Right, because sales and salesleadership you're often the
(10:14):
carrier of the product marketingartifact, which is the
narrative.
Right, you're the one talkingto it.
Product marketing is.
You know, they're at least thebest of the best, which, by the
way, great product marketersreally rare.
Product marketers are common.
Great product marketers arevery rare.
But if you're doing that jobwell, you craft the narrative,
(10:34):
but you're not necessarily theone carrying the narrative, and
sales and sales leadership oftenis.
And so there was there's a lotof learning curve.
It took me a little while tocondense my own model of sales
leadership and really understandit, and it's actually kind of
similar to the pillars that youlined up at the beginning of
(10:54):
this podcast.
The way I I think about salesleadership for myself is really
there's like three bucketsthere's manage the people,
there's manage the pipeline andthere's manage the business, and
most of what you think about asfar as a task or deliverable or
outcome of sales leadership atleast frontline and second line
sales leadership falls intothose buckets, right.
(11:16):
Manage the people, that's well,that's hiring, that's
onboarding, that's coaching,that's firing when you need to.
Pipeline management, that'sobvious.
Right, your job is to marshaldeals across a conveyor belt and
make sure they close, even ifyou're not the one closing them,
and then manage the business iskind of some of the things that
you mentioned.
There's a lot ofcross-functional chops that you
(11:39):
need to get used to.
There's business planning,there's developing scalable
playbooks used to.
There's business planning,there's developing scalable
playbooks.
That's the part I struggled withthe most was the
cross-functional stuff, becauseI can be very stubborn, right,
like if I have an idea or a wayof doing things, I just want to
marshal ahead and bring it intothe market, and sometimes that's
(12:00):
a very good trait to have,that's a really good trait for a
startup.
But when the company startedgrowing and I kind of forgot
that I have to align withcustomer success and marketing
and all that kind of stuff, Ithink I burnt a few.
I wouldn't say I burnt anybridges, but I scorched the
earth a little bit too much.
I was like a bull in a chinashop and I had to learn some
(12:22):
hard, cross-functional lessons.
The china shop and I had tolearn some hard,
cross-functional lessons.
And, uh, I actually rememberasking my boss to do an
anonymous 360 degree review ofme across all my peer set.
Right, they could like give mefeedback and it was painful,
like I still remember thatbecause I I got a lot of good
feedback, don't get me wrong,but there was a lot of like you
(12:45):
know, chris, just it's kind ofhis way or the highway type
stuff and it stung.
But I'm really glad I asked forall of that because it stung in
a way that helped me grow and Igrew fast because I was willing
to eat that glass, so to speakso you, I'm going to use your
(13:05):
framing of this.
Speaker 1 (13:06):
So was managing the people pretty natural thing,
because if I take it from myvantage point before you kind of
get into this, thecross-functional part I'm a
communicator and a little bitless of a kind of driver, so
that wouldn't be a pipeline.
Yeah, let's do pipeline.
Less of a kind of driver, sothat wouldn't be a pipeline.
Yeah, let's do pipeline.
(13:27):
I mean, I'm a sales guy.
But the people part was thearea that I was like, oh, they
don't want to do it the exactway that I just do it.
They're not clones of me.
This is a that to me was likewhoa, this is the hardest part.
So it's super interesting tokind of frame it that way.
Speaker 2 (13:51):
Yeah, well, one of the I mean, I still struggle
with this aspect of peoplemanagement today.
One of the things that I foundvery quickly is I like to think
I'm actually great at managingand leading people who are
already a players.
I'm good at coaching them.
I'm good at managing them.
Um, my co-founder here at Pclubs, so you can tell I'm still
like working through some ofthese opportunity uh areas.
He gave me feedback probably ayear ago where he's like Chris,
(14:11):
you're one of the best leaders Iknow when you're leading great
people and you're one of theworst leaders I know when you're
leading people that are not sogreat.
I like to think I've grownsince that conversation.
Right, it's not like a trainwreck anymore.
But that's something Istruggled with when I first
stepped into sales leadership,because not everybody likes to
(14:32):
admit this, but most sales teamshave B players on them and
sometimes C players, and I wouldget critical too fast of those
people and sometimes even today,I do.
Speaker 1 (14:43):
As by far my self-criticism is almost
identical to what you justshared.
Is it more of a patience thing?
What do you attribute thatdynamic to, this ability to work
incredibly well with motivatedhigh performers and a struggle
to help develop and have thepatience I mean that's the word
(15:05):
that comes to mind for me to,you know, almost slow down the
velocity of your individualexecution to help bring somebody
along.
Speaker 2 (15:15):
Well, there's a few.
I'll go in a few differentplaces here.
First, there is wisdom inknowing if somebody has the
potential and drive to work outright.
If somebody is quote unquotemediocre or a B player, that
doesn't mean give up on them.
That means assess their abilityto improve and their and their
drive to improve.
(15:35):
And if somebody is a B playerand they have those things, then
it's very high ROI time for youto coach them and develop them.
If they're not, you should justterminate them.
You should do itcompassionately and you should
do it non-emotionally andrespectfully.
But it doesn't make sense tohave somebody who's not great at
their job and doesn't have adesire to improve or an ability
(15:58):
to improve.
So that's like kind of thefirst bucket.
The second one is bucket.
The second one is I can'tremember who gave me this
feedback, but they said you dowant to be a challenging boss to
work for, but you want to makethe enemy the bar, not you.
And so the wrong way to do thisis you go into a one-on-one with
(16:20):
a B player and you're allemotional and critical and
you're kind of like attackingthem because now you're the
enemy.
Instead, you're completelyunemotional and you make the
enemy the bar, the bar forperformance or whatever, and you
just say something with theethos of, like, our bar's up
here and it looks like whatyou're doing is somewhere around
(16:41):
here, and so how do we closethat delta?
Right, that's being achallenging boss, but not being
an asshole or toxic about it,and I do like I hate to admit it
.
This is kind of painful to say,especially on a podcast.
I think sometimes I could havegotten toxic right, like in
those situations I was the enemyrather than the bar, and that's
probably one of the biggestgrowth opportunities I've had to
(17:05):
lean into over the last fiveyears or so.
Speaker 1 (17:07):
And is that concept making it less about what you
say and more about the standard,like an application that you
now are sort of prevalentlyusing?
Speaker 2 (17:17):
Yeah, 100%, and it comes.
I mean, this opens up a wholenew can of worms.
To be able to do thateffectively and fairly, you have
to document what your standardsare.
So good example of that todayis day three of my new VP of
sales starting, and before hestarted I put together what I
(17:39):
call a wiggle doc W-G-L-L, whatgood looks like and it's one or
two pages of of during yourfirst 120 days on the job,
between now and December 1st orDecember 31st.
Here's what great looks like,here's what mediocre looks like
and here's what off track lookslike.
And you can't really hold peoplerationally to a bar until
(18:04):
you've documented andcommunicated what those are.
So him and I you know, I sharedthat document with him a couple
of days ago, on day one, andhim, I was like go absorb this.
I want to make sure you feelgood about it.
And then, when you've absorbedit, let's talk about it at
length.
And that's what we did thismorning.
Right, it was like you know,he's walking through his
concerns.
He's walking through why Ipicked certain things the way I
(18:27):
did, I'm justifying them, and itwas just a little bit of a
healthy negotiation, right, likehere's what I expect, and now
he doesn't have to show up toone-on-ones with me guessing
about how he's doing.
We go well, let's look at thewiggle dock, and now I can refer
to that and say well, you knowwhat your ARR targets are, you
(18:47):
know what your monthly targetsare, you know what your revenue
per rep targets are.
Win rate, all that kind ofstuff Looks like we're a little
bit behind in this one area.
What do you think the plan isfor us?
Closing that delta?
That's holding people to a highbar and being a challenging
leader, but being a good leaderwhile you do it, instead of, you
know, freaking out and beinglike you're the problem and
(19:15):
being like all critical of themand attacking them, because now
you're not on their side andthey can sense that and you've
just done your first steptowards severing a relationship.
Speaker 1 (19:20):
First of all, love this idea of a wiggle dock.
What good looks like FantasticBrainstorm, or structured Like
like was it something you puttogether quickly, based off of,
like an exercise of 30 minutesof jotting things down, or is it
like no, I've honed in aframework of my definition of
(19:42):
good over months or years, or acareer Like how does that all
you?
Speaker 2 (19:46):
know it, it took me, I would guess, 90 minutes to
perfect it and get it to where Iwanted.
I needed to rely on all of mybusiness's context and history
to get there.
And so for me to perfect thatdocument two years ago I
probably wouldn't have been ableto.
I wouldn't have known what Icould have expected because we
were so early stage.
But now I can go look at someof my historic results and what
(20:10):
I'm paying him and therefore theeconomic lift I should expect
from somebody like that.
So you know, I spent a bunch oftime on it.
I, I thought, dumped a bunch ofstuff.
