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In a world of SEPs, automated emails, and now AI, it’s more difficult than ever for SDRs to stand out.
Personalization at scale doesn’t seem realistic if you’re working at a large company and reaching out to hundreds of prospects.
Persona-lization, not personalization. What’s persona-lization?
“Persona-lization or, you know, just relevance based on their role, and industry, and that kind of thing.”
To learn more and hear the rest of his insights, check out this week’s episode!
Hi everyone, this is Jordan, the owner and CEO of Greaser Consulting. On this episode, we have Jerry Pharr. Man, listen, early enablement guy at Outreach; he’s gone off to do great things at Redis. We talk about personalization versus persona-lization, the AI that’s coming for all of our jobs, and a lot of fun things in between. Anytime I have a chance to talk about Jerry, to Jerry, about tools, technology, and anything else in between, it’s always interesting and a ton of fun. I think you’ll enjoy this episode. Lean in and here we go.
Say you want some clarity in sales and marketing and SEP? Well, we have just the remedy: Our podcast, RevOps Therapy. Yeah.
Hi everyone. I’ve got Jerry with me today. Jerry, go ahead and introduce yourself.
Hey, thanks, Jordan. What’s up, y’all? I’m Jerry Pharr, Senior Director of Global Sales Enablement at Redis.
So I always like to give connections and feedback, how I may or may have met somebody in the past. And I think, Jerry, you are first back in the old Outreach days, our first enablement person. And, you know, I can put on the resume Jerry, that myself and another guy, we ran all the boot camps early on, blah, blah, blah, blah, blah. But the reality is, we may have done that, but then you showed up. So I’m just really curious, before we get into any of this, how bad were those boot camps when you first walked in?
Um, they weren’t terrible. They were okay. I mean, it was, it was a couple frontline managers doing their darndest to train new hires. And you guys were hiring quickly. So at least there was a structure to it. And you’re very entertaining. So two good things going for you there.
You know, it’s funny, you say very entertaining, though. Because did you ever meet or overlap with Tiffany French? [Yes] Okay. She told me a story once that just kind of blew my mind and made me like, rethink how I do trainings. She talked about being at this training, and it was like a landmark training or something. I can’t remember what it was. But she said a woman came up to her and said, “Wow, this, this training changed my life. This is the best three days of my life.” And so Tiffany said, “Oh, well tell me one thing you learned.” She said the woman just looked at her like a deer in the headlights and said, “You know, I can’t actually remember anything right now.” Tiffany was like, “How can I get these like rave reviews, and nothing actually stuck?” And that’s when she said some… this like, hit me at the core, because you know, Jerry, I’m an entertainer, right? She said, you can really lead an entertaining training that everybody loves that’s absolutely worthless. And I was like, “oh, no, that’s me.” Right? [Yeah.] And she said, she said, just because you can entertain people doesn’t mean the training was actually worth anything. And then she went into all this methodology, how to get people to actually change that. And so, Jerry, thanks for affirming what Tiffany’s fear that was in, stoked in me, that it was entertaining way back in the day; that means it was worthless.
Brief aside, I’ve actually gone through the three-day training that she’s referring to at Landmark forum; I went through about 20, 25 years ago, and I feel the same way.
But it was fantastic.
It was great. It was great at the time. Yeah.
Yeah. Well, so that’s why that’s my kind of like hidden segway into talking about things that are really popular, that may not actually matter. So you walk out of a training, right? It was amazing. But did it actually move the needle? And so when I reached out to you, and I said, “Hey, let’s talk about, let’s pick some topics you’re really interested in,” the one that sort of came to the top was this idea that personalization at scale doesn’t really work. And then you said, “Sometimes, maybe,” right? And so what’s your thesis statement here, Jerry, like, what are you? What are you trying to say with that?
