Outbound Sales Success Requires Complicated Systems. #ChangeMyMind
Brandi Starr is joined by Gabe Lullo, a sales and recruiting expert, and Rolly Keenan, CRO of Tegrita and seasoned revenue leader, who argue that outbound sales is failing not because of lazy reps, but because it's become far too complex for its own good. They challenge the conventional wisdom that ever-growing tools and metrics drive results, insisting that simplifying outbound and prioritizing authentic, intentional outreach is the only way forward. With real-world examples and sharp industry insight, Lullo and Keenan explain why revenue leaders must break away from complexity before it undermines growth. Will you rethink your outbound strategy or defend the old playbook?
This week on Revenue Rehab, Brandi Starr is joined by Gabe Lullo, a sales and recruiting expert, and Rolly Keenan, CRO of Tegrita and seasoned revenue leader, who argue that outbound sales is failing not because of lazy reps, but because it's become far too complex for its own good. They challenge the conventional wisdom that ever-growing tools and metrics drive results, insisting that simplifying outbound and prioritizing authentic, intentional outreach is the only way forward. With real-world examples and sharp industry insight, Lullo and Keenan explain why revenue leaders must break away from complexity before it undermines growth. Will you rethink your outbound strategy or defend the old playbook?
Episode Type: Problem Solving - Industry analysts, consultants, and founders take a bold stance on critical revenue challenges, offering insights you won’t hear anywhere else. These episodes explore common industry challenges and potential solutions through expert insights and varied perspectives.
Bullet Points of Key Topics + Chapter Markers:
Topic #1: Matching Buyer Complexity With Sales Simplicity [04:50]
Gabe Lullo challenges the belief that complex B2B buying journeys require complex sales processes. He argues that success comes from a multi-threaded, highly intentional approach rather than disconnected, over-engineered outbound systems. Lullo states, “Working on it very strategically… so those three departments are communicating correctly to talk to the right people at the right time,” pushing revenue leaders to simplify and sync their sales, SDR, and marketing efforts for real impact.
Topic #2: Why High-Volume Outreach Is Just Spam, Not Strategy [13:10]
Gabe Lullo argues that most outbound activity today is indistinguishable from spam, citing mass emailing and indiscriminate dialing as ineffective. He asserts, “Intentional outbound is what I think is really what is important. Authentic outbound is what I think is important,” reframing high-volume outreach as harmful rather than strategic. Rolly Keenan agrees and emphasizes the need to target the right prospects instead of treating outreach as a numbers game.
Topic #3: Technology Alone Won’t Fix Outbound [21:40]
Gabe Lullo pushes back on the reliance on technology and AI as quick fixes for outbound challenges, warning, “If you can use AI to just spam more, I don't think that's an effective way of implementing the technology.” He urges revenue leaders to use tech for preparation, research, and training rather than simply increasing activity. Rolly Keenan echoes this caution, reminding leaders to be thoughtful about whether their tools are genuinely helping SDRs connect in meaningful ways.
The Wrong Approach vs. Smarter Alternative
The Wrong Approach: “Trying to throw money at it. To Rolly's point, they're just trying to throw money at the problem to fix it.” – Gabe Lullo
Why It Fails: Simply investing more resources or buying additional tools doesn’t address the root cause of outbound motion issues. This approach often compounds complexity, increases inefficiency, and ignores the need for intentional strategy or meaningful conversations. It masks the real issues, making it harder for teams to achieve authentic engagement and sustainable revenue growth.
The Smarter Alternative: Instead of indiscriminately upping the spend or tech stack, leaders should focus on listening to what their competitors and the market are actually doing, rather than chasing analyst-driven trends. Prioritize intentional, authentic outreach and ensure your team is aligned and prepared to have relevant, high-value conversations that move deals forward.
The Rapid-Fire Round
- Finish this sentence: If your company has this problem, the first thing you should do is _ “Measure whether your connection rates and the quality of conversations are meaningfully tracked. If not, fix that first.” – Gabe Lullo
- What’s one red flag that signals a company has this problem—but might not realize it yet? “If your team isn’t having meaningful conversations—and isn’t tracking them authentically—issues will show up later in the funnel.”
