You Built It, They Didn’t Come — Now What? With Nate Broome

Nate Broome, a key architect of Outreach's early success, shares hard-won insights on navigating the complex jump from selling an SMB point solution to an enterprise platform. He highlights the common pitfall of assuming past success will seamlessly translate to new markets, emphasizing that strategic planning must be paired with teaching reps how to actually execute the new motion on the phones. The conversation tackles the evolution of outbound sales and the fading effectiveness of generic cold email sequences. Nate argues that while tools have proliferated, sellers have relied too heavily on dashboards and volume-based KPIs rather than the quality of work within those metrics. True success now requires authentic deal coaching, a shift away from spreadsheet management, and an omnichannel approach that leans heavily into brand awareness. Furthermore, Nate underscores the importance of the 'social contract' between leaders and their teams. By embracing a culture of coaching and focusing on reps' long-term career development—a 'tour of duty'—leaders can foster deep loyalty and high performance. He concludes with a powerful reminder for revenue leaders navigating tough markets: you are not alone, and reaching out to peers is a vital survival mechanism.

Discussed in this episode

How transitioning from a point solution to a platform requires completely re-tuning enablement, content, and business acumen.
The necessity of explaining the 'why' behind company strategies so sellers understand how transformations benefit both the organization and themselves.
Why hubris is the biggest obstacle when entering a new competitive space against established giants like Gong.
The distinct difference between brand awareness and demand gen, and why sales leaders must give marketing the space to build the former.
Why giving away the product or doing prolonged POCs might be necessary to earn early proof points in a new market.
How the over-reliance on generic cold email sequencing created a generation of sellers managed by dashboards rather than actual skill coaching.
The difference between pipeline inspection, like checking CRM dates, and genuine deal coaching that actually moves opportunities forward.
Why establishing a 'tour of duty' mindset helps align rep career development with company goals, even if they eventually leave for another role.

Episode highlights

0:00 — Introduction to Nate Broome and Outreach's growth
2:15 — Transitioning from point solution to platform selling
4:30 — The importance of explaining the 'why' to sellers
7:45 — Balancing transparency with the ugly truths of leadership
10:20 — Overcoming hubris when entering a new market
13:10 — Building brand awareness versus driving demand gen
19:30 — The downfall of generic cold email sequencing
23:45 — Dashboard management versus actual deal coaching
28:10 — Navigating the fear of being labeled a micromanager
31:00 — Creating a 'tour of duty' for sales rep development
33:45 — Rapid fire: Leadership mistakes and hard truths
36:20 — Why revenue leaders should never navigate challenges alone

Key takeaways

Teach reps how to execute the strategy.
Explain the 'why' during major organizational transitions.
Brand awareness requires time and distinct metrics.
Deal coaching goes far beyond CRM pipeline inspection.
Build a 'tour of duty' to accelerate rep growth.

Transcript

Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagine. We have Nate Broom with us today, who was a key architect of Outreach's success, building their commercial team which represented the largest percentage of revenue throughout his six years there. He moved on, most recently led sales at this little company called Captivate IQ that you might have heard about, uh, which is one of the leaders in the compensation management space, helping them transition and navigate the move that so many think is so easy, but actually isn't, and I'm sure we'll talk about this from SMB to Enterprise. Nate, thanks for joining the show, man.

Uh, thanks for, uh, thanks for having me. I'm excited to be here. So, you've gone through a lot of different iterations and changes, especially from SMB velocity type sales. Take us back to a moment where you felt like your, your go-to market strategy was out of control and then like what were you thinking about, like, how do I resolve that out of controlness feeling that you had?

Yeah. Yeah, I mean, like I think most sales leaders, a few of those just pop to mind. I think the, you know, the the the biggest one that really stands out to me was probably like later stage outreach, right? Um, you know, as you as Adam mentioned, had an incredible six-year run there.

