46 min

GTM Confessions: Truth About Being a Start-up Sales Leader


Stephanie and Kate talk about what it takes to work in a start-up, challenges facing sales leaders, how to think about measuring sales effectiveness, and more.



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(upbeat music)

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- Welcome to GTM Confessions,

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where we share what it takes

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to be a go-to-market professional today,

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because it's freaking hard,

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and it's far from the glamorous picture

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that social media often paints.

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Consider this show your weekly

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go-to-market therapy session.

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I'm your host, Stephanie Cox.

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I have more than 20 years of experience,

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and I've done almost everything

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go-to-market related in my career.

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In this episode, I chat with Kate,

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Vice President of Revenue at Audience Plus,

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about what it takes to work on a startup,

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the challenges facing sales leaders,

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how to think about measuring sales effectiveness,

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and so much more.

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- Welcome to the show, Kate.

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I'm so excited to have you.

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- I'm excited too.

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Good to see you.

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Thanks for having me.

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- So, for those of you that don't know Kate,

0:54

she is the VP of Revenue.

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So, all things tied to revenue at Audience Plus,

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and what I really wanna talk about is sales initially,

1:04

and how it's different at a startup

1:07

compared to a more established company.

1:09

'Cause I think sometimes there's a perception that,

1:12

well, if you're good at sales at a large company,

1:14

like a sales force Adobe, you could come to a startup,

1:17

and it's the same.

1:18

And you and I both know that's not the case.

1:20

So, talk to me about how you've seen it be different.

1:23

- For sure, I heard it referred to recently on LinkedIn

1:27

as the Magic Rep, which I had never heard before,

1:31

which I was like, of course in love with,

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'cause that's like just convenient for me.

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But yeah, it's extremely different.

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And I've been at enterprise, on enterprise teams,

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run enterprise teams, and then been progressively smaller

1:48

and smaller startups.

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And now, being really part of a founding team,

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and around from the beginning,

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I can, I think, speak pretty confidently

1:58

to how, like, how and why it's so different.

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And I think it comes down to just,

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everything is experimental all day.

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Nothing is done yet already.

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And that's like whether you're a leader or an AE,

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or whatever it is.

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Like, if you need a resource, guess what?

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Like, it doesn't exist.

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If you're looking for a narrative or a deck or a talk track

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that you can just come in and memorize

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and then learn how to personalize,

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guess what?

2:30

You first, you have to build it

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because it doesn't exist yet.

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And then depending on where you are on your product,

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product market fit, journey too.

2:40

Not only once you create those assets,

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or get it down and know what you're selling

2:46

and start getting good at it,

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it has to change again.

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And because you haven't figured it out yet.

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Like, we're finally at a place in our business

2:54

where we've got that now

2:55

and it does get a little bit easier,

2:57

it gets harder in other ways.

2:58

But like, yeah, just because you have figured out the story

3:03

doesn't mean you're telling it right

3:05

or that that's the story.

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So always having an openness and understanding of like,

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should I be doing this entirely differently?

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And you know, there's some ways to know

3:16

whether or not that's the case

3:17

and whether or not it's working.

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But, and then it's also just like nobody knows you.

3:23

So there's an incredible burden.

3:25

Like everyone's a bit of a marketer

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from a very early stage as well.

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So it's just, it's a lot, it's a lot.

3:34

Yeah.

3:34

- Well, I love that you said that you kind of have to come in

3:37

and build everything.

3:38

'Cause I think oftentimes people think,

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well, you're going to onboard a new team of burn

3:43

teach them everything.

3:45

And yes, but not everything exists.

3:49

There's not a process for everything.

3:51

There's not decks for everything.

3:53

You're releasing new product functionality

3:55

and things are changing.

3:56

You're constantly iterating on messaging.

3:58

It's not this kind of like beautiful little design box

4:02

that we give someone.

4:03

We're like, here, go do this.

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- Completely.

4:06

Yeah, when I joined, my mind tends to work

4:09

in like wanting to build a process for things

4:11

because then I don't have to like maybe F with it again

4:14

or I can like just then it's done.

4:16

And knowing I'd be bringing on a team at some point,

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there was like a lot of whole to document things early on

4:24

until I realized like, okay, I gotta stop doing this

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'cause this is like, yes, this is such a waste of time

4:30

because it's all changed already.

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And I can't keep updating all, like this is silly.

4:35

So finally let that go.

4:37

But yeah, that's a big part of it.

4:39

- It's interesting that you say that

4:40

'cause I do think we're all conditioned to like,

4:43

especially in a startup environment

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to think about when you start scaling

4:46

and to document the processes

4:47

and like create the training materials, which like yes,

4:52

but also.

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- Yes, but also like, yes, we'll just slow down

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and like, it's okay that not everything is in fact,

4:59

it shouldn't be scalable.

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Like nothing should be scalable for a while.

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And that's like takes a minute to really take that in

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properly, I think.

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- Well, I get everyone else on board with it too,

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especially like not just your kind of like team

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that you and colleagues that you work with,

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but also like a board who wants to think about,

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it was always thinking about what's next.

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- Yeah.

5:21

- Creating those scalable processes.

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- 100%.

5:23

- Yep.

5:24

- Very true.

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- So in this environment where it's very nebulous,

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things are constantly changing, you're iterating.

