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Even the most prominent voices in Sales were crap at Sales once.
Join bestselling Author, Founder and Sales Coach Mark Ackers as he speaks with successful Sales professionals about their early Sales struggles, and how they overcame these challenges to become the people they are today.
mark ackers: current sales
manager at Klaviyo, co founder
of SDRS anonymous, a sales
coach, former outreach sales
leader. It's Kaitlen Kelly, did
you used to be crap on sales?
kaitlen kelly: Yes.
mark ackers: How crap are we
talking?
kaitlen kelly: If we only give
it on a scale of one to 10 I'll
be generous and give myself a
mark ackers: Christ cold calling
your parents for roleplay
kaitlen kelly: I was doing
everything I could to get
better. Because these gentlemen
that I was hired with were
extremely great as well. At our
age. I'm pretty fearless on the
phone. So I got my script
memorised. We're good to go.
They sent me to my first event
in Vegas, there's so much prep
work that I put into this. So I
had a pretty like bulletproof
plan of who I was going to
target. Once I got there. I'm
with my account executive that
I'm paired with at that time, I
walk up my personas there,
because I looked on his
LinkedIn. I know what his
picture looks like. And I go
straight up to him. And
literally, it was the weirdest
thing. I was like I turned into
a robot. I think it shocked the
account executive, you guys he
had to stop me halfway through
and was like, I'm so sorry. Um,
we're going to just take a step
away from here. And he had to
like pull me away from the
prospect and was like, Are you
still breathing? Like what's
going on here? So that is yeah,
a moment where I'm just like,
that was incredibly
embarrassing. I
mark ackers: wonder somewhere
else that they sometimes tell
the story, are you Oh, that
great. Kaitlen Kelly, you see on
LinkedIn. Let me tell you about
our first event. Imagine a sales
rep is listening to this gonna
join a business and a saas roll.
This is the Kaitlen Kelly
blueprint, the first six months,
everything you need to do to get
ahead. What does that blueprint
look like? Yeah,
kaitlen kelly: my first six
months I'm going to
mark ackers: welcome to another
episode of The I used to be crap
at sales podcast. I'm your host,
Mark Akers, co founder and head
of sales, my sales coach, and
today I'm joined by the current
sales manager at CLEVEO, co
founder of SDRS anonymous, a
sales coach, former outreach
sales leader. It's Kaitlen
Kelly. Caitlyn, Bill, welcome to
the podcast. How are you? I
kaitlen kelly: am doing
fantastic, what a great entry
that you just gave me. So I
really appreciate that mark,
lots of titles that you tacked
on there.
mark ackers: It's all credit to
UK and going for your LinkedIn
is loads of your work going on,
which is why I know you're gonna
be a great guest today. Let's
kick off with just a yes, no
question. Kaitlen Kelly, did you
used to be crap at sales?
kaitlen kelly: Yes.
mark ackers: How crap? Are we
talking?
kaitlen kelly: I mean, if we had
to give it on a scale of one to
10, I'll give. I'll be generous
and give myself a three here.
But it's I think sales is a
funny thing, if you think about
it, in hindsight, and I think
we'll dive into kind of how I
ended up here. But yeah, if I
think back to the first couple
of times, got some good
memories.
mark ackers: Let's start there.
And how you ended up in sales?
Because obviously, that was
quite a career switch view
brings bring to life. How you
went from working in fashion?
Yeah, to working as an SDR
outreach. How did that happen?
kaitlen kelly: Yeah, so I think
on So growing up, like I had
like my dream and all this
stuff, but then early like
switched over and I was like, I
want to be a buyer within the
fashion industry. So what I did
is I worked backwards from the
end goal to figure out okay, how
do I become a buyer at
Nordstrom? Nordstrom is like a
designer store similar to like a
Selfridges based out of the US.
And so they had like a
internship programme. And the
internship programme actually
started out on the sales floor
there. At the time, it wasn't
like it's literally setting up
like stylist appointments, and
then you're selling wardrobes
and outfitting people, but
you're based on commission
solely. So I went throughout my
education kind of ticking off
the boxes of how do I get myself
to the buying office, which was
my end goal. And so as I went
through that I went got into
sales at Nordstrom through the
internship programme. And that
kind of accelerated me through a
series of leadership roles and
then into the buying office as
an analyst, which was kind of my
end goal. And as I was in the
buying office, I was probably in
my mid 20s at the time. And I
knew that in order for me to get
to that buying role, it would
probably be another five to
seven years, just given how slow
career progression was
happening. And it wasn't
actually loving the role either.
And so kind of like looking
around trying to figure out
like, is there people that I see
here that I want to be in 510
years? Is this really where I
want to end up? So I was having
one of those moments that I
think a lot of people probably
have these that 2526 years old,
and and a couple of my friends
that I had started out in this
internship programme at
Nordstrom had actually made the
switch over to outreach and
outreach as a Seattle
headquartered company as well.
Nordstrom is headquartered in
Seattle too. So I had a good
friend who had went there a year
before I had kind of made the
transition over to outreach. And
he went in as an SDR and was
like loving it. He knew how
ambitious I wasn't motivated.
And so he kept trying, he's
like, just give it a shot, give
it a shot. And I was like,
Absolutely not like, I'm not
cold calling, I was like sitting
in my comfort zone, like I had
just invested four years of my
own money to pay for tuition.
And all of the years that I put
into, like getting myself on
this career track. So I'm like,
do I give up now? Or kind of
seven years into this? Or do I
wait it out for five years? So
it's kind of in that weird spot?
And yeah, I remember talking to
my family about it. And I think
there's also like, some
generational differences there.
So I remember, whereas like, my,
my dad owns his own company, he
was very hesitant with me where
he's like, you know, you've had
great progression at Nordstrom,
like just wait it out, like, you
don't want to just make this
switch over to an SDR role, like
they treated you so well. And I
think that has a lot to do with
like how his generation was,
were they stay longer at these
companies. And then I kind of
just dug deep on, like, what I
loved and like where I felt my
strengths kind of aligned. And I
was like, you know, I'm gonna
bet on me, I'm gonna risk it,
I'm gonna go and start as an
SDR. And I'm scared as hell to
do it. Because all I could think
about was the cold calling. And
then, you know, being in a new
environment, something I'm
familiar with. But that kind of
curiosity I think outweighed the
fear of failing. And so as I
say, worst case scenario, I
fail, and I have to move back
home and I figure it out from
there. But if I don't try it and
go for it, then I'd regret it.
So that's how I ended up at
Outreach and kind of giving it a
go.
mark ackers: So it was certainly
more conscious choice than
right, a lot of people fall into
sounds, but yours was a
conscious choice. And I don't
know that percent, but I'm gonna
guess it's 95% plus of people
that will listen to this will
will no saas outreach really
easy. Tell me if I'm wrong here.
