The Transaction

By the way, did you guys, someone was telling me about this.

I was in Chicago, Maria was telling me this story about the woman who got a dinosaur tattoo and shared it on Facebook or Instagram and said, you know, I just got this tattoo, like what dinosaur is this?

And it was essentially the Arc'teryx logo, and she didn't know.

And Arc'teryx found out about it and sent her all of this free stuff.

It is an amazing story.

That's awesome.

I was afraid you were going to say and it threw a cease and desist and you got to cover it up and you got to do something else, but I love that they did that.

They're like, sweet, thanks for advertising us.

So yeah, it's like Disney.

Remember when they were like dropping lawsuits on every piece of graffiti in the globally, if you weren't allowed to use the logo.

Anyway, all right, so.

From ABM to PLG, from medic to med pic, the world of business is constantly evolving.

We'll cover the who, what, where, when, why, and most importantly, how you get the transaction.

I'm Matt Amundson and he's Craig Rosenberg.

Let's get started.

I cannot wait for today's episode.

And Matt, you as well, was that an agreement shrug?

That was an agreement shrug.

We've been talking about this for three weeks.

I know, dang it, but look, I have listened to Doug, hung out with Doug, just taking it all in for, I don't know how long.

He's just one of those friends where you can't wait to talk to him, but also you learn a ton.

And that's like the perfect podcast.

And so, I think I started to really dig in with you when you were at Box doing the sales productivity there.

You spoke at our summits.

I tried to leverage them as much as I could.

And then, seven years like me in the venture business advising, go to market for portfolio companies, Salesforce before that, but really a thought leader.

And I hate to use that term because I feel like 90% have no new thoughts.

Doug always does.

Here's the thing that I've always loved is when you talk to Doug and it's been like a period of time, he'll just be like, you're sort of talking about his old methodology of book.

He's like, oh no, here's what I'm thinking about now.

And then he just amazes you for like an hour on his new methodology at the table.

So it's with great pleasure that the transaction is so, we're so honored to have Doug Landis on the pod today.

So thanks for coming, buddy.

It's, you know what?

Here's the thing, like Craig, Matt, the feeling is mutual, my friend.

It is, I think we, I just feel like there's, you get to, like if you go to school, you go to a company, you go to a party, you just, you try and find your people, right?

And those are your people that you can have really interesting conversations with and there's no judgment and there's a free flowing form of ideas and there's no element of like having to be right or wrong or whatever.

It's just like, you're just, you're just kind of like learning, exploring and sharing and having fun doing it.

And the reality is you two are two of those people.

So like, I'm always happy to jam with either one of you.

And I think, you know, I think, I think for me, it's like, I've got this like just insatiable thirst and quest for learning and curiosity.

And so, you know, Craig to your comment about like coming up with something new, it kind of comes out of left field, to be honest.

It's like, ah, I've been hearing this or I've been experiencing this like, holy cow.

What do you think about it?

What are you seeing?

Yeah, I love that about Doug.

I mean, for about, I love that about you, Doug.

The fact of the matter is, is like, you have every reason to be kind of, hey, I did it.

I did it.

And this is the way I did it.

And there's no reason to change because this, you know, I sort of built a blueprint for this and people can follow in my footsteps, but the constant evolution, the constant curiosity, that I think that's one of the things that I admire so much about you.

And I recall the very first time I met you, I was on stage and you were sitting front row, sitting next to John Barrows at the sales conference.

And like, I made a comment about you because you were right there and I was just like so blown away.

I'm supposed to be up on the stage, like in the limelight and I'm like, there's Doug Landis, holy shit.

And you know, it's very few, there've been very few like sales leaders who are truly been inspirational for me and you're one of those people.

But enough about you, let's dive in.

Craig, hit us with the first question because that's where we'd like to get started.

Did we lose you, Craig?

Hey, quick producer note, because Craig decided to record this on an internet connection that is essentially a wire between two tin cans, he had some issues towards the beginning of the recording.

Thankfully, we were able to figure them out and I made sure to save all of the most embarrassing and hilarious clips for an eventual blooper reel.

And now, we return to your feature presentation.

So anyway, look, what we try...

Well, first, let me ask you this before I ask you the main question.

Yeah.

Do you believe that today's go-to-market playbook is different than four years ago?

And then I'll ask you the big question.

100%, has to be, no question, no question.

Is it different than a year ago?

Different than a year ago?

Closer to a year ago than four years ago, but it's definitely evolved.

From four years ago to today, it is dramatically different.

The challenge is I think everybody is still right now trying to operate and leverage the same kind of activities and the same motion and the same messaging and the same...

It's kind of the same of everything that they were doing back when it was frothy or even just four years ago when things felt like they were picking up again.

I think that is a real...

It's causing a lot of consternation for buyers.

I think the biggest thing, two biggest things that have really changed fundamentally is buyers, their bullshit meter is off the charts.