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What do you think is like critical skills

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to be successful in that like startup sales environment?

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Because I think oftentimes people think,

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"Oh, I'm really good at sales, I like doing it."

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And then they come into these environments

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and they're surprised, shocked,

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they don't realize like everything that they have to do

5:52

or how much they constantly have to iterate

5:55

on what they're doing as the company

5:58

is honestly being built.

6:00

- Yep.

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- You know, I think,

6:04

I think it helped for me for sure

6:08

that I have been doing this for a long time.

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Now that's not true for all eighties or sales,

6:14

anybody who's gonna come into maybe a first

6:17

or second sales role at a startup.

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But I'm like really used to hearing no from people.

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Like it's just like part of it.

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And it's in fact like it's a good thing.

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No means like you have an opportunity to turn it

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and do a yes.

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Like there's always no before there's yes.

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So like shedding the fear of that is the big deal

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'cause just like, I don't care, you know?

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Or like, I'll fix it, I'll turn it around

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if it makes sense to do that.

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And I trust that.

6:46

I think that's like, maybe that's just like confidence

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in itself a little bit that I know how to have

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those conversations and then prepared for them.

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I think just like then,

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curious like, you know, and I think that sales generally,

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but it's like an internal like with your team

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and you know, and external like that helps so much.

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And learning your business that helps you learn everyone

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else's while you're at it along the way

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and being close with your own CEO.

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And then I think just like, I don't know,

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being just fearless again back to the no thing,

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but like, I'm not afraid to fail.

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It will just make me smarter.

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Like it's okay.

7:33

You know, and you have to be willing to put on the work,

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which is duh, but I think, you know,

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for an A, especially someone that sells

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that's come from an enterprise organization

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that maybe seems to having meetings put on their calendar

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for them, that is likely not going to be your reality.

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So just being prepared, like even if you're told it will be

7:56

like, that's probably not true.

8:00

So being ready for the work.

8:02

Yeah.

8:03

- Well, I love what you said about being okay with no,

8:06

because I think in sales,

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no matter where you're at, you hear a no a lot,

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but I think you hear it more at a startup

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'cause you're trying to figure out ICP,

8:14

we're finding it, you're trying to figure out who to buy,

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who's gonna buy when they're gonna buy.

8:19

And additionally, like you don't have this brand recognition

8:23

that so many larger companies have.

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So oftentimes you hear no, because they just don't know

8:27

who you are.

8:29

100%, yeah.

8:31

It's like, it's so much education.

8:34

And it's one of those things too,

8:35

where there's like a 101 for a sales call

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that like exists for everybody.

8:40

It's how everybody gets trained, I feel like.

8:42

And yeah, there's iterations to it

8:43

and it changes over time when there's new methodologies

8:46

and all these things.

8:46

And it's cool, it's great, but, and it should evolve.

8:50

But also there's just like this very basic level of like,

8:53

you don't wanna have these monologues on a sales call.

8:56

Like a lot of even like recording software is like,

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you know, start yelling at you.

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If you've talked too much or if you,

9:03

but the thing about being in this kind of role

9:06

is that there's so much education that comes along with it,

9:08

especially if you are even somewhat of a category creator,

9:13

where you're not just like another solution for,

9:16

I don't know, you know,

9:20

call recording software let's say, 'cause I brought it up.

9:22

Or like something that people know

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that they have a line item for it's in their budget.

9:26

Like, and so you kind of have to throw some of those things

9:30

out the window that you know you're maybe not supposed

9:32

to do in this scenario also,

9:35

because this is just a different ballgame that you're playing.

9:38

- But I think that's an important differentiation

9:41

because oftentimes, right, you were taught to jump

9:44

on those first calls and do discovery and ask questions.

9:47

And the person you were talking to is like,

9:49

I don't know what you do.

9:50

- Yes.

9:51

- Can you please tell me what you do?

9:53

Because they're not, until you start to build a brand

9:56

and then demand's created from that,

9:58

you're typically the one reaching out to them saying,

10:00

I think you have this problem that I can help you solve.

10:03

Let me talk to you about the problem.

10:05

- 100%, yep.

10:06

And it's like, it's how most of my calls have started

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and my time, like where I am today, I would say,

10:15

is that just like, tell me about what you do.

10:18

And then of course you've got to weave the discovery in there

10:21

and all the other things you now have to be

10:23

have to be true to treat a prospect properly

10:27

and someone that's taken their time with you.

10:28

But yeah, there's some differences to it for sure

10:32

when you do it in this kind of situation.

10:34

- Well, and one of the things I always loved

10:37

about when we work together is you do love to turn nose

10:40

into yasas.

10:41

You think of them as like, not now's versus permanent nose.

10:45

And I think that's such an important differentiation

10:48

in the kind of like startup scale up world is most of the time,

10:52

it's you're doing outbound to these people

10:55

or you're getting introductions from other people

10:57

and they weren't looking for you,

10:59

they don't have a line item for you,

11:00

especially if you were, you know, this kind of new category

11:04

or a new product offering that they didn't know existed.

11:07

And so I think that's the part about being curious

11:11

that you mentioned earlier is so key

11:13

to being able to do that.

11:15

- Yeah, it's really true.