- What’s the most common mistake people make when trying to fix this? “Throwing money at the problem—more tech, more bodies—without actually addressing the core issue.”
- What’s the fastest action someone can take today to make progress? “Actively listen to what your competitors and the market are actually doing, instead of just following analyst advice and trends.”
Links: Gabe Lullo
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LinkedIn: https://www.linkedin.com/in/lullo/
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Website: https://alleyoop.io/
Links: Rolly
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LinkedIn: https://www.linkedin.com/in/rollykeenan/
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Brandi Starr [00:00:35]:
Welcome to another episode of Revenue Rehab. I'm your host, Brandi Starr, and we have another amazing episode for you today. Outbound sales isn't failing because reps are lazy. It's failing because we've made it way too complicated and we keep calling that strategy. And SDRs are drowning in tools they don't need, metrics they can't control, and quotas that don't really match reality. It's like giving someone a Swiss army knife and expecting them to perform surgery. So here's the real question. Is all of this complexity helping you close more deals or just helping you hide the fact that your outbound motion is broken? Today on Revenue Rehab, we are digging into the myth of the complicated outbound engine and.
Brandi Starr [00:01:26]:
And asking what it actually takes to build a system that works if your outbound isn't delivering. This episode is for you. Today. I am thrilled to be joined by two amazing guests, Gabe Lullo and Rolly Keenan. With me today is Gabe Lullo, a sales and recruiting pro who's trained teams, run his own firm, and now drives growth at Alleyoop with a sharp focus on culture and customer success. And also back in the studio, Rolly Keenan, Tegrida's CRO. He's led revenue at LinkedIn, Oracle, and Gallup. And yes, he's made over 500,000 cold calls.
Brandi Starr [00:02:10]:
So when we talk outbound, he's been in the trenches. Welcome to Revenue Rehab. You, your session begins now. All right, gentlemen, today we are tackling the common belief that outbound sales success requires complicated systems. This is the opportunity to change our mind. And Gabe, I know that you see this differently, so. So you've got 60 seconds. Convince the audience why they should rethink their current position.
Gabe Lullo [00:02:54]:
Yeah. So, you know, we have a Huge team, over 110sdrs, but it's not a single team for us. It's. It's fractionalized across many, many, many clients, from large enterprise all the way down to a founder led sales org. And you know, technology is of course, paramount to our success. Success. But it's all about the people. And I know AI is interrupting, disrupting, and making changes, but at the end of the day, people want to talk to other people and having humanized, authentic conversations right now actually is cutting through the noise versus just spray and pray automation type approach.
Gabe Lullo [00:03:34]:
And that's where we're finding success right now.
Brandi Starr [00:03:37]:
Okay, so my first question here that I'd like to ask is there's, you know, with B2B or B2B2C. You know, there are a lot of complexities. We are seeing all of the research show that buying committees are growing. You know, I've seen as much as 21 people in a buying committee. Sales cycles are getting longer. The number of touch points and you know, the amount of information that buyers need in order to make a decision and you know, really even get into the sales cycle. All of these numbers are growing. And because of this there is a belief that this complex journey requires a complex sales cycle.
Brandi Starr [00:04:34]:
And so what do you say to the statistics? How, how are the stats going in one direction if simplicity is the direction we need to go from a sales perspective?
Gabe Lullo [00:04:46]:
Is that my question?
Brandi Starr [00:04:47]:
Yes. Okay, got it right there.
Gabe Lullo [00:04:50]:
Yeah. I mean to your point, there is a lot longer sales cycles. There are more people involved in the buying journey and what our focus is multi threading, having the right conversations with the right people and being very intentional about every single piece of outreach where it's not just a spray and pray scenario and having emailing campaigns and SDR campaigns and full cycle sales campaigns work haphazardly and not connecting and being aligned, but working on it very strategically. So those three departments are communicating correctly to talk to the right people at the right time and then putting not only SDRs in front of the top of the funnel, but also throughout the entire journey. Whether it's following up, whether it's lost leads, whether it's rehashing and getting conversations back on the calendar. That's what we're seeing right now to speed up into continually create momentum through the sales cycle.
