Latest / I Used To Be Crap At Sales / From Sales Struggles to Sales Leader at Klaviyo | EP05 | Kaitlen Kelly

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From Sales Struggles to Sales Leader at Klaviyo | EP05 | Kaitlen Kelly · I Used To Be Crap At Sales

0:00
mark ackers: current sales manager at Klaviyo, co founder
0:02
of SDRS anonymous, a sales coach, former outreach sales
0:07
leader. It's Kaitlen Kelly, did you used to be crap on sales?
0:11
kaitlen kelly: Yes.
0:12
mark ackers: How crap are we talking?
0:13
kaitlen kelly: If we only give it on a scale of one to 10 I'll
0:15
be generous and give myself a
0:16
mark ackers: Christ cold calling your parents for roleplay
0:19
kaitlen kelly: I was doing everything I could to get
0:21
better. Because these gentlemen that I was hired with were
0:24
extremely great as well. At our age. I'm pretty fearless on the
0:28
phone. So I got my script memorised. We're good to go.
0:31
They sent me to my first event in Vegas, there's so much prep
0:35
work that I put into this. So I had a pretty like bulletproof
0:38
plan of who I was going to target. Once I got there. I'm
0:41
with my account executive that I'm paired with at that time, I
0:44
walk up my personas there, because I looked on his
0:47
LinkedIn. I know what his picture looks like. And I go
0:50
straight up to him. And literally, it was the weirdest
0:54
thing. I was like I turned into a robot. I think it shocked the
0:59
account executive, you guys he had to stop me halfway through
1:03
and was like, I'm so sorry. Um, we're going to just take a step
1:06
away from here. And he had to like pull me away from the
1:09
prospect and was like, Are you still breathing? Like what's
1:12
going on here? So that is yeah, a moment where I'm just like,
1:15
that was incredibly embarrassing. I
1:18
mark ackers: wonder somewhere else that they sometimes tell
1:21
the story, are you Oh, that great. Kaitlen Kelly, you see on
1:24
LinkedIn. Let me tell you about our first event. Imagine a sales
1:28
rep is listening to this gonna join a business and a saas roll.
1:31
This is the Kaitlen Kelly blueprint, the first six months,
1:34
everything you need to do to get ahead. What does that blueprint
1:38
look like? Yeah,
1:39
kaitlen kelly: my first six months I'm going to
1:46
mark ackers: welcome to another episode of The I used to be crap
1:49
at sales podcast. I'm your host, Mark Akers, co founder and head
1:52
of sales, my sales coach, and today I'm joined by the current
1:56
sales manager at CLEVEO, co founder of SDRS anonymous, a
2:01
sales coach, former outreach sales leader. It's Kaitlen
2:06
Kelly. Caitlyn, Bill, welcome to the podcast. How are you? I
2:10
kaitlen kelly: am doing fantastic, what a great entry
2:13
that you just gave me. So I really appreciate that mark,
2:15
lots of titles that you tacked on there.
2:17
mark ackers: It's all credit to UK and going for your LinkedIn
2:20
is loads of your work going on, which is why I know you're gonna
2:22
be a great guest today. Let's kick off with just a yes, no
2:27
question. Kaitlen Kelly, did you used to be crap at sales?
2:32
kaitlen kelly: Yes.
2:33
mark ackers: How crap? Are we talking?
2:36
kaitlen kelly: I mean, if we had to give it on a scale of one to
2:38
10, I'll give. I'll be generous and give myself a three here.
2:42
But it's I think sales is a funny thing, if you think about
2:45
it, in hindsight, and I think we'll dive into kind of how I
2:47
ended up here. But yeah, if I think back to the first couple
2:51
of times, got some good memories.
2:54
mark ackers: Let's start there. And how you ended up in sales?
2:57
Because obviously, that was quite a career switch view
3:00
brings bring to life. How you went from working in fashion?
3:04
Yeah, to working as an SDR outreach. How did that happen?
3:09
kaitlen kelly: Yeah, so I think on So growing up, like I had
3:14
like my dream and all this stuff, but then early like
3:17
switched over and I was like, I want to be a buyer within the
3:20
fashion industry. So what I did is I worked backwards from the
3:23
end goal to figure out okay, how do I become a buyer at
3:26
Nordstrom? Nordstrom is like a designer store similar to like a
3:30
Selfridges based out of the US. And so they had like a
3:34
internship programme. And the internship programme actually
3:36
started out on the sales floor there. At the time, it wasn't
3:41
like it's literally setting up like stylist appointments, and
3:44
then you're selling wardrobes and outfitting people, but
3:46
you're based on commission solely. So I went throughout my
3:50
education kind of ticking off the boxes of how do I get myself
3:54
to the buying office, which was my end goal. And so as I went
3:57
through that I went got into sales at Nordstrom through the
4:00
internship programme. And that kind of accelerated me through a
4:05
series of leadership roles and then into the buying office as
4:08
an analyst, which was kind of my end goal. And as I was in the
4:14
buying office, I was probably in my mid 20s at the time. And I
4:19
knew that in order for me to get to that buying role, it would
4:22
probably be another five to seven years, just given how slow
4:27
career progression was happening. And it wasn't
4:29
actually loving the role either. And so kind of like looking
4:33
around trying to figure out like, is there people that I see
4:36
here that I want to be in 510 years? Is this really where I
4:39
want to end up? So I was having one of those moments that I
4:43
think a lot of people probably have these that 2526 years old,
4:46
and and a couple of my friends that I had started out in this
4:51
internship programme at Nordstrom had actually made the
4:54
switch over to outreach and outreach as a Seattle
4:57
headquartered company as well. Nordstrom is headquartered in
5:00
Seattle too. So I had a good friend who had went there a year
5:04
before I had kind of made the transition over to outreach. And
5:08
he went in as an SDR and was like loving it. He knew how
5:11
ambitious I wasn't motivated. And so he kept trying, he's
5:15
like, just give it a shot, give it a shot. And I was like,
5:19
Absolutely not like, I'm not cold calling, I was like sitting
5:22
in my comfort zone, like I had just invested four years of my
5:26
own money to pay for tuition. And all of the years that I put
5:31
into, like getting myself on this career track. So I'm like,
5:34
do I give up now? Or kind of seven years into this? Or do I
5:38
wait it out for five years? So it's kind of in that weird spot?
5:42
And yeah, I remember talking to my family about it. And I think
5:48
there's also like, some generational differences there.
5:50
So I remember, whereas like, my, my dad owns his own company, he
5:54
was very hesitant with me where he's like, you know, you've had
5:57
great progression at Nordstrom, like just wait it out, like, you
6:00
don't want to just make this switch over to an SDR role, like
6:03
they treated you so well. And I think that has a lot to do with
6:06
like how his generation was, were they stay longer at these
6:08
companies. And then I kind of just dug deep on, like, what I
6:13
loved and like where I felt my strengths kind of aligned. And I
6:18
was like, you know, I'm gonna bet on me, I'm gonna risk it,
6:20
I'm gonna go and start as an SDR. And I'm scared as hell to
6:24
do it. Because all I could think about was the cold calling. And
6:28
then, you know, being in a new environment, something I'm
6:31
familiar with. But that kind of curiosity I think outweighed the
6:37
fear of failing. And so as I say, worst case scenario, I
6:42
fail, and I have to move back home and I figure it out from
6:44
there. But if I don't try it and go for it, then I'd regret it.
6:49
So that's how I ended up at Outreach and kind of giving it a
6:52
go.
6:53
mark ackers: So it was certainly more conscious choice than
6:55
right, a lot of people fall into sounds, but yours was a
6:58
conscious choice. And I don't know that percent, but I'm gonna
7:03
guess it's 95% plus of people that will listen to this will
7:08
will no saas outreach really easy. Tell me if I'm wrong here.
7:13
But I can imagine when you're at Nordstrom, thinking about
7:17
outreach, saas, SDR, that must have been just like
7:20
gobbledygook, who absolutely no understanding or appreciation
7:25
for that world and that role, that must be quite daunting to
7:29
go from that. to that.