11:17

It's, you know, I think part of it has just been like,

11:21

and you know, you don't wanna,

11:23

like if I know someone's a good fit,

11:24

if I know we could help,

11:26

that's when I'm gonna work to turn that nose into a yas.

11:29

Sometimes it's just not,

11:30

that's likely where I'm not gonna be spending my time anyway.

11:33

And that's, you know, so important in the startup scenario,

11:36

but yeah, for sure, it's, it's just part of the evolution

11:41

of a conversation like this where, you know,

11:45

you're gonna try to talk yourself out of buying something

11:48

before you talk yourself into doing it

11:50

and being part of that is important.

11:52

- Yeah, well, and I think that's one of the big differences

11:55

when I think about like selling in a startup

11:57

versus selling in a more established company, right?

12:00

An established company, your kind of first call

12:03

is all about qualifying them in or out, right?

12:06

Do you have the line, do you have the buying authority?

12:08

Do you have the budget?

12:10

And you can't really do that in a startup environment.

12:13

So I think it's just completely different.

12:15

So obviously just kind of the entire sales process

12:19

and figuring out how it's gonna work for your business

12:21

is a challenge.

12:22

What are other challenges that you think someone faces

12:25

in a sales role at a company that's a early stage?

12:27

- Yeah, I think it's hard to get the attention

12:35

or the time of day.

12:39

And I'm trying to like, you know,

12:40

there's a leadership aspect to it

12:43

that I'm kind of like putting aside maybe a little bit

12:45

for this answer, which is just like thinking of it

12:47

from an AE perspective, but it's really hard

12:50

to get the time of day from anyone else on your team

12:53

and not in like a toxic problematic way even like,

12:57

you know, we've had the greatest culture.

13:01

We're a small team and a small team means that like,

13:04

if you need something done,

13:06

you gotta get scrappy and find a resource to do it.

13:10

Like again, and I touched on this earlier a little bit,

13:13

but like, you know, sales,

13:15

we always want like the perfect customer story

13:17

or the perfect asset that's gonna help support

13:20

what it is that we're doing.

13:21

And it's like, it takes them getting used to where you're like,

13:25

okay, we don't have that.

13:27

I can't ask for it.

13:28

No one's got time to spin it up

13:30

or even like the means to do that right now today

13:32

because maybe even like,

13:33

we don't have formalized customer stories yet.

13:36

So like, how can I support that actually getting done then?

13:39

Maybe like, you know, what do we think about having that written

13:42

and who could do that?

13:43

And like, sometimes you're really just like actually outsourcing.

13:46

I mean, I have a surprising amount of sales calls

13:48

where I'm the prospect because I'm like, okay,

13:51

is there a solution for something that I can just take care of?

13:54

It doesn't maybe fall under my technical job description,

13:57

but like, it would be a difference maker.

14:00

So like, you just have to be,

14:04

I'm trying to raise the same scrappy

14:05

'cause I feel like that's such a like,

14:07

goes hand in hand with the startup conversation.

14:10

But yeah, it's that.

14:12

It's just like being extremely resourceful

14:16

because no one has time to give you the extra time

14:21

or why you need.

14:23

That's not to say the coaching, you know, here and there,

14:27

but it's kind of like a pick your battle scenario,

14:29

I think on a small team.

14:31

- Yeah, that's why I like to say part of being successful

14:34

in a startup is doing the job that's needed,

14:36

which is may not be the job you were hired for.

14:39

I think that's what you just described is,

14:41

there's a lot of things that you're gonna realize you need

14:44

that maybe in a larger organization,

14:46

another team would do that you're just gonna have to figure out

14:48

and things that other people are gonna need help on

14:50

that you maybe have done in the past,

14:53

but it aren't part of your current job responsibilities

14:56

that you can just step up and kind of help.

14:58

Everyone is truly working together to figure it all out

15:01

as the plane is being built while it's in the air.

15:05

- That's exactly right, yes.

15:08

So we talked a little bit about like establishing processes,

15:12

documenting everything.

15:14

Well, let's talk about kind of the next part of that,

15:17

which is like pipeline.

15:19

It is the most important thing at a startup.

15:22

It is also, I think, probably the most frustrating

15:25

and challenging thing at a startup

15:26

because it is constantly evolving

15:28

and you don't have a ton of good data when you get started

15:32

even as you grow 'cause your product evolves,

15:35

that where you can create predictable forecasting.

15:39

So how do you think about creating pipeline,

15:43

forecasting in a way that is maybe also

15:46

like directionally accurate

15:48

and not going crazy while you're doing that

15:52

and trying to share that with your CEO,

15:54

with the board who want predictability

15:58

and a plane that is in the air and still being built.

16:01

- Yeah, this makes me laugh because

16:06

it's an art form.

16:09

This is a benefit of an art form

16:11

'cause there's the right answer

16:15

and then there's like the reality.

16:17

And then it's like a matter of figuring out

16:20

how to bridge those to the best that you can

16:24

with what you have to work with.

16:26

I think, you know, in any,

16:30

and like in every sales role I've ever been.

16:34

Let's say sales leadership probably,

16:36

but you can waterfall all day.

16:39

And like I do, like I know based on our wind, right?

16:42

And how much pipeline we need

16:46

and how many meetings that equates to based on the race.

