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

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 Captivate IQ, 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.

Yeah, thanks for having me. I'm excited to be here.

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

Yeah, I mean, I think most sales leaders—a few of those just popped to mind. I think the biggest one that really stands out to me was probably later-stage Outreach, right? You know, 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 a Gong Compete product, 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?

And so right away, like you have to retune the enablement, the content, the decks, the business acumen. You're solving bigger problems, right? There's more stakeholders, what have you. And you know, ultimately, you know, how we got through that moment and how we ushered in kind of this platform selling at Outreach was really aligning people on, you know, on the overall strategy, what we were trying to do, just trying to solve more problems, right? And you know, the framework that I've used for that, I'll drop it here, but happy to answer questions, is you know, first and foremost, we aligned everybody on like, hey, here's the strategy. Here's what we're doing as a company. Here's the direction. We had to get everybody clear on what their part of the strategy was, right? And then most importantly, we had to teach people how to execute the strategy, right?

I've seen this too many times where people 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 they do all the stuff and then we forget to teach people how to actually do the job on the phones. It's wild. It just happens over and over and over.

So that was the big thing for us and how we got through the moment. And I think one of the things that you were saying is like the why. The why is like super important.

Yeah, go ahead.

We'll go with the why, right? Start with the why, right? Like that's it, right? So, yeah, you know, look, I was talking to somebody yesterday, one of my advising clients, and you know, one of the things that we were talking about, related to the why, was that sellers 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 transformation within your organization, 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 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, a frontline manager, often times 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." And I tend to oblige. But generally speaking, I found that you get so much more when you do explain the why.

Having worked, you know, Nate, at all different size companies, how do you balance sharing the why with not oversharing? Because that's tough, right? Like you want to give the why, but sometimes the why isn't pretty. Yeah. And often times, how do you balance that as a leader?

Yeah, man. That's tough, right? Because especially in the last handful of years, the why has been to save off competition, to move from VC burning money to profitability and efficiency, to potentially RIFs in the organization. So the ugliness of it and the heartache of it is real.

You know, I think for me, you had a post about this today, Adam, and I'll shout that out, was about empathy, right? Is that like, you know, I think for me it's that you can only do so much, right? And I think if you can, if you're very consistent, if you're building up those equity points with your teams, with your leaders, 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. But that's what 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 and messed it up and mucked it up and I've had good examples as well, but it's really empathy and meeting people where they're at 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 mid-twenties-year-old 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 guide them and mentor them through the moment.

Yeah, 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 know 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 motion and your platform motion. What was the biggest gaps that you guys saw? Was it that it was the wrong team selling, you know, or you guys didn't do the proper transition to training them and almost like reonboarding them from the initial process into a platform motion?

Yeah, I would say we eventually figured it out, but it was clunky in the beginning, right? And I might get some fire texts after this, but I'll say it anyhow in the confines of 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, SalesLoft, who did a masterful job, really strong go-to-market. It was a pleasure to compete with them because they kept the bar high, right?

But we did really well, right? Yeah, we were doing really well in our niche and our space. We were well thought of with our sequencing and kind of that orchestration tool that we had. That was our point solution, our first real product, right?

And then when we ventured into Clary's world, into Gong's world, into everyone's world, right, all of a sudden it's a knife fight on multiple fronts, right? We just assumed that we were going to have the same type of success and momentum, right? And really what we were selling was 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 definitely had success. Build it and they will come, yeah. Build it and they will come. And we definitely had success, but 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 ended up being two or three times longer, right? In part because we didn't start from a place of feeling like we were 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 want to double click on that. 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 or realize this as—

# Transcript

Important as it is. Dale, what's 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? Brand awareness, Nate. You know, there is. I find whether you are at one point the behemoth that is or was Outreach, whether you are, you know, Dale and Adams startup, I don't think people put enough emphasis on like you don't have a brand and you can't just build it. 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, be like, "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, you know, you're going to build go to market. How do you properly build and compound on brand awareness?

That's a loaded question. Loaded, loaded, loaded question. I feel like I need a marketing counterpart here to help with, you know, help whisper sweet nothings about brand awareness in my ear.