And, you know, to a point, we were selling a point solution, like everybody knows, we're selling sequencing, right? And then eventually we evolved into selling a platform that included, um, you know, a Gong compete product, uh, included forecasting, some data analytics. And all of a sudden, I had SMB and mid-market, maybe junior-ish type sellers trying to sell a platform after selling a point solution for so long, right? Um, and so right away, like you have to re-tune the enablement, the content, the decks, um, the business acumen, you're solving bigger problems, there's more stakeholders, what have you.

And, you know, ultimately, um, you know, how we got through that moment, uh, and how we ushered in kind of this platform selling and outreach was was really aligning people on, um, you know, on the overall strategy, what we were trying to do, which is trying to solve more problems, right? And, you know, the framework that I've used for that, and I'll I'll I'll drop it here, but happy to answer questions is, you know, first and foremost, we we aligned everybody on like, hey, here's the strategy, here's what we're doing as a company, here's the direction, uh, we had to get everybody clear on what their part of the strategy was, right? Um, and then most importantly, we had to teach people how to execute the strategy, right? I've seen this too many times where people moved make the move to platform or more of a sophisticated selling or solution selling, and then they do all the planning, the strategy, the ICP work, you know, Adam, you're familiar with this, right?

But like they they do all the stuff, and then we forget to teach people how to actually do the job on the phones. Right? It's wild that just happens over, over, over. So, that was the the big thing for us and and how we got through the to the moment.

And and I think one of the things that you were saying is like the why. So, I'll review. The why is like super important. I was already talking, dude.

Yeah, yeah. Go go go ahead. We'll go, we'll go to the why, right? Uh, Cynic, right?

Start with the why, right? Like that's it, right? So, um, yeah, you know, look, um, the I was talking to somebody yesterday, one of my advising clients and, um, you know, one of the things that, uh, we were talking about, uh, you know, related to the why, um, was that sellers are really can be really predictable sometimes, right? They're going to sell what's easiest, what's fastest, what makes the most money, right?

And sometimes, you know, while you're transitioning to any sort of, you know, transformation within your organization, um, it takes a minute for the sellers to catch up to that, right? Maybe it takes a minute for the comp plan to catch up to that, or the strategy, or the this, whatever, right? And so, it's really important that, hey, you talk everybody through, here's what we're doing, here's why we're doing it, here's why it matters to the organization and our customers. And then, oh, by the way, here's why it's going to matter to you, right?

So I agree that the why 90% of the time, sadly, is not explained, right? Whether it's a CEO, a revenue leader, uh, a frontline manager, um, oftentimes it's literally like, okay, go do this. This is what we have to do. Why?

Well, because the CEO said that this is the goal. Um, Dale tells me all the time that he wants me to do something, I say, why? And his answer is, because I said so. Um, and I I tend to oblige.

But generally speaking, I've found that you get so much more when you do explain the why. Having worked, you know, native at all different sized companies, how do you balance sharing the why with not oversharing? Because that that's tough, right? Like it's you you want to give the why, but sometimes the why isn't pretty.

Yeah, and oftentimes the why How have you balanced that as a revenue leader? Yeah. Man, that's tough, right? Because especially in the last like handful of years, the the why has been to stave off competition, to uh, move from VC burning money to profitability and efficiency, uh, to uh, potentially riffs in the organization.

So, the the ugliness of it and and um, the heartache of it is is real. Um, you know, I think for me, you had a post about this today, Adam, uh, and I'll I'll I'll shout that out. It was about empathy, right? Is that like, you know, I I think for me it's that you can only do so much, right?

And I think if you if you're very consistent, if you're building up that those equity points with your teams, with your leaders, um, you're doing those heart check-ins, what have you, that sometimes you can explain everything perfectly and you're still not going to nail it, but there's an inherent trust in the decision-making, the track record, what have you, that can help kind of guide the moment. It might not make it any easier, it still might be messy and clunky and what have you. Um, but that's that's when I found to at least get me through the moment. Now, whether I'm sure I've had a hundred examples where I've failed miserably, um, and messed it up and mucked it up and and I've had good examples as as well, but it's really empathy and meeting people where they're at to to get through that moment.