One, because they're trying to filter out whether this was like, was this written by AI or human?

And number two, mostly humans that I talked to are adding such little value in the conversation.

So I'm just gonna go find my cohort of peers and talk to those folks and then boom, I'm gonna make a decision.

And I don't wanna rely on salespeople at all, period.

Yeah.

Okay, by the way, Matt, what did you think about that setup for the big question?

That wasn't bad.

That was great.

That was great.

You're improving.

I mean, you can give me a little positive feedback.

I have to grovel for it.

So here's the big question we like to start with.

What is something that the market thinks they're doing right?

Okay, what is the best practice or as a way of operating?

We're actually, you know what?

You're wrong.

And here's how you should be thinking about it.

So what is it and what should they be doing?

And then how do they go do it?

So let's start with that big one.

I mean, that was like a four part question, which I would argue to everybody listening to this, is the worst way to ever ask a question, whether it's to a buyer or a podcast guest, is like hammer it, hit them with four questions.

Be like, okay, where do I start?

Imagine I'm a buyer and you just did ask me this exact question like, tomatoes.

Doug, you get a producer credit.

Well, here's the thing, there's an easy target to answer this big question is like, what are we still doing that we shouldn't be doing?

Because it's pretty evident that it's not working, but we're still doing it, it's outbound.

I mean, it's just, it's still a thing.

And it clearly isn't really working the way in which it used to be working when we had people actually pounding their phones because everyone's now switched to email or other technology, whether it's LinkedIn or text or whatever it may be.

I feel like the reachability of people is also a really big part of that, right?

People are less reachable, right?

Part of this happened when people moved to their homes and they were working in other homes and they were in this like remote environment.

So like, you know, I was routing my work phone to my home phone.

It's like now, now it's even harder to find me.

But the old school tactics, you know, I'm working with a handful of companies right now and they're like, they're sending me their cadences and I'm reading them.

I'm like, what is this?

In every single cadence, every cadence I read, there's a pitch about the company.

Yeah.

Every cadence, every email.

I'm like, what are you doing?

Your job is to nurture a relationship here.

It's not to pitch.

I know who you are because I can look at your email and I can look at your signature.

I can click and go like, what's this company all about?

So quit pitching that you've helped do this to 18 other companies and just start sharing.

Help me think through this process.

Help me think through how I'm gonna get everybody on board that this is a problem that we actually want to solve.

And this is all kind of connected to outbound, right?

So one, the way in which we're like, what we're saying, what we're doing.

Two, I'd still say the vehicles, like the reliance on quantity over quality still, because, and Matt, I'm really curious your thoughts on this, but I feel like there's still this innate pressure from marketing, like we got to generate more leads.

We got to generate more pipeline.

And so we need to generate more activity.

And then the third thing is I just think that fundamentally the way in which we're approaching conversations with people, it has to change.

And look, technology should make this a lot easier and a lot better.

My expectations for somebody that's doing outbound to me are so high now, and maybe it's just me, maybe I'm just jaded, but it's like if anything doesn't meet this bar, it's just, I have no patience for it whatsoever.

Yeah, yeah, I mean, number one, I agree with what you're saying.

I think what's interesting is people will tell me all the time that their outbound isn't working, and I'll take a look at what's in their messaging, and it's so bad.

And so there's like the intersection that I'm sitting at with outbound is like, have we truly lost our way in terms of like the art of good outbound, and that's why it's not working, or is it not working because people are jaded and they're just like, people won't even get mad at an outbound message anymore.

They'll just hit spam, right?

So-

Totally, and now you're blocked, and now you can't reach back out.

Yeah, yeah, totally.

Yeah, yeah, and you're incinerating your sender scores.

The thing that I struggle with is like, I just haven't seen a good outbound message in a long time.

I just have, right?

Like it's a sea of sameness, and I think that's a thing that's hurting people.

You know, I've postulated for years that if a company had the budget and the guts to put out an all video nurture, that would be an absolute sensation.

And you're just like, hey, there's no written words here.

Like just every single thing we're gonna send you is a video.

Is it good, bad and different?

It's like copy, marketing copy.

But here's the thing though, Matt, it goes back to what is exactly you're trying to say.

And I think that's fundamentally where companies get this wrong.

Because I think fundamentally from an outbound perspective that even whether it's an AE or a BDR or a marketing leader, everybody still feels like the need to position their company.

Right?

And I think that's the fundamental flaw, which is like quit positioning your company because you haven't fucking earned it yet.

You haven't earned the right.

You just assume you have the right to actually make this statement about who you are when I don't really care yet because you haven't proven that you understand me, that you understand my world, that you understand my competitors, that you understand what I'm trying to accomplish or some of the problems I might have.

Until you can prove that you get me, I don't care who you are.

I completely agree with you.

I'm gonna ask you a tricky question here, which is what is the right way to do it?

And have you seen companies do it well?