I did my own editing.
I got it 90% of the way there.
And then I mean, at this point,chat GPT is like my, my
executive coach.
I'd put it into there and I'mlike how do I make this like
(20:31):
apex level?
How do I make this as good asyou've ever seen when it comes
to an expectations document?
And I would take its feedbackand redo it and probably went
through that process 15 times.
Wow, and you know it's, it's abulletproof document.
Speaker 1 (20:46):
Now, Can you share a little bit about it?
Speaker 2 (20:49):
Like you know, the maybe categories or just some
examples of in fact let me bringit up just so I can reference
it and I'm not going off memory.
So I've got let's see one, two,three, four.
I've got four categories underthe what great looks like
section.
So we've got revenue outcomes.
That's one category and thoseare the things you would expect,
(21:12):
right, like hitting certain ARRtargets along certain time
horizons.
Then I've got growth efficiencyexpectations.
So these are things likerevenue per rep right, because
if he hits the ARR targets byhimself and the reps are
struggling, that report to him.
Well, that's great that we gotour revenue.
But that that tells me it wasdone through heroics and we're
(21:35):
paying these other reps and sothat's inefficient.
And so I put that in place winrates, acv, sales cycle, right,
making sure we're hittingcertain efficiency metrics there
.
The third bucket was, or is,predictability and repeatability
.
So I'll give you one examplefrom that.
We've got this interestingdynamic in our business where
(21:56):
we've got two revenue streams.
We've got consumers who sign upfor our platform and we've got
businesses that we sell to andthere's this bridge we call
B2C2B, and we'll see a lot ofdeals, like business deals, come
through that right.
You get like six reps signingup from an account.
Word starts spreading aroundthat account and it can lead to
a meeting with a VP of sales.
(22:17):
We land those deals all thetime.
We've never done anythingpurposeful, we've never put a
process in place to maximizethat, and so I documented him,
kind of systematizing this, andI put like a number next to it
right, for every 100 B2C signups.
Here's how many B2Bopportunities I think we should
generate.
(22:37):
Let's put that as a target.
And then the fourth and finalbucket is qualitative stuff, a
little bit harder to measure.
But has your team taken to yourleadership or has the body
rejected the organ?
That's one thing.
Are you coaching your AEs?
Do you have coaching plans?
How are you showing up insenior leadership meetings?
Is your influence felt, or areyou quiet the entire time?
(22:59):
And a bunch of stuff like that.
And then after that I've gotthe same stuff.
But here's what mediocre lookslike and here's what bad looks
like.
Right, the car is driving off acliff.
The cliff is approaching veryfast and we need to intervene
now approaching very fast and weneed to intervene now.
Speaker 1 (23:18):
So, yeah, so a lot of this is metrics driven and you
have confidence in those metricsbecause you've done it before.
Yeah, so you know track record.
I think for our audience thatone of the challenges that they
get caught up in when they'rebeing evaluated on revenue
outcomes, as an an example, islike were the expectations set
(23:40):
appropriately?
And I'm sure as yourorganization gets much bigger,
that can become a bit morechallenging.
But probably right now you'relike I know that we can do this
with the right execution and soyou can have a lot more
confidence in holding someoneaccountable to that.
I think as a company with 30reps and so on, it becomes you
(24:02):
know, it does become a bit morechallenging to kind of think
through metrics that may notfully be within their control.
Speaker 2 (24:08):
It's just an interesting yeah, and you can
always leave those out, butthere's always metrics that,
unless you're a very early stagestartup, there's always some
metrics that you should havesome level of predictability
around.
Right, Maybe you can't do allof this, Um, but the whole point
is like this document empowersyou to be a challenging leader,
(24:28):
but the right kind ofchallenging leader, because now
you know you're beingchallenging in the sense of
here's the bar.
It's very clear and let's talkabout it.
It the wrong way to do it isI'm going to come after you
unexpectedly and you're going tobe like what the hell?
Speaker 1 (24:41):
like you never even told me that this was an outcome
I needed to achieve yeah, yeah,people don't necessarily
frequently don't know where theystand in an org and when they
get you know either let go orsomething happens and it's a
surprise like that.
Yeah, yeah, it has a realimpact.
Speaker 2 (24:56):
Yeah, and it creates unnecessary fear in your
organization, which stymiesperformance.
Speaker 1 (25:04):
I mean, I think to me that is like I've always had
this mindset of, you know,helping managers set clear
expectations for the team, but Iwill concede that it's always
easier said than done, but itseems like that work up front is
(25:25):
worth it because it allows youto follow through on the element
you said, which is it's notabout you, it's about the bar,
and that's such an easier placein which to give critical
feedback or to do it from.
So that effort is worth it.
And you can see that also likefor individual contributors with
their manager, like if there'sclear expectations, you'll know
(25:47):
where you stand.
We have the bar, the bars,right here.
We can look at how high it isat any point in time and sort of
see how you're doing against it.
Fascinating to me howinfrequently that simple tactic
is deployed.
Mostly, I observe thatmanagement and sales teams are
(26:07):
much more chaotic and just sortof running, running, running and
not necessarily having theexact roadmap and the report
card that sort of says whetherthey're on the right, you know
heading to the right city or not.
Speaker 2 (26:20):
Yeah, yeah, and don't look at me too close with all
this stuff.
Right, I've got a few thingsthat I do really well, but I'm
similar to most salesorganizations.
There are aspects that Ihaven't perfected yet, yeah, but
to your point, it is common.
Like most sales, there's plentyof best practice out there for
sales management, et cetera.
(26:40):
The amount of time you see thatimplemented well, it's pretty
rare.
How many sales organizations doI see that give lip service to
a repeatable sales process butdon't actually have one beyond
just having stages in your CRM?
That's the status quo.
Speaker 1 (27:00):
I want to pivot to that a little bit.
You know, when I was thinkingabout your journey and your
movement from product marketingto sales leadership and then,
sort of, you know, starting yourown company and now focused on
improving the quality of salesexecution in the world now
focused on improving the qualityof sales execution in the world
my thoughts went to coachingand something that, like
(27:21):
coaching, became something youbecame passionate about to the
extent that you started abusiness around it.
And you know, one of theobservations you might be seeing
is the fact that, like,repeatable sales process is lip
service and not something that'sactually adhered to.
Do you want to talk a littlebit about, like, how you
developed a coaching philosophyand how that turned into a sort
(27:42):
of like a passion in which tostart a business around?
Speaker 2 (27:45):
Well I, there were a number of things that just kind
of came together.
I think the right word for thatis a confluence.
My vocabulary is not.
Speaker 1 (27:56):
Hey.
Speaker 2 (27:56):
I'm down, we'll have to.
But.
But the first one is just theproblem I saw in the market,
right Like that.
That almost sounds um kind ofgeneric because like skills, you
know, skill development forsalespeople.
That's like the second oldestproblem in business, the first
of which is hiring salespeople,probably.
But there's we're in a uniquetime in history where skill
(28:20):
capacity across the revenueworkforce is probably lower than
it's ever been in history.
And that's not just likefounder hyperbole.
There are three like macroshifts that all happened at once
that made this happen.
Number one is the economychanged overnight.
We went from ZERP era, zerointerest rate policy, where
(28:42):
selling was easy, money was freeor cheap, buyers were buying
and therefore sellers did nothave to be very good.
They showed up.
If they could fog a mirror,they could close a deal, and
then immediately they werethrust into this new economy
where decisions were made at ahigher level, with more scrutiny
, bigger buying committees, morerisk-averse buying committees,
(29:04):
and skill capacity hasn't caughtup to meet that new demand.
So that's one, that's only one.
The second one is at the exactsame time, all of this was
happening, most of the revenueworkforce went remote and got
younger.
That's not me being a boomerand criticizing Gen Z and
(29:26):
millennials and all that kind ofstuff, but let's just call that
what it is.
You've got all these25-year-old AEs and 23-year-old
soon-to-be AEs coming into theworkforce, into a new economy,
selling from their bedroom,getting coached by a manager who
doesn't know what the hellthey're doing in their own job
and trying to sell in thiseconomy.
(29:47):
Right, that is a recipe fordangerously low skill capacity.
And then the third element is,while the revenue, workforce got
younger, a little bit lesssophisticated, just because
they're less experienced andremote, buyers got way more
savvy and educated and they knowmore, and so it's like an
unfair playing field.
You've got economy flipped,you've got workforce went remote
(30:10):
most of it, and you've gotbuyers who, essentially, you
know it's not even close to thesophistication.
And so now, like skilldevelopment, even though it's
one of the oldest problems inexistence, it's now one of the
most urgent problems inexistence.
It is I would call it ago-to-market skills crisis,
where AEs, sdrs, frontlinemanagers, csms, even marketers
(30:35):
hell.
I mean, they've always hadproblems.