But I can imagine when you're at
Nordstrom, thinking about
outreach, saas, SDR, that must
have been just like
gobbledygook, who absolutely no
understanding or appreciation
for that world and that role,
that must be quite daunting to
go from that. to that.
kaitlen kelly: Yeah, I think
that's super fair. And I this is
also why I'm like, like, SDR
synonymous community, and like,
why I'm so passionate about
mentoring and coaching people at
that beginning stage is because
it is you're not educated on it,
and you don't know the
opportunity, or at least I
didn't know what the
opportunities would have been
for me within a sales career. So
it was extremely daunting
because it felt like I was
walking in blind. Thankfully, I
did have a friend Justin Wright,
who was able to like, give me
some insight. And I did a fair
bit of due diligence, kind of
like testing it out going
through the interview process.
But it was a little bit of that.
I mean, earlier, right, I told
you, I'm either 0% or 150%. So
it was a little bit like,
alright, if I'm going to commit
to this, like, I got to jump in
and go at it full force.
mark ackers: I'm told him about
that, then you get offered the
job at Outreach. you're chatting
to your parents. They're just
the way you describe them. And
it's a very high level
description. But I hear that a
lot from people where they've
got a pair, obviously a
different generation, right. But
when you start talking to her
about SDR, they're like, What
the hell does that mean? saas?
What does that mean? Who's this
company outreach, they've grown
really fast. I'm leaving this
company that that, you know, in
an industry that you know, want
to be part of, and I'm taking
that role. How, how much did
they sort of doubt the move? And
you moving into sales where
you're going to be making cold
calls and emailing people trying
to book meetings? Like what did
they make of that for that 25
year old daughter at the time?
kaitlen kelly: Um, I think I
think my I think the biggest
thing was like I think my dad
was just nervous that I was
making a maybe like a an
irrational decision or a quick
decision without thinking things
already all the way through with
the opportunities I had at
Nordstrom. So I think that was
what it is he always believed in
me and trusted that I would be
able to figure it out and he was
confident that I would like I
had that skill set to do it. But
yeah, they he didn't really
understand he doesn't didn't
know what I was selling, but to
be fair, he owns his own
business. And so like, if I
think back to like my first cold
calls were when I was calling
down his customer list selling
the certifications and lessons
for his industry that they would
host at the the training centre.
So he under stands the need for
pyrogen and the relationships
and stuff, but it's just a
different way of going about it.
I think. So.
mark ackers: So that was
interesting. Did you use to make
those calls on behalf of his
company?
kaitlen kelly: Um, yeah. So when
I was in high school, because,
you know, I'm a fashion girly,
and I wanted my designer bags,
and he's like, I'm not buying
you any of that at that age. So
he gave me the opportunity to
basically sell these courses or
certifications. And then I got
paid a commission on every
single one. So I would literally
figure out the bag that I wanted
work backwards of how many
classes I need to sell, then go
get the bag. That's kind of
Yeah, when I think about the
first call call that I made. So
I think ironically, I was I was
doing the selling before I even
knew I was doing it. You know
what I mean?
mark ackers: Yeah. And lots of
people, when they have that
realisation, I realised that
they they've been selling their
whole lives. And we can't not
talk about that. And so what was
that? Like? Not only is your
boss, your dad, your 1516? You
say? You're picking up the
phone? That must have been scary
as hell?
kaitlen kelly: on it? Yeah. I
mean, when I think I don't, I
wasn't that scared. I think
there's this something about
being that young and being a
little bit naive of going into
it. So yeah, I would I can
picture I had literally like a
pack of papers with the list,
I'd go through with my
highlighter of the ones that
I've already called, and just
continue to work my way down it.
And yeah, then would just say
like, Hey, your guyses
certifications are coming up.
Like we've got a course it's
launching on May 18. We'd love
to get you in it's $350. And
then see how many people they
needed to sell or not sell but
sign up for it. And then I would
get them signed up for it. I'm
mark ackers: Did you have a
script? Did you create one
yourself that I didn't want to
sort of train you on what to do,
or I'm
kaitlen kelly: not really
trained. But it wasn't rocket
science either. Like if I knew
what the Course wasn't
certification, and they were
running on a quarterly basis,
then I knew I just had to call
the list. And if you can read
the person's name, then I would
just pitch what the
corresponding there's like a
little description. So
mark ackers: help me understand
that the gap here with 1516. And
I get that when you're younger,
you maybe have just you don't
have that self limiting belief,
you are more confident you've
got less, I suppose attached to
the outcome. But you get to a
point where outreach is floated,
and you're like, No way I'm not
cold calling I'm scared as hell.
Where's the disconnect? Between
that Kaitlen at 25? And Kaitlen
are 15. And 16 is like, give me
the list. I call them up. I'll
make the money. Yeah,
kaitlen kelly: I think what I
was envisioned, probably because
when I was is because it's like
family run business. It's been
running for 30 years, a lot of
these companies know my dad's
business. And so maybe it's that
it felt more familiar to me.
Whereas Kaitlyn at 2526, it was
me walking into a tech company
selling b2b Tech. And speaking
to VPS. And I guess it's just a
different persona. And now that
I have the experience that I do
know, I can kind of frame it
that way. Whereas when I'm 1516
year old, 16 years old, I'm just
calling like, the owners of
these companies that are like my
dad that I would talk to you
every day. Now,
mark ackers: I know, I know,
you'll know this, but so much
that it just comes down to
mindset, doesn't it? Yeah. And
that's the thing. It's
channelling the right mindset
and making sure that really,
you're, you're aligned to what
it is you're trying to do,
rather than who it is you're
calling. And so we join
outreach. And unless I've got
this wrong, it was like promoted
within four months, promoted
eight months later promoted
eight months later again, how
did you make it look so easy?
