The Transaction

Yeah, well, we're recording.

Ladies and gentlemen, coming in from the San Francisco Bay Area with Dan Gottlieb.

Dan, can I just point out a couple of things?

I hope so.

Well, one is, is that some kind of topographic map in the background?

Yeah, I'm very curious about this as well.

Thank you, Craig.

Okay.

No problem.

The map.

So you said you're going to point out a couple of things.

What else?

Well, two, also, right under the map, which I'm sure you use constantly all day.

I love those kind of blankets.

What are those blankets called?

I have no idea what the blanket is called.

But so my wife is, this is her desk, although I'm temporarily using it.

She is a tribal attorney for a tribe that's based in Montana, and she's in-house council for them.

It's called the Confederated Salish and Kootenay Tribes of the Flathead Nation.

So if you drive the Missoula, and you drive up the Glacier, you're driving through their lands.

So that's a map of their lands.

Flathead Lake is there.

It's actually really cool to talk to her about work at the end of the day.

Yeah.

That is amazing.

Yeah.

We're not crazy in the world.

She is.

Yeah.

Oh my God.

That's cool, man.

Fun fact, Big Missoula, Montana guy myself also spent a little time in Whitefish.

Yeah.

Yeah.

We Glacier National Park is I'm going to go ahead and say it.

I think it's the best national park we have in the country.

Oh, hot take right off the bat.

That's right.

By the way, I have to be a better dad.

I don't like national parks and I should take my kids to them.

Probably.

Your thoughts?

Yeah.

I haven't taken my kids there.

I went there as a child.

My parents were better parents than I am.

Yeah.

My parents were too.

I used to have to go to that all the time.

You know what?

I got to do it.

Here's my take.

You can't coach somebody to appreciate nature.

All you can do is lead by example by bringing them there and appreciating it yourself and hope they figure it out.

Because it's natural to appreciate nature.

I think the only way to do it is just to give them the at-back.

That would be my unsolicited parenting advice as the parent of a three-and-a-half-month-old to a couple of guys that have some teenagers.

There you go.

See?

You're listening to The Wind and The Fury with Craig and Doug.

Doug, there he is.

From ABM to PLG, from Medic to Meddpicc, 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.

By the way, can I just, as this is a good opportunity to introduce our guest today.

So Dan, who we will deliver at the end his full name, we're just going with Dan, codename Dan, also Doug.

Well, Doug Gottlieb.

Yeah, Doug Gottlieb.

Doug, Dan.

Controversial basketball analyst, Craig.

Yeah, he got all, I've known that guy for a long time.

Dan, his brother, isn't his brother Dan, that went to UCLA with him?

Are there two Dan Gottliebs?

I connect with them on LinkedIn.

I find them, I hit them up and I go, hey, I should be connected with the other Dan Gottliebs.

Yeah.

In fact, there's a doctor in Philadelphia, his name is Dr.

Dan Gottlieb.

He's a quadriplegic and he writes all of these books about his experiences and he's a therapist.

I connected with him and he sent me a book called Letters to Sam, which are all the stories, his grandson is autistic and they're all the stories that he wishes he could tell Sam.

Dude, what?

I'm going to cry.

Dr.

Daniel Gottlieb.

That is the greatest story of all time.

It's just what happens when you connect with people with your same name, random stuff.

When LinkedIn used to have groups, I had a Matt Amundson LinkedIn group for the two other Matt Amundsens and I on LinkedIn.

Well, I'll give you guys the Craig Rosenberg.

So this bastard is a director, producer, director, and I've been battling this son of a gun for the top ranking on Google.

When I was going crazy on the Funnel Holic, I got above him and now I'm just destroyed.

I mean, he's just destroying me, this guy.

The other day, Co, his baseball coach, is like, hey Craig, are you a director from Australia?

This bat poorly played by him, but I was like, damn it.

It just reminded me that Craig Rosenberg, the director, is still kicking my ass on Google.

Anyway, so Dan and I worked together.

How long did we work together?

Three years, four years, five?

Yeah, I would say it was four years.

Wow.

So Dan worked with us at Topo.

He started as a gritty, excited young man and ended as a grizzled veteran.

But he was amazing and there was a couple of things about him.

One is, he did a lot of standup comedy and today's podcast, he'll be testing out new material, a la his days of doing standup.

Nice.

Two, we didn't really enable that well at Topo and we threw him into some accounts out of the gate and he just absolutely destroyed it.

It was a sight to see.

It was amazing.

Yeah, it was great.

Three, the amount of time that we spent together, it was probably double that because we were doing decks until one in the morning and it was the greatest time doing 10 p.m.

to 1 a.m.

preparing for a presentation at 7 a.m.