16:48

Me and I know ourselves like going thin

16:50

so I know what we need in order to produce acts.

16:54

And that's not a difficult math.

16:57

And then you're like, okay, you can dig a layer deeper

17:01

and you're like, what are the sources for meetings

17:04

that convert better?

17:05

And how we focus on those to make sure we're feeding

17:09

the feeding myself really ultimately.

17:12

But, and then you know,

17:15

but there's a, at the end of the, like,

17:20

so you can do all that.

17:21

There's only so many levers you can pull.

17:28

With very finite resources in a startup.

17:31

So it's kind of a situation where like even if I,

17:36

okay, so like I do all that work and I'm like, okay,

17:38

here's the number reality tells me is attainable right now.

17:43

Okay, so what can I do to affect that?

17:48

Right, first of all, like, can I throw more money at this,

17:51

more time at this, do we need to get in market?

17:53

Do we need to, whatever?

17:56

And like often there are things that can be done always.

18:00

And like, you know, but like to a point

18:04

and also like considering resources are extremely strapped.

18:09

And so it's, and then it's a little bit of a game of just

18:11

like, okay, what's the number that like I absolutely can't go,

18:15

like say we're gonna go below?

18:18

Like what's just like looks right and pretty?

18:21

'Cause I could never walk into the boardroom

18:24

and justify this number in a million years.

18:27

But like what also am I not gonna like put myself

18:30

in a tough spot by over promising?

18:33

So you know, it's a bit of a, again, an art form.

18:39

I will also say though, like again, I kind of laugh

18:43

and I love doing that work.

18:44

I think the waterfall, I think all that modeling

18:46

and all that data and those numbers are so fun.

18:49

I love that part of my job.

18:50

But at the end of the day, like our forecast

18:55

is our plan is our runway and is our forecasted NRR.

18:59

Like there's really not like just tell me

19:02

what number you need me to hit.

19:03

And then let me like let me,

19:06

doesn't look like cute when I'm asked what we're gonna hit

19:11

'cause I'm like, let's just save a little bit of time.

19:15

Just tell me what you need for me

19:17

and what we've committed to in our plan

19:18

and like let me find a way to get there

19:20

and that's when I'll model it and that's when I'll figure out

19:24

what I can do to make sure we get there.

19:27

And you know, sometimes we blow it out.

19:30

Like we've had like two of our best quarters in a row

19:35

and like that just keeps continuing to happen.

19:37

So like there, you know, it's not all,

19:38

it's not like a big negative party by any means,

19:42

but it's like a little bit of like a pool there

19:45

and to be like putting together my forecast.

19:48

It's like just maybe what you want.

19:50

We'll do my best.

19:51

- So I love that 'cause it's true.

19:54

Well, it's true.

19:54

And I think it's, I love when you say there's kind of

19:56

like the right answer and then there's reality

19:58

'cause I think, you know,

19:59

I think what it boards wanna hear is that we have

20:01

this really well-defined process

20:04

that where we can forecast with great certainty

20:07

what's gonna, we can make commits

20:09

of what's gonna close and all these things

20:11

that we can pull forward deals and I'm like,

20:13

okay, the reality is like best case,

20:16

best case is like all of this closes.

20:18

Worst case, none of it closes.

20:20

And the reality is somewhere in the middle

20:21

and we're still trying to figure it out.

20:23

And over time it gets better, right?

20:27

But I think because there's so much iteration

20:29

and ICP, the product, the pricing,

20:32

we can even talk about like market conditions

20:35

that have changed, that changed dramatically over time

20:39

that you can't force economy.

20:41

It's hard to kind of get into that predictability

20:44

that I think everyone wants startups to have

20:47

that I think fundamentally don't exist.

20:49

So I love what you think about,

20:51

tell me what the, tell me what's in the financial model.

20:53

What is like the bare minimum that we need

20:56

and from like a cash runway standpoint?

20:59

And I think that's important.

21:00

I also think it's really, really important

21:04

for sales leaders and marketing leaders and the CEO

21:09

at startups to work on that together.

21:11

I think oftentimes the financial plan

21:13

is kind of put together in this vacuum

21:16

and then like you're told, hi, your sales goal is this.

21:19

We need to three act, you know,

21:21

it's what triple, triple, double, double,

21:22

like we need to do this and that's great.

21:25

But then there's reality.

21:27

Reality is like here's what I think I could actually

21:30

reasonably deliver with the resources that we have,

21:33

the market that we have, what we've been able to prove.

21:35

I will strive to go above and beyond this.

21:37

But if you want to talk about like what should be

21:39

the bare minimum that you can feel confident

21:41

to build a model off of, here it is.

21:43

- Yeah, yeah.

21:44

I think more of that needs to happen.

21:46

'Cause I think that's where companies end up

21:48

putting unrealistic quotas on sales leaders and AEs.

21:52

And then marketing's, you know,

21:55

expected to help drive demand for an unrealistic quota

22:00

for sales and it just isn't successful.

22:02

And it's just, I think it really hurts culture

22:05

when you do it that way.

22:06

- It does hurt culture.

22:08

I also think like with risk and all those things are true.

22:11

I think with respect to a startup,

22:12

there is a degree of like, I don't know,

22:15

I don't think this has ever been harder than it is today.

22:18

And everybody's competing right now more than ever.