Well, so I have some companies that are testing this out because I'm testing it out.

Yeah.

Because this is what I do.

Yeah.

So I'm like, all right, well, if I've been a buyer before, what would I respond to?

Mm-hmm.

Right?

And so look, there's the typical frameworks that you wanna make sure you follow, whether it's like, show me you know me, or why you now, or whatever.

Lavender's kinda coming out on the daily.

And I think following the framework makes a ton of sense, right?

Have the right subject line, right?

Have some sort of hook.

Like, what the hell am I reaching out to you, Matt, right now?

Like, why does this make sense?

And so yeah, we have to be paying attention to signals and what's going on, so that there's a compelling reason for me to want to engage with you.

But I think beyond that, the problem is, is most people take that compelling reason, and they take that hook, and then they go right into, well, we have done this, right?

And it's like, no, no, no, I don't want that piece.

The hook is interesting because it's like, oh, great, you're paying attention to me.

Kind of, it feels a little manipulative, so I'm just gonna be leery of that.

The next thing I wanna know is like, give me a hunch, a hypothesis.

I swear I'm gonna write a book called Hypothesis Selling because I talk about this all the time, but give me a hunch or a hypothesis of what you think my world might be like.

Yes.

And here's why, because again, it's about, if you're gonna earn the right to have a conversation with me, if you're gonna earn the right to actually share more about who you are and what you do, then you gotta build that.

You gotta earn that right, right?

So how do you do that?

You share a hunch or a hypothesis with me because you talk to people like me all the time.

And say, you know what, if I was reaching out to Sam, you're like, hey, Sam, my hunch is that you might be in a similar position that my friend Matt here was in, and this is what he shared with me.

Yeah.

If you wanna have a conversation about what else, how Matt resolved this, are you open to a 15-minute conversation?

Yeah, I love that.

Do you know what I didn't do?

Do you know what I did not do?

I didn't pitch my company at all, whoever I'm with.

Because here's the thing, and I'm constantly going to be sharing hunches and hypotheses based on what I'm learning and I'm seeing and I'm hearing about what I would consider your peers.

Yeah, yeah.

Right?

I love that.

And for you, you're gonna be like, oh, that's interesting.

I mean, it's similar to the idea of like, if you're doing a cadence, what, you should only have an ask and maybe like 20% of your outreach, right?

Because half the time you want to be nurturing this relationship, well, what does that look like?

It's like sharing things like, hey, you know, hey, Matt, I just, in fact, I just read this report from Norwest Ventures.

I literally just posted it like an hour ago on LinkedIn.

Like you know, that I think marketing expects are gonna generate 50% of the pipeline where sales leaders expect they're only gonna generate or their expectation for marketing is 40% of the pipeline.

What I've heard from other marketing leaders like, you know, Sam, it's more along the lines right now about 20, 30%.

My hunch is you kind of have a perspective on this.

Are you open to having a conversation about it?

I love that.

The reason why I love that so much, it's the absolute antithesis to the stuff that I heard for the last decade as a marketer, which is, hey, what's keeping you up at night, right?

Like, I don't want to answer that question.

I don't want to answer that question, but I will 100% have a 15, 30 hour long conversation with somebody who's saying, hey, Matt, I've been talking to a lot of your peers and this has been what's keeping them up at night.

I'm guessing based upon what I've seen about your organization or your business that you might be experiencing the same thing.

And I just want to talk to you about how they're solving that problem.

Yep, and by the way, now you're the messenger of what they said, not what you think or believe.

It's what they said.

I'm just all I'm doing is sharing, right?

Yes.

And here's the thing, Matt, you as a buyer, you want to learn from your peers.

And if I can be the vehicle to help you learn from your peers, then guess what?

I earn so much credibility.

I earn the right to now say like, hey, can I share with you?

And even over time, some of the options, by the way, I'm not going to talk about my company, but some of the options that these other leaders were considering as they were thinking about trying to solve the problem.

Because that's what you're going through.

You're like, well, I'm not quite there yet ready to make a decision.

So why the hell don't I talk to you?

I'm still in this process of like, well, is this a priority?

Can I get internal support for it?

Can I get everybody on the same page?

If I do get everybody on the same page, what are our options that we might have in order to actually try and tackle this thing?

Let alone, you know, and by the way, there's a whole slew of options.

And as we all know, the biggest one is like, well, do nothing because I can't get everybody on board.

So like, let's address that.

You know, like if you're in market and you're like, hey, you know, did you know what I've seen?

And did you know like more than 60% of the time, you're going to end up sticking with what you're currently doing?

Yeah.

My hunch is you're probably in that, but you're at that point right now where you're like, you're not sure which way it's going to go.

The reason why I love this pitch so much is it is a mirror reflection of the way people are consuming information as individuals.

They're taking part in communities.

You know, they're with Sam in Pavilion or they're in a myriad of Slack communities and they're trying to learn from their peers how they're solving problems.