Brandi Starr [00:05:45]:
Okay Rolly, I'd like to hear your perspective on our complex sales cycle. The role of outbound, whether we've over complicated this. What are your thoughts?
Rolly Keenan [00:05:58]:
Well, I think, I think the different. I, I always kind of laugh when I mean it happens like every year or so there'll be like a flurry of articles and posts. You know, sales has changed forever and I'm just like, oh, it changed forever again. You know, like the so. So there's more op. It's kind of like with our kids and social media and my kids are adults now but you know, there used to being no noise. You know, I got on my mom, you know, now I'm getting into Gen X stuff but you know, I Got on my bike, I left the house in the morning, I showed up for dinner and I was like six, you know, like I didn't have. There was not a lot of noise around me.
Rolly Keenan [00:06:43]:
I was just doing things. And that hasn't changed today, except there's a lot of noise. I really. My kids, if I had little kids now, should go out on their bike and keep themselves busy, even though there's a lot of noise. And I, And I feel like in sales it's the same way. Like there now there's buying committees and they've complicated things kind of on a buyer end, that doesn't mean I have to copy that. On the sales end, the basics are still the same. I've got to be relevant.
Rolly Keenan [00:07:16]:
I've gotta. When I get my moment, you know, and we have throw in your sales cliche, you know, my at bat, you know, whenever I show up, I still have to be amazing in that moment. Move thing, move something forward, get more information. Whatever I'm doing. And if the buying committee is two people or 20 people, or the, you know, situation is complex, or the deal is big, whatever, those are just details. The core of it hasn't changed. So I, I just feel like the noise is louder and louder. The more tools we have, the more tech we have.
Rolly Keenan [00:08:01]:
But that doesn't change kind of the how deals get closed, really. And it makes for a lot of consulting contracts to say things have changed. Let me help you implement this very complicated thing because you know how complicated it is now. I mean, it definitely drives business for consultants and, you know, make kind of gives heads of sales and heads of revenue a bit of like, oh, you know, such a complicated thing, you know, CRO now CRO, the futures know so complicated things, you know, but it's really the same thing. You just have to figure out how to weave through more noise over time. And yes, some of that has changed. Like with more tech and stuff, the buyers have more information earlier. That's true, yes.
Rolly Keenan [00:08:54]:
Are they pick. Are they picking up our cold calls anymore? Not really. I mean, I haven't picked up a cold call in 15 years, so you're not getting me on the phone. But yes. So some of that's changed. But still in the moment, the relevance, the talent you have that's in that role so important. But I, I really don't think the complexity has to match, I would say the nonsense that we see on the buyer side.
Brandi Starr [00:09:25]:
Gabe, anything you want to add to that point?
Gabe Lullo [00:09:27]:
I mean, I agree with most everything, actually. You know, my kids aren't adults, but I'm old enough to, to know what he's talking about and, and relate it definitely when I was a kid riding bikes. But it's funny because, you know, to his point, you know, back in the day when we were just calling off a list and a soft phone, right, Marketo and pardon and all these market automation platforms came out and then they just started wiping out sales words because marketing automation was going to change the world and everyone's going to buy things off of an email. And then what happened is they rehired all those people. But it's interesting. Every seller uses marketing automation today for their normal course of business and that was a massive shakeup but it really kind of all came back to normal. AI a year and a half. I was on John Barros's podcast two years ago and we were talking about how AI is going to wipe out sellers next year and he was just on mine about two weeks ago and we kind of reflected about how that has not changed.
Gabe Lullo [00:10:35]:
And so there's a lot of things that come in and I think to Riley's point, it's just more companies trying to sell you software to really get their foot in the door in regards to their revenue. But at the end of the day, sales is still sales. And that's to his point is being relevant when you show up. And what I'm really seeing right now is when I'm on the buyer side and vendors are selling me, nobody's prepared. AES are just know winging it. No one's knowing I'm talking about why I'm talking about it. They don't know why I'm there. I mean to point, he doesn't answer cold calls.