22:22

And for attention, if not, you know,

22:27

also the same buyer or the same budget or whatever.

22:32

With AI, it just, it just never been tougher.

22:37

And the reality is like, the runway is what it is.

22:41

And also, or like, you know,

22:44

if you're on attractive profitability

22:47

and don't wanna fundraise,

22:48

like those numbers just are what they are.

22:50

So I do think like part of the startup team mentality

22:55

means like you brace yourself and you do what you gotta do

22:59

to get there and you have to go the extra,

23:01

whether that's just like harder or smarter or whatever.

23:04

Like, you know, you've gotta have a good team

23:07

that can support being told what the number is

23:10

and finding a way to it.

23:11

Because I do think more often than not,

23:13

like in a perfect scenario,

23:14

there is alignment on what those numbers look like.

23:18

I think more often than not for a lot of teams today,

23:21

it's just like, this is what it is,

23:22

or we're not here anymore.

23:25

So it is, it's how to like handle,

23:30

handle that and not go into panic mode

23:32

and build your way to it.

23:33

- Well, and I think one of the things

23:36

that you just said around, like you're competing

23:38

for attention and for dollars in the past, you know,

23:42

a few years ago, it was you were competing for that

23:45

against competitors.

23:47

Now it's like you're competing against that,

23:49

at least if you're selling software,

23:50

against all other software that exists as well as--

23:53

- 100%.

23:54

- Even resources and it's really challenging.

23:59

And I don't know if everyone has caught up

24:03

to what that's like across any size of company,

24:06

let alone what it's like in a startup

24:08

when you don't have the brand recognition,

24:09

you don't have the resources to build or the time honestly

24:14

and runway to do that successfully.

24:19

- Yeah, although I think like it's so hard.

24:21

I think like sometimes we remind each other

24:24

that like, you know, there are a lot of bigger,

24:28

more well-known brands in the last couple of years

24:31

that don't exist anymore or have taken it on the nose

24:36

to merge or have been acquired on pennies on the dollar,

24:40

if that, you know, because of these huge fund raises

24:45

in these huge rentals in these huge teams

24:47

and all these things and it's impossible back out of that

24:52

once you're there.

24:53

So I think there is also like a bit of a,

24:55

we're like, as hard as this is, we consider ourselves lucky

25:00

as often as we can manage that, you know,

25:03

we like are doing this now today

25:06

and have the opportunity to do it the way that we are

25:08

instead of kind of being stuck.

25:10

Like I think some brands that came before us are right now.

25:14

- I think there's a lot of brands that are in that position

25:16

even right now, which is really hard.

25:19

So kind of tied to goals, I know you've, you know,

25:23

I've been in the situation, you've been in this situation.

25:26

What do you do when you have a board

25:29

that once you had a triple, triple, double, double

25:31

and grow, grow, grow and the reality is

25:35

you only have so much pipeline to work with.

25:39

When you pull things forward, that means now you have a gap

25:43

and like the next quarter, the next two quarters.

25:45

How do you try and have like those realistic sales target

25:49

and like quota conversations that, to help them understand

25:54

like it's not that you don't want to have to hit

25:57

these huge numbers, but the, you want to also set

25:59

like realistic expectations of what's going to happen.

26:02

- Yeah, I think this is where like data comes into play so well

26:07

and I think this is where lucky that like I have,

26:10

like I have the ability to manage, gather like own this part

26:15

of our business and A.E. of course, maybe isn't having

26:20

a board conversation anyway, but it's in a tougher position

26:22

to kind of justify that delta a little bit.

26:25

But I think like understanding what that delta looks like,

26:28

calling it out, like here's where we are today,

26:30

here's where we came up short, maybe in pipeline last quarter

26:33

and therefore that's what this quarter looks like realistically.

26:36

Here are, again, like our best sources for me.

26:41

Here's what closes when we got them on the line

26:43

and here are the following, here's like what,

26:45

here's how the numbers break down,

26:47

here's what we're going to need incrementally

26:48

in order to make it happen and quickly because of sale,

26:52

like so, you know, we've got this month

26:54

that it's extremely important to start this conversation.

26:56

So we've got time for the quarter

26:58

and like this is how we're doing that.

27:00

And so it being like just like extremely,

27:02

I think very proactive both with communication

27:06

and what we're doing about it.

27:10

I think the bigger problem is like the surprises.

27:15

So, you know, it's like, it's not a fun conversation

27:20

no matter what, but it's worse to over promise

27:23

and under deliver than just a like,

27:26

and duh, but like then to say like, hey,

27:28

here's like we've got, we've identified a gap.

27:31

Here's how we're working a result already today.

27:34

And here's how we're holding ourselves accountable to that.

27:37

And here's what we're going to adjust maybe as well

27:39

if like we're falling off track of that.

27:42

So, and then you got to do it.

27:45

But I think like the beginning of that

27:48

is like having good data that tells you those things.

27:51

So I'm a pretty, I'm a pretty big like stickler

27:55

with like Salesforce cleanliness as my team knows.

28:00

And, but it's for a reason and it's because then

28:04

it allows me to speak intelligently about my business

28:08

and be able to address those things and answer questions

28:12

and not like sound like an idiot

28:14

'cause I don't know the reality of what's going on

28:16

or can't identify those problems.