At that time, it's just like fighting through it together.

You know, it's funny because towards the end, like I felt really good about, it's like we would do a lot of back and forth and towards the end of our time, like he just would come with incredible insights and whatnot.

And so, and now he's a Gartner analyst and one of the best guys at the about sales and sales tech at GoToMarket.

So I'm here to introduce today's guest, Dan Gottlieb.

Craig, that is probably the nicest thing you have.

Ever said to me.

I really appreciate that introduction.

And, you know, it's funny because I could relive many Topo stories that that would capture some of the things you said.

And I really appreciate that.

I think one of the most interesting periods in Topo was the period of 2020 when we had just become acquired by Gartner.

And so that carried some operational constraints.

And we still were operating independently.

And so we had to find a way to completely pivot, not just, you know, how we delivered our current product, but also create product on the go to get through 2020.

And that was probably one of the, like, you know, wildest professional experiences, any kind of expert based person could have gone through.

That was super fun.

And I think the best deliverable that came from that was the state of the market, which is this thing that Craig just kind of used to do, Craig's crystal ball, but he let me into the crystal ball.

And it definitely is the secret sauce that I use today.

So thank you.

I appreciate that.

And one other side note for you, Matt, a great memory was the Outreach Conference.

This was the year it rained, by the way.

I'm like, Dan's like, hey, come into dinners, I just want like the conference.

They're like, no, bro, dude, save yourself.

You and I are going to JV's taco shop.

And he's like, I'm in.

So we go there and they are known for the surf and turf burrito that's like this big.

I mean, it is huge, dude.

We're talking San Diego.

San Diego style, yep.

And by the way, anybody who likes to meal should go there.

And so we get in there and I've been a mealer my whole life, but I at that point, this was like a moment for me to realize that Dan had passed me like in everything.

There's a metaphor because that dude ate the whole burrito, dude.

Incredible.

Where does it go?

No one knows.

Oh, I knew where it went.

I know where it went.

That's not an issue.

I ate maybe 40 percent of the thing.

It's delicious, by the way.

It's hard to stop eating.

But Danny told me he didn't eat again for four days.

Rest of the conference, I'm like, now I'm good.

I'm not hungry.

But that was my metaphorical turning point where I'm like, Dan's now passed me, he's better than me.

Yeah.

It was because he took down the JV, he's talking about shop surf and turf burrito.

By the way, surf and turf, I mean, dude, you just, I mean, let's go.

Let's go.

Let's ask the big question of Dan.

So Dan.

Clarence, Clarence.

By the way, what movie is that from?

The Airplane.

Airplane.

Thank you.

Jeez.

All right.

What's your vector, Victor?

By the way, on a side note on Airplane before I ask the question, I've been doing little snippets of highlights from Airplane and the Kentucky Fried Movie to send to my brother.

Dude, re-watch those movies.

It is, you would not find movies like that today.

I mean, it is amazing.

So funny.

So Dan, what's something that the market thinks is right?

It could be an approach methodology, best practice, you know, tech, whatever.

And they're actually wrong.

What is it?

And what should they be doing differently?

Is the way we lead off?

And so let's start there and let's see where we go.

Yeah, I've been thinking about this question in preparation for this.

And I feel like the big bets that you see CROs making in their sales organizations to try to address a lot of the challenges that they face right now, they really fail to see the big picture of what's going on, not just in sales, but with this work in general, and are continuously frustrated by the results because they're not seeing the big picture.

And I think that this is a really unique moment in time where, you know, labor and like trends around people and what people value and how they want to work, which translates to how you want to sell and how you want to buy.

Tech and like the role that tech can play and helping you do your job is, you know, there's a lot of new hype around that conversation.

And then, you know, the way we think about using information and data is also evolving as a relationship with that.

And so I just feel like the big bets that we're making are rooted in like the last decade of how you change a sales organization with talent, with enablement, but it's not working because they're not seeing the big picture and making bigger bets that take advantage of the trends in talent, in tactics, and in tech.

And I'm excited to kind of unpack that a little bit because I know Craig is going to say, okay, but can you give me an example?

Because that's how all of our conversations went when we worked together for several years.

But I mean, before we go into that, I don't know if you have any reactions to my kind of big picture call out that I think we're missing it.

No, I think, I don't know, I won't speak for Matt.

But no, I just need to hear you unpack it a little bit as we like to say.

Let me put it to this way.

If this opening salvo, like that one.

Yeah, I want to, is to tease me into a conversation about this, it worked.

Yeah, my interest has peaked and, you know, I cannot wait to hear the unpacking of this because I agree with you, but I think people are having people struggle to understand what is the big picture in the way that you're talking about it.