kaitlen kelly: I wouldn't say I
made it easy. But I think given
I had the previous leadership
experience that I did have, and
my analysts background, I think
I had a lot of skills that
allowed me to set up processes
when I did jump into that role,
so I could stay organised and
execute efficiently. So I think
that kind of like when I think
about when I first came into the
SDR role, I was like, heads
down, I have a photographic
memory. So I like wrote that
script out, like so many
different times, I would call
call my parents to practice my
pitch. And I was just like, all
in until I had it perfected. And
I think I always have that
mindset. Whenever I start a new
role. I always go in knowing
like, okay, the six months is
gonna be like heads down,
absorb, absorb, absorb. And so
when I went in and did that and
started getting momentum and
rhythm, I also had like great
peers around me and some coaches
that were just like, super
motivated and inspiring to be
around as well. So kind of from
there, and then my leadership
background that I had had, I
think set me up nicely as an A
candidate essentially to lead
and build out the team here in
EMEA. So
mark ackers: there's two things
I want to talk about there. One
One is the peers and coaching
you had naturally I'm curious
about that. But Christ cold
calling your parents for
roleplay. That I mean, it's
amazing. I love that. I reckon
Have you said to 99% of sales
reps, we're gonna roleplay, let
alone with your parents. They
had run for the hills. How did
how did you like? How did you
cope with that? It feels like it
was fine, the way you described,
it was just like it was no
problem at all, just calling my
mom and dad up. But talk to me
about the mindset that you need
to have to get to do that, and
why that was so helpful. I
kaitlen kelly: think it's the
drive that's within me, I'm also
extremely competitive. So one of
the things that I loved about
outreaches, when they hire you
on they hire you on as part of a
class and it go G class. And me
being extremely competitive
means that I have peers that
start at the same time as me. So
if I'm not booking more meetings
and beating them on the
leaderboard, then that's
probably not going to be good
enough. And so I was doing
everything I could to get
better, because these gentlemen
that I was hired with were
extremely great as well. And so
that was something that I would
do in my spare time, I've
listened back to tonnes of Gong
calls. And I still do this as a
leader as well, if I like when I
started at Clay VO, I would just
on my way to work at the gym,
I'm constantly listening so that
I can pick up the product
knowledge as quick as as I need
to be. But um, yeah, so in my
spare time, I, if I'd be at home
in the evening, call my parents,
I would hate scaling from
outreach on a recorded line. And
I would just go straight into
the pitch, they'd be like,
Kaitlen. But yeah, and I would
just keep going through and
doing it. So did I give you
feedback? Um, no, not really. So
it depends on how far they'd let
me take it, like give up on it.
But it was more such as getting
in the rhythm. And the more I
kept doing it, the more natural
it would feel. And I'm
definitely I would say, like the
sales culture at Outreach was
extremely call heavy. So and we
were out on the floor too. So I
had mentioned like some of my
peers like we would gamify and
make these call blitzes like
extremely fun and competitive.
So I think that also kind of
broke down some of the barriers
and had the fear of the phone.
mark ackers: Fascinating that we
don't need to dive into it. But
I'm a massive advocate for cold
calling. Like, it's really the
only way I book pipeline for
myself. And not to sound
terrible. But if you want to
book a meet with me is really
the only way that gets through
to me. Like, if you've got me on
the phone, you've got my
attention, you're getting
emails, it's harder, but my
point is outreach, a tool that
sped up the amount of emails,
the delivery, the cadence, the
sequences, whatever you want to
call it being called heavy. It's
interesting, isn't it? You feel
like they'd be sequence in
cadence heavy. But as I say, I'm
a massive advocate of cold
calling. And it's just that was
interesting. You said that. So
talk to me about day one, that
you're part of a group, you're
in a classroom, are you I
suppose? How many people are you
sat with in this cohort on day
one outreach.
kaitlen kelly: So when I started
an outreach, the cohorts were a
little bit smaller. So it was
three of us. So I, me and then
two other gentlemen. And but
then as it started growing, and
I became one of the team leads
and managers, those cohorts
started to grow bigger. So
oftentimes, we would be in rooms
with up to like, eight, new
SDRS. But yeah, so it was quite
intimate. And then it got to be
to a point where it was like
getting bigger. When
mark ackers: you sat there with
the other two gentlemen. Where
did you rank yourself? Like,
first impressions? How did you
rank yourself versus the other
two? Um,
kaitlen kelly: I would like in
reflection, I would say probably
in the middle of Yeah. Okay, so
mark ackers: if one was better
than you one ad, the big one
kaitlen kelly: had more
experience he'd been doing it
before who was familiar with it,
another one came from kind of a
different background like I did.
So I think kind of what
separated me and maybe gave me
that that nudge for me to feel a
little bit more confident in my
abilities was my resilience.
Okay.
mark ackers: And then I love how
you described like, I'm either
out or I'm all in and then just
just listening to what you said
there you know, listening to
call recordings on the way the
gym in the morning. So as a can
role playing my parents, great
peers, great coaches taught me
more about that the first six
months where you're like, This
is a critical period. Almost
give me like your blueprint. So
imagine a sales rep is listening
to this going to join a business
and a saas role. This is the
Kaitlen Kelly blueprint for the
first six months. Everything you
need to do to get ahead. What
does that blueprint look like?
kaitlen kelly: Nice. Um, yeah,
so this is just going to be kind
of like off the cuff of what I
would do. But if I am getting my
first role Well as an SDR BDR
and joining a company, I would
Yeah, in my first six months,
I'm going to basically execute
on the onboarding or bootcamp
that they give to me, that's
probably going to take up about
two weeks or so during that two
weeks when they are throwing
tonnes of product knowledge at
me and all the information I
need. At that same time, I'm
probably going to set up coffee
chats with basically like key
personas, I know that are going
to help me within my role so
that I'm building like a little
bit of a resource pool behind me
of people that I can lean on
when I may need them. So that
could be other peers that could
be top performing account
executives, maybe it's other
sales leaders, but it's trying
to understand the different
facets of the entire
organisation and where my impact
is going to drive. So I'll be
having coffee chats with
different people trying to
understand their roles, what
they love about their roles,
challenges they're currently
facing, and if it's something
that I'm going to like, as an
SDR BDR, you're probably booking
meetings for AES. So you're
trying to understand any
challenges or friction that is
happening that you can help
solve for. At the same time, I'm
doing role we are role plays, I
don't know why that came out. So
we're doing tonnes of role
plays. I'm asking for feedback,
I'm listening to the gong calls,
I'm listening back to my own
Cole calls, and checking the
leaderboard to see where am I
stacking up against my peers. So
I think like, it's gonna be
heavy on listening back and
absorbing probably in those
first three months and making
sure that you're kind of
practising practising. And in
that three to six month mark,
you should have a pretty strong
foundation of like scripts
objection handling, the omni
channel approach, so like
LinkedIn, social selling, social
selling, and I'm referring to
video as well voice notes, and
then phone and email and have a
good grasp of the ICP. And then
from that three to six months,
it's how do you like double down
on where your strengths are to
drive your results forward,
you're probably going to start
tearing out your accounts or
heat mapping them. So that you
know, okay, which ones are
likely to convert? This guy gave
me an objection last week? Do I
follow up with them this week?
And how do you start to build
kind of a process around that
last
mark ackers: a blueprint to
success? What was interesting
is, I know you're taking the
right way. Nothing you've said
there is like revolutionary,
right? But but it's all the
right things to do. But here's
my point. loads, people say
that, but so if you do it, and
it does that surprise you? Um,
kaitlen kelly: I mean, I don't
think it surprises me because I
see it all the time. I think
what, yeah, it surprised me that
more people don't do it,
especially if you're given a
framework or a process. I think
I mean, organisation, if you can
be organised, then you're going
to be miles ahead because you
can execute on a plan
efficiently. And so that is
something that I'm that is
something that I'm, I would say
I'm extremely good at and doing
it. That's why I can execute
like that. But I think you're
just leaving opportunity on the
table if you don't, and you're
wasting your own energy and
actual brain space to buy trying
to do that. If you don't get
yourself organised.
mark ackers: I think that is
just on the money, a pool of
money, so to speak, if you've
seen the quickfire round, you'll
get the reference. So when I
think back to reps I've managed
over the last eight years or so
why of the things that would
frustrate me and I see different
between the top performers, and
those are trying is they've got
just big holes in their
calendar. I think when you look
at your calendar, that that
tells me if someone has got
their shit together or not, I'm
guessing there for you
meticulously plan your day and
your time and where you spent
it. And so few reps do that.