28:19

- Yeah.

28:19

So what metrics do you find are most essential then

28:22

for measuring like sales effectiveness at the stage?

28:25

- Yes.

28:28

- So I think ultimately G-R-R is actually like the biggest thing.

28:35

I think it's also the toughest,

28:43

like it's the toughest at a startup.

28:48

And that is like how much are you,

28:51

and you don't want to just be replacing churn with more deals.

28:55

Right?

28:56

Like that doesn't solve anything.

28:59

You want to be continuing to growing,

29:01

retaining the revenue that you have

29:03

and adding on top of that.

29:04

So like, but you know, talked about product market

29:09

fit earlier, that can be hard to do for the first couple

29:12

of years, potentially first year, first whatever it is

29:15

because you've not like quite figured out

29:16

the right way to do it yet.

29:19

That number identifies whether or not you're starting to,

29:23

I think first of all, like what's happening with renewals

29:27

is the signal for whether or not you're selling the right way.

29:33

So that's a big, a big, big thing.

29:37

And then I don't know, the other things are just like

29:41

some of the more basic, I think stuff,

29:46

they're still really finding makes sense and whatever,

29:48

but like a CV, how much are you selling for?

29:52

What's your win rate?

29:53

What percent of meetings booked if you're measuring that way?

29:57

Which is, I think the way it should be measured are

30:00

and in a close one and like knowing what's good

30:04

and what you're aiming for and knowing again,

30:08

and like as you get a little bit smarter

30:11

and a little bit more sophisticated,

30:13

what do you need in terms of pipeline?

30:16

What has been your like month over month

30:19

or quarter of quarter average in terms of meetings booked

30:22

and where have those meetings come from?

30:24

And what can you do to maybe automate some things

30:29

and channels a little bit better

30:30

so maybe you can focus on some other areas?

30:33

So just like following the journey of where the revenue

30:39

is coming from beginning to end is really important

30:43

and then again paying really close attention

30:47

to renewal cycles and who's happy and who's sticking with you.

30:52

- So when do you think about, you mentioned renewal cycles,

30:57

where do you think in a startup,

31:00

renewals should sit because oftentimes you have like

31:05

a sales team which is responsible for bringing new customers,

31:07

customer success is responsible for retaining and upselling,

31:11

but so much of what you're trying to figure out

31:14

is not just how to bring on new customers

31:16

but how to make sure you're bringing on

31:17

the right customers long term.

31:19

So yeah, and I know it's different for every organization

31:22

but how are you thinking about that today

31:24

and how would you suggest others think about it?

31:27

- Yeah, I mean, it's definitely,

31:29

we're lucky we've got like an all-star CS leader

31:33

shout out Clayton who is experienced

31:39

and owns the number ultimately.

31:42

We spend a lot of time one by one.

31:49

In fact, I have that meeting this afternoon.

31:51

Like going through customers one by one

31:54

and just talking about like where we are,

31:57

we've got a bit of a matrix we've been able to build

31:59

that takes into consideration like product utilization

32:03

and then just like the things you can't quantify

32:06

like how much do they like us?

32:08

Like, you know, there we have that helps us measure

32:12

like who is maybe at risk a little bit

32:16

'cause that can fall into a different,

32:18

a couple different buckets

32:19

and how you identify those individuals.

32:21

But it's, I mean, it sounds like so cliche

32:24

but it's such a team effort.

32:25

I would say probably like least of all mine,

32:28

although I'm bringing in the initial business,

32:31

I truly have to like kind of and I stay involved

32:35

and I'm in market a lot.

32:36

We do a lot of like customer dinners and visits

32:39

and all those things, but I largely have to focus

32:41

on top of funnel for us to continue to hit those goals

32:45

but our CEO is hugely involved in our customer meetings

32:50

and journeys and then also I didn't say

32:56

but our CS leaders also our product leader

32:58

which I think is also just extremely beneficial.

33:02

Would it be great if his workload didn't look like that

33:05

and that was two people's roles?

33:06

Yes, it would still be extremely important

33:08

that both of those roles are very, very much involved in

33:11

in the customer relationship

33:16

because of how much that affects signals ultimately.

33:18

- Well, I know you just mentioned how your CEO

33:24

and your CS leader and you are involved in customer knows

33:27

but how do you think about the roles that they can play

33:29

like in the initial sales process?

33:32

Like when do you think about bringing someone in?

33:35

- Yeah. - And does that always happen

33:38

or does it really depend on the situation?

33:40

- Definitely dependent on the situation.

33:43

Our sales cycle length is often fairly short.

33:52

It's not unheard of to have a turnaround to be within

33:57

a week or two by any means and we've even had like

34:02

significantly shorter than that at times

34:04

because if it's a good fit, it's a really good fit

34:06

and it like makes so much sense kind of thing.

34:08

So, and also I think just like in this world of

34:12

self service and information and like,

34:17

if I hear one more person tell me,

34:19

no one wants to talk to a sales person,

34:21

you know, like kind of process you have to be as easy

34:25

as possible to buy from.

34:29

And that means like, I tackle it all

34:33

in a first-meltz meeting.

34:34

Like you're gonna get pricing, you're gonna get a demo

34:36

and like thankfully our product,

34:38

we have a lot of enterprise customers.