7:32
kaitlen kelly: Yeah, I think that's super fair. And I this is
7:34
also why I'm like, like, SDR synonymous community, and like,
7:37
why I'm so passionate about mentoring and coaching people at
7:40
that beginning stage is because it is you're not educated on it,
7:45
and you don't know the opportunity, or at least I
7:47
didn't know what the opportunities would have been
7:48
for me within a sales career. So it was extremely daunting
7:53
because it felt like I was walking in blind. Thankfully, I
7:56
did have a friend Justin Wright, who was able to like, give me
7:58
some insight. And I did a fair bit of due diligence, kind of
8:02
like testing it out going through the interview process.
8:05
But it was a little bit of that. I mean, earlier, right, I told
8:09
you, I'm either 0% or 150%. So it was a little bit like,
8:13
alright, if I'm going to commit to this, like, I got to jump in
8:15
and go at it full force.
8:18
mark ackers: I'm told him about that, then you get offered the
8:21
job at Outreach. you're chatting to your parents. They're just
8:27
the way you describe them. And it's a very high level
8:29
description. But I hear that a lot from people where they've
8:31
got a pair, obviously a different generation, right. But
8:34
when you start talking to her about SDR, they're like, What
8:37
the hell does that mean? saas? What does that mean? Who's this
8:42
company outreach, they've grown really fast. I'm leaving this
8:46
company that that, you know, in an industry that you know, want
8:48
to be part of, and I'm taking that role. How, how much did
8:54
they sort of doubt the move? And you moving into sales where
8:59
you're going to be making cold calls and emailing people trying
9:03
to book meetings? Like what did they make of that for that 25
9:06
year old daughter at the time?
9:09
kaitlen kelly: Um, I think I think my I think the biggest
9:12
thing was like I think my dad was just nervous that I was
9:16
making a maybe like a an irrational decision or a quick
9:20
decision without thinking things already all the way through with
9:23
the opportunities I had at Nordstrom. So I think that was
9:27
what it is he always believed in me and trusted that I would be
9:31
able to figure it out and he was confident that I would like I
9:33
had that skill set to do it. But yeah, they he didn't really
9:39
understand he doesn't didn't know what I was selling, but to
9:41
be fair, he owns his own business. And so like, if I
9:45
think back to like my first cold calls were when I was calling
9:48
down his customer list selling the certifications and lessons
9:52
for his industry that they would host at the the training centre.
9:58
So he under stands the need for pyrogen and the relationships
10:02
and stuff, but it's just a different way of going about it.
10:05
I think. So.
10:06
mark ackers: So that was interesting. Did you use to make
10:08
those calls on behalf of his company?
10:10
kaitlen kelly: Um, yeah. So when I was in high school, because,
10:13
you know, I'm a fashion girly, and I wanted my designer bags,
10:17
and he's like, I'm not buying you any of that at that age. So
10:21
he gave me the opportunity to basically sell these courses or
10:25
certifications. And then I got paid a commission on every
10:28
single one. So I would literally figure out the bag that I wanted
10:32
work backwards of how many classes I need to sell, then go
10:35
get the bag. That's kind of Yeah, when I think about the
10:39
first call call that I made. So I think ironically, I was I was
10:43
doing the selling before I even knew I was doing it. You know
10:45
what I mean?
10:46
mark ackers: Yeah. And lots of people, when they have that
10:48
realisation, I realised that they they've been selling their
10:50
whole lives. And we can't not talk about that. And so what was
10:54
that? Like? Not only is your boss, your dad, your 1516? You
11:00
say? You're picking up the phone? That must have been scary
11:04
as hell?
11:06
kaitlen kelly: on it? Yeah. I mean, when I think I don't, I
11:10
wasn't that scared. I think there's this something about
11:12
being that young and being a little bit naive of going into
11:15
it. So yeah, I would I can picture I had literally like a
11:20
pack of papers with the list, I'd go through with my
11:23
highlighter of the ones that I've already called, and just
11:25
continue to work my way down it. And yeah, then would just say
11:30
like, Hey, your guyses certifications are coming up.
11:32
Like we've got a course it's launching on May 18. We'd love
11:35
to get you in it's $350. And then see how many people they
11:39
needed to sell or not sell but sign up for it. And then I would
11:43
get them signed up for it. I'm
11:45
mark ackers: Did you have a script? Did you create one
11:47
yourself that I didn't want to sort of train you on what to do,
11:50
or I'm
11:51
kaitlen kelly: not really trained. But it wasn't rocket
11:55
science either. Like if I knew what the Course wasn't
11:57
certification, and they were running on a quarterly basis,
12:00
then I knew I just had to call the list. And if you can read
12:03
the person's name, then I would just pitch what the
12:06
corresponding there's like a little description. So
12:09
mark ackers: help me understand that the gap here with 1516. And
12:14
I get that when you're younger, you maybe have just you don't
12:17
have that self limiting belief, you are more confident you've
12:20
got less, I suppose attached to the outcome. But you get to a
12:25
point where outreach is floated, and you're like, No way I'm not
12:30
cold calling I'm scared as hell. Where's the disconnect? Between
12:33
that Kaitlen at 25? And Kaitlen are 15. And 16 is like, give me
12:38
the list. I call them up. I'll make the money. Yeah,
12:40
kaitlen kelly: I think what I was envisioned, probably because
12:42
when I was is because it's like family run business. It's been
12:46
running for 30 years, a lot of these companies know my dad's
12:49
business. And so maybe it's that it felt more familiar to me.
12:54
Whereas Kaitlyn at 2526, it was me walking into a tech company
13:00
selling b2b Tech. And speaking to VPS. And I guess it's just a
13:06
different persona. And now that I have the experience that I do
13:09
know, I can kind of frame it that way. Whereas when I'm 1516
13:13
year old, 16 years old, I'm just calling like, the owners of
13:16
these companies that are like my dad that I would talk to you
13:19
every day. Now,
13:21
mark ackers: I know, I know, you'll know this, but so much
13:23
that it just comes down to mindset, doesn't it? Yeah. And
13:27
that's the thing. It's channelling the right mindset
13:30
and making sure that really, you're, you're aligned to what
13:35
it is you're trying to do, rather than who it is you're
13:37
calling. And so we join outreach. And unless I've got
13:43
this wrong, it was like promoted within four months, promoted
13:47
eight months later promoted eight months later again, how
13:50
did you make it look so easy?
13:53
kaitlen kelly: I wouldn't say I made it easy. But I think given
13:57
I had the previous leadership experience that I did have, and
14:00
my analysts background, I think I had a lot of skills that
14:04
allowed me to set up processes when I did jump into that role,
14:06
so I could stay organised and execute efficiently. So I think
14:11
that kind of like when I think about when I first came into the
14:14
SDR role, I was like, heads down, I have a photographic
14:18
memory. So I like wrote that script out, like so many
14:21
different times, I would call call my parents to practice my
14:24
pitch. And I was just like, all in until I had it perfected. And
14:29
I think I always have that mindset. Whenever I start a new
14:31
role. I always go in knowing like, okay, the six months is
14:34
gonna be like heads down, absorb, absorb, absorb. And so
14:38
when I went in and did that and started getting momentum and
14:41
rhythm, I also had like great peers around me and some coaches
14:44
that were just like, super motivated and inspiring to be
14:47
around as well. So kind of from there, and then my leadership
14:52
background that I had had, I think set me up nicely as an A
14:56
candidate essentially to lead and build out the team here in
14:59
EMEA. So
15:00
mark ackers: there's two things I want to talk about there. One
15:03
One is the peers and coaching you had naturally I'm curious
15:06
about that. But Christ cold calling your parents for
15:10
roleplay. That I mean, it's amazing. I love that. I reckon
15:15
Have you said to 99% of sales reps, we're gonna roleplay, let
15:19
alone with your parents. They had run for the hills. How did
15:24
how did you like? How did you cope with that? It feels like it
15:28
was fine, the way you described, it was just like it was no
15:30
problem at all, just calling my mom and dad up. But talk to me
15:33
about the mindset that you need to have to get to do that, and
15:37
why that was so helpful. I
15:39
kaitlen kelly: think it's the drive that's within me, I'm also
15:42
extremely competitive. So one of the things that I loved about
15:46
outreaches, when they hire you on they hire you on as part of a
15:49
class and it go G class. And me being extremely competitive
15:54
means that I have peers that start at the same time as me. So
15:57
if I'm not booking more meetings and beating them on the
16:00
leaderboard, then that's probably not going to be good
16:03
enough. And so I was doing everything I could to get
16:06
better, because these gentlemen that I was hired with were
16:09
extremely great as well. And so that was something that I would
16:13
do in my spare time, I've listened back to tonnes of Gong
16:16
calls. And I still do this as a leader as well, if I like when I
16:19
started at Clay VO, I would just on my way to work at the gym,
16:22
I'm constantly listening so that I can pick up the product
16:25
knowledge as quick as as I need to be. But um, yeah, so in my
16:30
spare time, I, if I'd be at home in the evening, call my parents,
16:33
I would hate scaling from outreach on a recorded line. And
16:36
I would just go straight into the pitch, they'd be like,
16:38
Kaitlen. But yeah, and I would just keep going through and
16:42
doing it. So did I give you feedback? Um, no, not really. So
16:47
it depends on how far they'd let me take it, like give up on it.