And so if you're, Craig always makes fun of me for saying this phrase, but if your approach vector is similar to the one that they would use in order to solve their problem, I think you get a nice in there and you break down that wall of here comes somebody who's trying to sell me something versus here's somebody who's showing up with an idea.

Yeah, yeah.

And that's why I say it's a hypothesis, right?

You're coming up with a hypothesis, a point of view, a perspective.

And you know, look, I see a bunch of people talking about this because look at the end of the day, if there's not enough of a compelling reason for you to want to actually change what you're currently doing, then you're not gonna change.

And therefore you're not gonna take the risk of building the momentum inside your organization to get other people on board.

Because the amount of times that I brought something-

By the way, I did pick up the approach vector.

Yeah.

Welcome back to the party, old man.

Hey, by the way, I want to say I-

No.

Nope, can't say it, Craig, because you just died again.

I can't even do this.

I'm enjoying this, but I will say I'm enjoying the conversation you guys are having.

Well, yeah, because it's freaking Doug.

Given our earlier conversation before we started recording, this what Craig is experiencing right now with his technology is one of the most, I mean, I feel like this belongs in a Sinead O'Connor song.

Like, isn't it ironic?

Or I don't know who sings that song, but like-

Alana's song.

Isn't it ironic?

We're talking about age and technology and how we have to help our parents now do all this.

And like, Craig with his Elton John suite of glasses, you know, can't seem to sort out his own internet.

It's just the best.

Oh man, and the kids aren't even home on Fortnite.

I don't know what's gonna happen then.

Anyway-

Oh yeah, you're toast.

You're toast.

Anyway, keep going, Matt.

I've enjoyed this thoroughly.

I just wanted to literally got my internet going just so I can compliment you on including approach vector in the pod.

Go.

Oh, well thank you.

Thank you.

As much as that approach vector to me feels so it's tap dancing on the line of buzzword bingo, but I kind of appreciate it.

Yeah.

I kind of appreciate it.

So when you think about the most successful sales organizations out right now, what is the one thing that they are really getting right?

Are they thinking about this kind of hypothesis selling motion or are they powered by a company that has a great message right now?

Do they do discovery really well?

Yeah, go ahead.

You know what they're getting right?

They've got a badass product that everybody needs.

That's what they're getting right.

I mean, look at the end of the day right now, product wins, the best product wins.

And if you look at what like Kyle Coleman's doing on LinkedIn right now, is he's trying to showcase every day how badass copy.ai is, right?

And he is like, he's just showcasing like, here's a problem, here's a way to think about it.

Here's a problem, here's a way to think about it.

And he starts to think, and I've been talking to him behind the scenes, he's like, oh, I might want to use this.

I'm like, what can it do?

Because like, if I just see it's like, this is a writer, an AI writer platform, kind of like writer.ai, he's like, no, no, it's so much more.

And then he sends me some links.

I'm like, ooh, that's kind of cool.

So first and foremost, to be honest, it's the product.

The product that wins because at the end of the day, we could have a great conversation.

You could come in with a hypothesis and it's be an amazing sales experience.

But once I actually get in the product, if it doesn't really do what I need it to do, plus, you know, times a hundred, you know, it doesn't matter.

Like it just doesn't matter.

Like, cause we're at the age in the day right now where like I can only deeply invest in something that is an absolute must have.

If it's not, if it's a nice to have, might be a little side project.

I might test out, but you're not going to get a whole lot of, you know, money or revenue out of me.

But it's like, if you've got to, if you've got a killer product then, then you're, you're way ahead of the game.

Yeah.

Yeah.

That seems to be very true.

The transaction is presented by Ringmaster, the go-to branded podcast team.

You know, when Craig and I were thinking of starting this podcast, we had all the ideas in the world, but you know, all the ideas in the world won't get you a great podcast.

That's where Ringmaster comes in.

They handle the creative, book guests and do all the production for the podcast so we can focus on what we do best, talk to one another and our amazing guests.

To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com today.

What would you say to maybe a company that's competing in a space where they have a slightly inferior product?

Woof.

Good luck.

I mean, it's true.

Like, come on, Craig, we're in the world of venture.

Like, you know, companies right now that can't figure out how are they gonna go continue to grow and scale beyond 20, 30%.

We're gonna have a hard time raising their next round of funding.

And if you can't raise your next round of funding, then like, where are you going?

Are you gonna sell?

Are you gonna merge?

What else are you gonna do?

So look, if you're an inferior product, you're a hyper competitive space, and there's just a lot of parity in terms of products out there, that could be a good thing because look, at least there's a market, right?

So it kind of goes back to first product, and then second, is there an actual market?

Because I think what's happened in this environment is we've seen a lot of markets just kind of disappear.

Right?

And markets shift.

And so it's like, the first thing is, do you have a killer product?

Product second, do you actually have a market that is, there's market pull?

We call this market pull, right?