Like, I don't want to talk about
STL specifically here, but that
would be a great example where
you look in their calendar, and
you might literally see Town
Hall on a Wednesday and that's
it. Nothing else and it's It
puzzles me. Yeah,
kaitlen kelly: this is um, this
is something I speak to as well
as like time prioritisation, but
it's also just time blocking out
and then well as one thing I do
with my calendar is I also
colour code it. So as an SDR I
would time block specific tasks
that I need to execute on. And
then on top of executing on
those tasks, I would attach a
goal to it. So if I knew I had
to reach a goal by the certain
time at the end of the week, or
maybe I wasn't patient, because
I don't know about you, but I've
had one of those months, where
you're in towards the end of the
month, and you're pretty far off
of that target and you've got
like five days to figure it out
and you panic. So you're like,
how do I figure this out? The
answer to that was I literally
sat in a room and cold call till
I got the meetings booked in.
But I'm working backwards from
what the end goal is and setting
goals against the calendar
blocking is like key and I carry
that through even as a leader
today on all the little tasks
that way nothing drops, like I
can't drop the ball in anything.
mark ackers: We speak the same
language. I think we could
compare calendars, and we've
complemented each other mines
colour coded time blocked. I've
got to go All set to it. And so
what I sort of teach people to
do as well and encourage people
to do. Okay, so when I asked you
at the start the podcast, I
said, Did you speak like this?
As you said, Yes. Was there a
specific moment in your career
that rushed to the front of your
mind? When you answered that
question?
kaitlen kelly: Yeah, there is.
So there's one big one in like
tech sales, and then there's one
that just actually came to my
mind as well. So do want me to
share both of them love that.
Alright, so my first day as an
intern on the sales floor at
Nordstrom, I was terrified. I'm
actually like an introverted
person, I have to force myself
to go to these networking
events, and kind of get out
there to talk to people. And
it's a skill that I had to
develop, but to the point that
like, my shoulders, and my arms
will literally go numb, because
I'm so nervous. So when I want,
it's my first day on the sales,
I don't even know how to
approach a person. And I just
remember my manager coming up,
and like literally pushing you
on the back, like, You're gonna
be fine. Just go say hi, and ask
how they day how their day is.
So that is something where I'm
just like, almost like the fear
of talking to somebody or the
fear. But the rejection maybe
held me back there a little bit,
until someone else kind of
pushed me forward and kind of
believed in me before I believed
in myself. So that was kind of
in the fashion industry. And
then software, yes, so at our
age and made the transition over
b2b, I'm cold calling I'm like
four months in, and I'm pretty
fearless on the phone. So that's
I'm like doing the phone thing.
That's great. Got my script
memorised, we're good to go.
They sent me to my first event
in Vegas. And the way that we do
these events, it's incredible,
because there's so much prep
work that I put into this. So I
would like map out the entire
showroom floor, understand all
the brands that would have their
booths there. And then I would
research each of the brands and
understand which ones were
prospects, which ones were
potential customers. And then
from the ones that were
prospects, I would then figure
out who were with my personas,
I'd map all this out. So I had a
pretty like bulletproof plan of
who I was going to target once I
got there. And so for example,
it could look like alright, I'm
going to booth three team,
because x companies there. And I
know, Jeff, the CMO will be
there after lunch. So they I go,
and I'm with my account
executive that I'm paired with
at that time. And the way that
the kind of the play works is we
go up to the booth, we start
chatting and trying to
understand their play. And then
that's easily tee up a
conversation for the account
executive. And this is my first
event and my first time going to
the booth in person. And I walk
up my personas there, because I
looked on his LinkedIn, I know
what his picture looks like. And
I go straight up to him and
literally pitch a script, a cold
call script at him. So I
mentioned my photographic
memory. And it was the weirdest
thing. I was like I turned into
a robot and I just threw up this
script at him. It was so not
natural, so not human. And I
think it shocked the accounting
executive. Because he had to
stop me halfway through and was
like, I'm so sorry. We're going
to just take a step away from
here. Like, we'll come back in a
little bit. I apologise for
this. And he had to like pull me
away from the prospect and was
like, Are you still breathing?
Like what's going on here? So
that is yeah, a moment where I'm
just like, that was incredibly
embarrassing mark.
mark ackers: So okay, let's just
play that back up. Again,
meticulous planning is what's
coming through here. So many
people again, don't do that live
events. I love it. Right. So you
know exactly. Almost like the
Terminator, you got your list of
evil that you're going to find.
You go up to the booth you with
the AAA, you see, the person who
will speak to you start to pitch
like a robot. Your AE shuts you
down, almost like halfway
through, says to your prospect.
I'm so sorry. We're gonna step
away and we're come back. What
was going through your mind when
you heard that? That must have
been crushing?
kaitlen kelly: I think I would
say I was mortified. I was like,
oh my god, like, I think I'm
malfunctioning. Like what just
happened? So yeah, I want to say
it was like I think it both
shocked us and then I want to
say it was like, like, I didn't
feel like I let him down like he
didn't seem like he was
extremely I think he was
shocked. More so than like, let
down or disappointed. And then
for me, I think it was like a
huge Eye Opener where maybe I
was like overcomplicating it and
just needed It's like, calm
down. Like, it doesn't matter if
this is a CMO, like it's just a
person just have a normal
conversation. So I think that
was kind of how we took it back.
And we just kind of simplified
it again, it was like you're
human, like, just have a
conversation. And I think one
other thing that we did was
just, which is probably simple,
but I thought it was helpful was
just like roleplay, like a
couple of ways to open up a
conversation with somebody. So
that was nice. So
mark ackers: and you're totally
right. It's just another human
being, you can almost make light
hearted the moment and, and
almost people are happy to
forgive and move on. But yeah,
so you go away from the stand,
it feels like the AE is an
absolute friend there in terms
of trying to help you. Lots of
people wouldn't have gone back
to that CMO. Lots of people
would have gone, you can go, I'm
not going back or we don't go at
all. How easy was it for you to
go back for a second round?
kaitlen kelly: Yeah, so it took
a couple. I would say like
couple hours later, like we went
into other booths before we
circle back. And when we did
circle back, it was definitely
like a falling on my sword
moment where I was like, Hey,
I'm so sorry. This is actually
my first event. I didn't mean to
just like show up and pitch it
yo, but I am curious to hear how
you guys are handling your
leads, essentially. So
mark ackers: I think that it's
just you played a play that
absolutely right there almost
like free yourself under the
bus. It's my first event,
natural reaction is to want to
help you and give you that short
redemption, so to speak. Did
they buy?
kaitlen kelly: I don't think so.