I think there's a couple things to it, right? I think 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 people that are on the outer edges of your product and their advocacy or their feedback back to you, right? And so you're taking care of that core, right? 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 proof of concepts. You might just have to beg, borrow, and plead to get badged into their corporate headquarters to, you know, be ushered along, right? Get access to the reps, whatever the thing is, right? You mean people do this thing called in-person sales and actually go places. You're hopping on a flight tonight to do the same thing, right? So I think because we fundamentally believe that certain things have to be done in person, I think that you know, look, there's a place for the in-person and face to face for sure.

But I think that's you've got to create that. You got to do that initial work, right? And then you've got to have a really good go-to-market strategy and execution orchestration amongst your SDR to marketing department, product marketing, you know, sales and how sales is communicating to 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, we're formidable. We can provide value. We're an alternative to whatever was going on.

And I think more than anything, when we entered 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 so when we're inching in on their territory, they've got a high bar that we've got to cross a threshold on to provide value.

So yeah, that's I think part of it. And then as a sales leader, when your marketing lead, 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 generation, it immediately equals leads, right? Or has some sort of ROI on leads and opportunities and meetings. When I talk about brand, that doesn't necessarily translate to pipeline right away, right? And so sometimes it's hard for a sales leader to wrap their mind 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 tell sales leaders: 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. It's never going to happen. I got a funny story about that.

So when I first joined Outreach and hopped on that rocket ship, I came in as a sales development leader. I was the first external SDR leader into Outreach, right? So I was leading a team and what have you.

Did you have blue hair?

I did not. I was not.

But Sam Nelson was part of one of my early teams and, you know, Sam Nelson's got the Kobe Bryantesque 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. All those stories about Sam are true. So this community that he's built and his expertise are like, it's well earned and forged in the fire, if you will.

But yeah, when we first started going, when Sam was part of this team, you know, we were calling CROs and, you know, one was probably like, "Hey look, what is sales engagement and who is Outreach, right?" Yeah, like that was those early days of cold calling. And tell you what, it's really hard to book a meeting and get somebody's attention if those are the first two questions out of their mouth.

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Well, and you're building kind of a market like you're building a brand and a market, which is also difficult. I used to run sales for a company called Kitedesk and you've probably had Julianne Sweat that was in your group. She used to work for you. Yeah, the whole Tampa team. Yeah, those are. Yeah. That's funny. That's a small world.

It's, um, you're right. 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, Sales Loft, 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—we could have a separate conversation about that—have all this brand recognition and it's very easy to call a CRO on the phone when you're calling from Outreach or Sales Loft 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 fuck are you? You don't exist." And these reps struggle with that, right?

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 things. But the brand recognition part? Your job is going to get easier. Going from an Amazon or a Gong or an Outreach or a Sales Loft to Bob's startup? Like, I've yet to see very many people who could successfully go backwards like that. It's so hard.

You've got to—it's a mental shift for sure, right? It's not saying that it can't be done, but like there's a lot more examples of it not being done well and people flaming out by making that move.

I think, and by the way, I think in our market right now, like in just the marketplace I think that we are actually going through that type of moment where you had this generation of, call it, pre-AI technology, right? Where there's all these companies that are in this like 100 to 300, 400 million range that didn't go IPO, they don't have AI, have a strong customer base. And then now there's these upstarts of AI companies that are starting to flourish, right? And so now I think you have this marketplace of leaders and sellers who are now looking at the new hyperrowth companies which are going to be AI-type companies.

I think, you know, Nooks and Clay are great examples of those. Glean's a great example of that, right? You know, 11X, like all that stuff, right? And they're all going to have to contend with that, right? And so I think there's a mental shift.

That you have to work through—like, am I comfortable in ambiguity? Am I willing to actually do the work that's required? Do I have it in me to do that? I think that's a very real conversation that a lot of people are having. Right now, startups are just different. Jason Lumpkin actually posted about it the other day. You've got to be willing to just do whatever job it is and not get bogged down in the job description. You don't have a month to make a difference. You just have to come in and figure it out.