And I think the last thing I'll say is that, you know, look, most of my leadership career, I've been managing and leading, um, mid-20 year old, uh, sellers. Right? So there is a reality they've never seen some of these cycles that happen within organizations before. And so, you just got to like continue to like guide them and mentor them through the through the moment.

Yeah, I think that's I think that's a big challenge with a lot of even leaders. Like, you can be a good leader and still not know how to coach, still not how to pull through with empathy, the transparency that's needed to actually be successful. Um, as you look back in let's take outreach, um, since we were kind of going through that process. There must have been a fairly big gap from when you were going from a point solution to your enterprise, uh, motion and your platform motion.

What was the biggest gaps that you guys saw? Was it that it was the wrong team selling the, you know, or you guys didn't, you know, do the proper, uh, transition to training them and almost like re-onboarding them from the, uh, from the initial process into like a a platform motion. Yeah, I would say, we eventually figured it out, but it was it was clunky in the beginning, right? And I I might get some fire techs after this, but I'll I'll say it anyhow in in the confines of our our small circle here and whoever's listening, right?

Our biggest challenge was hubris. Right? You know, when we were selling a point solution, we had one primary competitor in in Salesloft who did a masterful job, uh, really strong go-to-market. It was a pleasure to compete with them because they they kept the bar high.

Right? Um, but we, um, we did really well. Right? Uh, yeah, we were doing really well in in our niche, in our space, uh, we were all thought of, um, with our our sequencing and you kind of that orchestration tool that we had that it was our point solution, our our first real product, right?

Um, and then when we ventured into Clary's world, into Gong's world, into Everyone's world. Yeah, everyone everyone's world, right? All of a sudden it's a knife fight on multiple fronts, right? Um, we just assumed that we were going to have the same type of success and momentum, right?

And really what we were we're selling a whole new product, whole new personas as we talked about. And that initial hiccup that we had was hubris, like we're going to turn this thing on, it's going to fly out the door, what have you. And we had, don't get me wrong, we had success, we had build it and they will come. Yeah, build it and they will come.

And we definitely we had success, but there was there was definitely whatever we thought our transition period was to enable the teams, to educate the market, to create brand awareness and all that type of stuff. It was it ended up being two or three times longer, right? Um, in part because we didn't start from a place of feeling like we are on our heels or that type of thing, right? And so, eventually we learned the lesson really fast, but we did have to learn the lesson.

Yeah. I I want to double click on that. You you said a phrase, two words, um, that Dale and I talk about a lot that I don't think people put enough stock into, um, or realize is as important as it is. Dale, what's do you do you know the phrase I'm going to say?

I'm going to put Dale on the spot. No idea. You say a ton of phrases, so who the heck knows what you're going to say? Fuck off.

Brand brand awareness, Nate. Yeah. Um, you know, there there is I find whether you are at one point the behemoth that is or was outreach, whether you are, you know, Dale and Adam startup, um, I don't think people put enough emphasis on like you don't have a brand. And you can't just build it, build it.

I I don't really care how good your product is. Let's assume you have a product that's going to solve whatever the problem is. You're not going to call Dale, tell them you have this product and Dale's never heard of it, never seen it, has no idea what it is and he's going to turn around and be like, shit, man, I've been waiting for this call my whole life. I can't wait to talk to you.

Yet, so many founders, CEOs, revenue leaders think that, oh, just do some outbound and like if you do some outbound and get outreach and put people in a sequence, um, that, you know, you're going to build go-to-market. How do you properly build and compound on brand awareness? Oh man. loaded question.

loaded loaded question. Uh, I feel like I need a marketing counterpart here to help with, you know, whisper sweet nothings about brand awareness in my ear. Um, as a Yeah, you know, I I think there's a I think there's a couple things to it, right? I think is one is you've got to have a high bar for the product.

You got to have a high bar to take care of your early adopters within your customer base, right? Those those people that are on the outer edges of you your product and and uh, their advocacy or their feedback back to you, right? And so you're taking care of the kind of core, right? Um, you got to get case studies.

