Jason Bay – Outbound Squad – Is It Harder to Hit Quota Now or Has it Been Happening Already?

Quote of the Show

In sales, you're starting from a place of skepticism. It's one of the few professions that we do where the people that we speak with on a daily basis are inherently skeptical of us. We're starting from behind the starting line and most professions are not like that.

Key Takeaways

  • The SDR model is not a good fit for many companies.
  • Understand how acumen will help you craft your messaging.
  • Don’t use AI until it can “think outside the box”.
  • In sales, if you don’t know how to write effective emails and it’s your main job, you are going to be replaced because the technology is already here.


Episode 104 – Jason Bay

Guest: [00:00:00] 1, 2, 3, 4,

Host: sales, marketing, and rev. It’s sink or swim out there. And yesterday’s strategies and tactics won’t help you today. This is revenue today, and

Guest: I’m your host, Jared Robin.

Host: Join me as we interview revenue leaders in our community to learn what steps we could take, right. To help you scale yourself and your company.

Revenue today is sponsored by Rev Genius, and we’re on a mission to bring inspiration and creativity to all revenue professionals in the world.

Wanna shout out our sponsored demand base Demand base to Smarter GTM for B2B brands, they help marketing and sales teams spot the juiciest opportunities earlier and progress them faster. By injecting account intelligence into every step of the buyer journey in orchestrating every action. For more information about demand-based, [00:01:00] visit demand-based dot com.

Hey friends. Welcome to another episode of Revenue. Today I’m joined by a special guest, Jason Bay, who’s the founder and c e o of the Outbound Squad. He’s on a mission to help reps and sales teams turn complete strangers into paying customers, and he is worked with. Many companies like Zoom, C B R E, Medallia, Xfinity Gong, and so many more.

Jason, welcome. Good to be here, man. I’m so excited to have you followed your journey a bit since, at least since I leaned into Rev Genius and yeah, really, really proud of what you’ve accomplished. Really excited to, to learn from you today.

Guest: Yeah. Yeah. I, I think we connected. on LinkedIn. We were sent, I sent a DM to you or something cuz you liked something.

I posted, I can’t remember. And you’re like, yeah dude, I just got laid off. I’m about to go start something else . And that feels like an eternity ago, right? [00:02:00]

Host: I wish. And, and this is actually possible Darren McKee told me how to do this. I wish I could get. From, let’s say, the time I’m laid off till I added Rev Genius on my LinkedIn profile.

Yeah. All my dms I sent, because that would probably be an interesting an interesting blog post, at least, right. .

Guest: Yeah. Cause things have been freaking cooking in your world too. Man. Lot has changed. I’m grateful. So yeah. I’m, I’m excited to catch up, dude.

Host: Yeah, man. So I’m, I’m grateful and grateful to have you, grateful for our journeys.

Coming out with it, like debunk a myth about generating revenue today?

Guest: Yeah, I mean, I spend a lot of my time working with both account executive teams and SDR and BDR teams, and I, I’m gonna pull something out I think that people might not like to hear, but. I don’t think the revenue, the s e r model is a fit for most companies, and it’s not because the [00:03:00] model itself is broken.

I don’t think that most teams have the expertise to execute on it. And when I say that it doesn’t work, I’m not implying that prospecting and outbound, that’s, that’s what I’ve made my living off of, you know, in the last five, seven years, whatever it’s been. I think a lot of companies, what they’re starting to scrutinize, right.

I’m literally have clients laying people off and doing all that other kind of stuff. What I notice is that when companies lose people and the companies that are hiring great, now, they’re hiring fewer SDRs than their account executives. Mm-hmm. and the SDR two account executive ratio has held pretty steady at like one to 2.6 according to Bridge Group over the last three years.

And I think we’re gonna see that grow. I think we’re gonna see less SDR support for account executives. So the myths I. based on the data. And then from what I’m seeing in the marketplace is that I need SDRs in order to grow and scale a sales organization. [00:04:00] I have a client with, I think they have 450 account executives, zero SDR support everyone’s self sources.

Mm-hmm. Pipeline. That’s just how they do it. That’s called

Host: 2012, by the way, .

Guest: And the the other thing that I see too is, I think that this method, as an account executive, I don’t need to prospect that I’m above that. I’ve already done that. I was hired under the expectation I wouldn’t have to do that anymore.

You’re just not gonna, you’re not gonna hit and surpass quota right now unless you got a company that’s really well positioned and it’s just got a, like an inbound marketing machine. You’re just not gonna hit and surpass quota in an the environment that we’re in right now. So I, those are the two big things that I see in my line of.

when, when

Host: did this transition from SDRs to being effective and efficient to not happen and, and what do you think caused that? Or were they just never efficient in your opinion?

Guest: So, [00:05:00] yeah, I mean, everything, I’ll speak to my opinion and then I can speak to the data as well. Sure. Because it’s really hard to tell.

There’s not a, it’s easy for me to talk about and correlate things that. , you know, or to point to causation when it’s correlation, right? Sure. So what we’ve seen here in the last 15 years, I think for 11 of them, it’s the longest bull run in American history. The economy has not been better this many years in a row up until now.

So what that caused is venture capitalist firms to start investing in all of these companies. There’s just so much money to go around and what do they want to do? They want people to. that’s in their mind. This is how we scaled this business. We need to double headcount this year. And you hear things like that and it’s like, wow, we need to go from a hundred to 200 reps.