The delta between where theirskill capacity is and what is
needed to win today in 2025,very big delta compared to what
that delta looked like inprevious decades.
Speaker 1 (30:50):
And so you observed this and said, hey, I think I
can bring a unique perspective,because you know it's been this
dynamic, been around a reallylong time.
But you saw the need.
Maybe the need increased or didyou have like, hey, I've got
the good, I've got the actualsolution vis-a-vis everything
else I'm seeing out there.
Speaker 2 (31:08):
Yeah, well, that led to the next piece.
So there's a few passions thatyou know kind of play with this.
One is passionate about sales,passionate about the market and
passionate about learning.
Right, which is our, what ourbusiness is.
But then, like, our uniqueangle on the solution is we're
not your typical sales trainingcompany, right?
This isn't a one and doneengagement.
It's not one size fits all.
(31:29):
It's not theoretical, where weteach you what to do without
without teaching you how to doit, and it's not a bunch of
trainers who haven't closed thedeal since 2014.
Instead, we have a platformwhere you learn from number one,
the best of the best, right?
No professional trainers, no,guys who sold Xerox in the 1980s
and are still teaching the sameway today.
(31:50):
You've got, you know NateNesrella, kyle Norton, kyle
Coleman all these like best ofthe best revenue experts
teaching.
The second thing, and what makesthis unique, is we make a
distinction between skills andsales process.
Right, sales process is what todo, it's what do you do in this
stage, then this stage, thenthis stage.
Skill capacity is deeper it'swhat to do, why to do it and how
(32:14):
to do it, and so every courseyou take in our platform is
dedicated to one skill and itgoes deep on that.
So instead of learning how tosell enterprise good, which is
going to be a mile wide and aninch deep, you take one short
course on every component ofenterprise selling
Enterprise-grade discovery,enterprise grade multi-threading
(32:36):
enterprise grade C-suitemeetings, negotiating with
procurement.
And when you do that now youcan go really deep on each skill
and by the time you're done youhave a very different skill set
than the people who got like asurface level sales process
training that dabbles across allof those topics.
Speaker 1 (32:54):
Yep Makes sense to me .
I want to move, though, to likewhat you're seeing in the world
.
When you now cause, you'reinteracting with sales leaders
on a regular basis.
What is something that you'reseeing?
Any patterns that you're seeingin how sales leaders are being
effective today versus whatyou've seen in the past, or any
glaring hole that you arelooking to solve as it relates
(33:14):
to leadership impact?
Speaker 2 (33:16):
I mean, I think that is a subset of the problem I
just mentioned, right, likerevenue skill capacity across
the revenue professiondangerously low.
Frontline managers inparticular are struggling more
than others and it's not theirfault, like.
(33:36):
This is not me throwing stones,it's our current way of
promoting people is broken,right, you take your super rep,
who loves working alone andclosing deals, you turn them
into a manager and then thereisn't really any rite of passage
in training and development forfrontline managers.
You just I mean, there wasn'tfor me.
That's not a hit at gong, butit's the truth, right, I went
(33:58):
into sales leadership and yeah,no, I.
I'm with you.
You know I read every salesleadership I book I could with
within like a 90 day sprintbecause there wasn't any other
option.
So I think like there's a lotof problems in sales leadership,
it's a really big opportunityfor people.
Speaker 1 (34:17):
What advice are you giving to sales leaders right
now?
Like, is there anything you'refinding yourself saying?
Like you're you're interactingwith sales leaders at a far
greater velocity than I am, andthis whole, uh, this whole, like
, everything that I'm doing isaround trying to define like am
I good at my job?
Speaker 2 (34:33):
So what are you?
Speaker 1 (34:34):
what are you seeing?
What are you saying Like?
What are people asking you forhelp?
For I certainly know thatyou've got a lot of your
business focused on how do weget sellers to be great at
skills, and I'm all for it.
I mean, I think this could be atool to help leaders get their
team to up level like fantastic.
But in those interactions withthe leaders themselves and their
ability to impact, I would loveto just get a synopsis of any
(34:55):
advice you're giving or anythingin the world we live in now,
august 2025.
Speaker 2 (34:59):
Yeah, I mean it's not all that different than what
I've already mentioned, right?
Like I'm not training them onhow to do their job or anything
like that.
The conversation I'm havingwith them is you went from a
world of growing at all costsand hiring, and hiring and
hiring, regardless of whatrevenue per rep looks like, and
now you're in a world whereyou're being asked to do more
(35:19):
with less.
That's not going away anytimesoon, right?
This isn't a fad.
This is going to be a stickymode of operating for a while,
and so your brag metric is notheadcount, it's revenue per rep.
Now, I'm not saying you need tojack up revenue per rep to the
stratosphere, because if revenueper rep is too high, then
(35:41):
you're probably not growing asfast as you could.
Right, if you got a milliondollars revenue per rep, well,
you're probably hedging a littlebit.
But revenue per rep gettingthat in the right balance
probably one of the mostimportant metrics today and one
of the many ways like probably atop three way to pull that
lever.
Skill capacity Now, I don't wantto oversell that.
(36:01):
There are other things you needto get right beyond skill
capacity to drive up revenue perrep.
Right, if you're targeting thewrong accounts with the wrong
message.
You got to fix that first.
But if you've got your strategyin place and you've got some of
the basics of your go-to-market, now skill capacity becomes a
board level metric right.
This is something you can talkabout with your board saying
(36:23):
here's where my skill capacityis.
It's at the right level, whichmeans we should hire more, or
it's low, which means hiringwould be a stupid idea.
Let's get more out of what wecan, first by increasing that
number, skill capacity, and thenwe can start hiring again.
I think this is more of aprediction rather than something
(36:44):
I'm consistently seeing, but Ithink, because of the macro
environment we're in, we'regoing to see skill capacity
become not a nice to have jobperk but like a requirement.
Speaker 1 (36:57):
So number one, chris Orlob advice to leaders is like
you have to figure out a way toincrease skill capacity of your
team, like you need to upskillthem based on the you know
dimensions that you described,the three things coming together
the world we live in, the morediscerning buyers, the
experience levels, the things.
What's the second thing?
Speaker 2 (37:19):
I don't know if I have a second thing.
All of my conversations arefocused around that.
So, um, yeah, I mean the firstthing is like make sure you have
your go-to-market strategybaked right.
Are you targeting the wrongright accounts?
Because having a great, highlyskilled sales organization
talking to the wrong people,it's not going to solve your
problem.
That's coming from the guy whosells skill capacity.
(37:39):
So I know how to belevel-headed here.
But, assuming that's the case,it's pretty rare that I hear
pushback on it, because if I did, I would go.
Well, go listen to your reps'gong calls and tell me what you
hear and if they're great, right, like you, don't have that
problem.
But you're one in 20 and mostleaders I talk to they say my
(38:01):
reps are doing surface leveldiscovery and then transitioning
to a pitch, or they're singlethreaded or they don't even know
what the word champion actuallymeans.
Anybody who likes the productremotely, that's a champion in
my, in my, rep size.
So you know most of myconversations are pretty focused
within that world.
Speaker 1 (38:19):
And do you have like learnings that you're offering
around the leadership aspects,things around people, pipeline
and business?
Speaker 2 (38:28):
We do have sales, like frontline AE manager
curriculum yeah, we don't quiteyet have second line leadership
or like VP of sales and CROlearning paths and stuff like
that.
We plan on doing that.
That's probably a 2026 thing,but we've got the foundations in
place for AE managers to learntheir job and do it well.
Speaker 1 (38:49):
And what are some of the high level concepts in
frontline manager?
You know, skill upskilling.
Speaker 2 (38:54):
Yes, similar to what we've talked about.
Right, we've got courses thatsupport those three pillars I've
mentioned right.
Speaker 1 (39:01):
The people.
Speaker 2 (39:01):
Pipeline and the business yeah, like there's
hiring and recruiting, there'sskill coaching for AE managers
how to run team meetings, someof the basic stuff.
Then you go into pipelinemanagement.
We've got deal strategy, allthat kind of stuff.
Manage the business we're alittle bit lighter in that
bucket.
Right, we don't have like deepcurriculum yet on you know how
to do business planning or stufflike that, but we'll get there.
Speaker 1 (39:23):
Well, chris, I got to say man I, you know I'm
inspired a lot by just thetenacity with which you bring to
the sport that you're playingin, like going after upskilling
of sales.
People have been doing thatsince the beginning of time and
I think the success is A havinga great product and having real
operational experience andhaving lived it, which clearly
you have, and then the rest isjust the rigor with which you go
(39:46):
to bring, and a lot of yourcontent continues just to be as
impactful and interesting andreadable in 2025 as it was in
2017.
So, eight years and counting.
I enjoy thoroughly, you knowlearning from you, you know
through the social media avenuealone.
So it was great speaking withyou.
(40:07):
Anything else you'd want toshare with the audience?
Speaker 2 (40:10):
No, I think that sums it up and you know I'm grateful
.