Like, you got to get proof points soon and early, right? That might, I think, maybe tactically speaking, give a tactic here is that you might have to give the product away. Right? You might have to go do prolonged, uh, you know, proof of concepts, um, you you you might just have to beg, borrow, and plead to get badged into their corporate headquarters to like, you know, ushered along, like get access to the reps, whatever the thing is, right?

Uh, but Do you mean people do this thing called in-person sales and actually go places? you're hopping on a flight tonight to to do the same thing, right? So, I think the Because we fundamentally believe that some of the things have to be done in person. Yeah.

I I think that, you know, look, I I think Yes, there's a place for the in-person and face in the place for sure. So, but I think that's you've got to you've got to create that that you got to do that initial work, right? And then you've got to have a really good, um, go-to-market, uh, uh, you know, strategy and execution and orchestration amongst, you know, your SDRs, your marketing department, product marketing, you know, sales, and how sales is communicating to, you know, get the word out there, right? Of like, hey, these are the types of successes that we're having.

We may be the new kid on the block, but, you know, uh, we're formidable, we can provide value, um, let's let's we're an alternative to whatever was going on. And I think we, you know, more than anything, like, um, when we entered like the call intelligence space at Outreach, right? Look, nobody has better brand equity, brand awareness than Gong. Right?

Gong is like universally beloved, right? And rightfully so, right? And and so when when we're inching in on their territory, um, they've got a high bar that we've got to we've got to cross a threshold on to to to provide value. So, um, so yeah, that's I think that's part of it.

And then, at a sales leader, when you're marketing the as as one last thing I'll give here, is as a sales leader, when your marketing leader comes and talks about brand, you got to give them the space. Because when they're talking about demand gen, it immediately equals leads. Right? Or has some sort of ROI on leads and opportunities and meetings.

When they talk about brand, that doesn't necessarily translate to pipeline right away, right? And so, sometimes it's it's hard for a sales leader to put their their, you know, to you know, to put their mind wrapped around that, right? But it's really important the farther down funnel you get, the bigger you get, new product, platform, all that stuff. I just I just tell sales leaders, if uh, if you don't understand awareness or brand, then just try to do cold calling with zero marketing, zero outbound, zero awareness of who you are.

Like it's never gonna happen. I got a funny I'll tell you can but so many people do it and think it's gonna work. I got a funny story like about that. So we uh, so when I first uh, joined Outreach and hopped on that rocket ship, I came in as a sales development leader.

I was the first external, you know, SDR leader into to Outreach, right? So I I was, you know, leading a team and what have you. Did you have Did you have blue hair? I did not I was not I did not have blue hair, uh, but Sam Nelson was part of of the one of my early teams and, uh, so, you know, Sam Nelson's kind of got the Kobe Bryant ask thing going, right?

Where it's like, you know, all these stories about Kobe Bryant being just a maniacal worker and doing all the little things and being a grinder, uh, all those stories about Sam are true. So, this community that he's built and his expertise are like it's it's well-earned and and uh, and forged in the fire if you will. But yeah, when we when we first started going though, when Sam was part of this team, you know, we were calling CROs and, you know, one, we probably called you Adam, like it's like, one was that like, hey, look, what is sales engagement and who is Outreach? Right?

And like that was like those early days of cold calling and tell you what, it's really hard to book a meeting, um, and get somebody's attention if those are the first two questions out of their mouth. Hard. People buy from people. That's why companies who invest in meaningful connections win.

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com. Well, and and you're in in your building kind of a a market. Like you're building a brand in a market, which is also difficult. I used to, uh, I ran the sales, I ran sales for a a company called KiteDesk, and you've probably had Julian Sweat that was, uh, in your group.

She used to work for me. Oh, yeah, yeah, yeah, yeah. I and the whole Campa team. Yeah, those were, yeah.

Yeah. Yeah. Yeah, that's funny. That's a small world.

It's um, you're right when you when those are the first two questions, I'd imagine it's very very hard to book a meeting. And now, you know, you have companies like Outreach, Salesloft, Gong, that have this brand recognition. And I think reps and like, we'll call it the next generation of revenue leaders who are going to go work at some startup because some founder thinks because they worked at Gong that they're great to go lead their startup. They're not.