Well, yeah.
mark ackers: Can you remember
that? You don't need to know
that. Can you remember who that
person was?
kaitlen kelly: I can like the
outline of the person. I can't
remember their name or the
company. But I have like, you
know, the vision? Yeah.
mark ackers: I wonder if
somewhere else they sometimes
tell the story. Are you Oh, that
great. Kaitlen Kelly, you see on
LinkedIn, let me tell you about
her first event. Okay, so let's
talk about other things that you
were crap at. Because there's so
many facets that even you
mentioned there as an SDR. It
feels like you had that fear of
cold calling. But for months, in
your words there. No fear
crushing on the phone? What
other aspects of the role? Would
you say you were crap out?
kaitlen kelly: I would I I mean,
I've never been like the best at
like the written words like
emails and stuff. I think that
was one of the benefits of
outreach was the we had so many
sequences and templates and
stuff. So I think when I first
actually this is good. So yeah,
I wasn't the biggest fan of the
email prospecting, probably why
leaned in so heavy on the phone.
And I if I reflect back on to
what made me so crap at that, I
don't think I put enough energy
into the relevancy of what that
first nugget was, I never had an
issue finding like a way to
personalise it or, you know, a
reason to reach out to somebody,
but like, how did I tie that
back to my solution of like, why
then why now? That was, that was
a learning curve that came
later.
mark ackers: Do you think and
I'm guessing, do you think part
of that might be down to your
personality, like, you're all in
or you're not. And if your, your
belief is, I'm not very good at
email, or don't enjoy email, I
get great success from cold
calling. Maybe the email didn't
get that 150% of you, so to
speak, during that was part of
it.
kaitlen kelly: Um, I mean, I
think that could have played
into it. I think the the true
driver behind it was down to
like speed and efficiency. And
so if I think back to like, what
that template was, it's like
that first line is like,
basically fill in your nugget.
And then there's like a
templated pitch. And this was, I
don't know, maybe five years
ago, right. Whereas I definitely
think the frame of cold email is
different now. But so I think it
was more of speed of efficiency,
where maybe I was just trying to
get out as many sequences as
possible. So I would just chuck
the nugget in there for that
first line, rather than taking
the extra minute or two to tie
it all the way through. Gotcha.
mark ackers: And you mentioned
coaches, so it feels like you've
had people that have walked in
your shoes before, had success
in that role that you can lean
on. Talk to me about some of the
coaches that you you've worked
with, and have helped you and
more about that. Yeah,
kaitlen kelly: so I think like
coming in at Outreach for that.
SDR role, like kind of Maher was
the one that kind of led that
entire Goji tribe. So Goji is
the new hires for the first
three months. And that's to make
sure that you have that strong
foundation of how to execute on
the job. So Ken was one of the
top performers as an SDR there
and he also learned through Sam
Nelson. So it was like this
funnel of learnings all the way
through. And so yeah, so that
was like kind of having that
coaching and that level of like,
drive behind you. Like I think
one thing Ken does well as he
believes in the reps that he
would bring on board and that
even before you would believe in
yourself and so you would just
kind of rushed through those
awkward moments where sometimes
it's easy to want to quit and
give up, right, especially if
you're not getting the results.
But he would continue to push
you through. So I think early
earlier days, that was fantastic
to see me and him ended up
becoming peers, and we're highly
competitive against each other,
which was also incredible. And
then from there, like when I
made the transition over to the
EMEA team over here in London,
like being able to work under
Tom Cassidy, I think that was
probably like an inflection
point in my career, because the
amount of development and growth
that I got underneath him, also
was incredible. And that helped
me form a lot of the processes
that I implemented within
growing out that region, but
also what I've been able to
carry over to clay vo to do the
similar thing within the account
executive org. I didn't
mark ackers: feel one of the
things that I think you've said
three times now, is this believe
in you before you believe in
yourself, like you mentioned
about your parents, you
mentioned at Nordstrom, you've
mentioned that there with with
your coach outreach. How
important is that? Do you think
for you that you've had someone
believe in you before? Maybe you
believed in yourself and the
journey of the career that
you've been on?
kaitlen kelly: Mark, you have
incredible active listening, so
that you picked up on that? Um,
how I think it is, I think it is
extremely important and even
like thinking back as a leader
to it's like, how do you
identify that in your reps as
well, so that you can pull that
out in them. So I think that's
something that I'm always
keeping top of mind. Because I
think if a lot of people didn't
tap me on the shoulders, and
some of these moments, I
wouldn't be in the roles that I
am in now. And I also want to
have that level of confidence
that I was able to build up by
the giving these opportunities
that I went for and failed and
then tried again and tried
again. So I think I was having
people believe in you. But
before you believe in yourself,
it does create that environment
where I can fail fast and be
okay failing, not be afraid of
it.
mark ackers: That makes sense to
sentence. Yeah. How do you do
that? With a backdrop. So you've
worked at our age in clay vo to
like Darling's in the SAS world
where pressure will be high.
Right? Results will be needed
and demanded. How do you create
an environment where people I
know we've jumped out to you as
a leader, and we'll come back?
But how do you create an
environment where people can
feel safe to fail? Know that
they're going to learn with a
backdrop of growth, growth,
growth investment? Gotta have
the results? How do you do that,
as a leader, that must be really
challenging.
kaitlen kelly: So I think as a
if I'm thinking about how do I
create an environment where it's
like safe to fail, I think if I,
there's a couple of things that
I would do, and I can kind of
like talk through how I coach my
team as well. But there's a
metric or a matrix that I use
called it's juicy 17. But juicy
is just the name of my team. But
17 is the role of the key here.
The idea here is looking at
frequencies and competency. So
giving my team a clear outline
of what the expectation of the
role is and metrics they need to
achieve, that will then result
to them hitting their target or
the metrics that they're held
accountable for. So frequencies
would be like KPIs and metrics
that I can quantify competencies
are going to be the soft skills,
and with a mixture of those
mixed together. So if you're
hitting all of your frequencies,
and you're mastering your
competencies, goes will drive
your results that we're tracking
to be successful. So that could
be your quota, your ASP, and
your win rate, top three off the
top my head. So I think that
helps create a environment where
we know that we're growing and
developing because we do that
month over month reflection
there. And that also tees up a
great conversation for me to
have with them is like talk to
me about your strategy. What are
we doing here? How can we pivot,
because I see it as like a
massive partnership. And then
the other thing that I'm doing
to create that safe to fail
environment is I vocalised, my
failures and I'm not afraid to
get in the weeds with them. So
like, I'm happy to do cold
calling with them. I'll jump on
discoveries, I'll get involved
in negotiations, but I want them
to feel like we are at the same
level and I'm here to support
them so they can reach their
goals. I never want it to feel
like that top down approach. And
I think if I can create an
environment where it's like, you
know, we win together that
creates a safe space. And I
think if somebody does fail,
it's like alright, what did we
learn off the back of it? Let's
take that move it forward.
mark ackers: I love you sound
like you've been incredible
person to work with in a manager
managerial capacity. The way you
describe that and talk to you
about how you got into that
manager manager role then so
we're an SDR as I say. We're on
my notes here. We were promoted
four months and eight months and
eight months later was Did you
just take his like a duck to
water once you got your first
six months under your belt? You
knew what you were doing? Was it
just Easy peasy for you.
kaitlen kelly: So my first
leadership role was at 23 years
old, with Nordstrom as an
assistant manager for a
division. And the route with
Nordstrom is you go intern and
then from intern to assistant
manager, and then you either go
to a bigger division or to a
manager of a smaller division.