Gabe Lullo [00:11:11]:
Well, I hang up on, on demos when I, I asked my first question, I say, listen, do you know what it is that we do? It's my first question in every demo if someone's selling me something and if they can't answer that without saying, yeah, I'm on your website right now, that's usually how they start the count. And I'm just like, I'm gone. And so there is definitely, I think, a, a return to normalcy that should be happening. And you're seeing it happen in a lot of orgs that are having success.
Brandi Starr [00:11:39]:
You both have hit on a couple things that I want to dig into. First, the role of outbound. So you know, we talked about Rolly. You're saying you haven't answered a cold call in 15 years. Gabe, in one of your answers you talked about SDRs being leveraged throughout the journey. And a key part of what SDRs do is outbound. So let's talk about the outbound piece, because it definitely has changed because there was a point where we were all in offices. You got that golden phone number.
Brandi Starr [00:12:16]:
People always answered the phone. You know, whether they talk to you or not is a different story. But you at least got someone to say hello. And I, you know, I can remember strategies around getting past the gatekeeper, the executive assistant or the receptionist and. And all those things. I think we're all sort of dating ourselves in terms of our age. But talk to me a bit about your perspective, because those two things don't go together. If we're saying outbound, that used to mainly just be top of funnel, should be used throughout the funnel.
Brandi Starr [00:12:52]:
But we're also saying no one answers the phone.
Gabe Lullo [00:12:56]:
And.
Brandi Starr [00:12:56]:
And we talked about some of the challenges of email works, but it's not a magic pill of, you know, you magically send and now everyone's buying. How do we resolve that? Like, in terms of the role of outbound.
Gabe Lullo [00:13:10]:
Right. I think outbound has changed definitions from when we were doing outbound to what we now look at as outbound. Because outbound right now is just spam, in my opinion. That's the new definition. Right. And so marketing automation, to my point, and just blasting emails with. Without any understanding, you know, if it says, you know, remove me or unsubscribe on the bottom of the email, that's spam. If you're using, you know, parallel dialers to just hit your total addressable market and reps are making thousands of dials to anyone and everyone.
Gabe Lullo [00:13:49]:
Yeah, that, that spam, you know, if you're just hitting pitch slaps and using, you know, phantom buster tools on to DM every single person. Your pitch on LinkedIn, that's spam. But is it outbound? Right. So I don't know. I have an SDR who's been here for six months and has booked 252 meetings in the first six months of working for me, I had an SDR on. My team has booked a $2 billion company literally two days ago and a $5 billion company yesterday. And we just closed Ingram Micro as a small agency off of a cold call. So intentional outbound is what I think is really what is important.
Gabe Lullo [00:14:29]:
Authentic outbound is what I think is important. But what we look at is outbound versus what really we think aboutbound is. It's very different, I think, these days.
Brandi Starr [00:14:40]:
Yeah. And I know Rolly just because we've had so many conversations, you feel the same in terms of the fact that most outbound is speaking spam. And so my question for you is because we know that outbound works. Because, Gabe, I've talked to other companies as well who have similar stories of those people who are doing it right. But I definitely have talked to way more companies where they kind of know that their SDRs are spammers. So, Rolly, my question for you is how do we help those listening to really understand what is the difference between, you know, how do you be. How do you have that outbound motion that is effective, that is not spam? What's that distinction? Because people don't seem to really understand. They know that there's a good and the bad, but they don't really have a grasp of what that line is.
Rolly Keenan [00:15:48]:
I feel like my answer is super inconvenient because the way I view this is the problem is the core purpose of what are you doing? And I think where people are spamming, slash outbounding thousands of people a month, their core purpose is to spam and outbound thousands of people a month. That is, that's the point with the idea that people are. Are just percentages on a spreadsheet. And if I call this many people, I'm going to get this many. You know, that's a formula. That's what we presented to the board. So if they give us more money and we get in more inboxes, then that should give us more revenue. I mean, so that's the problem.
Rolly Keenan [00:16:43]:
If the core, and I think the words were intentional. Outbound. Is that what you said? Yeah. So that is a different core purpose of what are you doing? And when your core purpose is they're a good fit, I'm going after them, they're a good fit, I'm going after them. That changes everything. That is no longer a spam. That is no longer. It's also a smaller number in volume, drastically smaller number, because to the point of, you know, people showing up unprepared on demos, I mean, it's, it's comical.