What I will say is like, this is becoming an increasingly popular conversation for people to have on our show, which is that like, people are so wrapped up in like micro tactics, whether that's, hey, I'm trying to make the subject line of my emails better, or I'm trying to get my landing page to convert one percent better, or I want to increase traffic to my website by five percent, you know, so there are these kind of micro tactics that actually suck up a lot of people's time, and the benefits really don't align well with the amount of time invested in solving for those problems.

So I'd love to hear what your perspective is on what is the big picture and what are the bigger things that we need to go after.

Okay, so we'll talk about it in, we'll break it down to talent, tech and tactics.

So from a talent perspective, I think that in general, we used to think that 15% to 20% of our sales team was top performers, but I think what we're learning is really only 5% to 10% are top performers in our organization.

And what that's turning into is this top down blame game.

It's a talent issue that we have, we never had great reps, we need to find great reps.

And that's actually translating to more conservative hiring, because that definition of a great rep is more about like relevant industry expertise, relevant motion expertise.

And it's more like safe bet than big bet.

And I think that's one challenge.

The other is you see organizations hedging against the performance of the sales organization.

And that's where this whole product led concept I think really came from.

I mean, obviously came from more than that, but that's one way to understand that trend.

And you also, now we better understand the interest in AISDRs as an example, right?

And I think that the missed opportunity here is in the way that you can just address your talent strategy to account for some of the more forward looking competencies or skills and just start slowly hiring for that more evolved version of a sales rep.

And so, I am prepared with some Gartner data, work of the job.

And we have an awesome research team.

I won't go into too much detail.

Craig understands.

But basically, with the Gartners, we have a team of social scientists, basically, that they pair with us, the subject matter experts, if you will, to collaborate on big research ideas.

And so, this group, they sought out across eight different data sources to try to understand the question of, what are the competencies of the more high-performing DNA of a seller?

And there's generally three topics, or three competencies that came from that.

And the first two aren't going to surprise you.

The third one might.

The first one is this concept we call mentalizing.

And this is really where you're able to take perspective of the different people involved in a deal.

And you're able to adapt situationally based on that perspective.

And you draw connections between concepts.

Jeremy Donovan, I don't know if you remember Jeremy Donovan.

He used to call this, it always cracked me up, general mental abilities, right?

He would evaluate general mental abilities.

And this is about just the capacity for dot connecting.

And so I think that that's not a new idea, but it is one that we can build into our talent acquisition process that can separate individuals.

The second one is tactical flexibility, which is knowing how to and feeling comfortable adapting both within a current call, as well as asynchronously outside of calls, our tactics accordingly.

And I think that this is not a new, this is like a yeah-duh to say out loud, but it's actually a competency that runs, you know, antithetical to the concept of a sales process or the concept of a sales methodology.

You know, we we've always had these methodologies that we govern, used to govern to qualify whether a deal is legit or not.

And we try to coach people into following that process, as opposed to knowing that high performance just figure it out deal by deal.

And it's always cracked me up that we like invest sales ops resources in the scaling of process and for but yet when we get into what do we need to do to hit the number this quarter, all that goes out the window.

And we all know that.

We all know that.

And so we can build that into the talent process.

And reps that demonstrate high competency of both of those things are three and a half times more likely to hit the number.

And so I don't think that these are surprising, but yet I don't see it more aggressively included in talent strategy.

And then the last one around talent, and this one's really interesting, is AI partnership.

And this is a more current analysis.

And reps that are, demonstrate a high competency in AI partnership, which you define as, they can dot connect between the workflow that they have in front of them, the AI tool that's available to address or improve that, and then they can execute against that pretty quickly.

They're 3.7 times more likely to hit their number, reps that demonstrate high AI partnership.

Out of 100%, how many reps do you think meet that specific competency?

What do you think?

Hold on, let me put on some women's glasses here.

Yeah, Craig, can we play Price is Right rules here, closest without going over?

Yeah.

So percent of out of 100.

Out of 100%.

2.5.

Okay, Matt wins Price is Right rules.

Craig is closest to the pin.

It's 4%.

Yeah.

Wait, what do you mean?

What is that?

Oh, that price is, wow, you son of a god.

He knew exactly.

Yeah, I should have said $1.

Yeah, he knew exactly what he was doing.

Not enough companies are taking advantage of the trends.

So another researcher on our team, Jared, who Craig knows, that he did this huge, huge job description analysis to try to figure out, are some of these concepts manifesting in hiring trends?

Basically, the concept of adaptability has probably been one of the more popularly rising.

It's now in about 10% of job postings.