So I was on that track and
leadership. And then at 24, I
believe I was running the third
largest trend division in the
US. And I had 27 Associates
underneath me. So when I made
the switch in the analyst's
office, and then over to
outreach I had already, I all
say crash and burn throughout my
leadership career, to be honest.
And I had some tough learnings
earlier on because you can
imagine being a 23 year old
trying to lead a 40 year old
that's maybe working part time
as a stylist, that's a hard
dynamic to master. So when I got
into outreach, and started out
as an Icee, as an SDR, it really
was like the first three months
and I started hitting really
good results. And then I started
breaking records. And right
around that, like four month,
four to six month mark, there
was conversations of you know,
where did I want to go? Did I
want to get back into
management, and audit, I want to
go account executive route. And
to be honest with you, based off
my previous leadership
experience, at Nordstrom, I was
like, I don't want to do that.
Because it was I just don't
think I had the best experience.
And so that wasn't my natural
route to go that direction. And
then some other people talk to
me, and I kind of thought it
through a little bit more. And
then that's when I started
leaning in and training on the
boot camps as a senior SDR. And
then the opportunity for London
came up. And I remember I got
the call as I was moving into a
new apartment in Seattle. And my
mom was with me at the time. And
they were just like, hey, we
just want to float this idea by
you do you want to take some
time to think it over? It was in
September of 19 2018. And I just
committed on the column. I
remember my mom looking at me
like I was crazy. And she's
like, you're just going to up
and move to another country. And
I'm like, it's only six months.
Here we are.
mark ackers: It's amazing,
though, like so so many people
don't get that opportunity. Or
they do that. They don't take
that. As as a father myself, I'd
be like, right? Well, I'm coming
with you. I'll just be I'd be
I'd be I might struggle to
actually because it could be in
different places. But let's talk
more about you being a leader,
then. You've obviously had
different experiences in and out
of saas. Let's just go with a
big question straightaway.
What's the biggest mistake
you've made as a leader?
kaitlen kelly: I think the
biggest mistake I've made as a
leader. I think it's like not
taking the time to understand
the why behind some things. So
like, if something's not we're
in this is I think I've learned
off the back of it. But I think
if something isn't working out,
it's not taking the time to
pause and maybe ask the rep why
or help me understand it would
I'd come in and try to diagnose
before trying to understand it.
So I'd say that's like one of
the biggest ones, I think the
other one is coming to like a
change management where it's
like, okay, if you're trying to
implement change, I'm good at
implementing the change. And I
noticed a trend where I would
not have like the accountability
bit, right. So it's like, okay,
I'm doing all these efforts for
changing were identifying it,
but there was a gap on getting
the results on the end. And that
had to do with the programme
that followed up to kind of
enable or like double down on
the skill or whatever we were
trying to train on. So I think
those are kind of the two
biggest ones was like slowing
down to understand the why to
get the full picture before
diagnosing and then ensuring
that there is a programme with
accountability when trying to
implement change.
mark ackers: And how did you
learn that? Was this? You
learned by yourself? Or did you
have someone to help you? Um,
kaitlen kelly: no, I think well,
there was a stark moment when I
was 23. That happened at
Nordstrom, where it glares at me
when I'm like, okay, pause and
like understand the behaviour,
understand there's some there's
something behind what's driving
someone's behaviour, typically
is what I would say. So there
was one of those moments that
had happened where I had had
like one of the one of my sales
associates on the sales floor,
like snap at me and like shocked
me. So that was like a moment
where I learned it the hard way.
And then for the other one where
it was like the accountability
bit, but this I think this is
working in tandem with Steve
Ross, who is the VP of the SDR
org outreach. And it's, um,
through having like talking
through some of the things that
I was implementing and my
processes and stuff. And then it
was the way he followed up with
me on account accountability.
And I'd be like, oh, yeah, this
isn't working. And so in
reflection, then it came about
where am I okay, he's running
this process with me. Why am I
not replicating that with my
team? There's a gap. Call.
Ignore
mark ackers: the word. A stock
moment. I know you saw me bite
my tongue. I could ask when they
start to you, or they say,
kaitlen kelly: Why are you being
such a bitch? It's like, oh my
gosh, and it was like down to
literally closing duties, which
if we want to, like, you know,
make that a cinnamon for a
sentiment a synonym for like
saas. It's like basically asking
someone to do their KPIs at the
end of their shift. So yeah, so
it was taking this like
understanding like, Okay, what's
actually going on with this
person? How can I take a step
back and be kind of have a
little bit of the empathy to
show through because there's
something else that's triggering
this, because it's not like
these closing duties were new or
something implemented on that
day, and she'd been with the
company for months. So there's
something else that I needed to
figure out. So that was the
moment that like, shook me,
because I think I think that
would shake it shake anyone?
Yeah.
mark ackers: And you're 23 at
the time you say? Yeah, how old
is this person?
kaitlen kelly: She was 19. So
she was young. Okay.
mark ackers: I think that's
important context. Because
you've obviously mentioned like
managing 40 year olds, for
example. So they're young,
they're emotional, etc. But they
said, Why you being such a bitch
in front of other people?
kaitlen kelly: No.
mark ackers: Okay. Just
privately. Yeah. Okay. How did
you deal with that? Because
that's not acceptable. How did
you deal with that?
kaitlen kelly: I just like
looked at her and walked away.
And then I went to my manager to
let him to loop in Milan, the
conversation to get support on
how do I handle this in that
context, because I'd never been
exposed to that. I don't know, I
didn't know at the time how to
approach a conversation without
elevating it or making it bigger
than it needed to be. It needed
to be kind of diffused at that
time. So yeah, I went to the
store manager, and then HR to
figure out a path forward. How
mark ackers: did you have the
maturity? Not to go back at them
straightaway? Um,
kaitlen kelly: I mean, I think
at 23. I mean, yeah, I think at
23, you know, that would have
been really immature of me. And
I, I don't know, I think to me,
if I'm thinking about it's like,
what is the outcome that I would
have wanted, if I would have
reciprocated or if I would have
went back, I don't think
anything good would have came
out of that situation, given
where the emotion was at and the
tone that she had used. So it
was just completely
inappropriate in my eyes. So at
that point, I'm like, I'm gonna
walk away from the situation,
and then go figure out how to
properly handle this.
mark ackers: I think you were
more mature at the age of 23
than I was. Obviously, sales
leadership can be quite a lonely
place. You're a sales leader.