Rolly Keenan [00:17:27]:
And also, the head of sales absolutely knows that's what's happening. Like, they're not dumb. They know that their guys are showing up. And the second they're on the call is the first time they looked at the company name, much less learned about it, because the core purpose is thousands of people. And if they actually show up to your meeting, now look at them. Because all we're trying to do is get a meeting. And I mean, I saw a Long post from, you know, somebody that I essentially jump on his posts on a weekly basis and put smh. I mean everything he says, I'm like, no.
Rolly Keenan [00:18:09]:
And he loves to put this whole thing and, and he's well known guy, everyone. Usually their answers to his posts are like, love it. You know, and it's like they're, you know, it's so, so articulate, you know, I'm like, no. But he does this whole thing of, of like when I get out, you know, I should do more outbounds, I should do more whatever. And this is, this is proof that there's a bigger market. And they're like, like, it's like this spiral of feeling better about what I'm doing, you know, and, and, and you know, if you're not getting enough, do more, you know, so there's a, there's a culture of pushing volume and a culture of yeah, yeah, yeah, tough it out. You're going to get a lot of no's, you're going to get a lot of hang ups, you know, no one's going to answer you. And there's a, and I said the VPs of sales, the heads of sales, they know this is happening.
Rolly Keenan [00:19:19]:
They're there going, yeah, I don't care. Like eventually timing's going to be right, we're going to talk to somebody and it doesn't matter how uninformed, unprepared and inexperienced my SDR is. That buyer is going to basically guide the sale at that point. That's all I want. I just want to find them. And I won't find them unless I do thousands of them.
Brandi Starr [00:19:43]:
And so I want to shift gears a little bit because I do agree that, that this is the challenge and the measurement is a key part of it because there are so many SDR teams that are measured on volume and it's not effectiveness, it's not if these meetings are good meetings. It is just how can we ramp up the volume as much as we can and that like that. It often comes back to measurement. We always say what gets measured is what gets done. So if you change how people are measured, it will change the behaviors. I want to shift a little bit and think about the technology because we talked about AI and of course that is the hot topic. You can't have any conversation without AI coming up. But there is this AI is going to replace the SDR team.
Brandi Starr [00:20:39]:
And even before AI there are different technologies. You know, we got the outbound dialer. There was a mentality of, okay, now we need less people because we're reducing the time to dial because it's something auto or there's this other technology that's going to make us more efficient, which means we can do more with less staff. You know, the do more with less is a constant theme. I think that comes up almost as often as AI. And so talking about the technology and how technology is not, you know, tech is great, but it does complicate the process. And so, Gabe, I'd love your perspective on how we make sure that our SDRs are, you know, having the right tools, using the right tools, but that we are not over engineering to our detriment.
Gabe Lullo [00:21:40]:
Yeah, I think to Rolly's point, right. Going back to the intentional outbound, if the tool is just promoting more spam and more, just this is an equation and go out and get more no's and it's just promoting that like, is the tool worth it? Sure. You can spam now more 10,000 more people than you can spam a thousand. Is that like, okay, is that great? I don't know. You know, if I owned a pool business and I installed pools and I used to use a shovel to dig the hole to put the pool in, and now I can use a backhoe to do it and it's a lot faster. That's exciting. But I'm in the pool business and my job is to give you amazing pools. Right.
Gabe Lullo [00:22:21]:
So it's the intention behind it. So AI is really a tool. If you can use AI to just spam more, I don't think that's an effective way of implementing the technology. But if you can use the AI to do research on the demo and the people and the company and the product and the website that you're about to go into and sell to, well, that's a significant opportunity. If I can use AI for my SDRs to do role plays every morning before they pick up a live call to make sure that they're sharp, like doing jumping jacks before you go lift weights at the gym. And they're on their game and they're doing the role plays from a training perspective, that's an amazing way to use AI to make sure our reps are capable and ready and excited to go into their day. If we can grade and check what they're saying and how they're saying and provide battle cards in real life time using AI tools so they can be more worthy, valuable and relevant and intentional. That's a great way of doing it.