16:52
But it was more such as getting in the rhythm. And the more I
16:54
kept doing it, the more natural it would feel. And I'm
16:58
definitely I would say, like the sales culture at Outreach was
17:01
extremely call heavy. So and we were out on the floor too. So I
17:05
had mentioned like some of my peers like we would gamify and
17:08
make these call blitzes like extremely fun and competitive.
17:12
So I think that also kind of broke down some of the barriers
17:15
and had the fear of the phone.
17:17
mark ackers: Fascinating that we don't need to dive into it. But
17:20
I'm a massive advocate for cold calling. Like, it's really the
17:24
only way I book pipeline for myself. And not to sound
17:28
terrible. But if you want to book a meet with me is really
17:30
the only way that gets through to me. Like, if you've got me on
17:33
the phone, you've got my attention, you're getting
17:34
emails, it's harder, but my point is outreach, a tool that
17:39
sped up the amount of emails, the delivery, the cadence, the
17:43
sequences, whatever you want to call it being called heavy. It's
17:46
interesting, isn't it? You feel like they'd be sequence in
17:49
cadence heavy. But as I say, I'm a massive advocate of cold
17:52
calling. And it's just that was interesting. You said that. So
17:57
talk to me about day one, that you're part of a group, you're
18:00
in a classroom, are you I suppose? How many people are you
18:04
sat with in this cohort on day one outreach.
18:08
kaitlen kelly: So when I started an outreach, the cohorts were a
18:10
little bit smaller. So it was three of us. So I, me and then
18:14
two other gentlemen. And but then as it started growing, and
18:18
I became one of the team leads and managers, those cohorts
18:21
started to grow bigger. So oftentimes, we would be in rooms
18:25
with up to like, eight, new SDRS. But yeah, so it was quite
18:30
intimate. And then it got to be to a point where it was like
18:32
getting bigger. When
18:34
mark ackers: you sat there with the other two gentlemen. Where
18:37
did you rank yourself? Like, first impressions? How did you
18:40
rank yourself versus the other two? Um,
18:44
kaitlen kelly: I would like in reflection, I would say probably
18:48
in the middle of Yeah. Okay, so
18:52
mark ackers: if one was better than you one ad, the big one
18:56
kaitlen kelly: had more experience he'd been doing it
18:57
before who was familiar with it, another one came from kind of a
19:01
different background like I did. So I think kind of what
19:05
separated me and maybe gave me that that nudge for me to feel a
19:08
little bit more confident in my abilities was my resilience.
19:11
Okay.
19:13
mark ackers: And then I love how you described like, I'm either
19:16
out or I'm all in and then just just listening to what you said
19:21
there you know, listening to call recordings on the way the
19:25
gym in the morning. So as a can role playing my parents, great
19:28
peers, great coaches taught me more about that the first six
19:33
months where you're like, This is a critical period. Almost
19:36
give me like your blueprint. So imagine a sales rep is listening
19:40
to this going to join a business and a saas role. This is the
19:43
Kaitlen Kelly blueprint for the first six months. Everything you
19:47
need to do to get ahead. What does that blueprint look like?
19:52
kaitlen kelly: Nice. Um, yeah, so this is just going to be kind
19:55
of like off the cuff of what I would do. But if I am getting my
19:59
first role Well as an SDR BDR and joining a company, I would
20:02
Yeah, in my first six months, I'm going to basically execute
20:06
on the onboarding or bootcamp that they give to me, that's
20:08
probably going to take up about two weeks or so during that two
20:12
weeks when they are throwing tonnes of product knowledge at
20:15
me and all the information I need. At that same time, I'm
20:18
probably going to set up coffee chats with basically like key
20:22
personas, I know that are going to help me within my role so
20:25
that I'm building like a little bit of a resource pool behind me
20:27
of people that I can lean on when I may need them. So that
20:31
could be other peers that could be top performing account
20:34
executives, maybe it's other sales leaders, but it's trying
20:37
to understand the different facets of the entire
20:40
organisation and where my impact is going to drive. So I'll be
20:44
having coffee chats with different people trying to
20:46
understand their roles, what they love about their roles,
20:49
challenges they're currently facing, and if it's something
20:51
that I'm going to like, as an SDR BDR, you're probably booking
20:54
meetings for AES. So you're trying to understand any
20:57
challenges or friction that is happening that you can help
20:59
solve for. At the same time, I'm doing role we are role plays, I
21:05
don't know why that came out. So we're doing tonnes of role
21:10
plays. I'm asking for feedback, I'm listening to the gong calls,
21:14
I'm listening back to my own Cole calls, and checking the
21:18
leaderboard to see where am I stacking up against my peers. So
21:22
I think like, it's gonna be heavy on listening back and
21:25
absorbing probably in those first three months and making
21:28
sure that you're kind of practising practising. And in
21:31
that three to six month mark, you should have a pretty strong
21:33
foundation of like scripts objection handling, the omni
21:37
channel approach, so like LinkedIn, social selling, social
21:41
selling, and I'm referring to video as well voice notes, and
21:45
then phone and email and have a good grasp of the ICP. And then
21:48
from that three to six months, it's how do you like double down
21:50
on where your strengths are to drive your results forward,
21:53
you're probably going to start tearing out your accounts or
21:55
heat mapping them. So that you know, okay, which ones are
21:58
likely to convert? This guy gave me an objection last week? Do I
22:01
follow up with them this week? And how do you start to build
22:03
kind of a process around that last
22:06
mark ackers: a blueprint to success? What was interesting
22:09
is, I know you're taking the right way. Nothing you've said
22:13
there is like revolutionary, right? But but it's all the
22:17
right things to do. But here's my point. loads, people say
22:20
that, but so if you do it, and it does that surprise you? Um,
22:26
kaitlen kelly: I mean, I don't think it surprises me because I
22:30
see it all the time. I think what, yeah, it surprised me that
22:33
more people don't do it, especially if you're given a
22:36
framework or a process. I think I mean, organisation, if you can
22:41
be organised, then you're going to be miles ahead because you
22:44
can execute on a plan efficiently. And so that is
22:48
something that I'm that is something that I'm, I would say
22:51
I'm extremely good at and doing it. That's why I can execute
22:54
like that. But I think you're just leaving opportunity on the
22:57
table if you don't, and you're wasting your own energy and
23:00
actual brain space to buy trying to do that. If you don't get
23:03
yourself organised.