First of all, thank you for allthe kind words.
I think you're giving me alittle bit too much credit, but
I had a ton of fun today and Ihope people got value out of
this.
And if anybody wants to connectwith me, you can find me on
LinkedIn.
Speaker 1 (40:26):
Yeah, I was going to say I know where to find Chris
on LinkedIn or at pclubio.
Chris, thanks for joining ustoday.
Speaker 2 (40:35):
We'd love to have you on Pillar Talk.
Talk to you soon, man.
Thanks, Rick.
Speaker 1 (40:50):
Reflecting on the conversation with Chris Orlob,
the first thing that reallystood out to me is that we have
the same self-diagnosedleadership gaps, this ability to
work really well with topperformers and really struggle
with folks that are coreperformers or below.
It's a very real thing and it'ssomething that has been a big
challenge for me for many yearsthat I've been in this
leadership position when tryingto improve as a leader in this
area.
Chris made this excellent pointabout step one determine if the
(41:13):
team member has the rawmaterial to succeed.
Determine that it makes sensethat if you do invest the time
and the coaching and find thepatience that's required, that
there's a benefit that you canget on the other side through
the skill development of thatindividual.
When you have a history ofperforming at a high level and
you're used to moving at like acertain speed, it's a real
(41:34):
challenge to slow it down, tohave the patience to maybe get
an answer that you didn't expectto a question and be good with
that and turn it into a learningopportunity.
One challenge that I'llcontinue to have is determining
who has the potential to performand who does not and is just
simply in the wrong role.
It's not always cut and dry.
At least, that's what I find.
One thing I have to say, though, is that a key determinant of
(41:56):
that is the will of theindividual to receive coaching,
versus the folks that areresistant to it.
Now, the leader has to be goodat coaching, and I've seen
situations where there's anindividual who just feels like
they aren't getting the rightcoaching.
I can't help you with that, butif we assume that the leader is
actually good and has valuableinformation to share with
somebody, that willingness toreceive it can be a key
(42:18):
determinant of whether they havethe raw material to succeed.
I personally adhere to acustomer engagement methodology
that helps me be consistent inthe coaching that I deliver.
I hope that helps my leadershipteam as well be consistent in
their coaching.
So I'm not saying one thing andthey're saying another, and the
rep's wondering what to doabout that.
Now, what stood out the most forme in this episode was Chris's
(42:39):
description of how he setsexpectations.
He talked about the wiggledocument, wgll.
He made an important pointDon't make the coaching about
you versus the rep.
Make it about the rep versusthe bar that was set.
And how do you set the bar?
Setting clear expectations anddefining them.
He talked about revenueoutcomes or growth efficiency,
win rate, process improvementsthat the individual make, the
(43:02):
team's response to a new leader,the coaching plans that were
created, leadershipparticipation.
The thing that stands out isn'tnecessarily those individual
points.
It's that he took the time todefine what success looks like
for the individual, sat downwith that person and walked
through it in detail.
As a result, everyone knowswhere things stand and the
(43:23):
relationship can be far moreproductive.
It can now be about theindividual versus the bar that
was set and can help sustainfocus and execution rather than
wondering where I stand and am Iperforming well in my role.
I provide leaders in my orgwith a top 10 list, almost like
David Letterman style at thebeginning of when they join
around key focus areas, and it'ssomething that we can keep
(43:44):
going back to and back to.
Now what I need to do is takean additional step of ensuring
that there are clarifiedexpectations as part of that Now
.
Lastly, chris did a nice job ofoutlining the sales skills gaps.
I'll say that 10 times fast.
That he sees in the market andis the basis behind his business
.
I got to say it is hard toteach reps the skills it takes
(44:08):
to succeed.
When I think about sports oranything in the arts, the amount
of practice that takes place isstaggering, and yet in B2B sass
the learning is almost entirelydone by doing.
Chris is passionatelyattempting to tackle that and if
you read his content online,look, he brings a ton of
credibility.
So check it out.
(44:28):
I want to thank Chris forjoining Pillar Talk this week.
I want to thank Ari Smolin forproducing my man, isler and Sons
of Summer for the tunes and Iwant to thank you, listener, for
joining.
We will see you next time.
Have a good one.
Speaker 2 (44:42):
It hurts in me Like a drug.
I can't shake, I can't quit.
Speaker 1 (44:54):
It's never really what you said it was.
All you're doing is breaking.
It's time to say something real.
Speaker 2 (00:04):
I've been waiting on you to tell me how you really
feel.
Just be honest.
Words in me Like the joke.
I can't shake.
Speaker 1 (00:13):
I can't quit.
It's never really what you say.
Hello everyone, and welcome toanother episode of Pillar Talk,
where we build the foundationsof sales leadership success and
attempt to create clarity interms of what good looks like
for current and aspiring salesleaders.
Before we jump in with today'sguests, let's review the six
(00:34):
pillars of successful salesleadership.
It starts with talent,identification and attraction.
Obviously, both are verydifficult.
It's also the operating rhythm,the environment that fosters
the balance between motivation,engagement and accountability.
Business planning, which isaround the cross functional
dynamics, so that the companycan play offense instead of
(00:54):
reacting and playing defense tothings that happen around us.
Mastering the craft, which isall about helping the team win,
communication and ownership.
Today we are lucky to have as aguest Chris Orlob, the founder
and CEO of pclubio.
That's a platform designed tohelp enterprise sellers
(01:20):
consistently break intoPresident's Club by mastering
winning sales strategies.
Now I know Chris as a thoughtleader focused on sales
performance and analytics.
He previously was an earlyemployee and senior leader at
Gong, where he helped shape,from my perspective, the
company's narrative onconversation intelligence, which
created a category Beforefounding P-Club.
(01:43):
Chris built a career at theintersection, really
interestingly, of marketing andsales, leadership and technology
, sharing his learnings publicly, and I was one of the
beneficiaries of that before itreally became the norm to do so
on platforms like LinkedIn.
So, chris, thank you for beinghere today.
On Pillar Talk.
Speaker 2 (02:03):
Yeah, thanks for having me, Rick, excited to be
here.
Speaker 1 (02:06):
Yeah, excited to learn from you.
I've been learning from you foryears.
I recall back in like 2017, youwere probably the only marketer
in my inbox that had a voice.
Like you were the projection ofannouncements of what was
happening.
Projection of announcements ofwhat was happening, you were,
(02:27):
you know, sharing all kinds ofstuff around your you know,
around the company's positioning, and then it moved to your own
sort of leadership journey andthat was all kind of public.
What made you decide to liketake that approach back then,
before it was the cool thing todo or a trend?
Speaker 2 (02:43):
It just seemed obvious to me.
I don't think there was anylike sophisticated insight that
went behind it.
It was just we were anonymousat Gong right, like we were a
tiny little company.
Nobody knew who we were.
Most of our market spent timeon LinkedIn.
I had happened to spend a fewyears before that crafting my
(03:07):
chops when it came to writingand public speaking and all that
kind of stuff and then we weresitting on top of this data at
gong right, like we're analyzingthousands and eventually
millions of sales calls, and wewere able to extrapolate what's
working according to data.
And so it was kind of like thisperfect storm of like this is
the ultimate thought leadershipplay and it would have been a
(03:30):
complete waste if we weren'tbeating that drum loud and
consistently.
And I also think like I can'ttake all the credit for that,
because a lot of senior leadersand CEOs will not be on board
for something so polarizing.
And it was polarizing.
We were very polarizing whereyou know, even today, I mean
(03:54):
like 90% of the people who wouldengage with our content loved
it, and 10% of them I mean ourfaces were on like a dartboard
that they would throw darts at,like it was very polarizing in
that way, and Amit and Udi rightCEO and VP of marketing at the
time were very on board withthat kind of narrative approach.
(04:15):
Right, let's be edgy, let's putsome polarizing messages into
the market that are going to beboth good for them and good for
our business.
And if that generates some youknow trolls online, that's the
price we pay.
So that's how it started.
Speaker 1 (04:31):
Yeah, I mean I remember they were insightful.
It was I wouldn't saycontroversial, but it zagged a
little bit from maybeconventional thought.
It must've gotten wonderfulengagement and certainly helped
with the brand as well as theswag, and I think it was a dog
associated in there at somepoint.
But then you know, you hadseemed to be a master of like
product marketing, messaging outto a large community, and then
(04:53):
all of a sudden I'm seeing thatyou're in sales leadership and
at the time I don't think thatwas a conventional move that
people made.
It's probably not aconventional move that people
make today.
Speaker 2 (05:11):
Love to hear, just like what drove that decision.
And you know what did you learnearly on that you didn't expect
?
Well, I think, even to this dayI'm I'm in a career where I
can't really explain to myparents what I want to be when I
grow up and and what I am,because my passion is not sales
or sales leadership or productmarketing, is not sales or sales
leadership or product marketing, it's all of it, it's business.