But there was very little mention of that not that long ago, as being part of a sales competency.

Then creativity is also on the rise as a capability.

It's important to think about this because while many companies are trying to double down on process and efficiency, the zagers are actually saying, well, let's throw that out the window.

Let's just hire really talented people, and let's just hire less of them.

I think that that's going to be where an exciting opportunity, one of the big bets that is missing is just being a little bit more specific about the kind of talent we're going to bring in.

I think that this is really big bet number one would be, hey, are we actually bringing in the kind of talent that's going to be more future-proof?

I love this dialogue.

I love this because this is something that I see because I work with a lot of startups.

Thank you.

Finally.

There you go, Craig.

I work with a lot of startups.

One of the things that can be challenging for their sales process is it's too rigorous, meaning it's too structured.

They let a lot of good deals go away because they hold the line around process or pricing or certain features that are included in a package.

They need to be creative, especially at that stage of a business, because what is a pricing model for a series A or for a series B company?

In a lot of cases, it is the prototype to what it's going to be when the company truly hits its inflection point.

The more data that you can collect around, well, how many people actually like our standard packaging, and how many people are actually looking for a combination of maybe these two things?

What goes out the window is when sales reps are like, well, I lost this no decision or I lost this to a competitor, but in reality, they lost it because the packaging wasn't sufficient or the sales process that they were running was too rigorous and didn't account for certain variables that people hadn't anticipated because we're just getting started.

I think the most successful sales reps at start-ups are sales reps who are creative and are focused on the ability to make a deal happen and can sort of see each sales cycle somewhat individualized as opposed to, hey, this is a standard sales cycle and generally it looks like this.

What that leads to is really, really low win rates.

So anyways, I love that.

And I think a lot of it is because it's great to hear.

And as someone who started selling, well, actually, that's not true.

I sold Cutco and then ads before I moved into software.

Cutco is one of the greatest training grounds for salespeople out there.

True, true.

Yeah, yeah.

Cutco is perfect because they do give you a process to follow, but emphasize the importance of walking into someone's kitchen, reading the room, and collaborating with them on, hey, show me your knives.

Let me use your knife to cut the rope.

Just little things like that.

But anyway, we can talk about that for hours.

Yeah, I think that this is a concept that I think large enterprises are also trying to invest in as well.

This isn't just a challenge for startups, but for startups, increasingly, it's even more high stakes of a decision, right?

So, okay, this I think is a good segue because you brought up sales process and its relationship with creativity.

And I think the second big picture is the way we think about tactics and process and the relationship between them.

And so in general, a lot of the challenges that we face in sales and tech sales especially, are rooted around challenges that buying teams have.

And I think a lot of folks cite Gartner data when framing this particular challenge.

They always talk about the desire for the rep-free experience and things like that, right?

But what a lot of folks don't do is they scroll past that statistic and realize that when you look at whether a deal was determined high quality or not, as defined by the person who bought it, working with reps and doing a lot of self-serve stuff yields the highest quality deals.

And so from a process standpoint, I don't think that as an industry, we have right-sized our understanding of what a sales methodology or a sales process can look like to address that, because it's too complex.

Meddpicc, Meddic, it's too complicated.

It's all about us and management qualification.

I think that what we need and the big picture is for companies to simplify radically their definition of a sales process and its utility in guiding reps to make decisions.

And I think it really boils down to two big overarching phases.

The first one is the point of view phase, where I'm developing a point of view either as an individual and then collaboratively early on with the different buying groups that we work with around why they should buy anything.

And the key to doing this well is creating a differentiated point of view about how our product can address some of the initiatives, priorities, mission critical challenges, whatever way you want to phrase it.

And I think that that's what great sellers do anyways, but they don't codify that as process.

But I think by focusing on point of view selling as part of our sales process and methodology, we can implicitly bake in the bias that you need to care a lot about the buyers that you're working with and tell stories to them about what they care about.

And I think that that would be the first half of it.

Then you kind of reach this traditional point of deal qualification.

Define more specifically by like the fact that, hey, look, they're probably going to buy something, right?

A lot of people tend to use deal qualification to hot topic.

But I think that there's a line that we often cross where it goes from exploring to, there's a deal here.

And when we cross that deal, we convert this point of view into a business case.

And we flip it from, okay, here's an idea that was like 70% ours, 30% yours based on my research, based on conversations with a few people, into let's make it a business case that is like 70% yours, 30% us, that 30% being the differentiated part of the business case that make us the preferred vendor.

And when you treat it that way, that's really what they're doing.

I mean, y'all have been a part of buying processes where you kind of have to put it all together and package it and sell it to different people and get different feedback on it.