That we're looking for is like, are people actually pulling?

Now, regardless of who's out there, it's just these two things have to exist in order for us to then start to think about how do we compete?

So if those two things exist and then there's our company and like five others that are all pretty similar, maybe there's a couple that are more advanced and got better technology, then it's up to how we go execute.

Then it becomes an execution game.

Right?

And so to me, if I'm CEO, if I'm a go-to-market leader, I wanna be really honest about, okay, how badass is our product?

What's it missing?

How much of the market demand is there?

And if there's not enough, then I gotta go find where there are pockets of demand.

Yeah.

Right?

And then the third thing is, like if I'm gonna go out there, let's say we've found some demand, now it's about execution.

Now I'm gonna go, how are we executing?

Yeah.

What are we doing?

What are we saying?

How are we positioning ourselves?

And this is something I think four years ago, we kind of gave it more runway, right?

Whether it was a campaign, whether it was some messaging, whether it was some cadences, we gave it more time to kind of like, I don't know, kind of show itself as to whether or not it's working.

I think the window for our testing is shrunk by a factor of 10.

Like you got a week to go test it out, right?

And then we got to determine whether or not this is working.

I think the other thing that's also really true right now is, and I've been saying this for a decade, but people are starting to now pay attention.

It's like, hey, if you just want to know if this is going to work, go talk to your customers.

Just go ask them, just go ask them.

Like, come on, it's not rocket science.

Be like, hey, this or this, what do you think?

When you see this, what does it say to you?

Yeah, by the way, how's my AOL working now?

Yeah, you're rocking.

Okay, I have two reactions, by the way, to your question.

I want to get Doug's feedback.

So, and I think you said it, I'm just going to say it in my way and you'll go, yeah, that's what I just said, but that's fine.

Is when you, it's not, you know, so there's inferior product and then there's just runaway.

Cause like, there's other thing is like, where you know you have better technology, but you're getting your butt kicked.

You know, but these folks take off.

The key is, I'm just going to make this word up so you guys can wordsmith it, but honest, truthful, ideal customer profile.

You have got to find, I'll give you the perfect, the example I love is Infor.

You know, that's a huge company that competes with SAP and Oracle and the ERP.

And years ago, those guys said, we're selling to five verticals and that's it, and do not run with any of them.

And I love that.

And yeah, I once asked Chris Ball, I was like, who are the best enterprise sales teams?

He goes on like, he's an SAP man, they're just great.

He's like, then you know, Oracle.

He's like, but then I'll give you the surprise, Infor.

Those guys can sell the crap out of a product and facing two gnarly competitors.

And part of that is ideal customer, they focused and they built around areas where they're, at the time there was weakness on the part of the incumbents.

Now they're in there fighting, but they've built themselves a rep.

So look, the key is survival right now.

And so like, where's your wedge?

Because even someone who's growing fast has a blind spot.

And so that's one, that's really important because I think our first instinct is to take on the beast.

And why?

Why?

No reason.

Like, yeah, let's look at the data.

Yeah.

And let's, like you said, I think pockets of demand, I think you used, Doug.

That's what we're looking for.

And then let's define it and let's build the company around it.

Yeah, totally.

And you'll get through it.

You can re-expand.

Yeah, go ahead.

By the way, Craig, what you're talking about is verticalization, which is fundamentally right now when things get difficult is the best approach to take.

It's like, own a vertical.

I mean, look at Viva.

Like Viva is the ultimate example of that, right?

Peter Gassner was at Salesforce.

He's like, hey, this Salesforce platform kind of sucks working for Life Sciences and Pharmacales.

And so he went after this tiny little market of 400,000 pharmaceutical sales reps and built a $30, $50 billion software company out of it because he was hyper focused and they did what's called layering the cake.

So once you own a vertical, you can start adding more capabilities, more products, buying companies and increasing your wallet size in that organization until it works.

Yeah, I mean, look, vertical is a beautiful one because you can live and breathe and understand how people live.

Yes.

Just segment decisions can be really good, especially early on.

You know, I just worked with a company, they finally gave up the mid-market, which they should have a long time ago because they were getting their butt, they weren't good there.

There was a brand more they were losing down there and they were actually, believe this or not, because most of our companies want to move to the enterprise, they had a beachhead in the enterprise that was strong and they spent all of their energy trying to win the mid.

Trying to go down market?

Why?

What's the point?

Yeah, stop.

And so, and then there's, you know, there's technographic use case, you know, gravitational pull where it's like, have you identified that use case that is in the market and happens over there?

There's different, you have to do that.

The second thing, though, is when you make those decisions, what you said, you gotta talk to customers all the time.

And customers broadly defined as customers, potential prospects, partners.

You just, yeah, it sounds crazy.

Everyone laughs at me and I'm just like, you guys, there's nothing to laugh about.

It's the easiest piece of advice that I give all the time.

And they're like, oh, that's a good idea.

