The Transaction

Can I just give you my personal Dennis story?

Yeah, go.

We want it.

It's your show, yeah.

Oh, that's true.

I appreciate that.

So, years ago, when Lars was at Cloudera, Lars Nilsson for everyone on the show, he's always done a good job of bringing outside people in to come talk to him.

So has Dennis picked that up too.

But for the sake of the story, I think Lars probably brought someone in every month or something, Dennis.

And he asked me to come in, okay?

I go in there.

Clearly Lars recruited from NC2A Division I football teams because these guys were gigantic, all right?

These sons of guns were so big.

But there's one guy, yeah, I don't think he was in SDR, but he was somewhere on the team, who sat in the front, was like wide-eyed with a zillion questions that were so smart.

And I'm like, remember just going, who is this guy?

And then I think we went to like a show later, me and Lars and Dennis came.

And he's just like grilling me.

And like, I'm an analyst, and he forget what's kind of tech he asked me about.

And he's like, well, have you looked at this, this, this, this?

Here's the plus, here's the minus.

Like it was like, oh my God, this guy's amazing.

So anyway, we became friends because I was just, you know, he was so impressive from a business perspective.

And he's an amazing guy.

So we became friends.

And then, you know, Dennis is like, hey, I'm my brother is like telling me about, or the Bessemer guys are telling me about this company down in Santa Barbara.

They do construction software and the numbers are off the charts.

I think about going there and I'm like, sounds good to me.

So he goes down there.

Procore is one of the most amazing stories in SaaS over the last 15 years.

And Dennis was so and then, you know, at Topo, we did a lot of work with him.

I watched him, you know, go in there and just it built use his.

It's a combination of magic, operational excellence and vision and his desire to always keep smart people around him, like he's always learning.

And and this team, man, I just remember going in there and like every time I went down there, there was new learnings and they were just moving.

I mean, like I, the speed at which they built this thing and the, the big company that they built was so amazing.

And so I've just, it's with like, I'm just honored and happy and excited that today's guest is Dennis Lyandres, who is now doing his own thing, but like we knew him as like we were able to say we knew him when he was building Procore.

And I knew him even before then when he was just an excited young man.

So Dennis, welcome to The Transaction.

I love it.

I'm so stoked you're doing this.

I think that it was just missing in my life, Craig, not being out on stage, putting content out.

So I am pumped that you're doing this.

I'm honored to be here and high bar.

So I hopefully have something useful to say.

You know what's amazing, you guys, speaking of which is like the speed at which you can become obsolete in the B2B sales and marketing world.

Like it's great to be back, but like, there's so many people that didn't, you know, know, you know, that, you know, I was on the circuit and doing all this speaking.

They're like, you know, what inspired you to go do this?

I'm like, inspired me.

I'm like, well, Matt inspired me, but it was so that both of us could get back, you know?

I met Matt because Matt spoke at a Topo Council, right?

Is that that was the first one and because everyone told me, well, you got to meet Matt and it's I'm like, all right, let's go.

And then I had him come up and talk about his program.

This dude, like he just knocked it out.

The priest cursed a lot.

No, no, no, no, no, no, no, not a Topo, not a Topo.

You can't you can't you can't curse there.

No, I cursed at a SalesLoft event because it was all sales dudes, right?

Like, yeah, come on now.

We can't be cursing like that on Sand Hill Road.

From ABM to PLG, from Meddic 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.

All right, so this is Dennis.

We're so excited to see you.

We wanted to record our, a long intro and conversation with you, but let's get into some, let's get into some B2B insights.

So here's how we like to start the show.

Ready?

Can I interject before and mess you up here?

Yeah, go.

That's how this show grows.

All right, let's do it.

I mean, I think your comment on relevancy and how fast things change, I have been beyond humbled because I am doing some advisory work now.

And almost every single workflow I'm trying to optimize, I'm like, you know what?

You guys got to go out and you got to learn and figure out these different ways.

Here's how two other companies are doing it, because it's already so fundamentally different.

And whether it's account planning or customer experience programs, whether it's AI or different kind of approaches to talent and technology, it is just so different.

So I couldn't agree more with you.

As you're saying that, I'm like, man, I got to not get obsolete.

So it's amazing.

It happens fast.

And by the way, doing this helps.

So what's something that the market thinks today that they're doing right, or is the best practice or methodology, and they're actually wrong, and they should be thinking about doing something different?

What would you, what would be your answer to that?

I mean, look, I do have to acknowledge my like admiration for technology companies is, you know, knows no bounds, right?

I think that technology companies are the coolest, most epic companies of my generation.

You know, that being said, like if there was something that I'm like, hey, let's do this differently or better, or like maybe this is wrong.

I would love to see the same level of excellence and thoughtfulness put into a people strategy that you see into a product strategy, or that you see into, you know, a get right program when enterprise sales isn't working.

And to add some color to that, right?

Because I think one magic I love about you is the specificity and action ability of what you offer, right?

That was always something that drew me to you.

And it was like, hey, I can actually like help my people grow faster, serve my customers better tomorrow because of this.

And, you know, the thing that I would say is like the most important thing in that people strategy that I would love to see people do better and or that I think they do wrong is how they train and develop and how they make that a part of how they hire, how they fire, how they promote and add a little more color.