I want to shift gears slightly because I do want to talk about cold email, just knowing where you came from. Cold email is rough, to put it nicely. I, to some extent, blame Outreach and Sales Loft for this. I'll take the hit. I'll take it and it's fine. But we went through this area where sequencing—I think it 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 X number of people, maybe enrich it, maybe don't. If you're not, shame on you. Drop people in a 36-email, 97-day sequence. Maybe email 35 is what's going to make me convert because one through 34 didn't. Like, what the hell happened to doing email the right way, and how do we fix it?

That's a loaded question that we could talk about for the next three hours. I'm going to get a call from Manny after this, talking about Outreach and all the things. I love Outreach and I love Manny. Look, what happened and how do we get through it? I think, like anything else, we had too much cake and now we're overweight and we have cavities. We took a good thing and we abused the hell out of it. As the tools proliferated, so did the emails and a generation of sellers who didn't have to grow up without it. I think that's part of it.

Look, I think like anything else, it's a channel that just isn't going to have the return that it once did. The landscape has changed. So if that's not working, a couple things: how do you take a six sense or a common room and intent-type data and start reacting to signals? Start to be smarter. I think the newest one is ChatGPT writing everybody's emails to look personalized, but it's still missing quite a bit. How do you still add the human element and stay relevant? I think the technologies will always shift. We saw that with ToutApp back in the day, to Outreach, to the next generation of things, but the humans have got to shift with it. You've got to be relevant. You've got to be timely. You've got to be omnichannel. You've got to be true ABM and working with your marketing teams and all that.

I don't think we're going to get these crazy conversions. And then I'm going to die on this hill: pick up the damn phone.

Well, everybody's got cell phones now, right? That's where sequencing does help, though, because it's just not emails. It's phone calls. It could be pigeon mail. There's a lot of things that you can do in a sequence that's not just emailing. People associate sequencing to emails. I think that's a disconnect.

Here's a thing I would say: as I coach sales leaders—I actually talked to somebody about this yesterday—they were talking about two reps. Both reps were hitting their KPIs. Let's call it 50 dials a day. These are AEs outbounding. One rep was having massive success: multiple meetings, progressing deals, all the things you would want to hear about. Rep B had the same activity, same KPIs, but wasn't having nearly the amount of success.

I think one of the things around all these tools and tracking is that you have KPIs for days, metrics for days, dashboards for days. We have a generation of sellers that are used to being managed to a dashboard and a KPI, maybe more so than even the revenue target and quota target, which is wild. But the real secret sauce is the quality of work within the KPIs.

When I look at those sales managers and frontline leaders, I ask: how are you coaching the reps within their KPIs? If they're doing outbound cold emails, how are you making sure it's not generic and it's personalized and timely? If they're making calls, are you call coaching and making sure they're looking for connects, doing quality objection handling, great intro lines? The rigor around coaching and managing—it's never been more true than today. I think we have a generation of sales leaders who haven't had to come up that way and they're learning the hard lessons in a tough macro.

VP is a spreadsheet. VP is a dashboard.

Look, I'll be honest. When it was zero era, that was the required skill. The required skill was: could you manage from a spreadsheet? Could you manage from a dashboard? Because it was about the engine, keeping the wheels on the plane, keeping everything flying. And then as pipeline decreases and macro stuff starts hitting, you've got to ask: wait, can you actually deal coach? Can you actually coach reps? Can you actually do transformation? It's just a part of the moment.

Deal coaching—there are so few leaders I know that can do it really well. Anyone could look at a Salesforce or HubSpot report and be like, "Okay, Nate, your next step is out of date and your close date looks good." That's not deal coaching. That's not pipeline inspection. That's looking at a report, and we could all do that. We don't need a meeting for that.

I think what most people think deal coaching is, is not deal coaching. To survive and thrive in today's go-to-market, what you've done in the past isn't going to work. You have to be in there. We talk all the time how we're not consultants. We don't hand you a pretty slide deck and tell you what to do. We're going to get all up in your business. I think a lot of managers don't know how to do that in a way that doesn't come off as micromanagey, but comes off as, "I want to help you. I want to coach you. I want to guide you and make you better."

I've got an interesting take on that, though. I was talking to one of my old leaders who's now head of sales at a pretty hot startup. We were talking about management, and she's got some young leaders on her team. I think for a period of time, we were really fearful of the idea of micromanagement. What is micromanagement? I think at its core it's managing from fear, and you're not pleasant to work with. You're not celebrating success. You're just all business, and you're not really providing value. That facilitates this hands-off approach of, "I don't want to be known as a micromanager."