But you know what, hold on, Craig, I have a question for you.

I want to challenge you, actually both of you on this.

I think when I say this to people like, oh yeah, that's a really good idea.

Why haven't I thought about it?

And then when you unpack it, you realize, well, they don't know how to go talk to their customers.

They don't know what to ask.

They don't know how to ask for that conversation.

If you're the CEO, pick up the phone and call any customer you're like, hey, listen, I just want to get some feedback.

But if you're a marketing leader, if you're a sales leader, you're an FDR leader, and you're trying to figure out what's working, what's not working, how do you actually have that conversation?

So how do you, what do you coach your companies, your teams on when it comes to having that customer conversation?

Because I think that's one of the challenges.

We say go do it, no, okay, what does great look like?

What am I supposed to say?

What's off the, what should I not talk about?

Yeah, and by the way, I would, to your point too, like if you go to a customer, actually, unless they're really pissed off, asking them you'd like to get feedback on the product, you won't get the meetings, all the meetings you want because they may not want to talk to you unless someone's just absolutely pissed, then they would do it.

So what you're saying is when they're in good shape and they're humming, they're like wait, I don't have time for this.

A lot of times, yes, a lot of times, yes.

Yeah, I mean, and I mean, look, those folks are like moving fast and they're ignoring these things.

I mean, so like, I think it depends on the scenario, but like, I do have one where, frankly, we needed the CEO and everyone else to go talk to everyone.

And what we did was we said, well, look, let's back up and like, why do we exist and what's our mission?

And can we go talk about that?

And it's worked really well.

So instead of going and going, hey, I just want to see, or like lost deals was the big one.

I just was like, go talk to them, find out what happened.

They're like, well, they're not calling me back.

Well, yeah, if you say, I want to find out why we lost, I'm not going to, I mean, like, they're moving on.

So then what do you say?

What's your hook?

What's your, when you reach out, what are you saying?

Yeah, they wrote and said, look, like, I hope things are going well.

Like we, this is the data.

It's the same, it's actually been, worked really well to do the same as what you said, hypothesis selling outreach, where they took their mission and said, look, here's three things we've heard from the market.

And we believe that this is happening.

On half of them, we did that.

The other half, we just did, here's what we're seeing on the market.

I'm an exec here at Dot to Dot.

I'd just love to talk to you about what you're seeing and what we're seeing and trade some notes.

And believe it or not, that worked amazing.

And we 50-50.

We also, through our hypothesis, our actual, like what we believe is happening, included some content with that and said, we'd love to talk about that.

They both worked well.

You know, roughly the same numbers.

So what we did was, in that case, I understood it, like it was hard, right?

Because we couldn't just talk to customers.

We had to talk to more than that.

And so that was the approach.

And then when we asked the CSMs for help, we armed them with something like, look, we want to have this conversation about some new things happening today.

I've sort of taken that approach, like that, we have something that's of value to you, and I'm an executive, and let's go have that conversation.

Well, it goes back to that, we want to share some things that we're seeing and hearing, and we'd love to get your thoughts on it, because you're in the middle of it.

And this is, and by the way, who doesn't want to, especially as an executive, who doesn't want to hear from someone who's out there in the market and hearing things from our competitors or about the market that like, they're being idiot.

In fact, that's their job.

That's their job is to pay attention to what's going on in the market.

So it's kind of like, if you speak, again, it's putting yourself in their shoes and speak their language.

I think it's, you'll get, you're apt to get a response.

Because again, it's by the way, it's also an outbound prospecting activity.

It's just done at a very different level, you know?

The other thing though, that's really important to that is, this thing, they all go full circle is that the thought leadership-ization of your executive team, you want to...

You have your new phrases, man.

The words that you're coming up with.

I'm just, I'm getting the stuff up as I go.

But, you know, if you want your executives to be able to pick up the phone and call someone, they have to already know that you know something they don't know.

Yeah.

Yeah, totally.

And that's part of this process here.

And that includes your customers, everyone.

Like, because the minute we turn them into customers, it feels like we just start going product.

And that's fine because they're using it.

But we're still building against, you know, creating, you know, people are so important right now to the brand and the message.

And, you know, you create your mission and your view of the world, and then you have to get out there and talk about it.

And not, you know, if they see that you're talking about things they don't know, and it's not talking about your product, because that's, I've seen now, everyone's jumping into LinkedIn.

It's like CEO person, please.

Like, if it's just announcements about your features, you're not gonna get, be able to pick up the phone and call the CTO of Goldman Sachs.

But if you go and tell them that you, you've seen the future of the modern infrastructure in FinServe enterprise, then, and you give them the tidbits, then you have yourself the ability to go in there and do that.

Those things, those things build on each other.

Yeah.

So Craig, I'm hearing two things that absolutely resonate with me clearly as the former chief storyteller, but like one, it's like build up your storytelling muscles.

Yes.