Like I think the most important thing that drives whether you win, and this was certainly the case at Procore was leadership, right?

And the leadership team.

And so I think training and developing leaders so they can build the next generation of leaders and having a real vision strategy and plan for that, that is the best plan in the company is what I would love to to see done differently.

Wait, is this a look back insight or is this how you build things at Procore?

It's both.

I think that look, we knew out of necessity, you know, when I joined Procore is 10 million in revenue and never hired an outside sales rep.

And Vertical SaaS was not the thing.

Right.

And certainly construction was not the thing.

And so out of necessity, we were like, hey, like if we want to win, people are going to be the most important thing to winning and we're going to have to train the talent because we're not going to be able to buy it and relocate it from Silicon Valley.

And so that necessity and sort of the clarity of like having mission, vision and values was there.

For me, the leadership piece really probably didn't hit me until like halfway through my Procore journey, when truthfully, I just realized like even things that I kind of knew how to do, you know, like SDR or enterprise sales, like things that I had actually spent some time like in the saddle doing.

And I'm like working with my leaders and I'm like, shouldn't they be stoked?

Like they actually have a leader who like knows a little bit about this.

And I'm a big advocate for this.

And I'm a champion.

I'm trying to help them.

And I'm like, why are they mad at me?

Like, oh, right.

Like I should be figuring out how to do a totally different thing, which is lead them, bring together, you know, a bunch of different teams.

And so to answer your question, you know, it was certainly a lot of clarity that attracted me to Procore about people, about, you know, vision, values.

It was a humbling set of failures that I think brought me to the clarity that like leadership is its own thing to learn and do.

And that, you know, my work was going to be all about like building the next generation of leaders and truthfully like making myself a better leader.

So I do think the market's not thinking about that.

So I would agree on I would agree on that opening salvo.

That was like dead off, right?

So let's, let's just go kind of through the various elements of it.

Is that cool?

Because I think like, I think it's one, you know, people's one of those things or culture is one of those things is like having a culture.

It's like, oh, thanks.

Yeah.

I mean, like that very helpful platitude.

Yeah.

Yeah.

Be smarter.

You're like, thanks.

Yeah.

Robert Koehler, who I don't know if you've met, he was old topo guy, works with me here at Scale Venture Partners.

It's like, he used to always equate it to the coach who brings the team in and says, okay, guys, here's the deal.

You have to run faster.

And he, okay, good tip.

Thank you.

Play harder.

Okay.

So is the, so you mentioned first hiring, I think, or should we start there?

Is, is there a big overview type of approach here that we start with?

And then we look at the various elements or should we start with?

Should we start from the start, which is like, who do you hire?

Well, let me try to build on the prompt you have, which is like, what am I seeing and believing that people are doing wrong as it relates to hiring?

And then we could talk about firing and I'll kind of put a radical thought out there that I used to think hiring was the most important thing I did and then I realized if I'm not great at firing, like maybe that's actually the most important thing.

And so, you know, and look, I mean, most of my work right now and most of my work at Procore was, you know, executive leadership, right?

So I think my hiring is gonna be a little, comments are gonna be a little more aimed at that.

And I think aiming at that is a little more aimed at winning, right?

Because of importance of leadership.

So, you know, I'd say within hiring, you know, like to me, what I'm seeing folks not doing as much is the deep vetting for the people skills.

And let me give an example again, because I agree with you.

It's like culture.

And you're like kombucha.

No, that's not it.

Right.

And you guys laugh and I walked into companies and they're like, let me show you my culture.

And it's a foosball table.

And you're like, OK, what is the plan to train and develop people?

Like, do we have a differentiated employee?

So let me get back to kind of where we were going here on hiring.

And so, you know, a lot of sales leaders are probably familiar with the questions around, like, tell me about a deal you lost and what you learned.

Right.

OK, well, how often are we asking about, like, tell me about a manager you hired that didn't work out, what you learned from it.

Right.

How often are we holding people to a really high standard for their ability to develop and train?

And have, you know, successors ready for themselves.

Right.

You know, and are we asking those questions?

I also think that you can actually vet for things like curiosity and humility and a growth mindset.

Right.

And yet I see this in almost no interview panels.

Right.

There's not like one or two humans who are like, my sole job is to vet this person on people, skills, leadership, growth mindset.

Let me just pause there because I wanted to offer some examples of what to think about within hiring that builds on this concept that I don't see people doing.

So the three things you named to get key, do that again.

So we have growth mindset, curiosity, humility.

But is that the first part of the recommendation?

Or is that your personal?

Is that how you guys, those are the traits you personally look out for at Procore?

Or is that something we should tell people?

It's like, look, like if you're in a growth company, these are three key traits that you should vet for, foster, right?

And build your company around.

So it was definitely Procore.

I have a working hypothesis right now that this is a fundamental truth that applies across industry.

And so what I've come to find is, look, the only constant is change.

And so, you know, your ability to learn and grow is existential, right?

And so that growth mindset is really important.

You know, I've tried to spend a lot of time, because I struggle with prioritization truthfully.

And it's an important skill of an executive.

So shit, you know, oh, I might, I'm not supposed to swear in here, right?

No, this is an NC 17 podcast.