So the way, the notion of personalization at scale is supposed to mean that you can personalize email content in sort of outbound prospecting, and do so in a way that you can do it with not just one person, but lots of people or time. So doing it at scale. And the way that’s implemented or the way people coach on it is generally, try to go find something relevant and specific for Jordan, and then go find something unique and specific for Jerry, and then find unique and specific for the next person. And so people come up with these kind of tricks and tips and tricks to try to do that and make it not so onerous on, on the rep doing it. But I’ve found that it’s virtually impossible to actually do that in large numbers, just pure raw number of times. And then this second reason, the second big challenge for it is even if you were to do that, in fact, go find something interesting and relevant and important to say about Jordan that I can see from his online presence. The next thing I’m doing is I’m saying, “Hey, you want to buy some software?” Like making that transition from this thing about you to this thing I’m trying to pitch.
“You like golf, what to take a swing at…?”
Exactly, exactly. So, given the technology that is currently available to us, and the way it’s kind of that notion is currently used, I think that the idea of personalizing when and specific to the specific to the person is better, or specific to the company, I think that is mostly nonsense. I think if you…
So what’s the alternative?
Well, there are, there are a couple. One is if you, if your business model and your book of business is such that you only have a handful of accounts or so, absolutely you can do that. You don’t, you only have to reach out to, you know, 5 or 10 or 20 people a day, sure, spend the time doing that. Or, you can not do, in my language, not do personalization, but do relevance. If you tailor the content that is specific to their role, their persona, their industry, their market segment, those kinds of things, you tailor the content for those sorts of things. And as long as you know your buyer, your buyer personas well enough, you’re going to be in the ballpark. You might be slightly off, and it’s not unique to Jordan, but it’s relevant for Jordan’s role as a small business owner.
So instead of personalization, it’s persona-lization.
Persona-lization or, you know, just relevance based on their role, and industry, and that kind of thing.
So I’m not even quite sure how to ask this question. But I’ve been thinking about this a lot over the last maybe like two months, okay. I’ve been thinking a lot about the technology and tools that exist. It feels like we’re still running on the 2015 tool stack in a lot of ways. Like when Outreach, SalesLoft, Yesware, was in there, when these companies came to fruition, like they came out, it was like, “Oh my gosh, like we can do automated emails, we can queue up call tasks.” And I’m about to make a statement that’s gonna sound really harsh, but it’s not as harsh as it sounds. Like it’s actually a pretty minor innovation, in a sense that like string some calls together, string some emails together, that doesn’t mean it didn’t have a major impact. But it’s like a pretty similar, simple concept. So a lot of people could get the huge value. Anyway, we put that together. And even back in the day, it was like, “Hey, don’t spray and pray, you know, whatever.” The reality was, though, if I’m just gonna be totally upfront about 2015, 2016, maybe ‘17. That was like the heyday of like, you can buy a list; you can do a little bit of what you’re talking about, even little personalization in there. And you could just like, let it rip, and people would be, act like that is relevant, or that is right on and like, wow. And man, we felt like geniuses, right? Like, Wow, we got this thing, but we had an actually like a pretty simple concept, which is actually the value of the innovation was that like, it was a really simple concept that people could connect with, right? But we could do this thing at scale and numbers we never did. And now that’s just like, everywhere. And so in a world where that’s everywhere, everybody’s running a really similar playbook. Like, how do you stand out? And I’m going to use that little term that we just use with persona-lization, where you’re getting that, but how do you still stand out? If that’s a playbook that looks, like, really similar that everyone’s just piling on in some way?
Well, I think in 90, 95% of the outbound out there, that’s it, the personal persona-lization isn’t happening. It truly is spray and pray, like they’re sending the exact same message to all 1,000 people that we’re reaching out to. So it’s not specific to this persona, specific to the industry, specific to the market segment, that kind of thing. So there is some work that has to be done. But as long as you segment your messaging, based on those kinds of different factors that are relevant for your business, I think you can get people say, “Yeah, oh, yeah, that does make sense to me.”
Are you a big fan of centralization of content, or rep-created content?