Because at the end of the day, like having your own why as a company, why do you exist, what's your purpose?

Why do your people work there?

Why are you unique and different and differentiated is hugely important.

I spent a ton of time with our companies all over the world on this, just building your own narrative.

And then the second thing is, and I think this is kind of interconnected to everything we've been talking about, is it boils down to great leadership.

Like the companies that have struggled, I know you and I know them all, the ones that have struggled state the path for too long, didn't adjust quick enough, didn't actually talk to their customers, it was leadership.

They thought they knew better, right?

But the leaders that really truly have a voice and a perspective on LinkedIn are talking to and engaged with their customers, understand how difficult it is to do outbound and are maybe not holding the outbound reps to the same level of metrics, if you will, as we used to.

It's like, I don't wanna see 100 dials, I wanna see like 10 meaningful conversations today.

That's what I wanna see.

If it takes you 100 to get there, cool.

And so it's like having a leadership that's actually in touch with what's going on.

Like one of the coolest things that I'm gonna give Nick Mehta a huge amount of props right now, because Gainsight's an old, I would argue, an old school company, it's been around a long time, they've got massive market share.

But Nick is like on this whole new, he's on this whole new thread of like really talking about how hard it is out there.

Some of the things that, you know, he just wrote today about how like, dude, I hate to say this, but you know, there is no differentiation in SaaS.

It's all about, you know, how you differentiate the experience and the conversation.

And kind of Craig, to your point, it's like, you know, like that outreach as a CEO to another executive in a company, you've got to have some, you got to have a platform that you've been talking from and about for a long time.

You know, it's like, it's like, it's why an Aaron Levy can have a conversation with anybody in the world, because he's one of the most famous people on Twitter.

But there are a bunch of CEOs out there that are executives that people don't know.

You're right.

Yeah.

Yeah, Nick Mehta is the perfect example, you know, of an imperfect product.

I know they'll shoot me on that, but like, you know.

That's true.

But yeah, but he transcended, he was the mission.

Yeah.

And he could talk, anybody knew they could talk to him.

Now, here's the follow-up question.

Who has more swag?

Nick Mehta, Matt Amundson or Doug Landis, in terms of their dress?

I'm third.

Well, Jesus.

Matt just pulled himself out of the running.

Pulled himself out of the running.

Landis versus Mehta, who's better dressed?

Well, I would say right now, Nick is kind of a little bit more public.

I'm going through some of my own stuff right now.

So like, I honestly don't really care.

I'm also in the process of growing my hair out.

So it's in this weird middle stage.

So yeah, give me a couple more months and yeah, you'll see the new me coming out.

So if I can answer this question and stay classy.

One, I've always admired the way both of them dress.

The thing I'll say is, I've always wanted to dress like Doug.

And then like I look at Nick and go like, I wonder if I could ever have the confidence to dress like Nick.

So that's-

Like I just-

I wouldn't have the guts to wear those clothes.

He looks great in them, but like that couldn't be me.

And then like Doug is just like good approachable style.

You know what I mean?

It's like he looks great.

You want to talk to him.

Do you Matt, that is, I appreciate you saying that because I literally thought about starting my own little Instagram.

I'm like, hey, how do you like, how do you, as a 40, 50 year old man, how do you dress to go to work?

How do you, how should you think about it?

You're going to a conference.

Don't wear the typical shit that everybody else wears.

The Craig, you know, plaid button down with jeans and a blazer.

We call that, we call that, what is that the old?

I put myself in the, yeah.

Silicon Valley mullet.

You know, well, what can you do, like kind of mix it up, but still look, you know, classy, professional and approachable.

There's a whole ton that you can do out there.

And it also doesn't mean you have to go out and buy crazy expensive brands.

I've always had, I actually got best dressed in high school and there's nothing surprising about that.

Fun fact.

And I've always believed like fashion and style actually helps the way you feel and how you feel shows up in the conversations that you have.

And it shows up in like how you engage with people.

And yeah, some things don't work, you know, and some things do.

It's like, I think we tend to, and this is kind of to Nick's credit too, is I'd say Nick and I both have a lot less attachment to what other people think and feel.

And therefore we can be a bit more free willy about it.

Craig, you do too, because of these glasses, man.

I'm digging them.

I know I gave you shit for them, but I like them.

I like them.

By the way, I did want to throw in a fun tidbit on the, you know, your executives.

Like the other thing about Aaron, let's just say, is they had an insatiable desire to meet as many, not just customers, but smart people as possible.

Yes.

So I don't know if you remember Amy Chang had a company called Accompany.

She sold it to Cisco and she had taken a model, not his real thing.

She couldn't show me that of Jamie Dimon, his schedule, because she wanted to build some ambient listening around scheduling.

And she's like, here's what Jamie does.

He meets with people every 15 minutes, seven hours a day.

Because he's admitted, yes, the guy's just going through and meeting as many people.