Separate conversation we could have. Um, have all this brand recognition and it's very easy to call a CRO on the phone when you're calling from Outreach or Salesloft or Gong. And while you may or may not book the meeting, you'll at least get the time of day. They know who you are.

And then you go work for, you know, Nate's startup and you want to book the meeting for your new conversational intelligence tool and they're like, who the f are you? You don't exist. Yep. Yep.

Yep. And these reps struggle with that, right? It's I I I often say to revenue leaders and founders, it's very easy to go from no-name startup to big company. Like your adjustment is, you're going to have a lot more policies and procedures and you can't just wing shit, but the brand recognition part, your job's going to get easier.

Going from an Amazon or a Gong or a Outreach or a Salesloft to Bob's startup, like I I don't I've yet to see very many people who can successfully go backwards like that. It's so hard. It's so hard. You've got to it's a mental shift for sure, right?

It's it's not saying that it can't be done, but like, um, there's a lot more examples of it not being done well and people, you know, flaming out by making by making that move and you I I think and by the way, I think it in our market right now, like in just the the marketplace, I think that we are actually going through that type of moment where you had this generation of call it, I don't want to call it Zurp era, but call it like pre-AI technology, right? Where there's all these companies that are in this like hundred to 300, 400 million dollar range that didn't do IPO, they don't have AI, have a strong customer base. And then now there's these young upstarts of AI companies that are starting to flourish, right? And so now now so I think I think you have this this marketplace of leaders and sellers who are now looking at the new hyper-growth companies, which are going to be AI, uh, type companies.

I think, um, you know, Nooks and Clay are great examples, those Gleans are a great example of that, right? Um, you know, uh, 11X, like all that stuff, right? Um, and, um, they're all going to have to contend with that. Right?

And and so I think that there's a a mental shift that you have to work through of like, am I comfortable, you know, in ambiguity? Um, am I willing to actually do the work, right? Like that's required. Do I have it in me, right?

To do that, right? Um, like I think that's a a very real a very real conversation that a lot of people are having, right? You know, so, uh, right now. Yeah, startups startups are just different.

Um, you Jason Lemkin actually posted it about about it the other day, right? You you you got to be willing to just do whatever it is you got to do, whatever job it is, and not get bogged down in the job description and you don't have a month to make a difference, like you just got to come in and figure shit out. Yeah. I I I want to shift gears slightly because I I do want to talk about cold email, just knowing where you came from.

Okay. Um, cold email is fucked. Like to put it nicely. Uh, you know, and I and I to some extent blame Outreach and Salesloft for this.

I'll I'll take the hit. I'll take the hit. And and it's fine. But like we went through this area.

Dale's going to have a stroke because I just saw my camera flash and it's going to move. So, I'm going to do it just to annoy him for a minute. Um, and then I'll put it back. Um, sequencing, I think had a valuable place.

I still think it has a valuable place. But I think these tools have created this mindset of go wherever you're going to go, buy a list of, you know, X number of people, maybe enrich it, maybe don't. If you're not, I mean, shame on you. Um, drop people in a, you know, 36 email, 97-day sequence, um, and maybe email 30 like Dale's nodding because we all get them.

Maybe that maybe that 35th email is what's going to make me convert because 1 through 34 didn't. Like, what the hell happened to doing email the right way and how do we fix it, man? Uh, man. How's that for a loaded question that we could talk about for the next three hours?

Yeah. All my Yeah. I'm going to get a call from Manny after this. You're talking about Outreach and all the all the things, right?

I love Outreach and I love Manny. Um, Yeah, I think, um, and I do as well. I think, uh, look, what happened? And and how do we get through it?

Um, you know, I I think like anything else, right? Uh, we we we had too much cake and now we're overweight and we have cavities, right? Um, we we took a we took a good thing and we abused the hell out of it. Um, and as as the tools proliferated, right?

Um, so did the the emails, so did, uh, you know, a generation of sellers who, um, had didn't have to grow up without it, right? Um, so I think that's part of it, right? Um, look, I I think like anything else, it's it's a channel that just isn't going to have the return, uh, that, um, that it once did, right? And so, um, so how do you and so the landscape has changed, right?