We're good.

Okay.

Okay.

I've come to believe that the most important trait of a leader is humility.

And I've spent a lot of time soul searching on this.

And my thinking is that it takes humility to want to keep learning, growing, to have the ownership, to admit that it's sort of all your fault, right?

By the time you're a C-suite executive, like you can't blame anybody.

You know, like that was on you, the market you're in, the product strategy you signed up for, even as a sales leader, right?

You should be in that room.

You should be influencing those conversations.

You should have built the relationship and the trust to have a say.

And you shouldn't sign up for a plan that you think is, you know, suicide.

And so to your question, curiosity, humility, growth mindset, ability and aptitude to learn, I think are fundamentals everyone should be vetting for and that they are things you can't bet for.

All right.

And then how do you now go through?

So how do we vet for it?

Those four things.

You know, look, one, truthfully, I'm a fan of just track record, right?

I think it's no guarantee of the future.

But by the time you're hiring a senior executive, I mean, they're usually, you know, known entities and you can figure out at least the extremities, right?

Do you talk to five different people and they all are like, that person's really curious or really humble?

I think you should look at the own experiences that you have with folks, right?

So like, is someone curious?

Are they asking questions?

Look at the way you described that human at TOPA, right?

You can tell there's a curious individual.

You know, for humility, I found that there are some cool questions I like.

Like, tell me something you changed your mind about recently.

And I don't always say the recently, I say recently when they're like, OK, well, seven years ago.

And I'm like, sure, seven years ago.

Oh, my gosh.

Right.

I mean, there goes the growth growth mindset, guys.

Seven years.

Everyone else changed their mind about having an exercise ball, but someone else is stuck on.

You know what I'm saying?

You pay attention to your surroundings and you can make observations.

Yeah, I really like the vest.

I really like the vest.

What can I say?

Look, our growth mindset.

I mean, I'm plagiarizing quite significantly from Carol Dweck's work at Stanford, and she's got a lot in there.

Right.

I wouldn't do it justice.

I'm a student of all these things, not a teacher.

But she talks about like, hey, I haven't learned how to do this yet.

Right.

And to build on that, I find the people who bring together curiosity, humility, a learning mindset, they usually have stuff they're working on right now.

They could tell you what they were trying to learn a year ago.

There's a lot of specificity to that.

And so those are some of the ways that I think you can bet for these fundamental leadership and people attributes.

So Dennis, one of the things that I'm hearing from a lot of people is that as they're hiring sales reps, they are really trying to determine their level of curiosity.

And I think this is especially true in like, sort of emerging markets, right?

Where you have to ask a lot of questions.

You have to be curious, not just about like, what is somebody trying to solve with the product that they're trying to buy, but like, what is their strategy?

And like, what is happening within their organization?

Where are they in their digital transformation journey?

What's getting them stuck and whatnot?

But I feel like there is a lack of, here's actually how you test for curiosity.

Because, you know, when you're hiring sales reps, like are they asking questions on the calls, right?

Like, but I think so much of that has become a canned portion of an interview process, where sales reps are just going to ask lots of questions.

And then you sort of get them in seat, and they're not all that curious.

They're like, hey, actually, I would need to follow this playbook, and I don't know why I would want to ask that question.

And it doesn't really seem like they're curious.

And I don't know if it's, I don't know if the problem is that they want to adhere to a process, or we didn't actually figure out if they are a curious person or not.

So, did we beat the curiosity out of them with a rigid process?

Or were we unable to determine in the midst of our evaluation cycle of them as an employee, if they were actually curious or not?

I'd love your thoughts.

It's hard, you know, and I think that, you know, to build on a sort of seed I planted earlier, I mean, I think this is why firing is so important, right?

Because you can vet for it throughout the hiring process.

I do think, and I know this is a horrible answer, but, like, curiosity sort of has a scent to it.

And when it's inauthentic, you sort of know, you're kind of like, are these like the same questions you ask everyone?

And again, I think that, you know, in addition to behavioral situational interviewing, like asking folks, what are some things they're curious about right now?

And like, where has their curiosity let them to passion and let them to excellence?

Again, even with sales reps, they've usually got some track record in the workforce and asking about that.

But truthfully, I haven't found like a sort of panacea where I'm like, hey, it's this thing.

What I have found is that if you build a culture of learners who are very curious, right?

Because you can't decouple curiosity and learning.

And if you make that the bar in your organization where you're like, hey, we don't tolerate people who aren't learning, who aren't curious and who aren't showing up great for your customers, you will get enough signals.

A lot of times, honestly, before onboarding is even done.

But if not, certainly, before their ramp period is over.

And that's where I think investing in someone's training and development, being specific and clear, we expect you to be curious.

Here are examples of what great looks like.

That hasn't been happening.

Coaching to that.

And then just if you've done all you can, then hey, part ways with that individual, do it beautifully and gracefully.

And then take the learning exercise and say, was there anything in the hiring process we saw?

If it's your culture and the environment that you have, usually that'll mean that whatever sort of good apple you put in it will rot in the barrel.

And that'll be its own debugging.

I sort of see this a lot, and this is why I'm so passionate about leadership, which is like, what is going on here?

Like, the segment's performing, but the Eastern region isn't.