Gabe Lullo [00:23:17]:
But if I'm just going to use it to email everybody and Fire my entire SDR team. I don't know if that's the best way of using it.
Brandi Starr [00:23:26]:
Probably not. You know, just a little indicator, a.
Gabe Lullo [00:23:30]:
Little opinionated on this topic.
Brandi Starr [00:23:31]:
Sorry Wally. Anything you want to add related to tech and how it impacts the process and complexity?
Rolly Keenan [00:23:43]:
I just, I, I just a brief one of. I just think you have to be careful about, you know, is what you're doing helping. And in some cases, you know, it's really important in professional services in particular that we do and then, and is the industry that I have the most love for sales process and client understanding and all these things, they may be at the point of the arrow for someone in sales or customer success or something, but they, the more everyone sort of in the modern front office, everyone in the client facing jobs, the more they know about what the sales team knows, the better. And so there's tech. Over the years I've been at this that can make that better and easier and basically make you your brand stronger with clients. I love all that tech, but you got to be careful what you're going for. I mean there was an, a reference to some things with SDRs and you know, just doing more spam and you know, most of the time, you know, when I, I'm, I'm in a, you know, like a lot of us are, I'm in a membership group with a bunch of execs and I watch questions come through all the time and a lot of them are, man, you know, I'm spamming everybody and it's like breaking stuff. Anybody know how to fix this? And I just want to say stop spamming.
Brandi Starr [00:25:31]:
But that's never the solution for anything.
Rolly Keenan [00:25:36]:
So yeah, I just think you got to be care as all be thoughtful about it.
Brandi Starr [00:25:42]:
And so I think the, the hard part here is there's so much historic pressure of like this is the way that it's always been done. And one of the things that I think about so again going back to how it used to work where they were dialing for dollars because it's almost like you had a yellow pages of who you could sell into and I'm using real old language and you picked up the phone and you made those conversations and there was a point that volume was what we needed because that was what we had. We didn't have all the intelligence. We didn't know as much about the prospects. We just kind of knew who was in our TAM and we had phones. And if I fast forward to today, the same fundamental need exists, but the mentality of how to approach it is where people haven't caught up. It's like, because now these things are spam, now we can, you know, have a situation where we don't go into a demo and all we know is the company name. And so how do we.
Brandi Starr [00:26:58]:
It's like breaking that old mindset because there are a lot of people I will talk to that they'll be like, yeah, I hear you. And like, we, you know, they're comped on volume. They're, you know, it's like, this is how it's always been done. You know, we've got to go through a whole transformation to do anything differently. And it's like, how do we. Like, how do we break that? How do we really get through to people that. That in order to be effective, they've got to remove this complexity and be fundamentally different. Like, this is a question I keep coming back to.
Gabe Lullo [00:27:39]:
Well, my. My training with every one of our sellers is if you sound like a salesperson, you're doing it wrong. Right. You have to sound like the exact opposite of everyone else. So whatever's trending, just don't do that. Because guess what? Everyone else. Everyone else is doing it, too. And so I think it went from, like, relevant is everything in sales.
Gabe Lullo [00:28:01]:
That's how I think we were raised, based on the age stories so far. And then it went into personalization. And then personalization kind of like went off on this tangent where it didn't become personalization anymore. And now it's. Someone just sends me an email saying, hey, I saw you went to the University of Hartford. Do you still do Spring Fling? I'm like, I graduated 25 years ago. Right. And will, by the way, buy this new CRM, right? And so that.
Gabe Lullo [00:28:27]:
That's personalization now. And so I think it's all going back to relevance. I don't know if it's the exact answer you're looking for in the question, but I think that's where we're having to head back to. To sound different and to not do what everyone else is doing. And. And that's what we see actually having the most success. I. I'm saying right now, you know, the old school is new school again in regards to a lot of the ways, not just the tools, but the ways in which we are approaching the marketplace, if you will.