23:05
mark ackers: I think that is just on the money, a pool of
23:09
money, so to speak, if you've seen the quickfire round, you'll
23:11
get the reference. So when I think back to reps I've managed
23:15
over the last eight years or so why of the things that would
23:20
frustrate me and I see different between the top performers, and
23:24
those are trying is they've got just big holes in their
23:27
calendar. I think when you look at your calendar, that that
23:31
tells me if someone has got their shit together or not, I'm
23:35
guessing there for you meticulously plan your day and
23:39
your time and where you spent it. And so few reps do that.
23:43
Like, I don't want to talk about STL specifically here, but that
23:45
would be a great example where you look in their calendar, and
23:48
you might literally see Town Hall on a Wednesday and that's
23:51
it. Nothing else and it's It puzzles me. Yeah,
23:56
kaitlen kelly: this is um, this is something I speak to as well
23:58
as like time prioritisation, but it's also just time blocking out
24:02
and then well as one thing I do with my calendar is I also
24:05
colour code it. So as an SDR I would time block specific tasks
24:10
that I need to execute on. And then on top of executing on
24:13
those tasks, I would attach a goal to it. So if I knew I had
24:16
to reach a goal by the certain time at the end of the week, or
24:19
maybe I wasn't patient, because I don't know about you, but I've
24:22
had one of those months, where you're in towards the end of the
24:25
month, and you're pretty far off of that target and you've got
24:28
like five days to figure it out and you panic. So you're like,
24:31
how do I figure this out? The answer to that was I literally
24:34
sat in a room and cold call till I got the meetings booked in.
24:38
But I'm working backwards from what the end goal is and setting
24:42
goals against the calendar blocking is like key and I carry
24:44
that through even as a leader today on all the little tasks
24:47
that way nothing drops, like I can't drop the ball in anything.
24:51
mark ackers: We speak the same language. I think we could
24:53
compare calendars, and we've complemented each other mines
24:57
colour coded time blocked. I've got to go All set to it. And so
25:01
what I sort of teach people to do as well and encourage people
25:04
to do. Okay, so when I asked you at the start the podcast, I
25:10
said, Did you speak like this? As you said, Yes. Was there a
25:14
specific moment in your career that rushed to the front of your
25:18
mind? When you answered that question?
25:22
kaitlen kelly: Yeah, there is. So there's one big one in like
25:25
tech sales, and then there's one that just actually came to my
25:28
mind as well. So do want me to share both of them love that.
25:31
Alright, so my first day as an intern on the sales floor at
25:36
Nordstrom, I was terrified. I'm actually like an introverted
25:40
person, I have to force myself to go to these networking
25:43
events, and kind of get out there to talk to people. And
25:45
it's a skill that I had to develop, but to the point that
25:48
like, my shoulders, and my arms will literally go numb, because
25:51
I'm so nervous. So when I want, it's my first day on the sales,
25:55
I don't even know how to approach a person. And I just
25:59
remember my manager coming up, and like literally pushing you
26:02
on the back, like, You're gonna be fine. Just go say hi, and ask
26:05
how they day how their day is. So that is something where I'm
26:09
just like, almost like the fear of talking to somebody or the
26:12
fear. But the rejection maybe held me back there a little bit,
26:17
until someone else kind of pushed me forward and kind of
26:19
believed in me before I believed in myself. So that was kind of
26:22
in the fashion industry. And then software, yes, so at our
26:28
age and made the transition over b2b, I'm cold calling I'm like
26:34
four months in, and I'm pretty fearless on the phone. So that's
26:39
I'm like doing the phone thing. That's great. Got my script
26:42
memorised, we're good to go. They sent me to my first event
26:46
in Vegas. And the way that we do these events, it's incredible,
26:51
because there's so much prep work that I put into this. So I
26:55
would like map out the entire showroom floor, understand all
26:59
the brands that would have their booths there. And then I would
27:01
research each of the brands and understand which ones were
27:03
prospects, which ones were potential customers. And then
27:07
from the ones that were prospects, I would then figure
27:09
out who were with my personas, I'd map all this out. So I had a
27:13
pretty like bulletproof plan of who I was going to target once I
27:16
got there. And so for example, it could look like alright, I'm
27:19
going to booth three team, because x companies there. And I
27:23
know, Jeff, the CMO will be there after lunch. So they I go,
27:28
and I'm with my account executive that I'm paired with
27:32
at that time. And the way that the kind of the play works is we
27:35
go up to the booth, we start chatting and trying to
27:37
understand their play. And then that's easily tee up a
27:42
conversation for the account executive. And this is my first
27:46
event and my first time going to the booth in person. And I walk
27:51
up my personas there, because I looked on his LinkedIn, I know
27:55
what his picture looks like. And I go straight up to him and
28:01
literally pitch a script, a cold call script at him. So I
28:07
mentioned my photographic memory. And it was the weirdest
28:11
thing. I was like I turned into a robot and I just threw up this
28:14
script at him. It was so not natural, so not human. And I
28:19
think it shocked the accounting executive. Because he had to
28:23
stop me halfway through and was like, I'm so sorry. We're going
28:28
to just take a step away from here. Like, we'll come back in a
28:30
little bit. I apologise for this. And he had to like pull me
28:34
away from the prospect and was like, Are you still breathing?
28:38
Like what's going on here? So that is yeah, a moment where I'm
28:41
just like, that was incredibly embarrassing mark.
28:45
mark ackers: So okay, let's just play that back up. Again,
28:48
meticulous planning is what's coming through here. So many
28:52
people again, don't do that live events. I love it. Right. So you
28:55
know exactly. Almost like the Terminator, you got your list of
28:57
evil that you're going to find. You go up to the booth you with
29:01
the AAA, you see, the person who will speak to you start to pitch
29:08
like a robot. Your AE shuts you down, almost like halfway
29:14
through, says to your prospect. I'm so sorry. We're gonna step
29:19
away and we're come back. What was going through your mind when
29:23
you heard that? That must have been crushing?
29:27
kaitlen kelly: I think I would say I was mortified. I was like,
29:32
oh my god, like, I think I'm malfunctioning. Like what just
29:35
happened? So yeah, I want to say it was like I think it both
29:40
shocked us and then I want to say it was like, like, I didn't
29:43
feel like I let him down like he didn't seem like he was
29:47
extremely I think he was shocked. More so than like, let
29:50
down or disappointed. And then for me, I think it was like a
29:55
huge Eye Opener where maybe I was like overcomplicating it and
29:59
just needed It's like, calm down. Like, it doesn't matter if
30:02
this is a CMO, like it's just a person just have a normal
30:06
conversation. So I think that was kind of how we took it back.
30:10
And we just kind of simplified it again, it was like you're
30:12
human, like, just have a conversation. And I think one
30:16
other thing that we did was just, which is probably simple,
30:19
but I thought it was helpful was just like roleplay, like a
30:22
couple of ways to open up a conversation with somebody. So
30:26
that was nice. So
30:28
mark ackers: and you're totally right. It's just another human
30:30
being, you can almost make light hearted the moment and, and
30:33
almost people are happy to forgive and move on. But yeah,
30:37
so you go away from the stand, it feels like the AE is an
30:41
absolute friend there in terms of trying to help you. Lots of
30:46
people wouldn't have gone back to that CMO. Lots of people
30:49
would have gone, you can go, I'm not going back or we don't go at
30:53
all. How easy was it for you to go back for a second round?
30:58
kaitlen kelly: Yeah, so it took a couple. I would say like
31:01
couple hours later, like we went into other booths before we
31:03
circle back. And when we did circle back, it was definitely
31:08
like a falling on my sword moment where I was like, Hey,
31:10
I'm so sorry. This is actually my first event. I didn't mean to
31:14
just like show up and pitch it yo, but I am curious to hear how
31:17
you guys are handling your leads, essentially. So
31:20
mark ackers: I think that it's just you played a play that
31:23
absolutely right there almost like free yourself under the
31:25
bus. It's my first event, natural reaction is to want to
31:29
help you and give you that short redemption, so to speak. Did
31:33
they buy?
31:35
kaitlen kelly: I don't think so. Well, yeah.
31:38
mark ackers: Can you remember that? You don't need to know
31:39
that. Can you remember who that person was?