And then I go do some skip levels and I'm realizing like, hey, this manager's not investing in their people.

They're too strict on process.

They're not working towards outcomes well enough.

And I do the coaching and all this stuff and it doesn't work out.

And then the only change I made was the leader in the Eastern region.

And that team starts performing.

And so you usually can see if it's a structural, like every sort of apple in the barrel, if that makes sense, is not performing.

You know what's interesting on this, you guys, is by the way, this year we had Dagnan speak at the GoToMarket.

So we had...

God, he was awesome.

He was amazing.

And he didn't talk about this exactly, but you're bringing it back to his...

When he initially was building the sales team there, I remember asking him, this was actually initially, it was like, he was in the hundreds of millions of revenue.

But I said, what does product led mean to you?

Because everyone was asking me about product led growth and he twisted it and said, well, look, product led means that my sales reps have the curiosity and desire to understand everything about the product.

And I was like, okay, so you didn't say product, Dennis, but that's curiosity and learning.

And he's like, and we interview for that.

I'm looking for that.

I wanna know that you just are gonna just love and embrace this thing.

And you can show me that that's what you wanna go do.

Really interesting, right?

Because I think, you know, there's no magic bullet for how you figure it out yet, is what you're saying.

But you will be better at it by making it a point of emphasis.

So he said it in a different way, but it's the same idea, right?

They're testing to see, for them, it was something about product, but it was still a test against the desire to be curious and to learn and to embrace and to do that in the interview cycle.

And then the second part is like, he said, look, I'm going to go out and personally certify every single frontline manager.

I love that.

Yeah.

Yeah.

And he's like, I don't want anybody who's just going to push spreadsheets managing my team.

I want people that love and embrace the product and can pitch.

They're not going to be able to train anybody if they can't pitch.

And so anyway, just a second example that sort of falls into it, not said the way you said it, but the same concepts and ideas.

Yeah, I mean, he's a really talented individual, and I'd love to get Matt's thought on this, but to build on what you're saying.

One thing I've encouraged CEOs to do as they're hiring executives is have a mix of stuff you expect this executive to come in and know and see how epic that is, right?

That's just kind of horizontal, like, you know, any marketing leaders should have a good understanding of how to create unique value based messaging that's really differentiated, really compelling, but also test and challenge for their learning and their curiosity towards your specific business.

And so plant some stuff in there.

It's like, Hey, we're struggling with this problem, and it's not a problem you could have faced before.

And I want to hear and understand how you think through solving this, and you'll learn a lot.

I like that one.

Yeah, so I've been building that in to the hiring processes I'm working with as I'm advising so that they get to see both of those things like, Hey, you should be really good at this.

I want to see some mastery, and you should be able to be curious, hungry, learn and think through this.

And I want to see that curiosity and truthfully, you see humility too.

Sometimes people come back in the process.

They're like, I don't know, I nailed it.

Like, here's all the stuff I did.

Like, would you mind helping me?

And I love that from a senior executive.

Yeah, I think what was interesting about Chris' story was it really plays on a couple of points that we've made during the course of this conversation so far, which is, you know, in a lot of ways when or in a lot of cases, when companies start, they start founder led and the founders are the ones who are going out and doing the conversations and they're sort of gathering information.

Hey, we're thinking about building this.

You have this other solution.

What do you not like?

What do you like?

What do you think about, you know, this thing that we're going to build?

And Chris went out and did that, which is unusual, right?

So they hired him on at a seed round and he was just having conversations.

That was his goal.

He's just have as many conversations as he could with people.

Yeah, eight a week.

And what I think that that did is it created a culture in sales of curiosity because here's the sales leader who, you know, X number of rounds, IPO success out the wazoo.

And it's still their leader was the original person who is going out and being curious and asking questions.

And I think sometimes when you transition from founder led to sales led or to we have a sales leader, we have a go to market motion.

A lot of that early curiosity goes out the window.

And now people are in seat as a sales leader, as a marketing leader for scale.

And saying things like I just want to have conversations with people and ask their opinion does not line up well to, I need to create meetings that convert to opportunities, that create pipeline, that create customers, that create renewals, upsells, cross sells, right?

So I think a lot of companies lose that in the transition from founder led to go to market and they didn't.

And I think that that might be a superpower that they have and part of the reason why their culture is the way it is.

That's amazing.

You know, I'm going to bring up one other thing and that will be our transition here.

You know, I don't know if you've seen this, Matt, or, you know, by the way, Matt's like a startup CMO, which I'm not sure what's more treacherous.

This the startup set seed or the startup marketing leader.

I think the CMO, having managed both of like, I'll put my vote towards, you know, yeah.

The amount of Teflon that they need to get is incredible.

And so but but the thing that Chris brought up, you've brought up today and in the past.

And I've seen from successful leaders is it's it sounds like a really negative word, but firing.

So like, Chris brought up firing so much in the keynote that the first question the woman asked was besides firing them, his third name, I forgot what the rest was.

But like, you know, he was, you know, a yeah, I forget what analogy you use with apples.

But I do remember you used to say no assholes.

And like, now you're sort of making even more scientific, which is I'm looking for specific traits that I build into the organization.

And then Chris was like, you know, if you don't do this and this, then I'm going to let you go.