Well, that’s sort of a leak, an unfair advantage for me because I actually have a team that manages that, that is our responsibility. [I’m leading the witness here.] Yeah you’re leading the witness here. Yeah, that’s a great question, Jordan, I think it’s best to… If it is centralized, and I, I do still believe that very, very strongly today that if you want sequences to work, because like in 2015, 2016, as you were suggesting, you know, a well-trained monkey could probably do it and get some meetings. These days, I think you do have to really understand deeply best practices around, around human behavior, around persuasion techniques, around user experience, all those sorts of things, to figure out what is the best sort of architecture or sequence and muscle, what’s the best way to, you know, write emails that are going to land well in and arrive with a pain hypothesis and those kinds of things. And that, that takes quite a bit of background knowledge. So I firmly believe that you’re way better off having it centralized with one person or a handful of people who know how to do that well, rather than having, you know, a couple SDR managers or God forbid, individual SDRs doing it. I think that’s a terrible waste of time for them.
Do you think though, like, just, you know, reps used to write everything, and now there’s a little bit more command and now, now we’ve got ChatGPT; some folks use Lavender, uh, you know, religiously tools like that? Do you think there’s a day… and I’m actually thinking more about the folks who work on these committees, right? Like, should they be nervous right now of like, “oh, my gosh, like, I might not have a job in… the way that we’ve move, six months, six, you know, whatever, like, this whole machine is going to take over and now I’ll be replaced?” Or is that something that’s just gonna, it’s gonna have to, right, just become part of the motion?
So I purposely used, I inserted a word in my last answer; I said “today”. Today, I think it does make sense for it to be centralized, to have someone who’s knowledgeable. But I think, I don’t know how long maybe it’s 18 months, maybe it’s three years from now, that’s probably not going to be true. Because I think generative AI is going to take over and, and make those things I’m describing today, not really necessary; you’re going to be able to tell your, your bot to say, “hey, I want to go after DevOps directors who work in gaming companies in northeastern United States, at companies that are not current customers of ours. Please write me some emails that would shine a light on a pain they likely have that we can solve.”
So do you think the, like, the content writers of today will just be wholesale replaced, or do you think those people will then shift into becoming just like fantastic prompters of the machine?
Well, the machines are gonna have to learn from somebody; they’re not gonna be able to just go out and search Google for the things that are unique to your business. So my guess is there are going to be technologies out there, that will have the, the automation for it, but someone some admin internally, is going to have to populate that as an admin setting. What those personas are, what the persona-based pains are, and those kinds of things in order for it to, you know, automatically craft these emails.
So there’s a natural sort of progression in our thought here of in the back of the day, everybody was writing emails themselves, queuing up phone calls, keeping it on their Post-it notes, then their managers made them put it in CRM, and then you got sales engagement, that would relieve the burden and then we could do more. Now we’re talking about how AI can do some of these things for you. But that all stays in that very linear path of like, we’re doing the same thing; we’re calling or emailing, you know, maybe we’re checking out LinkedIn or something. Is there any part of you though, that thinks that like, the whole paradigm, at some point, is just going to like crack and shift? And like, instead of us talking about personalization versus persona-lization, and whether or not the person or the AI should do it? Like, there’s just going to be a brand new sales motion that doesn’t even involve any of this? Like, we’re not just doing email, email, phone call, phone call? There’s actually a new way to operate?
Well, I yeah, I think in the not-too-distant future, the notion of cold outbound is going to go the way of the dodo bird. I never really understood why people say that because what dodo bird is still around right? There. It’s going to be…
No they’re not; come on.
The sort of… the still cold, cold, outbound is probably not going to exist in any meaningful sense. What is going to exist is reaching out to people with kind of messaging that is produced by some AI bot, that is based on some sort of intent signal. Now that intent, intent signal could be them going out and searching things on the web; it could be them using your product in a certain way. And then which is more like sort of PLG kind of motion. But I think it’s going to be based on those signals. And you really only invest time going after those people, if it makes sense based on their intent.