And so just like focusing on that is what we have seen to accelerate sales cycles when it's done really well.

I think if we just simplify all of the tactics underneath of it, discovery, technical discovery, the disco demo, the demo, you know, the technical demo, the proof of concept, the free trial, the negotiate, the proposal, the negotiation phase, they're all are downhill activities that stem from our core ability to have a point of view that is differentiated and have a compelling business case.

And I think that if we just simplify to those two things, we would free up a lot of pressure that sellers face in trying to get deals done.

So that's sort of my high level sort of big bet number two.

And that's a radical idea, I think, to the conventional CRO.

But those two things go together.

Yeah.

Yes.

One and two.

By the way, side note, have you ever seen the movie Let's Be Cops?

Yeah.

Jake Johnson, the actor, he looks like.

Thank you.

I mean, both are striking young men.

Wow.

Thanks, guys.

Look at this guy.

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 hand out 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.

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Okay.

So I'm just going back.

This is actually really, really deep where you're delivering, even though in many ways, even on the talent where you ask them to rethink, the core skills, you know, that's kind of a simple, in many ways, in a good way, you know, sort of simple.

It's hard to tease it out, but you know what I mean.

And then you're, you're saying we're going to simplify the problem.

But if I had to sum it up, it's like, can we get the types of reps who have the ability to custom craft by, you know, by making left turn judgment calls on their own.

But combining that with a more simplified sales process is kind of when we're, as we're thinking about the big swings, like the combination of those two things are part of the solution.

Or a way to go.

Because in one, though, I thought you were going in a direction, sorry to go back to one, but I thought you were going in a different direction, which was, well, we have a talent problem.

And so, and I thought you were gonna say something different.

I'm not sure what I thought you were gonna say.

But what you said made a ton of sense for me.

And you have the data to back it up.

Okay.

The thing about it is figuring that out, though.

Like, for example, do you have, have you seen anything on your number two in that section on how we figure out if someone can make adjustments?

Is it your exercises or, sorry?

Definitely, it's all about exercises.

It's all about exercises in the sales process, where you want to give them tasks that can demonstrate that they can develop a point of view.

Then, you want to give them a scenario in a interviewing environment, where they have to mentalize the situation and adapt.

I think an example of this could be also, from a mentalizing standpoint, you're talking about what are they going to do with the answers that you provide in a discovery role-play, would be a great example.

How might the follow-up email incorporate everything that you talked about?

That would be an example, a very simple one.

But another on the more adapting scenario would be to ask them, what are three potential audibles that you could run based on the follow-up from this?

You could even tell them, we value multi-threading.

If you wanted to multi-thread this deal based on this call, give me three different things that you would try to multi-thread for this product.

I think that would be an example just to see what they come up with.

Yeah.

Those are a couple that would be insightful, and based on your product and your industry and the people that you sell to, there's going to be some real specificity there that you might expect, right?

What you're not looking for is like, well, I'd get them all on a big demo.

Yeah.

Right.

I got it.

I got that was a well-planned.

Did you define point of view selling or is this all part of this idea?

Is this a new thing?

I don't think any of the ideas are new one to themselves.

I think packaged this way, they are, and I was hoping that the three of us would maybe figure out what to call it on this podcast.

Well, but you said, but point of view selling, Matt was nodding like he knew what he was.

I loved it.

Yeah, so, I mean, you kind of already hit there.

But the issue with point of view is, another good thing about point of view and the issue is you're arguing for the rep having a point of view on what we should do next and how to play this.

Is that right?

Great question.

I would say that it is a point of view on why they would work with us.

Point of view at the brand level.

Correct.

It's a point of view on why you should, why you would work with us.

And you think about what great prospecting is.

It's all about finding a point of view and delivering that in a time that makes sense with a message that makes sense.

But it originates from a point of view.

And that you, there are a lot of interesting ways that you can make it easier for a rep to develop a point of view.

I think that's where the third bucket of tech excites me.

Because I'll talk about that at a minute, but I'll give you one example.

And Craig, I've actually, we've talked about this a lot in the past.

So one would be instead of framing discovery as a like verbal-only exchange, and I've heard Matt talk on this podcast about his experiences in discovery, right?

It's more like interrogation when it's done poorly.

And we all know that great reps do discovery.

It's a value add.

It's a thoughtful conversation.

But we can take that bias and we can bake that into more of an interactive experience.

So I know that you had the woman from design thinking selling, Ashley.

Yeah, Ashley Welch.

So let's take her concepts.

A really good example of this, and I had a client that sold single sign-on to implement this idea.

And what they did was they took the discovery process and they moved it into a virtual whiteboard.