And not he's not cold hearted.

He's the one in the night.

I mean, you two guys are two of the nicest guys I know.

Well, of course, Matt, but like, we don't address each other on the ship.

Yeah, you're right.

It depends.

And then, but like, you know, multiple leaders have said the same thing.

And especially as you're building and growing.

I don't know, Matt, you picked that up too.

You were nodding vociferously until I insulted you.

So like, are you?

Yeah, no, no, no.

Yeah, I mean, I'd love to get.

So Dennis, you brought up hiring and then you said, but firing might have been the more important thing.

Dig in on that, because that's really interesting here.

And we'll ask questions after you sort of lay out your thought process.

Look, I'm willing to bet that leadership is the most important thing to winning, that training and development is super important.

I'm not quite ready to plant the flag that firing is more important than hiring, but it's something I'm playing around with.

And, you know, truthfully, part of my thinking is like, hiring is like pretty fun, right?

Like it's awesome, it's exciting.

You're looking forward to getting these people on board, right?

At least you should be, you know, making a hire.

Firing sucks, right?

It's the worst part of the job.

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And I used to tell folks, like, you're not actually a manager or a leader, right?

You sometimes, you know, we were big on promoting from within a broker.

And, you know, we'd promote these managers and they can be like, I'm a leader.

And you're like, you are.

But actually, your first day as a manager or leader is the day you let someone go.

I mean, for me, it's treacherous.

I take it really personally.

I feel like I brought these folks on to the organization.

I always know things I could have done better to make them successful.

And frankly, I have a lot of examples where, you know, I managed wrong or I hired wrong.

Either way, I held on too long.

And the cost to the business was so significant and so tremendous.

And what happens to the culture when you have someone that's not performant, they're not putting the work in, they're not learning, they're not curious, right?

And everyone else around sees that it just degrades so fast.

And then, you know, for us, we were so kind of brand and customer obsessed and the trail of death and destruction internally and externally that, you know, bad field sales leader can leave, it's bad.

And so for me, I, you know, I started to realize like, OK, there's all that.

The other side of it is like, look, I'm an immigrant to this country.

Like I have so much to be grateful for that people just gave me an opportunity.

And some of my very best hires and you've seen these people, Craig, right?

Because we've worked together for so many years.

They're not the person you would have thought should have gotten the nod.

And so I'm a big believer that if you're really good at firing, right?

And that doesn't mean you treat people poorly.

That's no.

Yeah, of course.

Yeah.

But if you're really good at firing, then you can give people a heck of a lot more opportunities, right?

And people will amaze you if you give them the opportunity.

And so for me, I've just come to appreciate like firing might maybe be more important than hiring and that there are steps to do that exceptionally well.

And I'm going to keep coming back to my like training and developing thing.

Like you should be training and developing your folks to understand.

Am I either promoting this person or am I firing them?

Yeah, I would say for me personally, like rifts aside, and lots of people experienced rifts over the course of the last couple of years, I want to set that aside and put it in its own bucket.

But I have never, the only thing that I've ever regretted in firing somebody is not doing it faster.

I've never regretted firing them and been like, gosh, I wish that person was still here, never.

And that doesn't mean that the process of letting someone go isn't stressful, isn't painful, isn't emotional.

We're human beings, that's not, that's no one's favorite thing.

But I have never regretted letting someone go unless it was, I waited too long to let them go.

Same.

Yeah.

And again, we'll caveat everything with, it sounds cold, but these are not cold people.

And the compassion by which you handle this scenario is really important.

But yeah, no, I think that's right.

I mean, you know, and by the way, I would just say just on a side note to get soft is like, oftentimes, it's the right thing for the person.

I was going to say that I was totally going to say that.

Yeah.

Yes.

Yes.

Yes.

Oftentimes, it opens up a great next opportunity for that person.

And if you're doing it with dignity and you're like, hey, you know, you can still be a reference for them in cases where you can, that can be a great thing for them and it can be a real learning experience.

Sometimes, you can't always do that though.

Yeah.

No, for sure.

Yeah.

Okay.

I love that.

And then, all right.

So the learning and development, this was intriguing because you spoke last year at our Good Work at Summit.

And what was really interesting was that sort of how your steady state and how you develop leaders fit those traits that you're looking for, curiosity and learning, et cetera.

And so, I'd love to hear about that because that also, so we have all these sort of segments of your initial statement.

This is also an area where we don't spend enough time thinking about on the people side, which is like learning and development is very traditional.

It's like, can you go through the new products and all the sort of various features and functions and enhancements?

But you talk about something different, which is continuing to sort of foster those traits that you believe drive a growing organization.

So, I'd love to hear more specific examples around that and how you built the learning and enablement environment to support those things.

Gosh, I can go a lot of places with this.

So, maybe if you two could help guide me on what might be most useful.

I mean, I've, you know, my last several years at Procore poured all my energy into learning and development around leadership, right?

It doesn't give you a pass on your technical skill, right?

So, I mean, if you're doing, you know, brand marketing, like you got to be good at brand marketing, right?

But most of the folks I was working with, and again, because it was my mental model for how could we drive Procore to repeatability and winning, right?

Was around developing leaders.

And so, I think there are a set of core competencies in addition to attributes, right?