I like category definingbusiness and that if you're
(05:33):
going to do something like that,you need command over all of
those functions.
And so my background.
Funny enough, like a lot ofpeople in the world think like,
oh, chris was a product marketerwho went into sales leadership.
It's actually not true in theworld.
Think like, oh, chris was aproduct marketer who went into
sales leadership.
It's actually not true, it was.
Chris was a sales guy and thenhe tried his hand at product
marketing by joining Gong andthen went back into sales and
sales leadership.
My career before Gong was beside, you know, being an
(05:57):
entrepreneur was sales and Iwanted to try my hand at product
marketing because at the timemy goal was to be a CEO and one
of the patterns I identifiedamong many CEOs is they didn't
come from one function.
They had kind of like a windingcross-functional rise or ascent
(06:19):
up to the CEO position.
Many of them had salesbackgrounds, many of them had
product management backgrounds.
A CEO position Many of them hadsales backgrounds, many of them
had product managementbackgrounds and many, if not
most of them, spent some time ina couple different functions.
And so that's where that camefrom.
Right.
When Gong hired me, they weredoing about 200 grand in ARR and
Amit reaches out wanting totalk and he wanted me to be an
(06:41):
enterprise seller, right, thatwas like his first offer and at
the time I just wasn'tinterested.
I was like I, you know, I've,I've done this job.
It's not what excites me rightnow, at least at this point in
life.
And so he came back and he'slike look, I like how you
marketed your own business on ashoestring budget, how about you
lead product marketing?
I was like great, that's that.
And so I did product marketingfor a couple of years and I
(07:02):
still love product marketing,not necessarily as the job, but
like the craft right, narrativedesign and all that kind of
stuff.
Love that stuff.
I think about it all day, evenin my current role.
I didn't love the role as muchthough I liked being accountable
to a revenue number, I likedbeing well I'll put it the other
way and hopefully I'm notoffending any product marketers
(07:23):
out there I didn't like to besecond fiddle.
I wanted to be the sales leaderwho was, you know, your head's
on the chopping block.
But if your head's on thechopping block, that also means
you've got some authority,hopefully to call the shots, and
I was craving that kind ofdynamic again, and so I can't
even remember how all of thathappened.
I think I just started to talkto my boss about how I was
(07:46):
getting bored in the currentrole, but I didn't want to leave
the company, and so we lookedfor different roles.
Leading a segment of our salesorganization was the next one.
Speaker 1 (07:56):
I will say that that foresight that you had to take a
product marketing role in andof itself had to take a product
marketing role in and of itself,coming from a sales background.
And, truth be told, myknowledge of your background
starts with the productmarketing and gong.
So it's a lot of people fullyprevious.
(08:16):
It's just not conventionaleither.
So the storytelling and I getit.
I mean I just looked at a postyou put on today and look, I
scroll through LinkedIn, likemany people that listen to this
do.
It's a ton of amazing contenton there and you do just have
the knack for engrossing content.
I mean I'm immediately like,yeah, people do blow their shot
with the C-suite in the firstfive minutes.
(08:38):
Yeah, these are the reasons.
So you do have a natural knackfor an ability to do that and I
do like that.
In my career also, I didn't likehave purpose behind what I was
going to do.
I had the basis of like, okay,where can I make the biggest
impact in the organization?
And naturally, if I'm making abig impact in the organization,
they'll likely be a lot oflearning that is happening
(09:00):
associated with that.
So it's not like I want to getthe next role.
I just want to make sure that,as time passes, my impact is
growing in the org and then Iwill evolve to whatever that
ends up being.
Rather than having this likepurposeful journey of art.
I want to do this, spend thismuch time and then it's just you
can plan a pretty picnic, butlike life and the changing
dynamics of go-to-market aresuch that, like it's really hard
(09:22):
to follow a predeterminedtrajectory associated with it.
So it makes sense to me that itwasn't like purposeful, it was
like that's where you wereneeded and it made sense.
And then you started to talkabout what that was like.
And since this podcast is a lotabout the sales leadership
impact, I'd love to go back to,like when you moved into that
role, anything that stood outthat you didn't expect it.
(09:44):
When you had to like becomestoryteller to people manager,
quota carrying people manager.
Speaker 2 (09:51):
Yeah, I mean it's, it's just a totally different
job.
Now I will say, being a productmarketing leader made me a
better sales and salesleadership professional and, on
the other hand, being a salesand sales leadership
professional at the time made mehand.
Being a sales and salesleadership professional at the
time made me a better productmarketing leader, because these
aren't totally distinct skillsets.
Right, because sales and salesleadership you're often the
(10:14):
carrier of the product marketingartifact, which is the
narrative.
Right, you're the one talkingto it.
Product marketing is.
You know, they're at least thebest of the best, which, by the
way, great product marketersreally rare.
Product marketers are common.
Great product marketers arevery rare.
But if you're doing that jobwell, you craft the narrative,
(10:34):
but you're not necessarily theone carrying the narrative, and
sales and sales leadership oftenis.
And so there was there's a lotof learning curve.
It took me a little while tocondense my own model of sales
leadership and really understandit, and it's actually kind of
similar to the pillars that youlined up at the beginning of
(10:54):
this podcast.
The way I I think about salesleadership for myself is really
there's like three bucketsthere's manage the people,
there's manage the pipeline andthere's manage the business, and
most of what you think about asfar as a task or deliverable or
outcome of sales leadership atleast frontline and second line
sales leadership falls intothose buckets, right.
(11:16):
Manage the people, that's well,that's hiring, that's
onboarding, that's coaching,that's firing when you need to.
Pipeline management, that'sobvious.
Right, your job is to marshaldeals across a conveyor belt and
make sure they close, even ifyou're not the one closing them,
and then manage the business iskind of some of the things that
you mentioned.
There's a lot ofcross-functional chops that you
(11:39):
need to get used to.
There's business planning,there's developing scalable
playbooks used to.
There's business planning,there's developing scalable
playbooks.
That's the part I struggled withthe most was the
cross-functional stuff, becauseI can be very stubborn, right,
like if I have an idea or a wayof doing things, I just want to
marshal ahead and bring it intothe market, and sometimes that's
(12:00):
a very good trait to have,that's a really good trait for a
startup.
But when the company startedgrowing and I kind of forgot
that I have to align withcustomer success and marketing
and all that kind of stuff, Ithink I burnt a few.
I wouldn't say I burnt anybridges, but I scorched the
earth a little bit too much.
I was like a bull in a chinashop and I had to learn some
(12:22):
hard, cross-functional lessons.
The china shop and I had tolearn some hard,
cross-functional lessons.
And, uh, I actually rememberasking my boss to do an
anonymous 360 degree review ofme across all my peer set.
Right, they could like give mefeedback and it was painful,
like I still remember thatbecause I I got a lot of good
feedback, don't get me wrong,but there was a lot of like you
(12:45):
know, chris, just it's kind ofhis way or the highway type
stuff and it stung.
But I'm really glad I asked forall of that because it stung in
a way that helped me grow and Igrew fast because I was willing
to eat that glass, so to speakso you, I'm going to use your
(13:05):
framing of this.
Speaker 1 (13:06):
So was managing the people pretty natural thing,
because if I take it from myvantage point before you kind of
get into this, thecross-functional part I'm a
communicator and a little bitless of a kind of driver, so
that wouldn't be a pipeline.
Yeah, let's do pipeline.
Less of a kind of driver, sothat wouldn't be a pipeline.
Yeah, let's do pipeline.
(13:27):
I mean, I'm a sales guy.
But the people part was thearea that I was like, oh, they
don't want to do it the exactway that I just do it.
They're not clones of me.
This is a that to me was likewhoa, this is the hardest part.
So it's super interesting tokind of frame it that way.
Speaker 2 (13:51):
Yeah, well, one of the I mean, I still struggle
with this aspect of peoplemanagement today.
One of the things that I foundvery quickly is I like to think
I'm actually great at managingand leading people who are
already a players.
I'm good at coaching them.
I'm good at managing them.
Um, my co-founder here at Pclubs, so you can tell I'm still
like working through some ofthese opportunity uh areas.
He gave me feedback probably ayear ago where he's like Chris,
(14:11):
you're one of the best leaders Iknow when you're leading great
people and you're one of theworst leaders I know when you're
leading people that are not sogreat.
I like to think I've grownsince that conversation.
Right, it's not like a trainwreck anymore.
But that's something Istruggled with when I first
stepped into sales leadership,because not everybody likes to
(14:32):
admit this, but most sales teamshave B players on them and
sometimes C players, and I wouldget critical too fast of those
people and sometimes even today,I do.
Speaker 1 (14:43):
As by far my self-criticism is almost
identical to what you justshared.
Is it more of a patience thing?