He would sit in the Harvard club or wherever, and it was fast.

And part of the reason she was talking about it, they created these dossiers for him.

So he would get, but think about his life.

He needs to meet with every great economist, every great politician, every great CEO.

And founders laughing at me all the time.

I'm like, no, man, you should meet with every great founder, every great, and the one I'll add to that was, I think I've told this story years ago.

Remember Sean McLaren from Connect and Sell, that dude?

Oh yeah.

He's just everywhere.

And I once asked him, what's something I can learn from you?

He's like, anybody you talk to, ask them who's the best salesperson you've ever worked with and ask for an intro and who cares if they're looking, meet them.

Yeah.

And he's like, every breakfast at the Rosewood is with the best sales rep someone knows.

And he's like, because when you got to hire them, you want to know the best ones.

And he's like, I never stop.

So just think about that, but how human that is, Matt, just going with the human touch.

That's a good piece.

But I gotta say, man, I might have to adapt that because it's like when I'm heading into San Francisco and I know I've got an afternoon, it's like, I'm gonna reach out to all the people that I know there and be like, who's the best salesperson in your company?

By the way, the hard part about that is though, I can't say in San Francisco anymore because who knows their best sales rep maybe in Denver.

And I'm like, all right, well, I gotta go.

Maybe I'll write that down.

And when I'm out in Denver, I'm gonna make a point of meeting up with them.

But I love that idea of like, hey, who are your best reps and why?

Yeah, and like, you know, because I know you're sort of taking it all in and then coming back with your new methodologies.

And I will say on the hypothesis selling, you know, you told me about it I think a year ago.

I've been trying to incorporate it into everything that folks bring to the table.

And so, you know, I've got my sales consultants, Robert and Brandon.

They come to every meeting with hypothesis.

Nice.

And that's not sales, they're consultants.

They're like, no, man, they don't have time for me to ask them what keeps them awake at night.

Like, I'm going to create a hypothesis.

And people appreciate it and they have the conversations they want to have as a result.

So thank you.

Yeah, they love it.

It's a big win.

It just proves what that does.

And so you heard it from Doug a year ago and we heard it earlier on another episode of this show from another sales, very, very smart person.

So it's starting to be a bit of a trend.

Like, we're starting to hear it.

I mean, I came up with this thing like probably five years ago and I've been teaching it for a long time.

So I love the fact that it's coming out there.

I was talking to our buddy, John Barrows, because somebody else is actually out teaching their own class, they're a consultant and they're out teaching their own class.

And they were saying some of my exact words and I was like, huh, that's interesting.

And so I was talking to John, I was like, I feel like there are no, like, it doesn't matter if you came up with it or not, cause everyone's just gonna use it regardless.

It was like, all right, well, hey, what is it?

Was it copying is the best form of flattery, as they say?

Yes.

Yeah, yeah, for sure.

By the way, so I would say we're doing a roundup show, Doug.

So Matt, I think like signal-based selling has come up a lot or signal-driven selling or whatever.

And then hypothesis selling, we will give full attribution.

I think those are two big themes that would definitely help the market.

And by the way, on the hypothesis side and the signal side, both of those things are not just for sales.

No.

No.

If marketing.

For every conversation you're gonna have with somebody.

If I'm going to meet with Matt and he's my boss and be like, so Matt, I've been working on this hypothesis.

Boom, here's what I think.

And here are the options.

I'm gonna suggest we do this.

You'd be like, awesome.

You laid it out for me.

It was thoughtful.

You've given me options.

You're taking a choice, right?

You're making a choice.

And cool.

Here's the thing, like leaders, we hire people to go make decisions.

That's right.

Because as leaders, that's what we have to do all day long, is make decisions.

Yeah.

Right?

Love that.

So make it easy for me to make a decision.

Doug, you've given us so much of your time.

We're so thankful for your generosity.

I shit you not.

Craig and I have been talking about this episode for the last three weeks.

So we're so excited.

Craig, no thank you to your internet service provider.

They'll be listed in the show notes.

Please don't choose that as your home provider.

Yes.

So what not to do?

Leave sign-in alone, please, yes.

Sign-in.

I tell you, and Sam, good luck on the editing of this one.

You know, it's gonna be fun.

Craig was like absent for like 20 minutes of this thing.

I know, Jesus.

Hey, by the way, I will say, you got, we're gonna have you on again because you're gonna be a regular because this is great.

Thanks for joining us for another episode of The Transaction.

Craig and I really appreciate the fact that you've listened all the way to the end.

What are you actually doing here?

For show notes and other episodes, please visit us at thetransactionpod.com, like and subscribe on Spotify, Apple podcasts, or any other place you get your podcast from.

The Transaction is sponsored and produced by Ringmaster, the go-to branded podcast team.

To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com now.

Either you have walked away from your podcast device or this is playing somewhere in the background.

Someone in your house would really like for you to shut this off now.