So, you know, the Miro, Lucidchart, murals of the world, right?

And the enablement team just built this template.

And they had like on the right side of the box, they had a series of common challenges and pain points.

And then in the middle, they had a sample diagram to fill in.

And so the beginning of the conversation was about dragging and dropping the challenges that they had over into the box.

And all the rep had to do was just be like, okay, listen, like, our job together is to figure out how and why we would work together and developing a point of view on why working with us would be, would be worth your time.

And so they start by instead of turning it into a verbal discovery, they turn it into a visual activity where the reps were dragging and dropping the common challenges and then mocking them up like they were taking notes.

But the buying team was like leaning forward and being like, oh, no, no, no, no, this is what I meant.

This is what I meant.

And then one of the challenges too was around technical discovery.

Instead of relying on their sales engineers to do like deep technical discovery, they had this architecture diagram and they were like, okay, well, what are you using for this?

What are you using for this?

And they were able to fill in the technical diagram to gather on what they're using.

And then they took the pain points and they dragged and dropped them to the certain points and the technologies that they had.

And they now had co-created in 30 minutes, this like point of view on the problems that they were going to be solving for together.

I was like that, which he told me about it.

It was so cool.

And all they had to do was just teach the reps how to turn the conversation into just drag and drop experience.

That's it.

So that's like an example, I think, that we could anyone could do today, but it's outside the box thinking that only comes from these kinds of restrictions.

And you need the talent to be able to do that.

I went dark while you were talking, just going, I can imagine some reps being provided that kind of tool, just go, no, bro.

Yes.

Okay.

That was great.

Sorry.

I know, Matt, it's very important to Matt.

I'm going to speak on behalf of him that you quote, quote, land the plane with all your points.

So I will refrain from jumping in on said point of view, selling presentation by you and let's, let's continue to move forward as you work.

Yeah.

Number three is like we, like sales sucks at buying sales tech.

It is like, it is so brutal to participate in.

And that is my core of my job right now at Gartner.

I do a lot of calls with sales teams of, of all sizes talking about sales tech.

And over the last 18 months, that conversation has completely changed to AI for sales.

And I, you know, it, it is what is remarkable is how vendor led the purchasing is, how I'm looking at these companies.

What do you think that it's a very devoid of adequate internal analysis, especially at the executive level on like, what do we need, right?

And, you know, the folks that do debt well are the like, world-class rev ops practitioners that scope out the sales process.

But this becomes even more important now because AI is, in theory, capable of handling far more granular tasks.

And if you don't know the granular tasks that are actually required to get a deal done, it's going to be far more difficult for you to make a decision about how AI can help a sales rep get 10% more productive to quota just by introducing tech.

So I think that the big bet here, right?

There's like a, the big bet here is about putting in the hard work that's necessary to figure out, like, what our reps actually need, as opposed to your kind of point of view on what they need.

And if you, I would love to give you some examples of how we could think about applying that to this point of view selling concept, because the answer isn't always AI, without a doubt.

So I'll give you, I'll give you a couple, right?

So, but some of them will include AI, by the way.

I'm sorry in advance.

I think one of the coolest, immediately valuable use cases right now is AI led sales research.

It's very practical.

The role that it can play in synthesizing information.

But the real value comes in when you're able to prime through the prompting at a company level, how to look at these sources of information from a point of view.

So I'm not just like summarizing an earnings transcript.

I'm summarizing an earnings transcript from a point of view of someone is trying to sell X, Y, or Z.

We can do that at scale now.

That's like a kind of a big breakthrough, assuming the rep knows what to do with the information.

I gave you the example of visual collaboration apps instead of PowerPoints and part of the early conversation.

And I think another one in tech that I'm really bullish on for its value, maybe not as a billion dollar category, for its value is the interactive demo market in the way that I can take my point of view and apply it to a product story that I sent to you.

Think about the amount of bureaucracy that goes into getting somebody into a demo to learn about a product, especially from an outbound prospecting point of view, when I can take the burden of that and say, I've used AI to help me arrive at a point of view faster, and now I can put that time into creating a hyper-targeted piece of content that is a demo, by the way.

The demo is a piece of content now, and share that with you, and see that's why you want to have a conversation.

Way better intent early in the sales process, and then further down the sales process, and then I'll pause.

When we sort of transition from a point of view to a business case writing, I feel like the relationship between a large language model and all of that activity data and recorded calls are going to make it a lot easier for me if I'm recording calls to collaborate with a large language model on getting a wire frame of a written business case put together a lot faster.

Then same tech, I can use that visual collaboration space to get somebody that's not involved with the deal up to speed.