So, if that's not working, so a couple things is like, hey, how do you take a six-sense or how do you take a common room and that intent type data and, um, start reacting to signals, right? Um, start to be smarter, right? Um, how do you I think the newest one is like ChatGPT's writing everybody's emails to look personalized, but it's it's still missing quite a bit, right? So, how do you still add the human element and and stay relevant?

And so, I I think there's going to be, I think the technologies will always shift. I think we saw that with with Taudapp back in the day to Outreach to, you know, the next generation of thing, but the humans have got to shift with it. Right? And so, you've got to be relevant, you've got to be timely, you got to be omni-channel, you've got to be true ABM and working with your marketing, you know, teams and and all that, right?

Um, and so, I think that's the way to go. I I don't think we're going to get these crazy conversion, even with that said, I don't think we're going to get these crazy conversions, right? And then I then I'm going to die on this hill. Pick up the damn phone.

Well, and that's the thing I think that All he does is pick up has everybody's cell phones now, right? That's where sequencing does help though. Like, because it's just not emails, it's phone calls. It could be, you know, pigeon mail.

It could be like, there's a lot of things that you can do in the sequence that's not just emailing. So, people associate sequencing to emails, but I think that's a disconnect. But we made it. But I would And then And then, I would say, but I would Yeah.

Yeah, but here's the here's the thing I would say that I as I as I coach sales leaders to, and I actually talked to somebody about this yesterday, where they're talking about two reps, both reps were hitting their KPIs. Let's just call it, you know, 50 dials a day. These are AEs outbounding, right? One rep was having massive success, right?

Multiple meetings, uh, progressing deals, like all the things you would want to hear about a rep, right? You know, rep B, same activity, same KPIs, but wasn't having nearly the amount of success, right? And I think that one of the one of the things around all this this these these these tools, the tracking is that you have KPIs for days. You have metrics for days.

You have dashboards for days, right? And so, we have a generation of sellers that unfortunately are used to being managed to a dashboard and to a KPI, right? Maybe not even maybe more so than even the revenue target and the quota target, which is wild, right? But the real secret sauce is the quality of work within the KPIs, right?

And so, I go back and looking at those sales managers and those frontline leaders of like, how are you coaching the reps within their KPIs? If they're doing outbound cold emails, how are you making sure that it's not generic and it's personalized and it's timely? If they're making calls, you know, are you call coaching and making sure that, you know, they're looking for connects, that they're doing quality objection handling, great intro lines, all that type of stuff, right? And so, with all this, you know, I think I don't know what the saying is, but, um, that but the the the rigor around coaching and managing like it's never been more true than today.

It's just I think we've had a lot of I think we've had a lot of a generation of sales leaders who haven't had to come up that way and they're learning they're learning the hard lessons in a tough macro environment. VPs of spreadsheet. VPs of dashboards. Yeah, yeah, and look, let's be I'll be honest.

Like, you know, it's like, hey, look, when when it was when it was Zurp era, that was the that was the required skill. Sure. It was the required skill was, could you manage from a spreadsheet? Could you manage from a dashboard?

Because it was about the engine and keeping, you know, keeping the wheels on the plane and keeping everything flying, and then as pipeline pipeline decreases and it gets harder, macro stuff starts hitting, away, can you actually deal coach? Can you actually coach reps? Can you actually, you know, do transformation? Um, and yeah, that's just, uh, it's it's, uh, part of the moment, right?

Yeah, the the deal coaching, there's so few leaders that I know that can do it really well. Yeah. Um, you know, anyone could and and I think what most people think deal coaching is is not deal coaching, right? Anyone could look at a Salesforce or a HubSpot and we're going to be like, okay, Nate, your next step is out of date and, you know, you have your next yes, uh, your close date looks good.

Like that's not deal coaching. That's that's not pipeline inspection. That's looking at a report and we could all do that and we don't need a meeting for that. Um, so I I think that to survive and thrive in today's go-to-market, what you've done in the past isn't going to work.