31:42
kaitlen kelly: I can like the outline of the person. I can't
31:44
remember their name or the company. But I have like, you
31:47
know, the vision? Yeah.
31:49
mark ackers: I wonder if somewhere else they sometimes
31:52
tell the story. Are you Oh, that great. Kaitlen Kelly, you see on
31:55
LinkedIn, let me tell you about her first event. Okay, so let's
32:01
talk about other things that you were crap at. Because there's so
32:04
many facets that even you mentioned there as an SDR. It
32:08
feels like you had that fear of cold calling. But for months, in
32:11
your words there. No fear crushing on the phone? What
32:15
other aspects of the role? Would you say you were crap out?
32:18
kaitlen kelly: I would I I mean, I've never been like the best at
32:22
like the written words like emails and stuff. I think that
32:24
was one of the benefits of outreach was the we had so many
32:28
sequences and templates and stuff. So I think when I first
32:31
actually this is good. So yeah, I wasn't the biggest fan of the
32:34
email prospecting, probably why leaned in so heavy on the phone.
32:39
And I if I reflect back on to what made me so crap at that, I
32:43
don't think I put enough energy into the relevancy of what that
32:47
first nugget was, I never had an issue finding like a way to
32:51
personalise it or, you know, a reason to reach out to somebody,
32:55
but like, how did I tie that back to my solution of like, why
32:59
then why now? That was, that was a learning curve that came
33:03
later.
33:05
mark ackers: Do you think and I'm guessing, do you think part
33:07
of that might be down to your personality, like, you're all in
33:10
or you're not. And if your, your belief is, I'm not very good at
33:14
email, or don't enjoy email, I get great success from cold
33:18
calling. Maybe the email didn't get that 150% of you, so to
33:22
speak, during that was part of it.
33:24
kaitlen kelly: Um, I mean, I think that could have played
33:27
into it. I think the the true driver behind it was down to
33:31
like speed and efficiency. And so if I think back to like, what
33:34
that template was, it's like that first line is like,
33:37
basically fill in your nugget. And then there's like a
33:39
templated pitch. And this was, I don't know, maybe five years
33:43
ago, right. Whereas I definitely think the frame of cold email is
33:47
different now. But so I think it was more of speed of efficiency,
33:51
where maybe I was just trying to get out as many sequences as
33:55
possible. So I would just chuck the nugget in there for that
33:57
first line, rather than taking the extra minute or two to tie
34:01
it all the way through. Gotcha.
34:04
mark ackers: And you mentioned coaches, so it feels like you've
34:08
had people that have walked in your shoes before, had success
34:12
in that role that you can lean on. Talk to me about some of the
34:15
coaches that you you've worked with, and have helped you and
34:19
more about that. Yeah,
34:21
kaitlen kelly: so I think like coming in at Outreach for that.
34:23
SDR role, like kind of Maher was the one that kind of led that
34:26
entire Goji tribe. So Goji is the new hires for the first
34:29
three months. And that's to make sure that you have that strong
34:32
foundation of how to execute on the job. So Ken was one of the
34:37
top performers as an SDR there and he also learned through Sam
34:40
Nelson. So it was like this funnel of learnings all the way
34:43
through. And so yeah, so that was like kind of having that
34:47
coaching and that level of like, drive behind you. Like I think
34:52
one thing Ken does well as he believes in the reps that he
34:55
would bring on board and that even before you would believe in
34:58
yourself and so you would just kind of rushed through those
35:00
awkward moments where sometimes it's easy to want to quit and
35:04
give up, right, especially if you're not getting the results.
35:07
But he would continue to push you through. So I think early
35:11
earlier days, that was fantastic to see me and him ended up
35:14
becoming peers, and we're highly competitive against each other,
35:16
which was also incredible. And then from there, like when I
35:22
made the transition over to the EMEA team over here in London,
35:25
like being able to work under Tom Cassidy, I think that was
35:28
probably like an inflection point in my career, because the
35:31
amount of development and growth that I got underneath him, also
35:35
was incredible. And that helped me form a lot of the processes
35:38
that I implemented within growing out that region, but
35:41
also what I've been able to carry over to clay vo to do the
35:44
similar thing within the account executive org. I didn't
35:48
mark ackers: feel one of the things that I think you've said
35:50
three times now, is this believe in you before you believe in
35:54
yourself, like you mentioned about your parents, you
35:57
mentioned at Nordstrom, you've mentioned that there with with
36:01
your coach outreach. How important is that? Do you think
36:05
for you that you've had someone believe in you before? Maybe you
36:08
believed in yourself and the journey of the career that
36:10
you've been on?
36:12
kaitlen kelly: Mark, you have incredible active listening, so
36:15
that you picked up on that? Um, how I think it is, I think it is
36:19
extremely important and even like thinking back as a leader
36:23
to it's like, how do you identify that in your reps as
36:26
well, so that you can pull that out in them. So I think that's
36:29
something that I'm always keeping top of mind. Because I
36:31
think if a lot of people didn't tap me on the shoulders, and
36:34
some of these moments, I wouldn't be in the roles that I
36:36
am in now. And I also want to have that level of confidence
36:39
that I was able to build up by the giving these opportunities
36:43
that I went for and failed and then tried again and tried
36:45
again. So I think I was having people believe in you. But
36:49
before you believe in yourself, it does create that environment
36:52
where I can fail fast and be okay failing, not be afraid of
36:56
it.
36:57
mark ackers: That makes sense to sentence. Yeah. How do you do
37:01
that? With a backdrop. So you've worked at our age in clay vo to
37:06
like Darling's in the SAS world where pressure will be high.
37:10
Right? Results will be needed and demanded. How do you create
37:14
an environment where people I know we've jumped out to you as
37:17
a leader, and we'll come back? But how do you create an
37:19
environment where people can feel safe to fail? Know that
37:23
they're going to learn with a backdrop of growth, growth,
37:27
growth investment? Gotta have the results? How do you do that,
37:31
as a leader, that must be really challenging.
37:33
kaitlen kelly: So I think as a if I'm thinking about how do I
37:36
create an environment where it's like safe to fail, I think if I,
37:40
there's a couple of things that I would do, and I can kind of
37:42
like talk through how I coach my team as well. But there's a
37:46
metric or a matrix that I use called it's juicy 17. But juicy
37:52
is just the name of my team. But 17 is the role of the key here.
37:57
The idea here is looking at frequencies and competency. So
38:01
giving my team a clear outline of what the expectation of the
38:05
role is and metrics they need to achieve, that will then result
38:09
to them hitting their target or the metrics that they're held
38:12
accountable for. So frequencies would be like KPIs and metrics
38:16
that I can quantify competencies are going to be the soft skills,
38:20
and with a mixture of those mixed together. So if you're
38:23
hitting all of your frequencies, and you're mastering your
38:26
competencies, goes will drive your results that we're tracking
38:29
to be successful. So that could be your quota, your ASP, and
38:33
your win rate, top three off the top my head. So I think that
38:38
helps create a environment where we know that we're growing and
38:41
developing because we do that month over month reflection
38:43
there. And that also tees up a great conversation for me to
38:46
have with them is like talk to me about your strategy. What are
38:49
we doing here? How can we pivot, because I see it as like a
38:52
massive partnership. And then the other thing that I'm doing
38:54
to create that safe to fail environment is I vocalised, my
38:58
failures and I'm not afraid to get in the weeds with them. So
39:02
like, I'm happy to do cold calling with them. I'll jump on
39:04
discoveries, I'll get involved in negotiations, but I want them
39:08
to feel like we are at the same level and I'm here to support
39:11
them so they can reach their goals. I never want it to feel
39:14
like that top down approach. And I think if I can create an
39:18
environment where it's like, you know, we win together that
39:22
creates a safe space. And I think if somebody does fail,
39:25
it's like alright, what did we learn off the back of it? Let's
39:28
take that move it forward.