We need to go from three to 600 and naturally SDRs. Hey, we need to hire more of these people. And what I saw with a lot of companies a [00:06:00] year or two ago was, wow, they have a ton of SDRs. yet very few. The, the quota attainment across the team is extremely low. Mm-hmm. , there’s a few superstars. It’s people like you and.

we’re gonna be good in no matter where you put us. Okay? We just have that . We run businesses, you know what I mean? Like we have that grit. Not everyone has that. You can’t build and scale a team off of the top 10% of people out there. That’s just not how it works. Andy, you just have these teams just, I have specific clients that I’m thinking of where.

They have tons of SDRs that do not hit their quota and by definition, not penciling from an ROI standpoint for that company, but they can afford to keep ’em and they’re getting pressure from their venture capitalist to hire. So I think that’s one really big thing is that we overhired and it was not effective to begin with.

At that company we, we created the role as compensation out of

Host: nowhere. And then overhired for it, [00:07:00] which is fascinating. Yeah. Are you seeing what, what I seem to be seeing is quotas in general are going down as well. Yeah. Or maybe I’m just, or maybe there’s a whole new level of s and b coming in at companies that I wasn’t aware of before.

Guest: Yeah, I honestly, I don’t have enough insight to really share a trend on this. I could tell you anecdotally right now, yeah, there are companies lowering quota, which I think is probably the right thing to do if, if companies are, you know, if you’re being really affected by the, by the the economy. But, . I, I, I think the other thing though, cuz we were talking about what BDRs and is this a good function or not?

Howard Dover, he’s a professor over at UT Dallas. He, I think he runs the sales school over there. He wrote a really good book called, Oh Man, the Sales Tech Paradox or something like that. Howard Dover, you can look it up. Really, really good book. What [00:08:00] it totally opened my eyes up to was the amount of tech.

and traditionally in most industries, when the, when people are investing in technology, so let’s take an outreach or a sales loft or whatever, outcomes increase, but efficiency also increases too. Sure. So in other words, what we start to see is a multiple. On how much more effective people are. So if we’re gonna spend twice as much, we don’t just get twice as much output from a rep.

When I say output, I mean actual outcomes. Meetings booked in this case. Pipeline generated. Mm-hmm. , you would expect to see 3, 4, 5, 10 x. The output and what he pointed to is, is actually not even like, there is no increase in efficiency at all. Reps and tech have actually become more inefficient as they more technology

I was gonna say,

Host: when I was a full cycle rep, I gold myself and we’re talking eight years ago, geez, 10 [00:09:00] years ago, on having 20 new enterprise meetings every month. First a, a lot of people are hearing that number. It’s like, oh, that, that’s as a full cycle rep. Yeah. And now I hear people saying, my goal’s 14, my goal’s 16, my goal’s 12.

like, yeah. Crazy.

Guest: Yeah. The, the other part to this, so the third layer of this is that there’s so much noise. Right now, I mean, the average prospect, according to statistics, the average person in 2022 spent like 10.7 seconds reading an email after they open it. It’s just insane. You know, Harvard Business reviews got a bunch of data on, you know, the typical office worker gets 150 emails every day.

So that’s not even a busy executive that people that we’re trying to get ahold of. So when you start to think about the barrier to. . So if you go on g2, I have this, this image if you go on G2 just [00:10:00] for sales engagement. I mean, it’s crazy. Dude. There’s, there’s like four dozen just on that chart. , there’s probably even more when you zoom in.

But you know, outreach wasn’t really a big company like six years ago. , there weren’t all of these mass email blast type of tools and dialers and all this other stuff. So where I’m kind of going with that is the barrier of entry to be able to 10 x or a hundred x, your activity level is extremely low right now.

I think I, you could probably get something for 20 to $50 a month, like a mail shake or something like that, that allows you to mass blast emails. So GMass

Host: is like $12 a month for anybody listening. Yeah, like,

Guest: so that’s the barrier of entry to get into people’s inboxes right now. Is if you have 12 bucks a month, well,

Host: well, two different things here.

That’s the barrier to entry, to sending as many emails as you want. The barrier to entry to get into somebody’s inbox is a different thing. Right.

Guest: [00:11:00] Well, okay. Explaining that. Yeah, yeah, yeah. Yeah. As assuming that, you know, basic stuff like I’m, I’m not gonna put a lot of hyperlink into an E because even that stuff’s easy to game.

Sure. Right. I have a domain that’s good, which any big company is, for the most part, gonna have, and I’m doing all the email deliverability things that I. And Mail Shake has like a tool that helps you warm up your inbox and check for all of this kind of stuff. It’s just, my point is that you don’t need to be a multi-million or multi-billion dollar company to be able to effectively do this stuff anymore.

It’s very accessible, so the noise is crazy. And then what you start seeing is email open and reply rates in general go down across the board. I mean, pickup rates for cold calls get lower and lower every single. Right now it’s, at least in the data that I see at the companies I work with, it’s three and a half to 5% pickup rate on a cold call.

That’s only gonna get worse. You know, apple, Android, they both have functionality. They have for the last three or four year, almost four years now, where you can send unknown callers [00:12:00] straight to voicemail. They won’t even ring your phone. It won’t do any of that kind of stuff. It’s so, it’s it. . It’s scary, man.

I, I , I, I think that we’re heading for a future with, with outbound, where you might see something like, Gmail and Outlook saying, we’re no longer gonna allow tools like Outreach or SalesLoft to even hook up to our inbox. You gotta do a private email server from now on. And it’s gonna get better at detecting where this stuff is coming from too.