What do you attribute thatdynamic to, this ability to work
incredibly well with motivatedhigh performers and a struggle
to help develop and have thepatience I mean that's the word
(15:05):
that comes to mind for me to,you know, almost slow down the
velocity of your individualexecution to help bring somebody
along.
Speaker 2 (15:15):
Well, there's a few.
I'll go in a few differentplaces here.
First, there is wisdom inknowing if somebody has the
potential and drive to work outright.
If somebody is quote unquotemediocre or a B player, that
doesn't mean give up on them.
That means assess their abilityto improve and their and their
drive to improve.
(15:35):
And if somebody is a B playerand they have those things, then
it's very high ROI time for youto coach them and develop them.
If they're not, you should justterminate them.
You should do itcompassionately and you should
do it non-emotionally andrespectfully.
But it doesn't make sense tohave somebody who's not great at
their job and doesn't have adesire to improve or an ability
(15:58):
to improve.
So that's like kind of thefirst bucket.
The second one is bucket.
The second one is I can'tremember who gave me this
feedback, but they said you dowant to be a challenging boss to
work for, but you want to makethe enemy the bar, not you.
And so the wrong way to do thisis you go into a one-on-one with
(16:20):
a B player and you're allemotional and critical and
you're kind of like attackingthem because now you're the
enemy.
Instead, you're completelyunemotional and you make the
enemy the bar, the bar forperformance or whatever, and you
just say something with theethos of, like, our bar's up
here and it looks like whatyou're doing is somewhere around
(16:41):
here, and so how do we closethat delta?
Right, that's being achallenging boss, but not being
an asshole or toxic about it,and I do like I hate to admit it
.
This is kind of painful to say,especially on a podcast.
I think sometimes I could havegotten toxic right, like in
those situations I was the enemyrather than the bar, and that's
probably one of the biggestgrowth opportunities I've had to
(17:05):
lean into over the last fiveyears or so.
Speaker 1 (17:07):
And is that concept making it less about what you
say and more about the standard,like an application that you
now are sort of prevalentlyusing?
Speaker 2 (17:17):
Yeah, 100%, and it comes.
I mean, this opens up a wholenew can of worms.
To be able to do thateffectively and fairly, you have
to document what your standardsare.
So good example of that todayis day three of my new VP of
sales starting, and before hestarted I put together what I
(17:39):
call a wiggle doc W-G-L-L, whatgood looks like and it's one or
two pages of of during yourfirst 120 days on the job,
between now and December 1st orDecember 31st.
Here's what great looks like,here's what mediocre looks like
and here's what off track lookslike.
And you can't really hold peoplerationally to a bar until
(18:04):
you've documented andcommunicated what those are.
So him and I you know, I sharedthat document with him a couple
of days ago, on day one, andhim, I was like go absorb this.
I want to make sure you feelgood about it.
And then, when you've absorbedit, let's talk about it at
length.
And that's what we did thismorning.
Right, it was like you know,he's walking through his
concerns.
He's walking through why Ipicked certain things the way I
(18:27):
did, I'm justifying them, and itwas just a little bit of a
healthy negotiation, right, likehere's what I expect, and now
he doesn't have to show up toone-on-ones with me guessing
about how he's doing.
We go well, let's look at thewiggle dock, and now I can refer
to that and say well, you knowwhat your ARR targets are, you
(18:47):
know what your monthly targetsare, you know what your revenue
per rep targets are.
Win rate, all that kind ofstuff Looks like we're a little
bit behind in this one area.
What do you think the plan isfor us?
Closing that delta?
That's holding people to a highbar and being a challenging
leader, but being a good leaderwhile you do it, instead of, you
know, freaking out and beinglike you're the problem and
(19:15):
being like all critical of themand attacking them, because now
you're not on their side andthey can sense that and you've
just done your first steptowards severing a relationship.
Speaker 1 (19:20):
First of all, love this idea of a wiggle dock.
What good looks like FantasticBrainstorm, or structured Like
like was it something you puttogether quickly, based off of,
like an exercise of 30 minutesof jotting things down, or is it
like no, I've honed in aframework of my definition of
(19:42):
good over months or years, or acareer Like how does that all
you?
Speaker 2 (19:46):
know it, it took me, I would guess, 90 minutes to
perfect it and get it to where Iwanted.
I needed to rely on all of mybusiness's context and history
to get there.
And so for me to perfect thatdocument two years ago I
probably wouldn't have been ableto.
I wouldn't have known what Icould have expected because we
were so early stage.
But now I can go look at someof my historic results and what
(20:10):
I'm paying him and therefore theeconomic lift I should expect
from somebody like that.
So you know, I spent a bunch oftime on it.
I, I thought, dumped a bunch ofstuff.
I did my own editing.
I got it 90% of the way there.
And then I mean, at this point,chat GPT is like my, my
executive coach.
I'd put it into there and I'mlike how do I make this like
(20:31):
apex level?
How do I make this as good asyou've ever seen when it comes
to an expectations document?
And I would take its feedbackand redo it and probably went
through that process 15 times.
Wow, and you know it's, it's abulletproof document.
Speaker 1 (20:46):
Now, Can you share a little bit about it?
Speaker 2 (20:49):
Like you know, the maybe categories or just some
examples of in fact let me bringit up just so I can reference
it and I'm not going off memory.
So I've got let's see one, two,three, four.
I've got four categories underthe what great looks like
section.
So we've got revenue outcomes.
That's one category and thoseare the things you would expect,
(21:12):
right, like hitting certain ARRtargets along certain time
horizons.
Then I've got growth efficiencyexpectations.
So these are things likerevenue per rep right, because
if he hits the ARR targets byhimself and the reps are
struggling, that report to him.
Well, that's great that we gotour revenue.
But that that tells me it wasdone through heroics and we're
(21:35):
paying these other reps and sothat's inefficient.
And so I put that in place winrates, acv, sales cycle, right,
making sure we're hittingcertain efficiency metrics there
.
The third bucket was, or is,predictability and repeatability
.
So I'll give you one examplefrom that.
We've got this interestingdynamic in our business where
(21:56):
we've got two revenue streams.
We've got consumers who sign upfor our platform and we've got
businesses that we sell to andthere's this bridge we call
B2C2B, and we'll see a lot ofdeals, like business deals, come
through that right.
You get like six reps signingup from an account.
Word starts spreading aroundthat account and it can lead to
a meeting with a VP of sales.
(22:17):
We land those deals all thetime.
We've never done anythingpurposeful, we've never put a
process in place to maximizethat, and so I documented him,
kind of systematizing this, andI put like a number next to it
right, for every 100 B2C signups.
Here's how many B2Bopportunities I think we should
generate.
(22:37):
Let's put that as a target.
And then the fourth and finalbucket is qualitative stuff, a
little bit harder to measure.
But has your team taken to yourleadership or has the body
rejected the organ?
That's one thing.
Are you coaching your AEs?
Do you have coaching plans?
How are you showing up insenior leadership meetings?
Is your influence felt, or areyou quiet the entire time?
(22:59):
And a bunch of stuff like that.
And then after that I've gotthe same stuff.
But here's what mediocre lookslike and here's what bad looks
like.
Right, the car is driving off acliff.
The cliff is approaching veryfast and we need to intervene
now approaching very fast and weneed to intervene now.
Speaker 1 (23:18):
So, yeah, so a lot of this is metrics driven and you
have confidence in those metricsbecause you've done it before.
Yeah, so you know track record.
I think for our audience thatone of the challenges that they
get caught up in when they'rebeing evaluated on revenue
outcomes, as an an example, islike were the expectations set
(23:40):
appropriately?
And I'm sure as yourorganization gets much bigger,
that can become a bit morechallenging.
But probably right now you'relike I know that we can do this
with the right execution and soyou can have a lot more
confidence in holding someoneaccountable to that.
I think as a company with 30reps and so on, it becomes you
(24:02):
know, it does become a bit morechallenging to kind of think
through metrics that may notfully be within their control.
Speaker 2 (24:08):
It's just an interesting yeah, and you can
always leave those out, butthere's always metrics that,
unless you're a very early stagestartup, there's always some
metrics that you should havesome level of predictability
around.
Right, Maybe you can't do allof this, Um, but the whole point
is like this document empowersyou to be a challenging leader,
(24:28):
but the right kind ofchallenging leader, because now
you know you're beingchallenging in the sense of
here's the bar.
It's very clear and let's talkabout it.
It the wrong way to do it isI'm going to come after you
unexpectedly and you're going tobe like what the hell?
Speaker 1 (24:41):
like you never even told me that this was an outcome
I needed to achieve yeah, yeah,people don't necessarily
frequently don't know where theystand in an org and when they
get you know either let go orsomething happens and it's a
surprise like that.
Yeah, yeah, it has a realimpact.
Speaker 2 (24:56):
Yeah, and it creates unnecessary fear in your
organization, which stymiesperformance.