34:40

So it's not that it's not an enterprise solution,

34:43

it's just like there's not like intense systems

34:48

and data and things that we're working with

34:51

that are scary which is what makes this possible

34:54

and makes it lucky for me,

34:56

which is 'cause it's a lot more fun for me personally

34:59

in this scenario, but like we move pretty fast.

35:02

So all that say like a lot of the time,

35:03

it's really just me that's doing it.

35:05

And then everybody comes in, you know,

35:08

when we do like a knowledge transfer,

35:10

everybody's involved in that conversation.

35:11

Our CEO, our product and sales leader

35:15

is involved in that conversation.

35:17

And then in probably about like,

35:21

I don't know 75% of the time,

35:22

we're all able to make the kickoff as well.

35:24

Like our CEO is involved in those calls too

35:28

as much as possible.

35:31

I will bring in the CEO though,

35:33

and this is a little bit of a startup thing too, I think.

35:35

Like, you know, sometimes I might not be the best person

35:39

to have the conversation though.

35:41

Like if I am talking to another CEO founder,

35:48

maybe Jonathan as the CEO founder should be having

35:55

the conversation and like I have to like let my go

35:57

of my pride and be fine with it,

35:59

which I'm over at this point.

36:01

Sometimes I'm like, I wish I owned this

36:03

'cause you're not like doing what I want you to do.

36:05

But he's pretty good about listening to me.

36:08

But so, you know, if anything,

36:10

it's usually like passing things off to him

36:13

or being like, I'm adding you to this meeting

36:15

and letting you take it.

36:16

And also just like for better or for worse,

36:19

sometimes there's like cues about like maybe the,

36:22

who the person is, you know, my founders and well,

36:28

not gonna like go on and on about, you know, that today.

36:33

But like sometimes he's the better person

36:36

to have the conversation,

36:37

depending on who the person is,

36:38

if it's the best interest in business.

36:40

So, and then also like just the typical maybe

36:44

if I've got like an entire leadership team,

36:46

just to balance things out,

36:48

balance things out, I'll have him join me.

36:50

Just so it's not just me maybe,

36:53

but I'd say like, you know, seven out of 10 times,

36:57

maybe even more than that, it's just me

36:59

and I'm not bringing anybody else in.

37:01

- So we've talked a little bit about some market conditions

37:06

and how they can impact sales.

37:08

How, and it's more crowded than ever right now.

37:13

What role do you think market conditions

37:16

just in general are playing right now

37:18

and how can you attempt to combat them

37:20

because they are so unpredictable?

37:24

- Yeah, that's such a tricky one because it's very real.

37:28

And you can ask anybody that is an enterprise staff,

37:33

same particular today, but a lot of other ecosystems as well.

37:38

Like it has a real impact, a real significant impact.

37:44

And I think everybody,

37:45

I mean, I think like for better for worse COVID helped

37:48

normalize that a little bit in that like,

37:52

are and not, you know,

37:54

there's a difference between the board understanding

37:56

that that's true and like giving you any room

38:01

to speak to that being true.

38:04

But I think at least like an outcome of the last few years

38:09

we've all been through has given the like kind of communal

38:13

understanding that like this shit's hard right now.

38:16

And it's hard for everybody right now.

38:19

But at the end of the day, it doesn't fucking matter.

38:21

Sorry, bye.

38:22

It doesn't matter.

38:26

So you can, 'cause it's like,

38:27

and I think it's ingrained in me too,

38:29

just from like time and doing this like,

38:33

you have to take ownership for what has gone wrong.

38:37

And like as much as the market is the elephant in the room

38:41

and there's always gonna be some mention of like that.

38:44

And I think it comes out by way of like,

38:45

here's the customers we've lost

38:47

'cause they've merged with each other.

38:49

Or like, here's the customers we've lost

38:52

'cause they went out of business.

38:53

So like, I can't affect that at all.

38:58

I wish I could have kept an emphasis.

39:00

I'm super busy over here.

39:02

So like, you know, I think like the,

39:05

it comes out in a variety of ways.

39:07

But again, at the end of the day, it doesn't matter.

39:10

Everybody's in the same boat.

39:12

I think there's like pros and cons to the stage of business

39:14

that people are in today and whether or not

39:16

that makes this easier or harder to get through.

39:18

And I think you could argue both sides of that

39:21

for everybody right now.

39:23

But it is just like a lesson in like,

39:28

put your head down,

39:30

maybe get off LinkedIn for a minute

39:34

and just like, keep going.

39:38

And think about how to break through the noise.

39:42

And then just like think about, you know,

39:44

if you're lucky enough to sell a solution

39:45

that is a difference maker from a business perspective,

39:49

which hopefully, you know, we all are,

39:53

we all know that's not true

39:54

or else there's a lot of competition for similar things.

39:57

But like, if you focus on like what people are,

40:01

what the pains are that can help people solve

40:04

the issue that they have that's like impactful

40:08

to their bottom line.

40:10

And you have relentless focus on that

40:12

and relentless focus on your ICT.

40:16

You gotta do what you gotta do.

40:18

- Well, and I think your perspective that,

40:23

you know, your example of there's companies

40:25

that are getting acquired merging together,

40:28

there are companies going out of business,

40:30

there are things happening, you know,

40:33

politically, economically, that are drastically

40:35

changing the landscape that we as software leaders

40:39

can do absolutely nothing about.