So I, I think we’re, it’s gonna be scary for, for outbound here in the next like five to 10 years. We’re, we’re approaching a time where I think there’s gonna be a lot of restrictions and it’s gonna be just incredibly difficult to get ahold of people.

Host: You had a, a pretty cool post on LinkedIn about Google, Microsoft, apple, and even the US government making it harder to hit quota.

Yeah. Can you expound on that

Guest: a bit? Yes. I already mentioned there’s a couple things in 2019 that Apple and Android did with the phones. , this is Gmail and Outlook. I’ve been doing this forever. [00:13:00] Outlook was kind of the first one in 2007, but just creating separation within your inbox. Mm-hmm. . So making it easier to sort out what’s mass blast versus what’s personal versus what came from your company versus what’s a newsletter.

That stuff’s been going on since 2007, so they’re already think. If I’m Outlook in Gmail, what I’m trying to do is provide the best user experience for the people using this because they’ll stay in this app longer. So them being able to sort out spam some, something that pisses everyone off, them being able to have.

A better experience on the product. That’s, that’s their goal. They want people to stay in the product so they can see their ads. And then 2003 was when the FTC introduced the can spam, you know, laws and how you gotta let people know how to unsubscribe. There’s a D and c, you know, so there is a consumer.

Do not call us. I’m surprised there isn’t one for b2b, by the way. And then yo, it wasn’t too long ago that there was. You know, [00:14:00] gdpr and then in California, if your business is over a certain size, there’s GDPR type rules. I don’t think we’re too far away in the United States from having a GDPR type of thing where it becomes really hard to just get people’s information and it becomes, , there’s gonna be a lot more regulation.

Like there’s already, this is had been happening. I come from call centers. This has already been happening on the consumer side. I think it’s like 70 plus percent of America’s on the do not call us. And there’s major, major fines. Dude, if you’re calling people on the, do not call us, there’s like a per call infraction that could put businesses out of business.

So I, I do think that we’re heading towards a, towards. Are are

Host: what’s, what’s next? Are we are we doing field sales reps again?

Guest: Yeah. I think that there’s gonna be certain fads and things like that. Like, I think that LinkedIn as a prospecting tool is not necessarily a fad, but sending voice memos and like videos through LinkedIn is, is, is, it’s a fad.

Video [00:15:00] is, I like it. It’s got its place. But it was insanely effective for like a year or two until everyone started doing it. Audio messages, same kind of thing. , if you’re getting messages or doing anything in sales, that’s effective if you’re getting meetings because the thing that you’re doing is a pattern interrupt, like the prospect has never seen an audio message on LinkedIn before.

That was cool until I started getting a lot of audio messages and I didn’t wanna fucking listen to ’em. . You know what I mean?

Host: is, is is LinkedIn. Ruining. Let me, let me refresh the, let me resay this a different way is, are people that are leaning into LinkedIn sharing their tips or rooting it for the re because how many tips are actually

Guest: left?

Yeah. I don’t think the people sharing tips are ruining it necessarily. So, so in other words, I don’t feel like someone like myself that’s a sales trainer has a responsibility to, to not teach tips. I think. [00:16:00] Salespeople. The luxury that we don’t have in sales is that we have to get results even in enterprise and Strat sales, like you need out quick outcomes.

Mm-hmm. , so you don’t have the opportunity to like afford to just wait and try stuff. So you want to do what’s gonna generate a quick result. The stuff that doesn’t go outta style is, Hey, when I’m reaching out to Jared, do I understand what people like him, what their priorities tend? What they care about.

So for me, it’s VP of sales. I know the VPs of sales right now, they’re not only trying to do more with less, but more specifically they’re trying to get account executives to Salesforce, more pipeline because they know they need four to five X pipeline coverage versus three right now win rates are down, sales are taking longer to close.

They just need more good opportunities in the pipeline, and they’re not hiring SDRs to help these AEs. So getting them to Salesforce more pipeline and getting more out of the AE I know is a really big focus. for just about any VP of sales that I’m speaking with. Mm-hmm. . So [00:17:00] I need to be able to lead with that kind of messaging.

I really needed to know my personas inside and out. So what are their priorities? What are the problems? So what are they trying right now and what is and isn’t working? So priorities, current solutions, how they getting the job done, the, the problems and, and what is it that they really want? I need to know all of those things and I need to know those things in their language.

That’s what helps the message cut through the. that’ll get my email to cut through the collateral. I might have to send more emails than I’m normally used to. I might get fewer at bats on the phone, but outbound is turning into a game of only elite. Like if you have elite skills at outbound, those are the only account executives especially, they can actually make it worth her while , because yeah, I might get, just do the math dude.

If I, if I can make 25 calls in an hour, let’s say, and that’s, that’s aggressive. And let’s say I have a 5% pickup rate, that means I’m having one conversation or less. And let’s say I can [00:18:00] do five of those blocks over the course of a week, because like I’m running, managing a sales pipeline. I gotta queue up emails, I gotta do all the other stuff.

That’s maybe four or five conversations a week. You better get two meetings out of that, two or three meetings out of that, because if you’re converting at the average, which is 1.5%, 1.48%, exactly according to gong versus a leg. How to study around top performers. I see this in my line of work too, where a top performer will secure 30 to 40% of the live cold calls they get.

They secure a qualified meeting from. So it’s becoming a game of you gotta be a ninja outbound in order to make this activity worth your while if you’re an account executive, cuz you don’t got all data, just sit there and and pound the phones.

Host: No, no more just plugging into somebody else’s sequence. .

