BONUS: 35%+ response rates through killer sequencing and follow up with Becc Holland
62m 55s
In this podcast episode, Jason Bay interviews Beck Holland, CEO and Founder of Flip the Script, to address the common mystery of outbound prospecting sequences. Beck explains that many reps feel lost after the first email, unsure how to craft unique follow-ups without annoying prospects. She argues that the rise of sales engagement tools has led to a culture of mass automation, where reps lose sight of their true goal: selling more effectively. The key is to personalize at scale, as most people don’t respond to unpersonalized messages.
Beck outlines a four-part approach to solving this. First, she advises finding your buyer by going beyond marketing personas: start with case studies, then interview those customers to learn the real reasons they bought. Next, interview industry peers in the same role to understand their daily challenges, without pitching your product. This helps craft relevant messaging. Second, structure a comprehensive playbook that maximizes lead conversion through personalized outbound plays. Third, learn to scale any sales technique by incorporating proven methodologies (like Sandler or Challenger) into your sequences and testing them. Finally, Beck provides her personal follow-up email sequences as a default template, showing how to maintain personalization across multiple touches. The overall goal is to help reps stop guessing and use data-driven, scalable personalization to achieve 35%+ response rates.
Today we're talking about back Holland, CEO, and Founder at Flip the Script. The big mystery with outbound prospecting to a lot of folks is, you hear this, you know, I need to reach out to someone 12 to 15 times. And that number keeps going up. Every time I see the new research that comes out every year, there's always more touches that requires to go hold to someone. And that's a whole nother topic in and of itself that kind of scares me a little bit. But what I always wonder, I don't know about you. And this is what I hear a lot is, okay, if I'm supposed to send, you know, six to eight emails to someone and make four phone attempts and a couple touches on LinkedIn, what do I say after the first email? How could I possibly come up with something unique and different every time that I reach out to someone? What do the follow-ups look like? How do I not be a pest? Won't this make people, I mean, these are just all the things that I hear. And one of the people that I look up to, and this is who we're going to be interviewing today back, one of the people I look up to in this is, you know, people like back that are out there actually doing this with their teams and they have a ton of data, right? In terms of response rates and when people respond and how many touches and how much to personalize. And that's what we're going to get into today. But before we do that, if you're tuning in to the podcast for the first time, my name's Jason Bay, I'm the host of blissful prospecting. And my goal with this show is really to help any rep or sales leader that's leading people that are out there prospecting and doing sales development or outbound prospecting on a daily basis. Help the folks that love crushing their quota, but hate it when they spend a ton of time personalizing an email and no one responds to it. Or they get asked a question or get an objection on a cold call and they don't know what to say and they freeze out. So if that's ever happened to you or that's something that you hate, you're definitely in the right place. So we're talking about Colin today, one of the people I look up to in this industry, like in terms of content, she's probably top three people that I want to know what she's talking about and what she's saying. That's working because it just works. And she's got the data to prove it. And one thing that I got to do with her recently was record her webinar together on the thing outside the script, some of her virtual tour. And what she is sort of infamous for is this flip the script content that she put out and it was this YouTube series. It was really awesome when she was working at course, and I, and one of the things she talked about a lot was personalization at scale. So definitely make sure to check that out, which there's a link here on the show notes if you're looking to check that out. But this is like part two, essentially, of that. So once you know what to say in that first email, how do you follow up? What are the sequencing best practices? How do we get 35 plus percent of people to actually respond to us? And how do we take things that we're learning? You know, sales techniques. How do we scale that? How do we take what maybe you've heard me share or maybe you've heard Morgan, ingram or John Barrows or Beck Holland or Mark Hunter inserted any other sales, you know, trainer, consultant, coach type person. How do you take their techniques and scale it with your own stuff? She's going to talk about all those things. So make sure to tune in here and then check out if you want the more visual part because she did have slides. Make sure to check the replay out at toward oblisful prospecting.com. That's linked up in the show