40:41

- Right. - With that, with that said,

40:43

I think, you know, there's the recognition of,

40:47

hey, these are market conditions impacting our business.

40:49

Here is what I'm going to do as a result,

40:52

not to fix those problems 'cause I can't,

40:55

but because like, hey, if we're getting a single lot

40:57

of customers go out of business,

40:59

I, you know, obviously our insurance going up,

41:02

we're gonna need to bring in more sales

41:04

to kind of compensate that from a revenue perspective.

41:06

Here's my plan to try and tackle that problem.

41:08

And I think that it's just an interesting flip

41:11

on this situation 'cause I think sometimes people want to say,

41:14

well, you know, use market conditions,

41:17

we can't do anything and unless you sell

41:20

into like one specific industry or buyer

41:23

that has been like a decimated,

41:25

chances are you can do something,

41:27

it's just not fixing that problem,

41:29

it's looking for a completely different solution

41:31

to address what the problem caused for business.

41:34

- Yeah, 100%, 100%.

41:36

Yep.

41:37

And there are those industries that have been decimated.

41:41

Like that exists too,

41:42

where like there are some that just like, hey,

41:45

but I think like taking the ownership

41:48

of controlling what you can add is all you can do.

41:53

And I think like emotionally and then also like,

41:56

quantifiably like that is the only way to get through it also.

42:01

- 'Cause it is a roll-up of Sir,

42:04

being an early stage company.

42:06

There are days, I know you and I've talked about this before

42:09

where you are like so excited,

42:13

you're gonna like eventually get acquired

42:16

for like billions of dollars and change the world.

42:19

And then there are days where it's like,

42:21

something happens like in the market

42:23

that you have nothing to do and you're like,

42:24

you didn't see it coming and it's like being punched

42:26

in the face.

42:27

And then 10 minutes later, you have a great sales call.

42:30

It's just constant up and downs.

42:32

And I think having like a positive like optimistic perspective

42:37

is important with also like a sense of realism.

42:41

So that balance I think is really critical

42:45

with every minute going on in the world today.

42:47

- That's 100% sense of realism,

42:49

like maybe sets a few more.

42:51

- Yes. - A little bit too.

42:52

- Oh shit.

42:53

- It does.

42:55

- There's only so much you can do.

42:57

- There is.

42:58

So last question for you,

43:00

what is your biggest go-to-market confession?

43:02

, okay.

43:12

I was thinking about this this morning

43:15

from a LinkedIn post speaking of LinkedIn that I saw.

43:18

I, and I don't know if like maybe this is like

43:21

a little bit more on the personal side.

43:23

I refuse to believe and I refuse to quote anyone,

43:28

anymore ever again.

43:31

Well, I have a team member at some point

43:35

who's tasked with doing that.

43:36

I don't know, never say never,

43:38

but like I have not made one cold call

43:43

at the Juice or Audience Plus.

43:46

I will not be doing it.

43:48

Maybe I've done so many that I can't anymore.

43:53

I've reached my limit.

43:54

Maybe I get so many that I refuse to believe.

43:57

And like I know people do it really well.

43:59

Maybe I just suck at it to you at this point.

44:01

I guess just not having done it in a long time.

44:03

And I don't, you know, but like I'm not going to.

44:07

- I'm not doing it.

44:09

- I applaud you for that.

44:11

Because I think it goes back to like the market.

44:13

Like I think things have changed.

44:15

That worked really well, but now it's,

44:19

and I think part of it's like software that has caused it.

44:22

This is why I feel like sales and marketing tech

44:26

gets regulated by the government so often

44:28

is because like we get new software

44:30

and then we make like poor choices.

44:32

- Yeah.

44:33

- And they have to do something about the poor choices

44:36

that we've made.

44:36

But right now it's just like there's so many people,

44:39

you know, that are constantly calling

44:42

with like parallel dialers and automated email sequences.

44:45

And it's, I don't know who you are.

44:48

I don't know where you got my information.

44:50

I am not interested.

44:51

Please stop calling me.

44:53

- Yeah, I know that there's a way to do it well.

44:57

- I do and I have done it for the record.

44:59

Like, you know, 15 years ago or whatever.

45:03

Well.

45:06

- So it was a different world.

45:06

- But it was a different world.

45:07

And also, but also like, I don't know.

45:10

If your first like opportunity

45:13

for an impression with someone is that you're annoying.

45:17

That's just not like there are better ways today

45:20

and smarter ways to like identify where to spend your time.

45:23

That's not.

45:25

I'm not trying, like, I'm not gonna bug people.

45:28

It's annoying.

45:29

Like there's no way around it.

45:31

- Yes.

45:32

- That's not how I want to start a relationship with somebody.

45:35

So I just, I won't do it.

45:37

I do, I will say though, like I really respect people

45:42

that do it all day because I have done it

45:44

and it's the worst and it's extremely hard work.

45:48

But it's not happening.

45:49

- You've been listening to G-Tame Conpassions.

45:53

If you love what you've heard,

45:55

make sure to subscribe, rate and review our podcast.

45:57

And don't forget to tell a friend.

45:59

(upbeat music)

46:01

(upbeat music)