Brandi Starr [00:28:58]:
Yeah. And something that I saw someone post on LinkedIn that speaks to that, that I think is really accurate is it says, we started with relevance being important, then we went to personalization, and now we're currently in the era of context, where it's like, you still got to be relevant, you still should be personal. And I hate those. Like, you saw the random thing on my LinkedIn. Like, that is definitely a box I could rant on all day. But now it is that personalization has to be done in a way of context, of you've got so much information at your fingertips related to businesses, what's happening in business and all those things, and that you've got to be able to use that to infer some context and. And speak to me in that way. And when I saw that, I was like, oh, that's a great word.
Brandi Starr [00:30:01]:
Because with AI, with all of this, it's like, there's certain things. I've seen scenarios where sellers have seemingly known about layoffs before the employees done. Like, they have. Like, there was a scenario a guy posted that he reached out and was talking about the impact of layoffs, and they were like, what layoffs? And it was like, oh, how did the Internet know before for the employees? But, you know, that kind of can be a thing. And so, yeah, that. That was one of those things that I was like, yeah, we have evolved in that way of, like, now it is context over everything. Put this into some relevant context that is about me and my business and not where I went to college or what random hobby you have, you know, found from my Instagram Rolly. Anything you want to add in terms of, like, how we really crack the nut, to use buzzword?
Rolly Keenan [00:31:01]:
Well, so first, let me pick apart something at the very beginning of the foundational question, because you went through kind of a context, right? And you said, you know, we started here, and. And people are used to, you know, the outbound, you know, you call. That was necessary to call a lot because we didn't have a lot of information. So I just want to say, for the record, I never did that. And I, you know, I was in as close to a boiler room movie situation as you could imagine. So I had managers that would walk on your desk, walk across the desk and step on your phone if you weren't on it. And, you know, their mentality was what you're saying, like, you got to pick up the phone. You got to pick up the phone, you know, because the more volume, more volume I had the Internet.
Rolly Keenan [00:31:56]:
I mean, it was somewhat new at the time in 1998. But like, I. After the guy walked across my desk, I turned my phone off again and I called. I researched companies, and then I called them with a fully informed mine. And I didn't Call a thousand people. I called a hundred to 150 a day of people that I knew something about. So fast forward to the point of your question. So I just want to say I never, I was never there.
Rolly Keenan [00:32:36]:
But, you know, how do you deal with it? I really think you've got two problems. One, you've got. If you own your own company, then you can skip the first thing I'm going to say. But if you don't, which is almost everybody, you're driven by investors who are like, get, here's the money. You can only spend it on this. And I mean, they're just sitting there going, I mean, what, what am I going to do here? I mean, I, I can't just take their money that they said, I got to put in ads to drive all this attention for my team who doesn't know anything. I can't take that and have more informed salespeople. They didn't pay for that.
Rolly Keenan [00:33:19]:
So their hands are tied a little bit. But if you kind of skip over that, either because you just want to go on that, an intellectual journey with me, or because you actually are not hand. Your hands are not tied. Then it's the guidance is what are you really doing in, in the business? Like, who is your product really for? You know, what's the real problem with like, why someone would pick a competitor over, you know, it sounds so silly dumb, like, well, of course I'm doing that. But I can tell you, most of the people I talk to who are ahead of sales CROs, they really don't know any of that because their board has their attention on. But what's my cac. What's, you know, how my deal cycle's too long and they're into all the things that have nothing to do with the business. They're the outcomes of how they're running the business.
Rolly Keenan [00:34:14]:
And yes, that could tell you stuff, but you're focused solely on making that number better. When really, you know, does your product even work? Do customers even want it? You know, are, are people showing up to your SDRs, you know, and moving on to that meeting thinking that they can buy your product for 10k and it's really 100k. But you're not addressing that like, you know, so I think that you. There's authenticity and realness that has to be interjected if anybody wants any of this to go away. And I understand that that's a big hurdle for most people because they have no control over what they're doing. They're just there for a couple years and they're going to move on to another startup and maybe one day they'll get an Uber and be rich and they'll be happy. But in the meantime, they're going to do what they're told. And I, I say that with all, you know, compassion for people that are in that situation.
Rolly Keenan [00:35:12]:
I'm. There's a lot of them, but that's, that's, I think, why it's happened so much.