Guest: Yeah.

So all of that, that kind of stuff. I think messaging is where it starts. . So the equation that I have for outbound, it’s, it’s quality times volume. So the number of meetings that I’m gonna get is a combination of quality and volume. You can’t have one [00:19:00] without the other. So outside of the volume and activity side, the quality side is really broken up into three areas.

And that’s fit, message and delivery. So fit is am I reaching out to the right people at the right companies that are a good fit message is what is my saying? And delivery is my soft skills. So that’s my ability to, when I get a prospect live on the phone, conduct a great cold call, my copywriting skills when it comes to writing an effective email.

So, the message. Really assuming that you know who you’re gonna be reaching out to, the message is so, so important. That’s what I spend a lot of time working out with companies, and I cannot tell you, Jared, I’m curious what you see too. Mm-hmm. from the clients you work with is just like, dude, there are still so many companies that they’re, they teach their reps to just pitch to people.

There’s no, I’m gonna speak to Jared and make sure that. What he’s working on and what he might have problems with right now aligns with the stuff that we can fix. There’s still [00:20:00] so many people using a sales approach that is just the opposite of modern .

Host: I spoke, I spoke with Ryan Scalara, who is an incredible BD leader, and he’s like, most people I speak to don’t even know the actual problem that they solve.

Guest: It’s crazy. It is absolutely crazy and. . I think when you have leadership that doesn’t understand that, of course you’re gonna have a team of reps that doesn’t, the messaging, so, so

Host: you come up with a different message and then you’re pounding the wrong proverbially, the wrong message down the throats of your prospects and it’s just not landing.

Guest: Yeah, so that’s the hard part I think about prospecting is a lot of it is a game of if your company’s not providing this stuff, you as a rep have to figure it. . So the tip I have here, it’s a very simple, straightforward one, especially if you’re a newer rep and you haven’t really done much of this before.

Is you want to [00:21:00] listen to two or three call recordings that are, are like discovery calls or demo calls with the ideal prospect. Mm-hmm. . And preferably if it’s one, if it’s one of yours or one of the best sellers on your team. You really wanna extract language that people use around how they talk about their problems.

in the specific language they use. And if you, if you listen to three, maybe five of these, you’ll find patterns in the prospects. It, and it’s, it’s like all of them talk to each other. It’s really interesting. So you wanna make sure that you’re niched down enough to where. I’m listening to a sales executive in SaaS, let’s say, at a company that’s 500 to 2000 employees.

Like if I can niche down by industry, by size of company and by role, you’d be amazed how many patterns there are and what those people are focused on and what they care.

Host: With, with everything. I was speaking to our COO today who runs a demand gen agency as a side hustle, and he’s like, Jared, you wouldn’t be [00:22:00] surprised at how many companies all buy branded keywords and they don’t take the risk elsewhere.

He’s like, it’s like consistent. I’m like, I think you have your LinkedIn purpose , like, like your direction here. Yeah. And, and your messaging. and, and light bulb just went on and he’s like, oh my gosh. You’re right. I said pick one new issue that you’re seeing directly every day. Yeah. And, and thank you. You just built us a, a demand gen funnel for you.

Guest: Yeah. So let’s make that a really practical example. So on a cold call, here’s where people make mistake. They say, Hey Jared, it’s Jason with ABC Demand Gen Company. We’re actually running paper click campaigns and doing demand generation for some of the top SaaS companies out there. And I was giving you a call.

I wanna see if we could set aside some time. I’d like to do a free assessment for you and come up with a keyword. What’s your schedule looking like? Click or we already have a demand agency or, hey, we lowered our budget or whatever, versus, Hey Jared, it’s Jason with ABC Demand Gen Company. Maybe I do a [00:23:00] permission based open or whatever.

But if I said, Hey, Jared, I’m, I’m really interested in, in hearing a lot of the CMOs, I’m talking to you right now, they’re investing a lot in demand gen strategies like pay per click. But one of the things they feel that is really risky is when they start to venture outside of using branded keyword.

Because they really don’t wanna waste any of their precious marketing budget right now. How are you thinking about that? Or what approach have you taken with doing X, Y, Z and your, your, you know, what approach does your team right use right now and picking keywords outside of your, you know, how are you

Host: capturing people that aren’t searching for your brand , right?

Guest: Shit like, yeah. And so that’s a completely different type of call where I’m talking immediately about your world. . So there’s a really interesting stat from Gong on percentage of talk time in a successful versus unsuccessful cold call. So they analyzed over 90,000 cold calls, and what they found a pattern in is that roughly a successful cold call.

[00:24:00] The rep is speaking about 55% of the time. So in other words, they speak more than the prospect. I was just at an sko, there was about 600 people there a couple weeks ago, and I asked that question. because before I showed the stat, I said, what percentage of the time do you think you should be talking or your prospect?

Everyone said 10%, 20%, you know, as little as possible. I’m like, no. It’s not about how much you talk compared to the prospect. It’s about how much you talk about yourself compared to the prospect. What is the content of that conversation? The content should be 80% prospect, 20% me. So if I can start the call, it’s gonna be me talking quite a bit in that first 30, 45 seconds.

But I need to show the prospect. I know something about people like you and if I’ve done research and it’s a large company, I might not even know something about, like if I was selling demand gen services like this, I would get on Google and start Googling things to see where they pop up. I mean, there’s probably tools that they help you do that too.