Speaker 1 (25:04):
I mean, I think to me that is like I've always had
this mindset of, you know,helping managers set clear
expectations for the team, but Iwill concede that it's always
easier said than done, but itseems like that work up front is
(25:25):
worth it because it allows youto follow through on the element
you said, which is it's notabout you, it's about the bar,
and that's such an easier placein which to give critical
feedback or to do it from.
So that effort is worth it.
And you can see that also likefor individual contributors with
their manager, like if there'sclear expectations, you'll know
(25:47):
where you stand.
We have the bar, the bars,right here.
We can look at how high it isat any point in time and sort of
see how you're doing against it.
Fascinating to me howinfrequently that simple tactic
is deployed.
Mostly, I observe thatmanagement and sales teams are
(26:07):
much more chaotic and just sortof running, running, running and
not necessarily having theexact roadmap and the report
card that sort of says whetherthey're on the right, you know
heading to the right city or not.
Speaker 2 (26:20):
Yeah, yeah, and don't look at me too close with all
this stuff.
Right, I've got a few thingsthat I do really well, but I'm
similar to most salesorganizations.
There are aspects that Ihaven't perfected yet, yeah, but
to your point, it is common.
Like most sales, there's plentyof best practice out there for
sales management, et cetera.
(26:40):
The amount of time you see thatimplemented well, it's pretty
rare.
How many sales organizations doI see that give lip service to
a repeatable sales process butdon't actually have one beyond
just having stages in your CRM?
That's the status quo.
Speaker 1 (27:00):
I want to pivot to that a little bit.
You know, when I was thinkingabout your journey and your
movement from product marketingto sales leadership and then,
sort of, you know, starting yourown company and now focused on
improving the quality of salesexecution in the world now
focused on improving the qualityof sales execution in the world
my thoughts went to coachingand something that, like
(27:21):
coaching, became something youbecame passionate about to the
extent that you started abusiness around it.
And you know, one of theobservations you might be seeing
is the fact that, like,repeatable sales process is lip
service and not something that'sactually adhered to.
Do you want to talk a littlebit about, like, how you
developed a coaching philosophyand how that turned into a sort
(27:42):
of like a passion in which tostart a business around?
Speaker 2 (27:45):
Well I, there were a number of things that just kind
of came together.
I think the right word for thatis a confluence.
My vocabulary is not.
Speaker 1 (27:56):
Hey.
Speaker 2 (27:56):
I'm down, we'll have to.
But.
But the first one is just theproblem I saw in the market,
right Like that.
That almost sounds um kind ofgeneric because like skills, you
know, skill development forsalespeople.
That's like the second oldestproblem in business, the first
of which is hiring salespeople,probably.
But there's we're in a uniquetime in history where skill
(28:20):
capacity across the revenueworkforce is probably lower than
it's ever been in history.
And that's not just likefounder hyperbole.
There are three like macroshifts that all happened at once
that made this happen.
Number one is the economychanged overnight.
We went from ZERP era, zerointerest rate policy, where
(28:42):
selling was easy, money was freeor cheap, buyers were buying
and therefore sellers did nothave to be very good.
They showed up.
If they could fog a mirror,they could close a deal, and
then immediately they werethrust into this new economy
where decisions were made at ahigher level, with more scrutiny
, bigger buying committees, morerisk-averse buying committees,
(29:04):
and skill capacity hasn't caughtup to meet that new demand.
So that's one, that's only one.
The second one is at the exactsame time, all of this was
happening, most of the revenueworkforce went remote and got
younger.
That's not me being a boomerand criticizing Gen Z and
(29:26):
millennials and all that kind ofstuff, but let's just call that
what it is.
You've got all these25-year-old AEs and 23-year-old
soon-to-be AEs coming into theworkforce, into a new economy,
selling from their bedroom,getting coached by a manager who
doesn't know what the hellthey're doing in their own job
and trying to sell in thiseconomy.
(29:47):
Right, that is a recipe fordangerously low skill capacity.
And then the third element is,while the revenue, workforce got
younger, a little bit lesssophisticated, just because
they're less experienced andremote, buyers got way more
savvy and educated and they knowmore, and so it's like an
unfair playing field.
You've got economy flipped,you've got workforce went remote
(30:10):
most of it, and you've gotbuyers who, essentially, you
know it's not even close to thesophistication.
And so now, like skilldevelopment, even though it's
one of the oldest problems inexistence, it's now one of the
most urgent problems inexistence.
It is I would call it ago-to-market skills crisis,
where AEs, sdrs, frontlinemanagers, csms, even marketers
(30:35):
hell.
I mean, they've always hadproblems.
The delta between where theirskill capacity is and what is
needed to win today in 2025,very big delta compared to what
that delta looked like inprevious decades.
Speaker 1 (30:50):
And so you observed this and said, hey, I think I
can bring a unique perspective,because you know it's been this
dynamic, been around a reallylong time.
But you saw the need.
Maybe the need increased or didyou have like, hey, I've got
the good, I've got the actualsolution vis-a-vis everything
else I'm seeing out there.
Speaker 2 (31:08):
Yeah, well, that led to the next piece.
So there's a few passions thatyou know kind of play with this.
One is passionate about sales,passionate about the market and
passionate about learning.
Right, which is our, what ourbusiness is.
But then, like, our uniqueangle on the solution is we're
not your typical sales trainingcompany, right?
This isn't a one and doneengagement.
It's not one size fits all.
(31:29):
It's not theoretical, where weteach you what to do without
without teaching you how to doit, and it's not a bunch of
trainers who haven't closed thedeal since 2014.
Instead, we have a platformwhere you learn from number one,
the best of the best, right?
No professional trainers, no,guys who sold Xerox in the 1980s
and are still teaching the sameway today.
(31:50):
You've got, you know NateNesrella, kyle Norton, kyle
Coleman all these like best ofthe best revenue experts
teaching.
The second thing, and what makesthis unique, is we make a
distinction between skills andsales process.
Right, sales process is what todo, it's what do you do in this
stage, then this stage, thenthis stage.
Skill capacity is deeper it'swhat to do, why to do it and how
(32:14):
to do it, and so every courseyou take in our platform is
dedicated to one skill and itgoes deep on that.
So instead of learning how tosell enterprise good, which is
going to be a mile wide and aninch deep, you take one short
course on every component ofenterprise selling
Enterprise-grade discovery,enterprise grade multi-threading
(32:36):
enterprise grade C-suitemeetings, negotiating with
procurement.
And when you do that now youcan go really deep on each skill
and by the time you're done youhave a very different skill set
than the people who got like asurface level sales process
training that dabbles across allof those topics.
Speaker 1 (32:54):
Yep Makes sense to me .
I want to move, though, to likewhat you're seeing in the world
.
When you now cause, you'reinteracting with sales leaders
on a regular basis.
What is something that you'reseeing?
Any patterns that you're seeingin how sales leaders are being
effective today versus whatyou've seen in the past, or any
glaring hole that you arelooking to solve as it relates
(33:14):
to leadership impact?
Speaker 2 (33:16):
I mean, I think that is a subset of the problem I
just mentioned, right, likerevenue skill capacity across
the revenue professiondangerously low.
Frontline managers inparticular are struggling more
than others and it's not theirfault, like.
(33:36):
This is not me throwing stones,it's our current way of
promoting people is broken,right, you take your super rep,
who loves working alone andclosing deals, you turn them
into a manager and then thereisn't really any rite of passage
in training and development forfrontline managers.
You just I mean, there wasn'tfor me.
That's not a hit at gong, butit's the truth, right, I went
(33:58):
into sales leadership and yeah,no, I.
I'm with you.
You know I read every salesleadership I book I could with
within like a 90 day sprintbecause there wasn't any other
option.
So I think like there's a lotof problems in sales leadership,
it's a really big opportunityfor people.
Speaker 1 (34:17):
What advice are you giving to sales leaders right
now?
Like, is there anything you'refinding yourself saying?
Like you're you're interactingwith sales leaders at a far
greater velocity than I am, andthis whole, uh, this whole, like
, everything that I'm doing isaround trying to define like am
I good at my job?
Speaker 2 (34:33):
So what are you?
Speaker 1 (34:34):
what are you seeing?
What are you saying Like?
What are people asking you forhelp?
For I certainly know thatyou've got a lot of your
business focused on how do weget sellers to be great at
skills, and I'm all for it.
I mean, I think this could be atool to help leaders get their
team to up level like fantastic.
But in those interactions withthe leaders themselves and their
ability to impact, I would loveto just get a synopsis of any
(34:55):
advice you're giving or anythingin the world we live in now,
august 2025.
Speaker 2 (34:59):
Yeah, I mean it's not all that different than what
I've already mentioned, right?
Like I'm not training them onhow to do their job or anything
like that.
The conversation I'm havingwith them is you went from a
world of growing at all costsand hiring, and hiring and
hiring, regardless of whatrevenue per rep looks like, and
now you're in a world whereyou're being asked to do more
(35:19):
with less.