Now, who do you turn to when
you're having those difficult
months quarters, moments, self
doubt, imposter syndrome? All
the things that affect all of
us, really, but who do you turn
to now? For help and guidance?
Yeah,
kaitlen kelly: I think that I'm
so I'm very lucky, because we
have a strong like sales manager
group at Clay VO. So I have a
lot of like great relationships
with within the team. So I can
lean on and kind of vet out
different challenges that I may
be facing. I also think beyond
just my internal team at Clay
VO, it's partnering with my
wider network. So when I first
moved to London, I think another
thing that's interesting is, I
didn't know anyone in London, I
literally moved out here for
outreach. And so I had to create
my own communities. And so this
also ties back to SDRs
anonymous, and how this kind of
kicked off the ground because I
knew the value of being able to
network bounce ideas off of
other people. But from being
able to do that I joined the
sales development leaders group.
And then from there, we kind of
spun out into a group of like
five of us. And so that also
helped me when I was just
becoming a leader within the
saas at outreach. And so now I
have a lot of people that I can
kind of like lean on bounce
ideas with, which is like
extremely helpful, because it's
good just to get viewpoints from
outside of your org, but also
internally as well.
mark ackers: And that makes a
lot of sense. Talks about SDRs
anonymous, let, let's just
imagine I've never heard of it.
And people listening to this
might not have heard of it. What
is it? And
kaitlen kelly: I mean, they may
have not it's been on hold for
the last three quarters. But SDR
is anonymous is a community that
me and she for nearly who was
one of the first account
executives at SIA, started up at
the very beginning of the
pandemic. So at the beginning of
the pandemic, both of us
recognise like there's gonna be
that stark shift to a remote
environment. And one of the
benefits of being in an in
office culture, especially
within SDR and BDR land was
being able to have your peers to
lean on when you do fail or
something completely awkward or
cringy happens on a cold call.
You want somebody next to you
that you can laugh about with
it, but also just learning
quickly from them and like how
do you think It'll thing. So it
started off as a Friday chat
where it was just like an open
zoom to anyone that was located
within the London area, it was
multiple companies that would
jump on. And we would do like
Spitfire round questions as
well. So we had a slider that
was set up, and people would
just type in questions
anonymously that we then would
address his leaders.
mark ackers: Amazing how many
people are in the community. Um,
so
kaitlen kelly: there's just over
7000 now. And what it turned
into is it turned in from that
Friday conversation, which ended
up being quite a bit of an
uplift into quarterly events,
and then sharing some like
content and stuff. So now as
we're kind of going through like
a refresh and a revamp, we will
be rolling that back out, again,
into hopefully quarterly events,
again, amazing.
mark ackers: How do people join?
If they wanted to sign up and
join? How do they do that? It's
kaitlen kelly: literally just a
LinkedIn community. Right? So,
so easy, just follow on
LinkedIn. And then you just
follow the content that we're
posting. If we do events, all
the events are linked through
Eventbrite there in person, some
of them are on Zoom. So it's, if
we do a global one, it'd be on
Zoom. But yeah,
mark ackers: okay. I can tell
just from some of the things
that you said, no previous
conversations, it's important
for you to help people to
develop them to coach them. What
about yourself, it can be really
easy to neglect yourself. Do you
feel like you do enough
personally, to help yourself and
develop yourself? Now?
kaitlen kelly: I think this is a
great question, because it is
definitely something that's like
top of mind. And if I think back
to probably like my first so
being at Cato, for the last two
and a half years, I'll say
actually, I'll just simplify
this, rather than giving you a
tangent, but um, I will set
goals against what I want to
achieve on my own professional
development. So at one point in
time, it was like, Alright, once
a quarter, I want to go get
certified in a specific tool or
a text within the tech stack. So
I did some outreach ones, I did
some Gong certification one. So
it's like, how do I kind of
build my skills in this way. Or
I went through the Harvard
programme for leadership as
well. So I'll set these little
goals of where I identify my
gaps are. And then there does
become a time where all of a
sudden, a quarter goes by and
you're like, oh, my gosh, I just
lost three months, what have I
done to develop myself because
things get busy priorities get
shifted, and if it's not top of
mind, or if you don't schedule
the time out on your calendar,
then it can get put in the
backseat. So it is something
that I have to be proactive
about. I will and to be
transparent. Yeah, in the last
two quarters, I have been
looking for a way to kind of
stretch and develop myself in
what is the direction that I
want to be stretching and
develop in?
mark ackers: Do you have like
someone outside of clay VO, like
a mentor or a coach that you do
work with currently?
kaitlen kelly: Yeah, so there's
like quite a few different
mentors that I will like partner
with kind of like bounce ideas
off of which is like super
helpful. So and they're from
different types of backgrounds
as well, which I think is
important too, so I can get
different insights.
mark ackers: So I love that. I
want you to talk to me about the
impact that's had one of the
things that never fails to amaze
me. I know you would have just
seen this your whole career is
sales. So first of all, sales is
a skill, right? Like when people
say it's gift of the gab it's
centralised, Nonsan sales is a
skill that can be fine tuned,
can be learned and eventually
mastered, right? But there's no
barrier to entry. Anyone can get
a sales job at a certain level,
like anyone can get in to sales.
But there's an ego there. And I
find lots of sales reps have no
I use the air quote for those
listening but qualification so
to speak, get into sales. Yeah.
They have the ego, though, that
they don't need coaching or
mentoring. They're going to do
this themselves. What would you
say to people in sales right now
that think they're too
experienced, they're too good.
They don't need a mentor. They
don't need a coach, when they've
got into a job that's got no
barrier to entry. And it is a
skill that can be learned and
fine tuned. And let's be clear,
the better you are, the more you
earn. But it always amazes me
when you speak to people and
they just look down on
mentorship or coaching is
beneath them. What do you make
of that?
kaitlen kelly: Um, I would I
would want to understand why
they feel like it's beneath
them. Or I think yeah, I think
that is interesting. I think if
I'm thinking to like my team and
like why they don't maybe go out
and get external mentors and
coaches. It's obviously because
I'm the bet No, just kidding.