This makes me think about when I first got into the sales world, I can’t remember what the guy’s name was, but the book was called New Sales Simplified. Yeah, that remember that? Mike Weinberg. I think that’s what it was. Okay. And anyway, he just, he wrote about the idea that before the 2008 crash, okay, basically all salespeople had become account managers. And all they did is fill orders that go to the golf course, or do whatever the crash happens, organizations get lean; all of a sudden, people are pulling out, they’re not just reorder, and we need to go and hunt. And one of his big comments was like, “We need to get out of the spreadsheets, out of the CRM; we need to roll up the sleeves, take people in the car, let’s go outbound, learn how to hunt again.” Okay. And the whole motion was this idea that hunting had died for a while; everybody was just a farmer. And now we need to hunt again. So we got to relearn the motion. And so we go through this massive shift where it’s like grow at all costs; we’ll just throw money everywhere, grow, grow, grow, outbound, outbound, outbound, whatever. And now this like product-led growth comes in; now you’ve got this intent-mapping; you got this whole AI piece. And like, is there a world where we can only either target people smartly, or just, you know, live off of the inbound that comes in for the product-led growth and whatever? But to me, it just seems like history is cyclical. Like, are we moving right now to a motion where, to your point, like you’re talking about the future, like some place where outbound doesn’t need to exist in the same way. But will that just run its course in 10 years? And the next thing you know, we’ll be doing outbound again?
Well, hard to imagine. Yeah, I agree. Things are cyclical, but it’s hard to imagine a world 10, 15 years from now when there’s a human responsible for getting outbound to B2B companies. I don’t know.
So I’ve heard, I’ve heard folks say, like the SDR… the future doesn’t live in cities; it lives rurally because you can pay cheaper prices and better, you know, same quality, cheaper prices. We’re all decentralized. So that’s the future. But what you’re telling me is the SDR position in general will just cease to exist.
I, I think if SDR is… if by SDR, you mean cold outbound, I suspect Yes, but I think the SDR role is still important and will remain so for, for from for some foreseeable future. But following up on intent signals, and then when you’re when your machine gods in your company telling you this is the right person to reach out to work out to sure there might be a bot that gives you some initial message that is going to, might resonate with them. But there is going to be a human who has to call on them. And it has to do other things and send a size 18 shoe to them in the mail and all these sorts of things that are sales techniques. So there, there does have to be a human even at the top of the funnel.
So let’s bring it back. I took us like way sideways; we’ll bring it back to today. Since neither of us can predict the future, but we’re trying, what would you tell an SDR today that and I’m sure you have this conversation all the time. They’re like, “Hey, listen, I read on LinkedIn, everything has to be personalized. I still have a job today; the bots haven’t taken over; I’m still writing.” Like, how do you convince them that this idea of doing things like 1) gives me control, okay, 2) we’re going to do things based off of sort of these signals or this or that, but we’re not, you’re not going to sit down and write to Bobby Sue some personalized thing about his blue suede shoes or something?
Well, I’d say let’s do some math. Let’s figure out how much time are you spending per person doing that personalization, writing the emails, and all those kinds of things. And then, you know, how would that… that’s your part of the equation. There’s also how many meetings are you getting from that? And, you know, is… Can you get more meetings by doing other things that don’t require you spending nearly as much time? I know that SDRs want to feel like they need to have some, you know, insert their personality and innovativeness and don’t want to just be a machine. But having been around this a long time, that sounds great in theory; in practice, it doesn’t really work. In practice, you get much better results by focusing on messaging that is related to the, the role, the persona of the industry market segment.
You get better results as a team. Okay. But then let’s think about the individual. And what I, what I mean by that is, I hate to use a sports analogy, but I’m gonna use it anyway. Right? There’s the guy that can guy or gal, I should say, can score 30 points, 20 assists, 20 rebounds, 20, whatever, their teams are gonna lose almost every game, but they look phenomenal. So they’re gonna get paid a whole heck of a lot more. Okay, so why would I go into team ball whenever my contract value is going to go up and make all these shifts? And whatever? Why am I saying this, every team that I’ve ever been a part of, there’s always the team mentality of, “hey, if we can, in the aggregate, get people to do this, the team is going to produce this way.” And then there’s always I’ll just.. I’ll name Jimmy Mac, James McTavish, who made one phone call a day, and would write seven personalized emails. And he outperformed everybody. Right? But if we tried to do that at scale across the whole organization, like like, that’s never going to work, because quite frankly, you don’t have the skills that James McTavish has in email writing, right? And we’re not even going to train that; you just don’t have it. He does, you know, how do you balance that sort of a, in the aggregate, the team needs to move this direction, with the individual aspirations of the person saying like, “Yeah, but I like, I want to be able to do this; I want to work on this. I want to train on this.” Like, that’s a tough thing to to like balance whenever you’re trying to push these things.