Here's in one PDF picture or JPEG or PNG, depending on your preferences, of the story that we're building together right now.

Here is a custom demo video that I've made for you based on your role in this deal before our meeting.

I think those are just very straightforward and, in my opinion, intelligently applied sales tech that solves more current buying problems.

It's not like AI is the answer to all of our problems.

Going back to the data point that set this up, so about 4% of reps are really good at AI, and of those, they are 3.7%.

What was the data point there?

3.7 times more likely to meet quota.

By the way, is part of the AI proposition in the three things that we talked about here, any of it that you are, because this is interesting, because I, you know, once again, I, that's how we haven't spent as much time together, because I thought you were going to talk about how AI can clear the path with some of the mundane things that the rep has to do in order to allow them to think in number two and be more, frankly, I guess, to use the word twice thoughtful.

Instead, you surprised me in a cool way, which was like, actually, the AI is facilitating the point of view process.

Or at least the first draft.

Yeah.

And here's the catch on this, right?

So like, what do you use to pull this off?

The market is in rapid transition for sales tech to do things like this.

That data that I think we captured is more of a reflection of the individual contributors that figured out Shatch-PTN perplexity.

They have more agency in figuring this out.

But now this year and into next year, we'll see more adoption of the more sales-specific iterations with more advanced rag to simplify this process on behalf of reps.

And we're already starting to see that.

And that, I think, is where, when you talk about thinking big, we're making a bet on a use-case first and AI second.

I think that's an important frame here.

Like, I would need reps to come up with a point of view.

How can I do that faster?

Well, AI is good at this part of it, but they still need to deliver it in this more interactive setting.

That's an example of, I think, an intelligent way to approach buying sales tech as opposed to, hey, look, I got a demo from ZoomInfo, Gong, Outreach, and Clary.

What do you think?

Right.

Yeah.

Yeah.

I think that's right.

Yeah.

We did, I don't know if you were there for this part, Dan.

Matt, I definitely haven't told you this, but without the data in front of me, it's not an exact quote, but we basically had asked like two or three questions about using AI.

In our RevOps group, you know, at scale we have councils, right?

So we have RevOps Council, Product Marketing, DemandJet, and we, and SDR.

And we asked them all the thing.

And like in RevOps, when they're talking about the sales reps, that the vast majority of AI usage was reps using it on their own.

And according to your data, four out of 100, that's about right, right?

I mean, those are folks that are going to go figure this thing out on their own.

And we had John Barrows on, who basically said the 80-20 rule flips, and that the top 20%...

Wait, what was his quote again, Matt?

I started good on the one.

I forgot.

But it was that the top reps will be supported by AI, and they're going to figure out themselves.

That's like that the new age, it's going to be that the ones who are proficient in AI are the ones who will win.

Yeah.

Yeah.

And I mean, OK, Dan is he's on the fence on that one.

He gave it this.

It's a nuanced caveat.

I agree with that statement over like this two to three year period where we're transitioning to figuring out what are the practices, what are the operational rigor around it.

Like, I agree with it in that sort of a limited definition, but it's not going to take very long for us to figure out as an industry.

OK, these are ways that we can spend money on this and implement it with some success.

That can allow for that small innovative group to scale what they've learned to their peers by the nature of the way that you, we figured out intelligent prompting for sales research for our product and company.

So now we can put that into the products that allow me to scale that on behalf of reps.

So I have a client who has built a account enrichment button in Salesforce for all of their reps.

When they get a new account, they don't go and do, the first thing they do is they press the Enrich Me Now button, and they're addicted to it.

They want to start from that because they're starting from an opinionated point of view for their research.

So they're a forward-looking group.

They figured this out a little bit faster.

But so I agree with that statement.

That statement will be true in perpetuity, I think, for tech-savvy sales reps.

Yeah.

Whether it's AI or whatever's next.

Yeah.

Yeah.

That's right.

Are you seeing in the four, I guess, 4% such a small number.

But like, is there AI adoption outside of tech sales teams?

So I promise you, I didn't, I promise you listeners that I didn't ask Craig to ask that question.

So the short answer is yes.

And I think that that's what's been the most interesting thing to me and my job at Gartner has been the speed with which all kinds of sales industries want to know about AI for sales.

And, and it's, it's wild to me because they're even more vendor led.

And so I think a good example of this, we just got back some really useful data from on what, how is it going with copilot for Microsoft copilot?

How's it, how's it going as an industry?

And the data that we got back was more focused on a wider range of knowledge work.

But the findings, if these findings apply to a wider range of roles, we can only assume that it's even worse for sales.

And the, there are a lot, a lot of challenges that they're facing.