39:30
mark ackers: I love you sound like you've been incredible
39:32
person to work with in a manager managerial capacity. The way you
39:36
describe that and talk to you about how you got into that
39:40
manager manager role then so we're an SDR as I say. We're on
39:45
my notes here. We were promoted four months and eight months and
39:48
eight months later was Did you just take his like a duck to
39:53
water once you got your first six months under your belt? You
39:57
knew what you were doing? Was it just Easy peasy for you.
40:01
kaitlen kelly: So my first leadership role was at 23 years
40:05
old, with Nordstrom as an assistant manager for a
40:08
division. And the route with Nordstrom is you go intern and
40:12
then from intern to assistant manager, and then you either go
40:15
to a bigger division or to a manager of a smaller division.
40:19
So I was on that track and leadership. And then at 24, I
40:24
believe I was running the third largest trend division in the
40:27
US. And I had 27 Associates underneath me. So when I made
40:33
the switch in the analyst's office, and then over to
40:35
outreach I had already, I all say crash and burn throughout my
40:39
leadership career, to be honest. And I had some tough learnings
40:43
earlier on because you can imagine being a 23 year old
40:45
trying to lead a 40 year old that's maybe working part time
40:49
as a stylist, that's a hard dynamic to master. So when I got
40:53
into outreach, and started out as an Icee, as an SDR, it really
40:57
was like the first three months and I started hitting really
41:01
good results. And then I started breaking records. And right
41:05
around that, like four month, four to six month mark, there
41:08
was conversations of you know, where did I want to go? Did I
41:11
want to get back into management, and audit, I want to
41:15
go account executive route. And to be honest with you, based off
41:17
my previous leadership experience, at Nordstrom, I was
41:21
like, I don't want to do that. Because it was I just don't
41:25
think I had the best experience. And so that wasn't my natural
41:30
route to go that direction. And then some other people talk to
41:33
me, and I kind of thought it through a little bit more. And
41:36
then that's when I started leaning in and training on the
41:38
boot camps as a senior SDR. And then the opportunity for London
41:42
came up. And I remember I got the call as I was moving into a
41:45
new apartment in Seattle. And my mom was with me at the time. And
41:50
they were just like, hey, we just want to float this idea by
41:52
you do you want to take some time to think it over? It was in
41:54
September of 19 2018. And I just committed on the column. I
42:00
remember my mom looking at me like I was crazy. And she's
42:02
like, you're just going to up and move to another country. And
42:05
I'm like, it's only six months. Here we are.
42:09
mark ackers: It's amazing, though, like so so many people
42:12
don't get that opportunity. Or they do that. They don't take
42:15
that. As as a father myself, I'd be like, right? Well, I'm coming
42:18
with you. I'll just be I'd be I'd be I might struggle to
42:22
actually because it could be in different places. But let's talk
42:25
more about you being a leader, then. You've obviously had
42:28
different experiences in and out of saas. Let's just go with a
42:31
big question straightaway. What's the biggest mistake
42:34
you've made as a leader?
42:35
kaitlen kelly: I think the biggest mistake I've made as a
42:39
leader. I think it's like not taking the time to understand
42:45
the why behind some things. So like, if something's not we're
42:49
in this is I think I've learned off the back of it. But I think
42:51
if something isn't working out, it's not taking the time to
42:54
pause and maybe ask the rep why or help me understand it would
42:58
I'd come in and try to diagnose before trying to understand it.
43:01
So I'd say that's like one of the biggest ones, I think the
43:05
other one is coming to like a change management where it's
43:08
like, okay, if you're trying to implement change, I'm good at
43:12
implementing the change. And I noticed a trend where I would
43:15
not have like the accountability bit, right. So it's like, okay,
43:20
I'm doing all these efforts for changing were identifying it,
43:23
but there was a gap on getting the results on the end. And that
43:25
had to do with the programme that followed up to kind of
43:27
enable or like double down on the skill or whatever we were
43:30
trying to train on. So I think those are kind of the two
43:34
biggest ones was like slowing down to understand the why to
43:37
get the full picture before diagnosing and then ensuring
43:41
that there is a programme with accountability when trying to
43:43
implement change.
43:45
mark ackers: And how did you learn that? Was this? You
43:48
learned by yourself? Or did you have someone to help you? Um,
43:53
kaitlen kelly: no, I think well, there was a stark moment when I
43:58
was 23. That happened at Nordstrom, where it glares at me
44:01
when I'm like, okay, pause and like understand the behaviour,
44:04
understand there's some there's something behind what's driving
44:07
someone's behaviour, typically is what I would say. So there
44:11
was one of those moments that had happened where I had had
44:15
like one of the one of my sales associates on the sales floor,
44:19
like snap at me and like shocked me. So that was like a moment
44:23
where I learned it the hard way. And then for the other one where
44:27
it was like the accountability bit, but this I think this is
44:29
working in tandem with Steve Ross, who is the VP of the SDR
44:33
org outreach. And it's, um, through having like talking
44:37
through some of the things that I was implementing and my
44:39
processes and stuff. And then it was the way he followed up with
44:42
me on account accountability. And I'd be like, oh, yeah, this
44:45
isn't working. And so in reflection, then it came about
44:48
where am I okay, he's running this process with me. Why am I
44:50
not replicating that with my team? There's a gap. Call.
44:55
Ignore
44:55
mark ackers: the word. A stock moment. I know you saw me bite
45:00
my tongue. I could ask when they start to you, or they say,
45:05
kaitlen kelly: Why are you being such a bitch? It's like, oh my
45:10
gosh, and it was like down to literally closing duties, which
45:14
if we want to, like, you know, make that a cinnamon for a
45:18
sentiment a synonym for like saas. It's like basically asking
45:21
someone to do their KPIs at the end of their shift. So yeah, so
45:26
it was taking this like understanding like, Okay, what's
45:31
actually going on with this person? How can I take a step
45:33
back and be kind of have a little bit of the empathy to
45:35
show through because there's something else that's triggering
45:37
this, because it's not like these closing duties were new or
45:40
something implemented on that day, and she'd been with the
45:43
company for months. So there's something else that I needed to
45:47
figure out. So that was the moment that like, shook me,
45:50
because I think I think that would shake it shake anyone?
45:53
Yeah.
45:53
mark ackers: And you're 23 at the time you say? Yeah, how old
45:56
is this person?
45:58
kaitlen kelly: She was 19. So she was young. Okay.
46:00
mark ackers: I think that's important context. Because
46:02
you've obviously mentioned like managing 40 year olds, for
46:04
example. So they're young, they're emotional, etc. But they
46:08
said, Why you being such a bitch in front of other people?
46:12
kaitlen kelly: No.
46:13
mark ackers: Okay. Just privately. Yeah. Okay. How did
46:17
you deal with that? Because that's not acceptable. How did
46:20
you deal with that?
46:22
kaitlen kelly: I just like looked at her and walked away.
46:25
And then I went to my manager to let him to loop in Milan, the
46:27
conversation to get support on how do I handle this in that
46:30
context, because I'd never been exposed to that. I don't know, I
46:35
didn't know at the time how to approach a conversation without
46:38
elevating it or making it bigger than it needed to be. It needed
46:41
to be kind of diffused at that time. So yeah, I went to the
46:45
store manager, and then HR to figure out a path forward. How
46:50
mark ackers: did you have the maturity? Not to go back at them
46:54
straightaway? Um,
46:56
kaitlen kelly: I mean, I think at 23. I mean, yeah, I think at
46:59
23, you know, that would have been really immature of me. And
47:03
I, I don't know, I think to me, if I'm thinking about it's like,
47:07
what is the outcome that I would have wanted, if I would have
47:09
reciprocated or if I would have went back, I don't think
47:12
anything good would have came out of that situation, given
47:14
where the emotion was at and the tone that she had used. So it
47:19
was just completely inappropriate in my eyes. So at
47:21
that point, I'm like, I'm gonna walk away from the situation,
47:24
and then go figure out how to properly handle this.