So, we talked about the attributes already that, you know, enable someone to be a great leader.

And I think the sort of, you know, kind of place I keep talking about with folks that they're like, really?

And I'm like, I mean it.

And I mean it because like, I'm not very good at this and I've had to work to get better at communication, at how you set a compelling vision.

Like something like relationships is a repeatable process that you can do, right?

People can tell when you truly care deeply about them and you've taken the time to understand their hopes, their fears, what they appreciate the most, right?

Trust is like the currency that you operate around as a leader.

So like you certainly, some people are like, well, I don't know how to build trust.

I'm like, well, one, I mean, you got to do what you're going to say you're going to do, right?

Yeah, yeah, yeah.

Right.

I mean, and certainly we know how you can lose trust fast, right?

And there are variables that I've learned to play with like, hey, when things aren't going well with my leadership team and I want to develop, I'll increase the frequency of communication because just, you know, similar to marketing, right?

Where it's like reach and frequency matter.

The same thing happens with people like, no, no, I've talked to this person lots and lots of times.

And so, you know, for me on the developing and training leaders, like there are some things that I'm like, I think everyone can do this, right?

Can everyone get better at communication?

Yes.

Can everyone get better at building and managing relationships?

Yes.

Can everyone get better at strategy and or prioritization and driving execution?

Like, I think so.

Can everyone get better at decision making?

Right.

And like, there's so many of these frameworks.

I can talk about the one that like we used at Procore that we liked.

Can everyone get better at resolving people problems?

I think so.

Right.

Like, you can seek to understand before being understood.

You can escalate things in a way that are awesome instead of not so awesome.

Right.

And I can talk about these things.

So I don't know if you want me to talk more about like sales competencies and how we built and enabled those.

But, you know, the thing that I think isn't being done, right.

The thing that I'm like, hey, this seems kind of wrong is the investment in repeatable ways to scale and develop leaders.

And those are some of the examples of what goes into like a leadership development program.

I'll let Matt sort of choose what he wants to dig in on.

But can I just tell you guys a funny one I thought of as you were talking?

So Keenan, you know, years ago, was talking about sales leadership with me.

And he's like, do you know, I was a sales leader for 20 years before I became a consultant.

And nobody ever asked me about my leadership ability.

But this is my point.

Why did you say that earlier?

We were talking about Larry.

I just obviously it won't be because, dude, you start talking to him like, do you like these things that you're talking about or things that we neglect?

Yeah.

Oh, yeah.

Yeah.

Well, the irony is there are also the most important things.

Sorry, Matt.

Sorry.

I get fired up.

Yeah.

Yeah.

Yeah.

I mean, I think one of the things is like, I believe wholeheartedly, you and I had a conversation the other day.

I believe wholeheartedly in the concept of developing strong leaders and also developing really strong second line leaders.

I think that is really important.

The thing that I think a lot of companies get wrong is, there's certain bits of information that they don't like to share with the company because they think the company doesn't want to hear it.

I don't mean like they're like, oh, what's the ugly truth?

What's hidden behind that closet in your living room?

It's a lot of dirty clothes or whatever.

I don't know what it is, like skeletons.

But one of the things that I found so beneficial during my time at Marketo was how transparent Phil and Fred and Bill Bench were around.

What was actually happening at our company and the process leading up to our IPO?

It's like, hey, we filed our S1.

This is what an S1 is.

This is what a process looks like.

This is what a road show looks like.

And I'm like, sitting there and I'm an SDR leader and I have no business being explained this to me.

And there's no reason why I should have been in the room for that other than they wanted to share that process with us.

And like, I learned what all those things meant.

And then later on in my career, when I was at a company being acquired by private equity, I got to learn what that meant because they were very transparent about the process.

And then, you know, as I was exiting companies as an executive, I knew what to do.

I knew what to look for.

And it's like, how do you get that level of experience?

You go through those process and people tell you the details about it.

And like, I understand developing leadership, but like, developing leaders for, you know, 10 years in the future starts with giving people access to this kind of information because it's really not out there.

You know, we're training our people to book meetings and send emails and, you know, ask for the clothes.

And like, here's what colors are complementary.

And, you know, put this above the fold and here's the CTA.

Like, that's the type of stuff we're training people on.

But like, we should also be training people to become executives.

And they don't just have to go to HBS or, you know, Stanford and get an MBA somewhere to learn this stuff.

They should be able to learn it by working at these awesome companies that they have the opportunity to work for.

I mean, we had this at Procore.

We had a series called Metrics That Matter, and it was essentially walking folks through a kind of up and out view of how we would be able to fund and enable our mission, our product strategy, you know, everything that we want to do for our people by delivering exceptional metrics and outcomes.

And we talked about, you know, rule of 40 or rule of 50.

We talked about, you know, gross margin.

And we tried to have support reps that understood like, hey, when we're trying to make you more performant, it's not because we want to obsolete you, right?

It's because you drive gross margin and we want you doing your highest and best use.

And it's really inefficient when you're doing some crummy manual process.

So I think that that like culture of learning and training and development and teaching people the things that matter most at the highest levels is what creates a generation of leaders.

And like, it's also, you know, the, the tactical suggestion I would offer here is like, it's actually not a ton of extra work to do that.