Absolutely. Yeah. So I can, I can. [00:25:00] By talking about the prospects world, and I think in sales, what we try to do is we try to start in our world and get the prospect to come over versus starting in their world and meeting them where they are at. . That’s what sales is. That’s what prospecting is. I’m gonna meet the prospect where they’re at.

I, I can’t expect a stranger to meet me where I’m at. That’s too much of a lift. They have too much other shit going on. Yeah. So I have to talk about them in their world first. That is the key. If there was one thing that you could do that you would get an immediate lift on all of your outreach, it would be that, how can I start with their world first and articulate it in a really concise.

That either they are unable to do themselves or that just shows them, oh wow, Jared, he really understands my world. Okay, cool. What do you got? That’s what do you get those cold calls? Okay. Yeah. What do you got? . And

Host: then, and, and then it’s even cooler. Like when, when you speak their language, but then when you speak like their company’s language, like, yeah, I saw that you’re, hi.

[00:26:00] Judging by the fact that you’re hiring for a head of demand gen or whatever trigger enter trigger like this. This seems to be like, it might be even more top of mind for you or might be more relevant is, yeah. Is is that the case, ?

Guest: Yeah. Yeah. I saw you’re hiring for a demand gen a director of demand gen right now.

And, and usually what happens when I see people, you know, advertising on the way you are, that are doing some hiring is they’re looking to venture outside of branded keywords. They’re looking to bring some expertise in house Yep. To help them venture outside and capture. Traffic in an audience that is not already proactively looking for them.

How did I do ? Yeah. Coming in with a hypothesis based on like, you gotta think about I always like to use, you know, personal trainer analogies. Think about a personal trainer someone that’s been personal training for five, 10 years. They’ve seen every situation. , they’ve seen the person that has trouble getting to the gym.

They’ve seen the person that is stubborn about their diet. They’ve seen every, they’ve seen the, the busy mom or dad that [00:27:00] has trouble prioritizing it or whatever. as a salesperson, you’ve run across situations that are really, really common. So I, I do want to put the prospect in a bucket. I’m not gonna be assumptive about which bucket they’re in.

Yeah. But they need to be in one of the two or three common buckets that prospects are in that we can actually help them with. You need to know what that is. Before you call someone. You need to know that before a sales call, especially, I can’t tell you how many discovery. . And you know, an intro call starts off with, Hey, tell me about your biggest challenges.

Right? And it’s like you should already kind of know what those are. And if they don’t have a common challenge that you help with, they’re probably, you’re probably not a good fit to help them out. So you have to think about what are the two or three very common situations that people are in. And I have to, I have to be really proactive about bringing this stuff up because in sales you’re starting from a place of skeptic.

It’s one of the few professions that we do [00:28:00] where the people that we speak with on a daily basis are inherently skeptical of us. Like we’re starting from behind the starting line . Oh yeah. You know, most professions are not like that. There’s a few industries that are kind of shady, like car dealerships or, or whatever, but most people, yeah, or mattresses, mattress sells people, you know?

Yeah. Most people are not going into a store or going to the doctor or whatever. and assuming the person is full of shit or that they’re gonna be taken advantage of, most people don’t go in like that. And in sales, that’s where we start. So we ha we do have to demonstrate business acumen and that we know their world and we gotta do it in their language.

That’s table stakes. You gotta do that immediately. .

Host: It sounds like that’s one of the biggest takeaways, like understanding that acumen will help you craft your messaging. Yeah. To, to best meet their needs. Now with, with all of this quality, like what, what’s the use of a sales engagement platform like?

Is, is it just for the follow up pings? Like what’s, what’s, is there, [00:29:00] is there a world. , they’re gonna go by the wayside or how do you see that? I

Guest: don’t see ’em going away anytime soon. I think that companies are gonna really rethink their, how they invest in tools like this. Mm-hmm. , what I’m already starting to see is consolidation of tech.

So people are, just to throw example vendors out, people are doing much less, I’ll have outreach and gong and they’re saying, you know what? Outreach already has most of gong’s functionality built in from a conversational intelligence standpoint. At least let’s just. It’s good enough gets us 80% of the way there.

So I’ve already seen consolidation of tech, so that’s already starting to happen. I think the amount that people spend on tech per rep will go down. So to answer your question though, there’s absolutely room for a sales engagement tool. It’s, it’s kind of, to me, kind of like asking what’s the future of the cr.

Yeah. The CRM is already doing stuff that you could do on a spreadsheet, but the fact that you have someone there to gather the data for you and to help you run [00:30:00] experiments and to like capture patterns across a bunch of data is extremely helpful. So I can test things. I can test subject lines, I can test value props, I can test problem-based messaging, I can test industry.

There’s all kinds of things that I can. that a sales engagement helps platform helps with. I think when people think sales engagement, they think automation and you don’t have to use all of the automated features well, so you could, you could customize all of the messaging and just pre-schedule it to go out.

You’re still taking advantage of automation but not being spammy. So I think it’s, those two things are very important to understand. I think the other thing that we’re gonna start to see too, in the revenue intelligence, we’re already starting to. Is, it’s starting to extract stuff across multiple, medium.

So like gong’s already got some really good stuff going on with Rev Intelligence, where, you know, clarity’s been doing this for a while. It’s like, I think [00:31:00] tying the pieces of the puzzle together is where the value is in tech right now. And I, I feel like we’re barely skimming the surface. So how can I find patterns all the way from messaging people resonate with in an email and a cold call to throughout the sales process and start to pick up patterns and get me red flag.

when the best practices aren’t being used. You can already use a chorus or a gong to see how tightly a team is following a methodology or if there’s certain things that they forgot to do around multi-threading or whatever. So I think the technology is more gonna be the thing that enhances the rep, and it’s gonna be table stakes to where you have to do things that are clearly not.