47:26
mark ackers: I think you were more mature at the age of 23
47:29
than I was. Obviously, sales leadership can be quite a lonely
47:35
place. You're a sales leader. Now, who do you turn to when
47:40
you're having those difficult months quarters, moments, self
47:45
doubt, imposter syndrome? All the things that affect all of
47:48
us, really, but who do you turn to now? For help and guidance?
47:54
Yeah,
47:54
kaitlen kelly: I think that I'm so I'm very lucky, because we
47:58
have a strong like sales manager group at Clay VO. So I have a
48:01
lot of like great relationships with within the team. So I can
48:05
lean on and kind of vet out different challenges that I may
48:08
be facing. I also think beyond just my internal team at Clay
48:13
VO, it's partnering with my wider network. So when I first
48:17
moved to London, I think another thing that's interesting is, I
48:20
didn't know anyone in London, I literally moved out here for
48:23
outreach. And so I had to create my own communities. And so this
48:27
also ties back to SDRs anonymous, and how this kind of
48:30
kicked off the ground because I knew the value of being able to
48:33
network bounce ideas off of other people. But from being
48:36
able to do that I joined the sales development leaders group.
48:40
And then from there, we kind of spun out into a group of like
48:43
five of us. And so that also helped me when I was just
48:46
becoming a leader within the saas at outreach. And so now I
48:52
have a lot of people that I can kind of like lean on bounce
48:54
ideas with, which is like extremely helpful, because it's
48:58
good just to get viewpoints from outside of your org, but also
49:02
internally as well.
49:04
mark ackers: And that makes a lot of sense. Talks about SDRs
49:10
anonymous, let, let's just imagine I've never heard of it.
49:14
And people listening to this might not have heard of it. What
49:17
is it? And
49:19
kaitlen kelly: I mean, they may have not it's been on hold for
49:21
the last three quarters. But SDR is anonymous is a community that
49:25
me and she for nearly who was one of the first account
49:28
executives at SIA, started up at the very beginning of the
49:33
pandemic. So at the beginning of the pandemic, both of us
49:35
recognise like there's gonna be that stark shift to a remote
49:38
environment. And one of the benefits of being in an in
49:42
office culture, especially within SDR and BDR land was
49:48
being able to have your peers to lean on when you do fail or
49:50
something completely awkward or cringy happens on a cold call.
49:54
You want somebody next to you that you can laugh about with
49:56
it, but also just learning quickly from them and like how
49:59
do you think It'll thing. So it started off as a Friday chat
50:04
where it was just like an open zoom to anyone that was located
50:07
within the London area, it was multiple companies that would
50:09
jump on. And we would do like Spitfire round questions as
50:13
well. So we had a slider that was set up, and people would
50:15
just type in questions anonymously that we then would
50:18
address his leaders.
50:20
mark ackers: Amazing how many people are in the community. Um,
50:23
so
50:23
kaitlen kelly: there's just over 7000 now. And what it turned
50:28
into is it turned in from that Friday conversation, which ended
50:31
up being quite a bit of an uplift into quarterly events,
50:34
and then sharing some like content and stuff. So now as
50:37
we're kind of going through like a refresh and a revamp, we will
50:40
be rolling that back out, again, into hopefully quarterly events,
50:44
again, amazing.
50:45
mark ackers: How do people join? If they wanted to sign up and
50:48
join? How do they do that? It's
50:50
kaitlen kelly: literally just a LinkedIn community. Right? So,
50:52
so easy, just follow on LinkedIn. And then you just
50:56
follow the content that we're posting. If we do events, all
50:59
the events are linked through Eventbrite there in person, some
51:02
of them are on Zoom. So it's, if we do a global one, it'd be on
51:05
Zoom. But yeah,
51:07
mark ackers: okay. I can tell just from some of the things
51:11
that you said, no previous conversations, it's important
51:14
for you to help people to develop them to coach them. What
51:19
about yourself, it can be really easy to neglect yourself. Do you
51:24
feel like you do enough personally, to help yourself and
51:27
develop yourself? Now?
51:29
kaitlen kelly: I think this is a great question, because it is
51:31
definitely something that's like top of mind. And if I think back
51:36
to probably like my first so being at Cato, for the last two
51:41
and a half years, I'll say actually, I'll just simplify
51:43
this, rather than giving you a tangent, but um, I will set
51:47
goals against what I want to achieve on my own professional
51:50
development. So at one point in time, it was like, Alright, once
51:54
a quarter, I want to go get certified in a specific tool or
51:57
a text within the tech stack. So I did some outreach ones, I did
52:02
some Gong certification one. So it's like, how do I kind of
52:04
build my skills in this way. Or I went through the Harvard
52:08
programme for leadership as well. So I'll set these little
52:12
goals of where I identify my gaps are. And then there does
52:16
become a time where all of a sudden, a quarter goes by and
52:20
you're like, oh, my gosh, I just lost three months, what have I
52:23
done to develop myself because things get busy priorities get
52:25
shifted, and if it's not top of mind, or if you don't schedule
52:29
the time out on your calendar, then it can get put in the
52:32
backseat. So it is something that I have to be proactive
52:36
about. I will and to be transparent. Yeah, in the last
52:39
two quarters, I have been looking for a way to kind of
52:42
stretch and develop myself in what is the direction that I
52:44
want to be stretching and develop in?
52:48
mark ackers: Do you have like someone outside of clay VO, like
52:52
a mentor or a coach that you do work with currently?
52:56
kaitlen kelly: Yeah, so there's like quite a few different
52:57
mentors that I will like partner with kind of like bounce ideas
53:00
off of which is like super helpful. So and they're from
53:04
different types of backgrounds as well, which I think is
53:07
important too, so I can get different insights.
53:10
mark ackers: So I love that. I want you to talk to me about the
53:14
impact that's had one of the things that never fails to amaze
53:18
me. I know you would have just seen this your whole career is
53:21
sales. So first of all, sales is a skill, right? Like when people
53:26
say it's gift of the gab it's centralised, Nonsan sales is a
53:28
skill that can be fine tuned, can be learned and eventually
53:32
mastered, right? But there's no barrier to entry. Anyone can get
53:38
a sales job at a certain level, like anyone can get in to sales.
53:43
But there's an ego there. And I find lots of sales reps have no
53:49
I use the air quote for those listening but qualification so
53:52
to speak, get into sales. Yeah. They have the ego, though, that
53:58
they don't need coaching or mentoring. They're going to do
54:02
this themselves. What would you say to people in sales right now
54:07
that think they're too experienced, they're too good.
54:09
They don't need a mentor. They don't need a coach, when they've
54:12
got into a job that's got no barrier to entry. And it is a
54:16
skill that can be learned and fine tuned. And let's be clear,
54:19
the better you are, the more you earn. But it always amazes me
54:23
when you speak to people and they just look down on
54:26
mentorship or coaching is beneath them. What do you make
54:29
of that?
54:31
kaitlen kelly: Um, I would I would want to understand why
54:35
they feel like it's beneath them. Or I think yeah, I think
54:39
that is interesting. I think if I'm thinking to like my team and
54:42
like why they don't maybe go out and get external mentors and
54:46
coaches. It's obviously because I'm the bet No, just kidding.
54:51
No, I think it comes down to like the time commitment and I
54:54
kind of view it as like it's a small like some While investment
55:00
for a big gain, and this is also high look at like podcasts or
55:04
webinars going to network events, like yeah, maybe giving
55:08
up one night a month to go and network with someone, but I can
55:11
walk away with one thing that I'm going to be able to use for
55:13
the next 10 years. So I think it's kind of getting them to
55:17
like understand that framework that there is value, maybe not
55:20
all of it is going to be a value, maybe you're not going to
55:21
get everything from a mentor or coach. But you may pick up just
55:25
that one thing, or even just setting up a conversation with a
55:28
peer that maybe is excelling in an area that you're not. I think
55:32
taking that 30 minutes yet, maybe it's going to take 30
55:35
minutes away from prospecting, or cold calling. But you might
55:39
learn something that can make it so that you have more meetings
55:42
on your calendar. So you don't have to do that. 30 minutes of
55:44
prospecting.