Well. So Jimmy Mac was doing that 2015, 2016, 2017. Do you think that same, those same tactics would have similar results today? I’m not convinced they would.
I’m not either. But the, the reason for the analogy is that was an individual behaving differently than the rest of the team. Sure. Okay. And there’s always, in my experience been, and that’s not just emails, it’s not just Jimmy, there’s always somebody that like, man, if you just put them on the phone, like, please don’t let them send an email, oh, my goodness, like, just, then there’s a person that like, I don’t even know how it’s possible. But on LinkedIn all day, they don’t even, they don’t do any of that other stuff. And somehow they’re, they’re still doing well, but other people can’t do that. You know what I mean? So how do you deal with the eagle? Right, that’s in the batch among all the pigeons. And I hate to say that, but that’s just, it’s just the reality.
So I once worked for a sales leader who said, after you hit your quota, three quarters in a row, you work for yourself; until then you work for me. So my position is, when people are brought on board, they, they do the proven method that works for the most people for you know, call it 80, 90% of the people, they do it like that. If they can be successful that then they earn the right to do it their own way.
Now you say three quarters…
I just threw out a random number.
Okay, well, three quarters. That’s more than the average lifespan of an SDR.
I was thinking AE but okay, for the period of time.
All right. I gotcha. So do it our way first. Yeah. And then we’ll, then we’ll shift. What’s the one thing though, like the skill, thinking in that phrase that you’re saying today, and you think about writing? What’s the one skill that SDRs should be honing right now, even in their position as an SDR that, you know, in three years when the bots take over, like this is still going to matter?
Learning how to learn about your buyers. If you don’t deeply understand who your buyers are, what their day-to-day lives are, what the workflows are, what the problems are, how they’re incentivized, what they’re, you know why they generally get pissed off at their bosses, if you don’t understand those things, it’s going to be much more difficult for you to have those conversations. If you learn about those things deeply, you can have those conversations with credibility; you can send those emails in a way that makes sense. And what I’m saying… I acknowledge it’s not easy, especially if you sell a really super technical product. You’re selling to super technical people. I’m not saying it makes sense for SDRs to learn about their products in detail, but to learn about the kinds of people they sell to absolutely and I think that phenomenon that skill set is transferable to any, any sales role.
I think that’s a that’s a really important delineation, not the product, per se, with the people, people, the people. I think I can understand why that is. But why is that more important to understand the people?
Well, anytime… any person in a sales role has a couple things against them. Buyers think… they don’t trust you, and they think you don’t understand them or their business. And if you don’t take time to learn about what the role is, and what their challenges are, that have nothing to do with your product, just learn about the role, you’re going to reinforce those preconceived notions.
So when… I remember when you took over boot camps, what you would do is you would have, it’s easy for us, because we had a VP of Marketing, a VP of Sales, those were bi… so you’d have them come and do a day in the life. So we do a day in the life and then we had persona cards that you could read through. And that was all, let me just be really clear miles ahead of what we were doing, miles ahead, it made a huge difference. The more we lived in that environment, the more I would see some people that even with the persona cards, even with people coming to the boot camp and talking through it, like they still couldn’t piece together, why it actually mattered. And so how are you today moving people, like beyond just the one conversation and the one card into this like state of like, “Yeah, but I know why that actually matters”?