You're already kind of thinking through that.

You're already like, and so now it's just package it up.

It's like the same way.

I don't know.

I'd love your guys' thoughts on this, but you know, with sales training, sometimes it's like, let's just get like the best rep or the best manager who does this and let's have them record what they do.

And you know, these days, and this is the kind of, you know, things are changing fast.

These things, now you can have an AI grade someone's certification and it's pretty good.

You know, right?

And so I do think that, you know, the way I kind of framed this was like, look, you know, the more you solve the most important problems in the company, the more you matter.

Yeah.

In order to understand the most important problems in the company, you have to understand business.

You have to have a financial acumen.

You know, and these are all the things when we talk about executives.

So you're like, look, this is how I can tell if someone's curious and hungry.

A lot of sales leaders, marketing leaders don't come up knowing this stuff.

It doesn't mean they don't have the potential to learn it, but there's a learning objective and something you can check back in.

And by the way, they're going to be so much more understanding where you're like, might have to do a riff, right?

If they truly understand the most important metrics in the business and how this does or doesn't enable you to keep driving the mission and mission forward.

Yeah.

So, but like what if for leadership enablement, let's talk about Procore at the hundreds of millions of bucks.

What does enablement mean?

I mean, are you talking about is it training it like, you know, and I know not traditional training, but I mean, like a lot of these things you're talking about.

What's an enablement program to foster these things?

And I know you can talk about any of the various traits that you'd like your leadership team to have.

But like, I want to be able to sort of think about, well, what would I recommend to to?

We've hired well, we've we've done these things.

We know what we want.

Like, what do we do to foster it?

Like, what is an enablement program look like?

Do we just fire a bunch of them first?

Then we do this?

No, no, I'm kidding.

I mean, according to the last couple of conversations I've had, maybe.

But like, yeah, no, we've got people in the seats.

So, you know, Procore, we had a leadership development program that kind of started all the way from when we were interviewing folks.

And it included our mission, vision, values, a deep understanding of our corporate strategies, some core competencies like relationship building, crucial conversations, radical candor, all the stuff that's out there.

You know, maybe it's a little bit of a recency bias, but in the executives I'm working with now, and what I think was the underpinning of what we did at Procore was we tried to be purposeful in people's learning and tailor it towards outcomes and winning.

And I know that sounds like some jargon, right?

But like, I'll give you an example.

You know, I have an executive right now, and this individual is like phenomenal in terms of intellectual capacity.

They get the company, they get the culture.

But you know, they didn't come up through heavy enterprise selling.

And so now there's a journey of like, hey, we've landed these logos at this company, and they should be 10 million ARR logos, right?

And like the company strategy is get, you know, 100 customers to pay us 10 million a year.

That's a billion in ARR.

And by the way, we already have two examples of this.

How do we make it proven and repeatable?

And so I'm chatting with this executive and I'm like, okay, so what are the things we need to know in order to be able to do that?

And how are we going to make sure we go learn that and start chunking it out?

And we came across, I was like, well, first, let's get some mentors who have done this really well, right?

In addition to that, are we going to build a leadership team that brings together some of these capabilities?

You can hire frontline leaders who are really epic at focusing on accounts and customer expansion.

And then some of these other fundamentals come in, like for this leader, which I actually love because I'm similar, they're like, well, I start the trust bank at 100, right?

With everyone.

And I'm like, that used to be me.

Now, I started at like 70 and I build in ways to build it up or down, right?

And honestly, for the same reason as this leader, because when you started at 100, sometimes it drops to zero a lot faster.

And that's pretty crummy, right?

And so at any rate, that's the purposeful learning we're doing to achieve a business outcome.

And we're just chunking it out as we're like, hey, what is the situation here?

And how come we're not landing?

And I know that's not as much of like a soup to nuts kind of framework, right?

And I think those are out there, but I found it's more appropriate and effective when it's very purposeful.

And it's very quick in terms of the loop of driving more revenue growth, more customer success, more employee engagement, etc.

Yeah.

But was that like a terrible unanswered?

No, I don't think so at all.

I think like the terrible answer to that question is like, you put all executives or all leaders through the exact same training, and you go to, you know, Boulder, Colorado, and go on a hike and climb a peak and do a truss fall for rock.

Yeah, exactly.

Exactly.

Like, that's what doesn't work, but that's what comes in a package.

Like that comes in the package when you go, we need training.

It looks like that.

I think where people miss is different people need different things and different people are in different parts of their journey.

And they come from certain strengths in their background, and they have certain gaps in their in their tool belt, you know, and you need to go fill those gaps, because that's what's going to make a better business, a better leader and ultimately a better business.

So whether that's the sales leader who's like, hey, this guy's great, he understands the space, or she, she's a high velocity leader.

And now we're moving up into the enterprise and things are going to change.

So we have to add that skill to that person's tool belt, or it's a, you know, it's a product leader who's killer at building and delivering on a roadmap, but like is not a great, you know, presenter.

And so they don't distill the information down from their vision well to the rest of the organization.

You know, those two different types of people don't need the same training.

And in fact, if you give it to them, you're not going to do much in terms of pushing the needle for your business.

But if you think about where those individuals need training and you provide that kind of training, that's when I think you really accelerate your business.