One is the IT organization delaying because of managing for risk.

So if you have poor information security practices, if you are information management practices, i.e.

like, hey, you have people's salaries in SharePoint, right?

And you haven't gone through the appropriate permissioning on that, but you just turn on Co-Pilot.

I could just do a quick, hey, how much is Craig Rosenberg making?

And if you haven't figured that out, you could return that answer pretty clearly.

So there is a whole information management part of the change management that's required to get value from this tech.

And for sales, that's even more challenging, given the state of CRM data.

And then the second more interesting, or there's kind of two other findings here.

One is that like reps are stoked about it, or people, users are stoked, I should be clear.

Nine out of 10 users are like, hey, I really like using this thing, and I want to retain access to it.

But three out of four users say they struggle to integrate this product into their daily routines.

And that shouldn't surprise anybody.

It's a new way of working.

I'm not used to like my heuristics of finding answers or to go into search, not a co-pilot.

And the third one is that the enablement side, like enable adoption has not been automatic.

They see a spike and then a dip in general with use of the tech.

And it all signals that we have a really long way to go organizationally.

And it's just like any sales tech, where you have to actually go through doing the hard work of dot connecting how this capability can solve for this use case.

And if you aren't doing that, back to my kind of that whole salvo or sub-salvo about the relationship between like more modern tactics and point of view selling and the tech to support it, we're just going to kind of be back to where we are right now with this tech.

And that's, it's just a great reminder.

But this data is, it is not specific to sales, but it doesn't sound that different from what I'm experiencing talking to clients.

Interesting.

Man, that was deep, bro.

What the hell, man?

Let me tell you a funny story about this.

Okay?

You might appreciate it.

I'm listening.

Okay.

So I had a chief sales officer, actual title, okay, for a insurance company of a big brand that we all know.

And there's, it's one of the B2B products that they have.

And he was responsible for three states worth of sales performance.

And he dials into our customer call, right?

Which is always a good sign.

Dials in, you can hear him on the phone, on the car phone, kind of like when you call Craig outside of work, right?

Oh, yeah.

Yeah.

The wind tunnel.

Yeah.

I don't know why it's the wind tunnel, but yeah.

So he's driving and he's like, listen, I'm on my way from a customer meeting and I'm going to meet with IT.

And they're about to tell me that we should buy Microsoft Copilot.

And I need you in 20 minutes or less to tell me what the hell it is and why I should or shouldn't buy it.

And what was incredible was A, the way that that situation represents how sales tech decisions are being made in other industries.

It goes to show how far we have to go still.

But I sat there and was like, okay, well, how am I going to answer this question?

And I just started talking about what I know about the insurance sales process, the relationship between the agent and the underwriter.

The underwriter is the sales engineer of the sales process.

And all we had to do was talk to him about the value of transcription, and transcripts from summaries, and getting summaries from really long order documents, and how you can get answers to those questions really quickly, and in all the meetings that you miss for big deals, and in trying to understand some of the key things that are happening in some of these documents.

He got so excited when I just said that.

I didn't have to say anything to the rest of the call.

His wheels were just turning on the value of just using call transcription.

But I think that the reason why he made that he felt connected to that story was because of the pain in the workflow of working with an underwriter, right?

Yeah.

And so it reminded me that we suck at buying sales tech, but if we just focus at the more aspirational role we want to play in guiding how we work with customers, and think about that really closely and critically, I think there's a lot of breakthrough ideas that are sitting right there.

Yeah.

Amazing.

That was a great story.

There was a few great stories in today's pod.

Yeah.

But like just to end on one, consider all things considered, I just had a talk with a guy, an ex-analyst guy, started his own thing.

He was just talking about how when he went and met with a bunch of enterprise marketers, they're like number one issue was storytelling, but not their issue, but like the ability to help everyone tell the right stories.

Dan has always been a great storyteller, which means he would be a very talented person for the first T.

That wasn't funny.

Yes.

But I tried to tie back to end everything.

Thank you.

Yeah.

Well, that's an interesting POV.

That is correct.

Please label this episode, Triple T POV.

Duly noted.

Anyway, Dan, that was amazing.

This was probably the least amount of talking Matt and I did, because it was deep stuff you were delivering.

It was great.

It was almost like we were chatting with a Gartner analyst.

An expert in the game.

Yeah, with real research to back up what he was saying.

You actually backed up what you were saying.

Dan, thank you, man.

This was a great episode of The Transaction, and we hope to have you on again.

Hopefully, next time we can continue to point out things in the background of your room, as well as you're here, potentially talking movies as well.

So thanks for coming on, brother.

Thanks for having me, guys.

Thanks, Dan.

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.

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