Like you you have to be in there. Like we talk all the time how we don't, you know, we're not consultants. We don't hand you a pretty slide deck and tell you what to do. Like we're going to get all up in your shit.

And I think that a lot of managers don't know how to do that in a way that doesn't come off as micromanagy but comes off as a way of like, I want to help you. I want to coach you. I want to guide you and make you better. Yeah, I find an interesting take on that though, because I think as uh, I was talking to, um, uh, uh, one of my old leaders who's who now head of sales at a at a pretty hot startup now.

And we were talking about management, right? And she's got some young leaders on her team. And I think for a period of time there, we were really fearful of this idea of micromanagement. Right?

And what is micromanagement? I think at its core is like micromanagement is like, uh, leading from fear, right? Or maybe managing from fear is a better way to say it, right? And you're, you know, you're not pleasant to work with, you're you're not celebrating success, like you've been able of every business, but you're not really providing value, right?

And it it it like facilitates this hands-off approach, right? Of like, I don't want to be a known as a micromanager, right? And I think that came true. I think I think for a lot of leaders that, you know, a lot of young leaders that that came true during kind of this like heyday, you know, Zurb era heyday, where people were getting poached left and right.

There was always like, you know, people were paying astronomical amounts of, you know, base and OTEs for first-time sellers, right? Like, I mean, I lost like a small army of SDRs to AE gigs. We couldn't promote them fast enough into roles where they were, you know, making tons of money in a first-time closing role, right? And and so, there was a fear of like, if I micromanage them too hard, right?

If I'm not, you know, whatever, um, I'm going to lose people because they they're going to have a there's another thing out there for them to to go. And unfortunately, though, it it it takes you away from coaching. And the hard truth and the feedback that you actually you actually need and to to to move your career, your your development, your deals forward. Coaching's important and I think it's it's as much on the rep as it is the leader, right?

Like I use the term culture of coaching a lot. Yeah. Um, and if you don't want a culture, if you don't want a culture of coaching, if you don't want to be coached, I'm the wrong leader to work for. Um, like if you're looking for someone who's just going to like, oh, yeah, cool, sure, whatever.

Like, I'm not going to be a hard ass, but like, I am going to coach you and it comes from a place like, I want you to be the best. I listen, it's been a long long time. It's been a hot minute since I've been in a full-time leadership role. Um, but I always said that the the the metric that I look at other than numbers up into the right is how many people can I get promoted into a leadership role?

Yeah. How many people can I get promoted where they want to go? If you're sales and you want to go to marketing, while it might suck for me, my job is to get you there, because that's what you want to do and that's what makes me a good leader or a bad leader. Um, so I love the emphasis on that.

Yeah. All right, we are come go ahead. No. please.

No. We we're we're we're going to go to rapid fire, but I want you to finish your thought. We don't have strict time limits here. I really quick, really quickly, right?

Like I think it was You don't have to be really quick. We don't have strict time limits. Oh, there we go. Dale's never on time for a meeting.

So even if he has one right now, he's going to be late anyway. So just keep I love it. The zinger towards Dale. Love it.

Uh, so Reed Hoffman wrote a book, uh, way back when with uh, CPHD uh, type and, um, this concept that they they talked about in that book was about the alliance, right? About the the company and and the employee, what have you. And and back in our dad's days, right? Like my dad worked, he got a job at 18 and he didn't leave till he was 60, right?

Like that was my dad's life, right? And what have you. And I think now that's not true for any of us, right? Um, that's not in this era.

And so, how do we make the tour of duty of uh, a two-year, three-year, four-year stint with our reps, with our leaders, right? Super valuable. Right? And I think that's actually your point.

It's like, yeah, it might be painful, but it's only painful on that first go. Because if you can establish the the the culture of like, hey, look, I'm going to develop you, which means that I need you to lean in, I'm going to lean in with you. We're going to have some hard truths and hard conversations. But guess what?

I'm going to get you wherever you want to go. You want to buy that first house? Awesome. You want the promotion?

Awesome. You want to go and be a leader in another company? Great. Let's go help you do that, right?