55:46
mark ackers: How big do you think mentorship and coaching
55:48
has been for you and your development? Oh,
55:51
kaitlen kelly: I think it's huge. Like I don't think that
55:54
because it I think it Yeah, I think it's like all of it even
55:56
like from day one, I had a mentor. So within outreach as an
56:00
SDR. And it's just somebody like bounce ideas off frustrations on
56:05
especially outside of your manager, who maybe you're
56:08
nervous to bring some of these things forward to, especially if
56:11
you're just starting out in a role because you don't want to
56:13
like disappoint them or make them nervous if you're not
56:16
grasping the ideas of something. So having like a mentor or even
56:19
like a network around you is going to be like extremely
56:22
valuable just to get that extra insight. So
56:25
mark ackers: you're obviously conscious of development and
56:28
working with people, etc. What would you say is the biggest
56:31
flaw in your game today that you're trying to work on? I
56:34
think
56:35
kaitlen kelly: what I'm trying to iron out right now is like we
56:37
have this awesome opportunity at Clay vo where we're launching
56:40
additional products. And I've never worked for a company where
56:44
I've been a part of that programme where you sell, you're
56:47
known for one product, and then you have additional ones that
56:49
you can attach on. So now we're trying to change that essential
56:54
discovery and pitch to how do we sell it as a suite rather than
56:57
just one piece of the puzzle. So when I'm thinking about in
57:01
reflecting on what the training and the coaching looks like, and
57:06
then one thing that we do really great is the training aspect. So
57:10
the transfer of the information and all the data points, the
57:13
skills, everything they need to know to sell it. But then
57:16
there's the coaching aspect in the programme that follows. So
57:19
this is something that I've been fine tuning for this quarter,
57:22
and it's okay, how do we then enable them and make sure that
57:25
we're coaching them on it week after week so that it stays
57:28
consistent and sticks. It doesn't just become something
57:30
where we run a training and then it falls off. So it's how do I
57:33
get the training here? And then what does the coaching programme
57:37
look like? And then what's the outcome I'm looking forward to
57:40
the team knows the Northstar that we're working towards. So
57:43
that's kind of the gap I'm filling right now.
57:46
mark ackers: And as a sales leader, you spend multiple
57:49
plates, right your your be recruiting and onboarding,
57:52
you'll be training and coaching, forecasting, one, one to one's
57:57
internal fires to put out, etc. How much time do you spend
58:02
coaching the team do you believe on on a weekly basis, I
58:06
kaitlen kelly: would say if I was looking at my calendar about
58:09
probably 60% of it is going to go towards coaching. And then
58:14
20% of it is going to be like forecasting calls pipe scrubs.
58:18
But within that coaching that one on ones that's call reviews,
58:22
it's running trainings, there's those all of that's gonna go
58:26
into it 6%
58:28
mark ackers: Amazing, most people spend less than 5% of
58:31
their time coaching. So that's incredible. What colour is
58:34
coaching in your calendar. So
58:37
kaitlen kelly: let me take a look. Actually, I have my
58:38
calendar also doesn't buzz on here. But it's going to be by
58:42
different colours. So all of the one two ones are going to be
58:44
purple coaching. Like if it's going to be like one of the team
58:48
trainings, it'll be a dark green colour. And then we have yellow,
58:51
which is going to be like outreach Deep Dive. So how are
58:54
we so that's basically I
58:56
mark ackers: always struggle when people use different
58:57
colours for different things like my my one, two ones are
59:00
blue, for example. And it would freak me out to change that my
59:03
discovery calls are green, my preps yellow, and I could not do
59:08
it another way. Like it almost be like a non negotiable.
59:10
Someone said to me, here's a job but your discovery calls, you've
59:13
got to be read. I couldn't go with that. Like, I've got my
59:18
callers and I've had him locked in for about 15 years.
59:21
kaitlen kelly: The reason why I colour code all the ones that I
59:24
control, and then all the meetings that are blue are like
59:27
the other people are putting on my calendar basically. Gotcha.
59:29
mark ackers: Okay. Um, so you were to start your career again?
59:36
What would you do differently?
59:38
kaitlen kelly: I think I'd get into software sales sooner. I
59:41
think that's like, the one thing that kind of kills me is I wish
59:44
I just knew about it sooner and the opportunities and I made the
59:47
switch at 27. And so I think that is I think just getting
59:51
involved sooner would have been amazing. What
59:53
mark ackers: do you think it'd be different like so you got
59:55
involved five years earlier? What do you think would be
59:58
different? Where would you But, um,
1:00:02
kaitlen kelly: I mean, I think I'd probably Yeah, that's a
1:00:04
great question. Maybe I would probably be further within my
1:00:08
career, maybe I'd be at a VP level of a company at this
1:00:11
point. But I still am developing some key skills here. So I
1:00:15
think, yeah, I think that would be one thing and full
1:00:18
transparency to is if I would have gotten sooner, then that's
1:00:23
like, essentially, six more years of making software sales
1:00:26
type of money versus fashion money. We're not going to go
1:00:29
into the difference there. But you can imagine. So one thing
1:00:34
that I like aspire to have is like a portfolio of like rental
1:00:38
homes and houses, that's something that I'm working
1:00:40
towards. So my investments, I think we'd be in a different
1:00:43
situation if we started a little bit earlier. Yeah,
1:00:46
mark ackers: the textiles money probably allow you to buy the
1:00:49
fashion items from the fashion world. Yeah, exactly.
1:00:52
Okay. We're starting to wrap this up. Honestly, I've just
1:00:58
missed so many questions that I could ask you. What I'm picking
1:01:02
up though, is that you're incredibly proud of the career
1:01:05
that you've got proud to be in sounds, which I loved, loved to
1:01:09
hear. And, obviously, your sad reality is lots of people fall
1:01:12
into sales don't want to be in sales, and would love to get out
1:01:14
of it. And you told me before, offline that you've got one
1:01:20
nephew and a two nieces or nephews and one niece
1:01:23
kaitlen kelly: was two nephews and a niece, let's imagine.
1:01:27
mark ackers: And I'm guessing they're obviously not at the
1:01:29
right age for this decision. But they're in different careers,
1:01:33
and they pick up the phones or auntie Kaitlen, and they say, as
1:01:37
a saas company. It's an SDR role thinking about going for it?
1:01:42
What would you say?
1:01:44
kaitlen kelly: I would say go for it. 100%? Yeah, I wouldn't.
1:01:48
I mean, I will support their honestly, I would support them
1:01:51
in whatever they want to do want them to know, all three of them
1:01:53
to like, have the world. So yeah, if they were to say that I
1:01:56
would probably I'd be like super excited about the fact that they
1:01:59
want to go down that career track. And then I'd probably ask
1:02:02
them a little bit more about it. And just make sure that like the
1:02:05
company that they are choosing maybe aligns with a passion or
1:02:08
something that they can get internally involved with?
1:02:11
mark ackers: What's the one warning you'd give them? I go
1:02:14
for it, but what's the one thing that you'd warn them about?
1:02:19
kaitlen kelly: I think it's important to look at I Know,
1:02:21
Like culture is a huge thing. But I always look at like the
1:02:23
leadership team that's there as well. And then the career
1:02:27
progression because it what I would hate to see is that they
1:02:30
go into a company and then it's they don't get the best
1:02:34
experience or they don't have the right development early on.
1:02:36
And then all of a sudden, they're turned off of sales
1:02:40
because they don't think it's for them or you know, some
1:02:42
people just don't get have the great off the jump experience.
1:02:45
Which thing puts a bad taste in their mouth. So that would be my
1:02:48
one thing is like, hey, it's gonna be really hard work but
1:02:50
extremely rewarding. Make sure you do your due diligence
1:02:53
throughout the interview process, so you know exactly
1:02:55
what kind of development training you're gonna get, so
1:02:58
that you are successful in your seat. That's what I'd say.
1:03:01
mark ackers: Fair enough. And again, I could ask three or four
1:03:03
questions about that, like what would you ask them to do? How
1:03:06
would you help them but time has got the better of us.