Well, in a company… so at Outreach, we would hold those, and I would arrange those interviews with our sales leader, our marketing later, our ops leader, who were the buyer personas, and I didn’t have to explain to those people why it was important for the people who are being trained on how to get the value prop; they would, they would very easily navigate, navigate those conversations. But if at a company that sells to some other persona, like here, internally, we sell to architects, to DevOps, to developers, engineers, those kinds of people. And you go find those people here internally at Redis, who work that have those roles. And if they had that role at some other company, we’d want to sell to them. Just bringing them on and interviewing them about their role, it’s going to be a difficult interview. Because they don’t really understand the rationale for why you’re asking these kinds of questions. So it takes more coaching. From the facilitator perspective, I actually have to have like a 15-minute prep conversation with them. Because okay…
Oh, heaven forbid, yeah.
Well do that a bunch of times; it becomes real.
No, no, I’m not making…I’m saying a salesperson is like “why do you want to meet with me for 15 minutes? Just put me in.” Totally different personalities.
Yeah, definitely. And the engineer’s like, “why would I wanna talk to a salesperson? I hate salespeople.”
And wait a minute, like, you only gave me one Google Sheet of the potential prompts. Like, why haven’t we gotten into the, that’s what I’m saying. It’s just it’s so funny. How I think this is even your point about like, hitting the different personas. Like, it’s so funny, not just the way the messaging relates with different people, the way people respond to things, even the touch points, like I… even in everyday life, like asking an engineer to come and like, sit down and do this thing. Let’s do a 15-minute, let me send you a brief. Let me follow up with you like all this, the salesperson, let me just pick up the phone and call you like, can you do it? Yeah, sure, whatever, okay, see you… like the way people want to be communicated to, the way that I like, I expect you to respond to me. Like, it’s not intuitively better or worse, to be more or less aggressive, or to be more or less prepared. It’s just the difference in personalities and people.
So we did a boot camp… several last fall. And we finished the session, it was kind of basic outbound messaging, how to, how to form a pain hypothesis and kind of incorporate that into a conversation and what it might sound like. And then, literally, the next session in the boot camp was these persona interviews. And so interviewing one of these DevOps guys, and we kind of asked him a question to be like, you know, does it ever work for like a salesperson like, prospecting you? Is there any kind of message that would resonate that you might get you to respond? And he said, “Well, I’ll tell you what I would hate is if they said this.” And the thing he said was exactly what I coached other people to say, like an hour earlier.
Yeah, but here’s the like, it plays out in the aggregate too, because like that one person who says “Don’t say it like that.” I mean, I can think about lines that I’ve used on cold calls that work 90% of times the wrong percentage, but my point is like, wow, this like really works. And then you say it to one other person. And they’re like, “oh, my gosh, I can’t believe you said that”. Same title, same whatever. And it’s like, “Well, you do need to know like, you’re the Oddball here like you’re the one who’s not…”
It reinforces my belief that anytime someone on LinkedIn says, “X, fill in the blank doesn’t work in sales.” Yeah, well, there’s a little should be a little asterisk next to that. “It doesn’t work for me, in this situation with this kind of person in this kind of company. But it could perfectly well work for a lot of others.”
Yeah, I mean, I’m, I’m convinced that there are still industries and companies out there that if you gave somebody a phone book and just said dial, like it would still work. Sure. I’m sure they still are. But Jerry, I appreciate you coming on. I know we’re right at time. But listen, I always appreciate your insights and thoughts on things. And for anybody listening, Jerry was always the guy, I’m going to get him in trouble for this. But he was the guy in his first boot camp with us. He said, “Listen, I was a decent salesperson, but I was a better tools and technology hack.” And that always stuck with me that anytime I did talk with Jerry, man, he was always innovating, always thinking about something new and unique to work on and noodle on. So I’ve always appreciated, you know, just an opportunity to talk to you about some of these things, because I know you know what you’re thinking on is, is probably two steps ahead of what anybody… because you’re a hack and you couldn’t do it. Do it otherwise.
Long live hacks.
Anyway, thanks for coming on, Jerry, and I’ll see you later.
31:45Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at www.greaserconsulting.com. Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.