We had, you know, what's funny is we had it made fun of Trust Falls until just now with 10 minutes left.

Yeah.

Well, because there's there's on Dennis's scale, which is like, well, we have good culture and you know, is like they start with the foosball table.

The level two is Trust Falls.

What we're saying is neither of those, you know, like we're saying is completely different.

But Trust Falls is part of the, oh yeah.

Well, we do, you know, they don't say we do Trust Falls, but we went up to the Redwoods and, you know, part, we went on a hike in the Trust Falls is a great example.

Yeah.

So, but like, like what, could we go through one role?

I don't know if you could do this, where we work backwards from the outcomes they're trying to achieve and then like an example of how you've modified a program to help them get there.

What did that, what did that look like?

Yeah, let's try it.

Give me a role.

What do you think?

Well, I was thinking you already sort of started there, but like, you know, you're it could be a sales or marketing person that's trying to elevate you into a new segment.

Maybe that's a good one in a common theme.

Is that a good one?

What if we do marketing?

Right.

And I mean, we were just talking about how hard the CMO is.

Like I the tenure seems shorter than a sales leader these days and conversations with marketers.

It seems like a worse gig.

Ten years shorter and the therapy bills are are higher.

Yeah, for sure.

Yeah, because we're we're emotional creatures.

Oh, geez.

Passionate.

Blame yourself.

Blame yourselves.

Yeah, you're supposed to blame the market, not yourselves.

But I appreciate it.

But passion's an emotion, Dennis, passion's an emotion.

Words matter.

Words matter.

Framing matters.

So look, you know, I think when I get a marketer online, especially again, most of my way too many years at this point are senior leaders.

Right.

You know, I think there are core areas of excellence in marketing that reflect on the technical skill side.

Right.

And no one person's going to be a master in all of those.

But I do think you have to have a working knowledge of those things.

Right.

And so like you two helped me out here.

But I think the pillars we could quickly align on right is demand gen, product marketing.

I mean, those are probably two really important crown jewels.

Depending on the marketing organization, comms and I would maybe frame internal comms, external comms and IR as some branches under that.

Brand would be another one.

I've only gotten more and more obsessive about kind of customer experience and being able to own and drive the entire customer experience.

Right.

And so we may say, okay, these are the technical areas.

Right.

Then I think there's the leadership things, right.

We talked about those.

And then there's probably the company specific things, right.

Our industry.

And so if I was trying to develop a marketing leader, and actually let me add one more that probably has been the biggest thing.

I think marketers, the things marketers are doing wrong, truthfully, is setting and owning the narrative and being able to say, like, hey, I have ownership of this metric and outcome.

It doesn't mean I can get there alone.

Right.

We all fail if, you know, product isn't working, if sales isn't firing, but like, I'm going to do this thing, whether it's pipeline, whether it's, you know, never tension, whatever thing is most important.

Right.

But how you prioritize and drive the narrative, because the thing I've noticed with marketing is like, everyone thinks they're a marketer.

The idea of factory is more robust for marketing than it is even product, right?

And the process of being like, that's awesome, but like, here's the most important thing.

Here's where you can hold me to in doing it.

So, you know, look, to answer your question, Craig, I would kind of look and say, okay, we've got the leadership bucket, got things underneath it.

We've got the marketing excellence bucket.

We've got things underneath it.

We've got the company specific bucket.

We've got things underneath that.

Now I'm a big fan of having folks self-assess, because I actually think that's again another way to test that humility and to test someone's ability to kind of self-heal.

And so it's like, hey, ideally the marketer would come and be like, I think these are the pillars, right?

If they don't, cool, no problem.

Like, let's help guide folks.

Once they do that, then it's like, hey, let's go through, because I love Matt's comment on like, you got to meet people where they are and where it's going to be helpful.

Otherwise, it's too much and it's not effective.

And so it's like, can you self-assess, scale of one to 10?

Where are you the most awesome?

Where are you the least?

Then can we overlap where you're the most awesome and the least awesome with the business need and where we're going to be able to get the most ROI?

And now can we take 30 days and let's start chunking this thing out and let's show how fast you can get to baseline.

You can get to good.

You can get to great.

And so that would, does that kind of answer?

That's great.

Yeah.

I love that.

That was, I realized that most of my questions are really bad.

I realized how big and broad that was.

No, that was a good question.

I think that one of the things I admire the most about working with you is it gives me an opportunity to actually get better at understanding these things.

It's like your question was, hey, the Procore, you have that clarity or is this something you're understanding in hindsight?

And they're just beautiful questions.

So no, it wasn't that.

It was, I could do better at answering it.

That's great.

All right.

So you've fulfilled the, what's the market doing today where they could think differently?

You fulfilled that part.

It was also incredibly engaging and conversational.

So like that is what we're trying to do at The Transaction.

So I gotta say, I just want to say it, man.

It's great to see you.

It's great to hang out with you.

We basically recorded catching up with you and thanks for coming on.

Yeah, I keep pumping up the pride in the 805.

I love that.

We're both from the same stop.

I'm actually from the Bay Area, but this is now my forever home.

So I love what you're doing.

I appreciate you guys.

It's one of the greatest places on Earth.

Thanks, brother.

All right.

See you guys.

All right, guys.

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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