That's not going away anytimesoon, right?
This isn't a fad.
This is going to be a stickymode of operating for a while,
and so your brag metric is notheadcount, it's revenue per rep.
Now, I'm not saying you need tojack up revenue per rep to the
stratosphere, because if revenueper rep is too high, then
(35:41):
you're probably not growing asfast as you could.
Right, if you got a milliondollars revenue per rep, well,
you're probably hedging a littlebit.
But revenue per rep gettingthat in the right balance
probably one of the mostimportant metrics today and one
of the many ways like probably atop three way to pull that
lever.
Skill capacity Now, I don't wantto oversell that.
(36:01):
There are other things you needto get right beyond skill
capacity to drive up revenue perrep.
Right, if you're targeting thewrong accounts with the wrong
message.
You got to fix that first.
But if you've got your strategyin place and you've got some of
the basics of your go-to-market, now skill capacity becomes a
board level metric right.
This is something you can talkabout with your board saying
(36:23):
here's where my skill capacityis.
It's at the right level, whichmeans we should hire more, or
it's low, which means hiringwould be a stupid idea.
Let's get more out of what wecan, first by increasing that
number, skill capacity, and thenwe can start hiring again.
I think this is more of aprediction rather than something
(36:44):
I'm consistently seeing, but Ithink, because of the macro
environment we're in, we'regoing to see skill capacity
become not a nice to have jobperk but like a requirement.
Speaker 1 (36:57):
So number one, chris Orlob advice to leaders is like
you have to figure out a way toincrease skill capacity of your
team, like you need to upskillthem based on the you know
dimensions that you described,the three things coming together
the world we live in, the morediscerning buyers, the
experience levels, the things.
What's the second thing?
Speaker 2 (37:19):
I don't know if I have a second thing.
All of my conversations arefocused around that.
So, um, yeah, I mean the firstthing is like make sure you have
your go-to-market strategybaked right.
Are you targeting the wrongright accounts?
Because having a great, highlyskilled sales organization
talking to the wrong people,it's not going to solve your
problem.
That's coming from the guy whosells skill capacity.
(37:39):
So I know how to belevel-headed here.
But, assuming that's the case,it's pretty rare that I hear
pushback on it, because if I did, I would go.
Well, go listen to your reps'gong calls and tell me what you
hear and if they're great, right, like you, don't have that
problem.
But you're one in 20 and mostleaders I talk to they say my
(38:01):
reps are doing surface leveldiscovery and then transitioning
to a pitch, or they're singlethreaded or they don't even know
what the word champion actuallymeans.
Anybody who likes the productremotely, that's a champion in
my, in my, rep size.
So you know most of myconversations are pretty focused
within that world.
Speaker 1 (38:19):
And do you have like learnings that you're offering
around the leadership aspects,things around people, pipeline
and business?
Speaker 2 (38:28):
We do have sales, like frontline AE manager
curriculum yeah, we don't quiteyet have second line leadership
or like VP of sales and CROlearning paths and stuff like
that.
We plan on doing that.
That's probably a 2026 thing,but we've got the foundations in
place for AE managers to learntheir job and do it well.
Speaker 1 (38:49):
And what are some of the high level concepts in
frontline manager?
You know, skill upskilling.
Speaker 2 (38:54):
Yes, similar to what we've talked about.
Right, we've got courses thatsupport those three pillars I've
mentioned right.
Speaker 1 (39:01):
The people.
Speaker 2 (39:01):
Pipeline and the business yeah, like there's
hiring and recruiting, there'sskill coaching for AE managers
how to run team meetings, someof the basic stuff.
Then you go into pipelinemanagement.
We've got deal strategy, allthat kind of stuff.
Manage the business we're alittle bit lighter in that
bucket.
Right, we don't have like deepcurriculum yet on you know how
to do business planning or stufflike that, but we'll get there.
Speaker 1 (39:23):
Well, chris, I got to say man I, you know I'm
inspired a lot by just thetenacity with which you bring to
the sport that you're playingin, like going after upskilling
of sales.
People have been doing thatsince the beginning of time and
I think the success is A havinga great product and having real
operational experience andhaving lived it, which clearly
you have, and then the rest isjust the rigor with which you go
(39:46):
to bring, and a lot of yourcontent continues just to be as
impactful and interesting andreadable in 2025 as it was in
2017.
So, eight years and counting.
I enjoy thoroughly, you knowlearning from you, you know
through the social media avenuealone.
So it was great speaking withyou.
(40:07):
Anything else you'd want toshare with the audience?
Speaker 2 (40:10):
No, I think that sums it up and you know I'm grateful
.
First of all, thank you for allthe kind words.
I think you're giving me alittle bit too much credit, but
I had a ton of fun today and Ihope people got value out of
this.
And if anybody wants to connectwith me, you can find me on
LinkedIn.
Speaker 1 (40:26):
Yeah, I was going to say I know where to find Chris
on LinkedIn or at pclubio.
Chris, thanks for joining ustoday.
Speaker 2 (40:35):
We'd love to have you on Pillar Talk.
Talk to you soon, man.
Thanks, Rick.
Speaker 1 (40:50):
Reflecting on the conversation with Chris Orlob,
the first thing that reallystood out to me is that we have
the same self-diagnosedleadership gaps, this ability to
work really well with topperformers and really struggle
with folks that are coreperformers or below.
It's a very real thing and it'ssomething that has been a big
challenge for me for many yearsthat I've been in this
leadership position when tryingto improve as a leader in this
area.
Chris made this excellent pointabout step one determine if the
(41:13):
team member has the rawmaterial to succeed.
Determine that it makes sensethat if you do invest the time
and the coaching and find thepatience that's required, that
there's a benefit that you canget on the other side through
the skill development of thatindividual.
When you have a history ofperforming at a high level and
you're used to moving at like acertain speed, it's a real
(41:34):
challenge to slow it down, tohave the patience to maybe get
an answer that you didn't expectto a question and be good with
that and turn it into a learningopportunity.
One challenge that I'llcontinue to have is determining
who has the potential to performand who does not and is just
simply in the wrong role.
It's not always cut and dry.
At least, that's what I find.
One thing I have to say, though, is that a key determinant of
(41:56):
that is the will of theindividual to receive coaching,
versus the folks that areresistant to it.
Now, the leader has to be goodat coaching, and I've seen
situations where there's anindividual who just feels like
they aren't getting the rightcoaching.
I can't help you with that, butif we assume that the leader is
actually good and has valuableinformation to share with
somebody, that willingness toreceive it can be a key
(42:18):
determinant of whether they havethe raw material to succeed.
I personally adhere to acustomer engagement methodology
that helps me be consistent inthe coaching that I deliver.
I hope that helps my leadershipteam as well be consistent in
their coaching.
So I'm not saying one thing andthey're saying another, and the
rep's wondering what to doabout that.
Now, what stood out the most forme in this episode was Chris's
(42:39):
description of how he setsexpectations.
He talked about the wiggledocument, wgll.
He made an important pointDon't make the coaching about
you versus the rep.
Make it about the rep versusthe bar that was set.
And how do you set the bar?
Setting clear expectations anddefining them.
He talked about revenueoutcomes or growth efficiency,
win rate, process improvementsthat the individual make, the
(43:02):
team's response to a new leader,the coaching plans that were
created, leadershipparticipation.
The thing that stands out isn'tnecessarily those individual
points.
It's that he took the time todefine what success looks like
for the individual, sat downwith that person and walked
through it in detail.
As a result, everyone knowswhere things stand and the
(43:23):
relationship can be far moreproductive.
It can now be about theindividual versus the bar that
was set and can help sustainfocus and execution rather than
wondering where I stand and am Iperforming well in my role.
I provide leaders in my orgwith a top 10 list, almost like
David Letterman style at thebeginning of when they join
around key focus areas, and it'ssomething that we can keep
(43:44):
going back to and back to.
Now what I need to do is takean additional step of ensuring
that there are clarifiedexpectations as part of that Now
.
Lastly, chris did a nice job ofoutlining the sales skills gaps.
I'll say that 10 times fast.
That he sees in the market andis the basis behind his business
.
I got to say it is hard toteach reps the skills it takes
(44:08):
to succeed.
When I think about sports oranything in the arts, the amount
of practice that takes place isstaggering, and yet in B2B sass
the learning is almost entirelydone by doing.
Chris is passionatelyattempting to tackle that and if
you read his content online,look, he brings a ton of
credibility.
So check it out.
(44:28):
I want to thank Chris forjoining Pillar Talk this week.
I want to thank Ari Smolin forproducing my man, isler and Sons
of Summer for the tunes and Iwant to thank you, listener, for
joining.
We will see you next time.
Have a good one.
Speaker 2 (44:42):
It hurts in me Like a drug.
I can't shake, I can't quit.
Speaker 1 (44:54):
It's never really what you said it was.
All you're doing is breaking.
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