I think that came true for a lot of leaders—a lot of young leaders—during the zero era heyday, where people were getting poached left and right. There was always a situation where people were paying astronomical amounts of base to first-time sellers. I mean, I lost a small army of STRs to AE gigs. We couldn't promote them fast enough into roles where they were making.

Tons of money in a first-time closing role, right? And so there was a fear of like, if I micromanage them too hard, right, if I'm not, you know, I'm going to lose people because they're going to have another thing out there for them to go. And unfortunately though, it takes you away from coaching and the hard truth and the feedback that you actually need to move your career, your development, your deals forward. Coaching is important and I think it's as much on the rep as it is the leader, right? Like I use the term culture of coaching a lot.

And 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. Like if you're looking for someone who's just going to say, "Oh yeah, cool, sure, whatever," I'm not going to be a hard ass, but I am going to coach you. And it comes from a point like I want you to be the best.

I listen, it's been a long time. It's been a hot minute since I've been in a full-time leadership role. But I always said that the metric that I look at, other than numbers up and to the right, is how many people can I get promoted into a leadership role? 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. So I love the emphasis on that.

All right, we are coming, let me finish my thought. We don't have strict time limits. 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 a jab towards Dale. I love it.

Well, Reed Hoffman wrote a book way back when with some PhD type and this concept that they talked about in that book was about the alliance, right? About the company and the employee. 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? That was my dad's life. And I think now that's not true for any of us, right? That's not in this era.

So how do we make the tour of duty of a two year, three year, four year stint with our reps, with our leaders, right, super valuable, right? And I think that adds to 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 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 at another company? Great. Let's go help you do that. Right? Whatever your thing is, right?

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

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

What's the hardest leadership lesson that you've learned?

Oh, 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. Not putting people first, putting the number first, right? And you might muscle your way through the moment and get that deal in, make that number, whatever, but you absolutely ruin credibility, you 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 a piece of advice that you once agreed with but now you completely disagree with?

Grow at all costs. It's a good one. Yeah, I think that was right for the moment, but we've all paid the lessons back. So yeah, grow at all costs is definitely something I don't believe that anymore. All about efficiency now. How things have changed.

What's a leadership mistake you made that looking back you still are like, man, I regret that?

You know, as I was prepping for this I was thinking back to just like a job interview. So my very first management gig, right, was at a small Seattle startup and I got promoted from being a top rep and I effectively came in as 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. This is how I like to be talked to. This is how I thought all management worked. I didn't read any management books clearly because that's what they all tell you not to do. That's what I did. And so for that first team that had to pay the price for my leadership development, I apologize. I apologize to Curtis, to Scott, to Paul, Megan, a bunch of others.

That's a great one.

Last one as we wrap it up. 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, especially for VPs, CROs, heads of, you know, you're one of one in an organization, right? Your peers have different metrics and things that they're held accountable to that maybe aren't as easily defined as revenue and ARR, right? And your CEOs and your boards have different things. You got to be the captain of your ship for your teams but you're not alone, right? So chances are if you call another sales leader, there's going to be a high degree of empathy and understanding. We all have those dark days, right? And I know as sales leaders, yeah, it's cold, but I think as sales leaders and then as men, we're taught to show no weakness, right? And so we kind of hold this facade. But there are dark days even in the happiest of revenue times, right? So phone a friend for sure.

I love that. I can't imagine as much as Dale drives me crazy. I was having this conversation with someone the other day like I don't know if I could do this if I had to do it alone. I in fact I know I couldn't for a variety of reasons. Phone a friend, get advice. Don't think you know everything. And don't be afraid to say I don't know either.

Yeah, it's it's crucial.

Thank you so much for joining, man. We appreciate it. I am excited to see what is next for you. And thanks for dropping all your advice and tidbits today.

Yeah, it's great. Adam, a pleasure. Dale, a pleasure. And if anybody needs any help or advice, I'm around. Just DM me on LinkedIn and I'm happy to help.

Cool. Thank you sir.