Whatever your thing is, right? Um, but then the people coming behind them is going to be like, oh, if I lean into Adam, if I lean into Nate, and to what they're giving me, I'm going to get to where I want to go and there's a track record there, right? Um, and so, and that's got to be the the the social contract, if you will, um, that we operate in in today's in today's era. At least at least that's what I believe.

That's a great way to look at it. All right, let's get into some quick rapid fire to wrap this up. It's never as rapid as I'd like it to be. Um, but but that's okay.

What's the hardest leadership lesson that you've learned? Oh, um, Not meeting people where they're at and treating people like a number. Right? Is that when you get stressed and numbers are tight and you got to make the number, you got to make the quarter, um, not putting people first, putting the number first, right?

Um, and you might muscle your way through the moment and get that deal in, make that number, whatever, but, uh, you absolutely ruin credibility. You, uh, ruin the long-term value of that relationship or what you could have got out of that team. That's a good one. What's the piece of advice that you once, uh, agreed with, but now you completely disagree with?

Grow at all costs. Oh, that's a good one. Yeah. Like I think that's the, uh, it was was right for the moment, but, uh, uh, we've all paid the lessons back, uh, so, yeah, grow at all costs is, uh, uh, I definitely don't believe that anymore.

All about efficiency. My, how things have changed. What's um, what's a leadership mistake you made that looking back, you still are like, man, I regret that. Yeah.

As I was prepping for this, I'm like, I'm gonna get that question and I was thinking back to Just like a job interview. So, so my very, so I'm going to apologize to Curtis, to Scott, to Paul, Megan, a bunch of others, right? But my very first management gig, right? Uh, was at a small field startup, uh, and, um, got promoted from being a top rep.

And I effectively came in and was a first-time sales leader, I was a terrible first-time manager because I was trying to replicate myself, right? I was trying to like, this worked for me. This is how I'm motivated. Uh, this is how I like to be talked to.

Uh, this is how all the every manager, like, I didn't read any management books clearly, because that's what they all tell you not to do. That's what I did. Um, and so, uh, for that first team that had to uh, to uh, you know, pay the price for my leadership development, I apologize. That's a great one.

Last one as we wrap it up, if there if there's a revenue leader listening to this right now and they're trying to bridge these gaps, these go-to-market gaps that they have, what's one thing that they need to hear right this minute? You're not alone. Like, I think that's the big thing is that especially VPs, um, CROs, right? Heads of, um, you're one of one in an organization, right?

Your peers have different, um, you know, metrics and things that they're held accountable to that's maybe not as hard, uh, hard to as as easily defined as revenue and ARR, right? Uh, and your CEOs and your boards have different things. You got to be the captain of your ship for your for your teams. Um, but you're not alone, right?

Um, so, uh, chances are if you call another sales leader, um, there's going to be a high degree of empathy and understanding. Um, so, uh, we all have the dark days, right? And so Call a friend. And I know as sales leaders, Yeah.

Yeah. Call out to them, but I think as sales leaders, and then as men, we're taught to show no weakness, right? Um, and so we we kind of hold this facade. Um, but there are dark days even in the happiest of revenue times, right?

So, so so phone a friend for sure. I love that. I I I it's it's so hard to do it alone. We talk about this all the time.

Um, and if you try to go out and do it alone, you I I I can't imagine. As as much as Dale drives me crazy. Um, I was having this conversation with someone the other day, like I don't know if I could do this if I like had to do it alone. I in fact, I know I couldn't.

Um, for a variety of reasons. Uh, phone a friend, get advice, don't think you know everything. Um, and don't be afraid to say I don't know, um, as well. Yeah.

It's it's amazing. May, thank you thank you so much for joining, man. We appreciate it. I am excited to see what is next for you.

Um, and thanks for dropping all your uh all your advice and tidbits today. Yeah, it's great, Adam, a pleasure, Dale, a pleasure. And, uh, uh, if anybody needs any help or advice, uh, I'm around, just DM me on LinkedIn and uh, I happy to help. Cool.

Thank you, sir.