Host: Yeah, I mean, it’s so funny that just the measurement part of emails going out isn’t handled by anybody outside of the sales engagement platforms. What do you mean the measurement part? Like, like AB testing different subject lines. Like clearly you can’t do [00:32:00] that straight in Google. That’s kind of the antithesis.

Or Gmail, or, or, or Outlook. That’s kind of the antithesis there, but why not HubSpot or Salesforce in the crm? HubSpot’s connected to every email that I’m going out. Maybe, maybe they are, maybe they could, or maybe I’m just not activating it. Well, they have, they, and I’m not using the automation part. Yeah,

Guest: they do track.

So I use HubSpot. They, it will track if emails are opened and how many times. But there isn’t a way to, unless you’re using the sequencing functionality there. Yeah. It’s not giving you the type of information that may be lavender or, or, or whatever it would. Sure. I think that , the thing that is, dude, look at chat, g p t, man and listen to Lex

Host: Friedman every morning.

It’s gonna be g p t four in due time. And yeah, it’s, it’s even more powerful than writing your sales email. But by far, like you could ask, tell me about Jason Bay in a, [00:33:00] in a negative light, and, and they’ll, they’ll pull out everything.

Guest: Yeah. So controversial. Yeah. And reggie.ai is already, was already using an older version of chat, G P t I believe so.

Both were, yeah. Here’s the thing that’s really crazy is it still relies on input of good data, though. . Mm-hmm. . So Reggie ai, for example, when I talked to Matt and I sought this most recent time in like November or something like that, November, December, I was blown away by, by the progress that they’ve made in there.

They’re not a sponsor or anything like that, by the way, ,

Host: I’m, I’m, I’m, I’m, I’m an advisor of Reggie, that guy. Okay. For disclosure, so, okay.

Guest: So he is, he’s a great dude, but. Where I was kind of going with this is that it still relies on good data to be inputted into the platform to spit out something. That’s good.

So in other words, so humans are the API

Host: for G

Guest: P T, fyi. Yeah. So api, [00:34:00] yeah. So if I’m reaching out to VPs of sales, I still need the acumen I have around that industry and really understanding that that persona. That’s, that’s a necessary first step in order to use chat. G p t, let’s say, where I found a lot of value in chat, G p T, and I honestly haven’t played around with it a ton, is, dude, it’s ability to get you 80, 90% of the way there.

Mm-hmm. is insane. You could just throw it together. A really just hear the kind of talking points. Here’s what the people care about. Give me an email and they tell it, to rewrite it and to make it more concise. And I, I was using it. I. Posted one of the LinkedIn posts yet, but I was messing around with having it repurposed my LinkedIn posts.

So I, I always, this is probably not a big secret to marketers. Might be a big secret to people that consume my LinkedIn content. Probably one or two of the posts I put up out of the five every week is something I’ve already posted before. Mm-hmm. . So take your best content, repurpose it, put it up. I’ve done [00:35:00] stuff with chat G B T.

Again, I haven’t posted these yet. I gotta start doing it, but I just had it for fun. Repurpose one of my more popular posts, and I was like, wow, that looks like something that I would write. And it’s the same core foundation of what that post was trying to accomplish. But it just reworded it, made it like freshened it up a bit.

So that’s, that’s what’s coming for. and email is gonna be one of those things. I think that right now is it’s gonna be something that, there’s just not gonna be a really big need to have individuals with great copywriting skills on a sales or marketing team. It’s gonna become table stakes. , you’re,

Host: that’s gonna come to cold calling too, when it could manipulate your voice.

Guest: Yeah, but, and listen, the only thing. The only thing with that is, I think we talked about this before, there’s gonna be heavy regulation around that. There’s gotta be, so it’s, there’s gotta be some sort of disclosure. If it’s automated and it [00:36:00] sounds like a person, there’s, there’s, Elon Musk is

Host: already like saying, we need to create a whole government agency to oversee this.

Because it, yeah, it could get, it could

Guest: get hairy. It’s scary. But the point being is, I, I don’t think that in our lifetime we’re gonna hit a point where AI could hop on a podcast like this and have a human conversation with you. But I definitely think they can make cold calls though, because it’s a pretty li it’s, it’s a pretty linear the content can only go in so many different directions, and you could have it respond in a way if it doesn’t know the answer in a really human-like way.

I definitely think that that could, that’s gonna happen here. I don’t know how long I, cause I don’t know much about the science and stuff behind this, about around the technology, but I definitely see that happening in our lifetime for sure.

Host: As somebody that listens to AI podcast Daily . And I do, cuz I, I love Lex Friedman strong recommend and plug Yeah.

He interweaves AI to like all his conversations even with like mm-hmm. , not scientific [00:37:00] folks. He said the technology is just about there. It’s just about the inputs and like the data. He is like we, we just need a few massive companies to like really take it on and like make it learn like Google.

You sure. . Well, so G P T is the biggest opponent, competitor for Google. Cuz think about it, Google’s based on algorithms of talking the search in part. Okay. Yeah. If GBT three knows the best answer, forget Google’s algorithm, which is based, you know, on a multitude of factors. If it knows legitimately, objectively the answer that you need.

And it could serve that up by Google. By Google. Like goo Google’s figuring out their own AI now like, like they are. Building AI fast because this, this is the first serious threat and they’ve had many threats, Yahoo, et cetera, et cetera. But this is the first like fundamental, like [00:38:00] crazy threat to the search algorithm and, and their whole business as a whole.