No, I think it comes down to
like the time commitment and I
kind of view it as like it's a
small like some While investment
for a big gain, and this is also
high look at like podcasts or
webinars going to network
events, like yeah, maybe giving
up one night a month to go and
network with someone, but I can
walk away with one thing that
I'm going to be able to use for
the next 10 years. So I think
it's kind of getting them to
like understand that framework
that there is value, maybe not
all of it is going to be a
value, maybe you're not going to
get everything from a mentor or
coach. But you may pick up just
that one thing, or even just
setting up a conversation with a
peer that maybe is excelling in
an area that you're not. I think
taking that 30 minutes yet,
maybe it's going to take 30
minutes away from prospecting,
or cold calling. But you might
learn something that can make it
so that you have more meetings
on your calendar. So you don't
have to do that. 30 minutes of
prospecting.
mark ackers: How big do you
think mentorship and coaching
has been for you and your
development? Oh,
kaitlen kelly: I think it's
huge. Like I don't think that
because it I think it Yeah, I
think it's like all of it even
like from day one, I had a
mentor. So within outreach as an
SDR. And it's just somebody like
bounce ideas off frustrations on
especially outside of your
manager, who maybe you're
nervous to bring some of these
things forward to, especially if
you're just starting out in a
role because you don't want to
like disappoint them or make
them nervous if you're not
grasping the ideas of something.
So having like a mentor or even
like a network around you is
going to be like extremely
valuable just to get that extra
insight. So
mark ackers: you're obviously
conscious of development and
working with people, etc. What
would you say is the biggest
flaw in your game today that
you're trying to work on? I
think
kaitlen kelly: what I'm trying
to iron out right now is like we
have this awesome opportunity at
Clay vo where we're launching
additional products. And I've
never worked for a company where
I've been a part of that
programme where you sell, you're
known for one product, and then
you have additional ones that
you can attach on. So now we're
trying to change that essential
discovery and pitch to how do we
sell it as a suite rather than
just one piece of the puzzle. So
when I'm thinking about in
reflecting on what the training
and the coaching looks like, and
then one thing that we do really
great is the training aspect. So
the transfer of the information
and all the data points, the
skills, everything they need to
know to sell it. But then
there's the coaching aspect in
the programme that follows. So
this is something that I've been
fine tuning for this quarter,
and it's okay, how do we then
enable them and make sure that
we're coaching them on it week
after week so that it stays
consistent and sticks. It
doesn't just become something
where we run a training and then
it falls off. So it's how do I
get the training here? And then
what does the coaching programme
look like? And then what's the
outcome I'm looking forward to
the team knows the Northstar
that we're working towards. So
that's kind of the gap I'm
filling right now.
mark ackers: And as a sales
leader, you spend multiple
plates, right your your be
recruiting and onboarding,
you'll be training and coaching,
forecasting, one, one to one's
internal fires to put out, etc.
How much time do you spend
coaching the team do you believe
on on a weekly basis, I
kaitlen kelly: would say if I
was looking at my calendar about
probably 60% of it is going to
go towards coaching. And then
20% of it is going to be like
forecasting calls pipe scrubs.
But within that coaching that
one on ones that's call reviews,
it's running trainings, there's
those all of that's gonna go
into it 6%
mark ackers: Amazing, most
people spend less than 5% of
their time coaching. So that's
incredible. What colour is
coaching in your calendar. So
kaitlen kelly: let me take a
look. Actually, I have my
calendar also doesn't buzz on
here. But it's going to be by
different colours. So all of the
one two ones are going to be
purple coaching. Like if it's
going to be like one of the team
trainings, it'll be a dark green
colour. And then we have yellow,
which is going to be like
outreach Deep Dive. So how are
we so that's basically I
mark ackers: always struggle
when people use different
colours for different things
like my my one, two ones are
blue, for example. And it would
freak me out to change that my
discovery calls are green, my
preps yellow, and I could not do
it another way. Like it almost
be like a non negotiable.
Someone said to me, here's a job
but your discovery calls, you've
got to be read. I couldn't go
with that. Like, I've got my
callers and I've had him locked
in for about 15 years.
kaitlen kelly: The reason why I
colour code all the ones that I
control, and then all the
meetings that are blue are like
the other people are putting on
my calendar basically. Gotcha.
mark ackers: Okay. Um, so you
were to start your career again?
What would you do differently?
kaitlen kelly: I think I'd get
into software sales sooner. I
think that's like, the one thing
that kind of kills me is I wish
I just knew about it sooner and
the opportunities and I made the
switch at 27. And so I think
that is I think just getting
involved sooner would have been
amazing. What
mark ackers: do you think it'd
be different like so you got
involved five years earlier?
What do you think would be
different? Where would you But,
um,
kaitlen kelly: I mean, I think
I'd probably Yeah, that's a
great question. Maybe I would
probably be further within my
career, maybe I'd be at a VP
level of a company at this
point. But I still am developing
some key skills here. So I
think, yeah, I think that would
be one thing and full
transparency to is if I would
have gotten sooner, then that's
like, essentially, six more
years of making software sales
type of money versus fashion
money. We're not going to go
into the difference there. But
you can imagine. So one thing
that I like aspire to have is
like a portfolio of like rental
homes and houses, that's
something that I'm working
towards. So my investments, I
think we'd be in a different
situation if we started a little
bit earlier. Yeah,
mark ackers: the textiles money
probably allow you to buy the
fashion items from the fashion
world. Yeah, exactly.
Okay. We're starting to wrap
this up. Honestly, I've just
missed so many questions that I
could ask you. What I'm picking
up though, is that you're
incredibly proud of the career
that you've got proud to be in
sounds, which I loved, loved to
hear. And, obviously, your sad
reality is lots of people fall
into sales don't want to be in
sales, and would love to get out
of it. And you told me before,
offline that you've got one
nephew and a two nieces or
nephews and one niece
kaitlen kelly: was two nephews
and a niece, let's imagine.
mark ackers: And I'm guessing
they're obviously not at the
right age for this decision. But
they're in different careers,
and they pick up the phones or
auntie Kaitlen, and they say, as
a saas company. It's an SDR role
thinking about going for it?
What would you say?
kaitlen kelly: I would say go
for it. 100%? Yeah, I wouldn't.
I mean, I will support their
honestly, I would support them
in whatever they want to do want
them to know, all three of them
to like, have the world. So
yeah, if they were to say that I
would probably I'd be like super
excited about the fact that they
want to go down that career
track. And then I'd probably ask
them a little bit more about it.
And just make sure that like the
company that they are choosing
maybe aligns with a passion or
something that they can get
internally involved with?
mark ackers: What's the one
warning you'd give them? I go
for it, but what's the one thing
that you'd warn them about?
kaitlen kelly: I think it's
important to look at I Know,
Like culture is a huge thing.
But I always look at like the
leadership team that's there as
well. And then the career
progression because it what I
would hate to see is that they
go into a company and then it's
they don't get the best
experience or they don't have
the right development early on.
And then all of a sudden,
they're turned off of sales
because they don't think it's
for them or you know, some
people just don't get have the
great off the jump experience.
Which thing puts a bad taste in
their mouth. So that would be my
one thing is like, hey, it's
gonna be really hard work but
extremely rewarding. Make sure
you do your due diligence
throughout the interview
process, so you know exactly
what kind of development
training you're gonna get, so
that you are successful in your
seat. That's what I'd say.
mark ackers: Fair enough. And
again, I could ask three or four
questions about that, like what
would you ask them to do? How
would you help them but time has
got the better of us.