Brandi Starr [00:35:18]:
All right, we've explored the issue. Now it's time to fix it. Gabe, welcome to the lightning round. Quick answers only.
Gabe Lullo [00:35:27]:
Let me get some water.
Brandi Starr [00:35:29]:
Goal is to help our audience walk away knowing if they have a problem and understanding how they can try to move in the right direction. So first question, what's the first sign a company is facing an outbound motion problem but hasn't named it yet?
Gabe Lullo [00:35:51]:
Well, you would think the quota attainment, but it's really not. It's our connection rates a problem right now and are they not having the conversations and are they not meaningful conversations? And if the meaningful conversations are not being measured in an authentic way, there's going to be a problem down the funnel.
Brandi Starr [00:36:11]:
Okay, what's one mindset shift that unlocks progress?
Gabe Lullo [00:36:20]:
Your team's probably smarter than you.
Brandi Starr [00:36:26]:
What's one common trap leaders fall into when trying to solve this?
Gabe Lullo [00:36:33]:
Trying to throw money at it. To Rolly's point, they're just trying to throw money at the problem to fix it.
Brandi Starr [00:36:39]:
And what's the most underrated move that actually works to fix it fast?
Gabe Lullo [00:36:49]:
Listening to what your competitors are doing and really realizing what the market is doing as opposed to what the analysts start telling you?
Brandi Starr [00:36:59]:
I love it. And before we close, let's have a little fun. Tell me, what's one book, podcast or tech tool that's been a game changer in your business lately?
Gabe Lullo [00:37:14]:
Gap selling by Keenan. He's a good friend of ours and he's done a really good job with that book and we really like it over here.
Brandi Starr [00:37:22]:
Awesome. We will have to make sure to link out to that. Well, yeah, Gabe, Rolly, this has been such a great conversation, but that's our time for today. But before we go, Rolly, I'm going to start with you. How can listeners connect with you?
Rolly Keenan [00:37:39]:
I'm the only cool Rolly on LinkedIn. A few of us, but just look me up on LinkedIn.
Brandi Starr [00:37:46]:
Awesome. And then Gabe, definitely tell us how that they can connect with you and do the shameless plug for Alleyoop.
Gabe Lullo [00:37:56]:
Yeah, LinkedIn as well. We, I post on my profile six days a week. So there's a lot of free content out there. We're hyper responsive. So reach out. We'll absolutely help you. And if you're a company that is struggling to find or keep SDRS in your funnel, doing the right things and generating the interest, the leads and the meaningful conversations in an intentional way, let us know. We can do an audit and see if it makes sense to work together.
Brandi Starr [00:38:23]:
Awesome. Well, thank you both for joining me and thanks everyone for joining us. I hope you have enjoyed my conversation with Gabe and Rolly. I can't believe we're at the end. Until next time. Bye Bye.
Gabe Lullo [00:39:13]:
Sam.

Rolly Keenan
Chief Revenue Officer
Rolly Keenan is a CRO who resides in Colorado. He is a born leader and the key growth specialist at Tegrita as our CRO. Rolly brings 25 years of diverse experiences at the likes of LinkedIn, Oracle, Gallup and the US Olympic Volleyball Teams. Graduating with his MBA in Marketing from Northwestern University’s Kellogg School of Management, Rolly has had some unique experiences in his career including making over 500,000 cold calls and he has even spent time in training for high-stakes negotiation protocol for hostage situations. He is a partner to the wonderful, Veronica, and a father to six children and one dog, Nala.

Gabe Lullo
CEO
Gabe’s expertise in sales, marketing, recruiting, and management began when he started his own business after graduation from the Barney School of Business at the University of Hartford. He owned and operated his own sales, training, and marketing firm for more than a decade. He excelled in training sales and marketing professionals, and additionally, Gabe has had a successful career in executive recruiting. He has been instrumental in expanding the company's search and placement for IT, Software Development, Sales, Customer Success, Marketing, and Executive leaders. Gabe's most recent success has been with us here at Alleyoop. For many years he has been working to build and grow the company by focusing on our culture, environment, customer success, and sales.