I don’t think Google’s gonna go anywhere in our lifetime, but it could eventually and picture, if everybody is on an ai. With G P T power, whether it’s lavender, whether it’s Reggie, whether it’s the five more that’ll come out in the next 12 months Jasper or or blah, blah, blah. And it’s learning what subject lines a success verse.

Not objectively test, like helping do this and like essentially being a so how things are now you have an outreach. And, and I’m not an AI expert, but I’ve sold AI once. You, you have an outreach ex thing. All that data’s your. Right, like the subject lines, all of that, you use that to human make better decisions.

Well, with G P T, it’s all going to a central place and it’s getting [00:39:00] everybody smarter. All the nodes smarter on that, right? So everybody’s sharing that and every, and, and it’s gonna become table stakes to be plugged in. Otherwise, you won’t be the best being human. That, that’s what’s so crazy about it. So the technology’s almost there.

They’re gonna have G P T four, I think next. Oh, I know. That comes after three and they’re gonna have different iterations. I think they’re close to releasing this one. Who is Lex was he was speaking on Joe Rogan today. Yeah, that thought I was listening. It’s fascinating stuff. And then there’s Neurolink, that’s something completely tangential, like fixing stuff, but what does, how does all this.

You know, go into the future of the sdr. Like how, how does that translate into the future of the sales

Guest: development rep? Well, I think what you’re seeing right now in general in the US working population at least, is I work with another, one of my clients sells. [00:40:00] I’ve worked with two robotics companies actually.

One of them though sells like imagine in an Amazon warehouse that’s a robotic cart that takes stuff on and off the shelves so that people don’t have to do it anymore. That’s completely being replaced. So I think the table stakes type of skills, , the stuff on the bottom is being replaced. Yep. So, well the stuff

Host: that you have to be insured for as well, like Right.

That there might be like a heavy like insurance implication so there’s more cost than just a person there.

Guest: Yeah. So, and it’s just an easy skill to replace. So you gotta think about, what am I doing right now that’s really easy to re. . Well, taking a really shitty sequence and then sending it out thousands of times a week, that’s a really easy thing to replicate.

Mm-hmm. . So what are you doing that cannot be replicated? Where I don’t see AI making a lot of progress is it’s, it’s, it is, it’s taking, Google is not suggesting things to me that are out so outside of [00:41:00] the box that I’m like, oh wow, this is great. It’s not pattern interrupting in any kind of way. . It’s not doing any of those stuff.

I haven’t seen any AI like suggest something that’s like, oh wow, that is so creative. It’s just serving up stuff that’s effective. So if you take cold emails, for example, and you got a tool that’s saying, these are the subject lines that’ll work the best, will help you kind of hunt it. Well, that’s just based on the data that’s already in there.

What about the outside of the box stuff? Like think of all the most clever marketing campaigns and ideas that you’ve ever heard of. But you could train it.

Host: No, like you could train it. You should say like, the first line needs to be provocative based on the downside of data. At this person’s role That relates in my demand

Guest: gen.

Yeah. I just don’t think that, at least from what I’ve seen, I just don’t see this getting to the point where it’s thinking outside of the box like a person does. The other thing that I don’t see [00:42:00] get getting replaced is stuff that’s Enterprise and Strat stuff that’s very strategic where, okay, cool. It can send an email.

sorry. No, no. SVP or C-level executive at a Fortune 5,000 company is going to sit on the phone and speak to a robotic cold caller. That’s not gonna happen in, in the amount of knowledge that you need to have in order to figure out what’s important to these people and the multi-threading and the multiple conversations and linking them together.

There’s just so much there that you need a person. and not to mention just because you get the meeting, dude, that’s the hard work has just begun when you get the meeting , I think

Host: I, I, I agree. I think, I think anything relationship driven, anything empathy driven. Yeah. Anything edge case driven, like, you’re making a left turn and a, and a dog runs in the road and you have to like, stop or whatever.

Like yeah, like I’m talking about electric electric AI driven bots or [00:43:00] cars rather. Mm-hmm. , that’s gonna be hard, but Exmark, you know, is crazy, man.

Guest: Yeah. I don’t think we’re gonna see that in our lifetime though. That’s, that’s, it’s so advanced. So, . Yeah. That’s scary dude. To think that that’s going to happen at some point.

If we don’t, if the human race doesn’t kill itself, something like that is eventually gonna happen. . So I

Host: was just listening to how this is all part of evolution. It’s so fascinating, right? Like when people were taking horse and buggy across the country, if you were to tell ’em, Hey, you could have done that in three hours at an airplane.

At the time, , they would’ve been like, what? Like evolution is like changing quite a bit. Yeah.

Guest: I, that’s the thing is with ai, I feel like we are so completely screwed If AI picture them back with the, the horse and buggy days. If they’re like, you know what? You guys should think about airplanes. like [00:44:00] that is so insanely like, it’s so far out of the box for people so far out.

I just, if AI is starting to do stuff like that, we’re just screwed as a race. If it’s starting to do stuff like that, we’re completely screwed. This is like some Terminator two judgment day shit. . Oh, there, there,

Host: I mean, and then you, at that point, you open your eyes to Elliots too, because you’re like, yeah.

Yes. Yeah. That’s what’s out

Guest: there. Yep. So I think in sales, what you gotta be really worried about is if you don’t know how to write effective emails, you’re j and and that’s your job. You are going to be replaced. Yeah. That is gonna be a really easy thing to do. It’s already there. The technology is already there.

Reggie AI’s got it. Lavender has got some really great stuff with, with emails, but that’s just, that’s table sticks right now. So I think the other thing too is that if you are not. If you’re not taking the time to really understand your prospects and to become that trusted advisor, if you’re not taking the time to become someone that could give advice to your [00:45:00] prospects like a coach does, like I do with my coaching clients, if you don’t have that level of acumen, you’re going to be replaced.

You’re not needed anymore. Yep. It’s already, there’s already a ton of data from Gartner. I think 91% of the time that buyers spend during the buying process is outside of speaking with a sales rep. And a lot of them would prefer not to interact with sales reps. That’s not because people hate sales reps.

That’s just because they don’t get value from it, and it’s like 55% or 58% or something like, According to Rain training group, they surveyed at like over 400 B2B buyers. They said 58% of the meetings they attended with salespeople were an absolute waste of time. They didn’t learn anything. They were just pitched and they were talking to someone that didn’t really have the ability to help them, like I helped my clients.

So that’s what you gotta really be thinking about in sales. I think we’re going to start to see it become a game. people with a lot of business acumen that want to become these trusted advisors. [00:46:00] These are the people that are gonna have jobs in sales. And your SMB rep that just is really good at taking 50 sales calls a week that’s gonna go outta style.


Host: that’s, that’s a mic drop moment. I mean, what, what gets you excited and hopeful for the future?

Guest: Everything I just said is, is that, yeah, is that, is that if you really invest in the craft, you’re good. You’re good. I don’t know about you. You’ve run a larger company than I do, at least by employee count, and I probably would imagine revenue.

Therefore, because of that dude, the outreach that I get is so bad. The sales calls that I attend, yeah, with companies trying to sell me stuff, it’s so bad. I’ve had one rep that I’ve really liked so bad. It’s so bad. The best, the best

Host: outreach I get is from an old position like that. I was in the e-commerce space, and the, the only one that they’re actually like, Hey, because you on Shopify and stuff.

I’m like, I make like one sale a month. I don’t care. Like, and, and actually I give [00:47:00] it for freedom, my employees, so I’m actually giving ’em a hundred percent

Guest: discount on that . Yeah. Yeah. It’s, it’s, it’s crazy. So I’m excited to see a world where people actually have to use their brains in exert effort. And I’m also excited to, I really feel like tech is leading the way with this in SaaS.

Mm-hmm. , I’m excited to see a world where the support and the training and enablement is much better for reps. I feel like we’re barely just skimming the surface. What I’m seeing right now is a lot of that, the layoffs are pretty heavy with the enablement side. And mine tickle did a, a really big survey.

I’m forgetting it was a large percentage. Senior sales leaders are believed that enablement should be tied more to revenue outcomes, sales outcomes versus surveys completed, and certifications given, and all of that other kind of garbage. I, I just. . And don’t get me wrong, people ask, I get outreach from enablement people that ask if we have a certification and I get there just checking the box for their [00:48:00] employer.

Mm-hmm. . But that is not the future of sales enablement. The future of sales enablement is are we actually helping them achieve a sales outcome? So I think we’re gonna see, that’s the stuff I’m excited for. I’m already starting to see a really good trend of that. The companies I work with outside of SaaS, I’m starting to.

which is the wild, wild West, by the way. There are so many companies, dude, 95% of companies, I would venture to a guest that have B2B sales teams don’t even know what outreach and sales loft is. Mm-hmm. like Regi ai, they’re like, what are you talking about? I have no idea what that is. They’re so, like the sophistication on the tech side is so low.

They don’t have an enablement department, so the managers have to do all the sales. , there’s no one that makes content and Dax and that doesn’t, any of that kind of stuff. So I’m excited because there’s such opportunity there, and I see tech really leading the way and really setting the standard for how do we support our sales staff?

How do we level these folks up? How do we give them the business acumen that they need to [00:49:00] educate customers and be trusted advisors? That’s going to be a necess. here very, very soon. That’s gon, that’s going to become table stakes. So that’s, that’s what I’m excited for, man.

Host: Nice. Jason. That’s, that’s the perfect note to end on, , how, how, how can folks get in touch with you?

Guest: Yeah, this has been great, man. Outbound squad dot com’s the best place. So we do a couple things. One, if you’re just looking for free content and you’re a rep, we talk about both outbound and selling. So we talk a lot about discovery and you know, multi-threading, that sort of stuff. So Outbound Squad podcast, you can find on outbound squad.com or wherever you’re listening.

I post every day on LinkedIn. There’s tons of free resources there. And then if you’re an individual rep, we have coaching programs, and if you’re a sales leader, we have training programs as well for sales teams. So outbound squad.com is gonna be the best place to check us out.

Host: Jason, what a great engaging conversation from Full cycle future of SDR to X Machina.

That was my [00:50:00] drop, but, and everything in between. This is it’s a fascinating state. Of sales development and sales in general. Thank you for coming today.

Guest: Yeah, you bet. Thanks for having me on, man.

Host: Absolutely. And thank you all for listening. If you learned something or you enjoyed it, tell a friend. Then we’ll see you next week.

Whoa, another great episode of Revenue Today. For show notes, links and mentions, visit revenue today.live for all my friends in the Rev Genius community. Thank you. It’s been awesome to spend this time with you. Please DM me any feedback and ideas in our Slack channel or on LinkedIn. If you’re not in Rev Genius, join [email protected].

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