notes. So she'll be able to open it up right on your phone here and take a listen to it. And lastly, before we dig in, we do have if you're listening to this in September, we do have a couple more weeks worth of people coming on to the tour to talk about prospecting. So folks just like Beck, it's free. It's live. I would definitely check it out at toward oblisful prospecting.com along with all the replays. So if 40 talks with 42 speakers. So check that out and let's get to the interview with Beck. And I'm super excited for the topic today because sequencing, I think is the big mystery when it comes to prospecting. It's like, hey, what do you say after you send that first cold email, right? Or how do you get phone and email like to work together? And then how do you optimize these sequences and what should they look like? And the reason why I invited Beck on the tour is her flip the script content is something that both my wife and I running our business have just studied religiously to improve our outbound. And she's one of my go to, I would say top three go to resources when it comes to sales development, outbound prospecting and that sort of stuff. And she's currently the head of sales development at chorus AI. So Beck, it's great to have you on. It's good to be here. Thanks for having me. Absolutely. I'm super excited for today. I know you got a lot of stuff. But before we dig into the content, this may be a longer-winded answer than you want to give right now. But what is the big challenge? Like, what do you feel like is like, why is it such a mystery when it comes to sequences? And what do you think are the challenges? Like when you work with people on this stuff? Like what's the big mystery and challenge when it comes to sequencing? Yeah. So that's a very, you're right. It's a very deep question. But I feel like, I mean, you saw in like sales culture, let's put it that way, you know, back in the 80s, back in the 90s, into the early 2000s. Like you just saw people, you know, go and door to door, right? Field sales was like the thing. That's how I started selling is, you know, a graduated from A&M came out in 2008 and started field selling. Like, I'm going to show up at this person's door. Actually, the term for the term bag was because sales physically used to take a bag of goods, you know, around from door to door and have to be responsible for selling those those goods. So that's actually what originated from is from sales people used to go door to door. You know, then the internet came along and then, you know, with the internet came automation with automation, you know, came a bunch of sales engagement platform. So people started selling over like, how do I, how do I do this over email? You know, then the question was, how do I speed this up? Yep. You know, by using sales engagement and so you saw an influx. This was probably back in, you know, 2012 where sales engagement was really getting. It's when was sales law, to groove outreach, yes, where, et cetera. And people started sending a whole bunch of messages at once. I'm like, oh, if I can get the, this amount of meetings of 150 emails, you know, what if I could send 4,000 or 8,000 and all these dynamic tags came in of like I can insert their company name or first name or, you know, industry segment or title or whatever. And so with the tool like sales engagement, I felt like it left it left sales culture into a place where we've kind of lost our North star. Or like, you know, what is our goal? You know, and then how can we achieve that? And so I've kind of challenged the programs that I've worked with of like the monomaniacal about what your goal is and don't ever lose side of that. Of like, your goal is to sell more, right? So if you send 800 emails or you send 80 emails and you're selling more like that is the North star that you need to, to guide yourself by. And so I think TLG already answered your question. I think that sequences are the most confusing because you need someone something, etc. to prove causation of what you can say to actually cause someone to take a meeting. And you've seen a couple of strides of that of like, you know, we're doing technologies, but I think that's the most confusing thing is. The things that really help conversion are the things that seem unscatable. And so today that I wanted to go into the content is like, how do you scale the things that work for your messaging and be constantly pushing that needle, you know, in terms of results? I love that. I learned a new word to monomaniacal. That's, that's a fun one. So before you get to that, I just just a quick comment on that's really the challenge. I think right now, like you said, I think you hit the hammer on the nail with. There's people, a lot of people are bought into personalizing the approach and adding relevance, but it's like, how do we do this at scale? And you put that whole series come out on that. And this is kind of like a sequel, you know, to that almost in like, what does the sequence in portion look like, but. Hey, with that further ado, I know you got a lot of content prepared for this. Yeah, go ahead. Let's get to it. I'm excited for this. What on I go ahead and share my screen or make sure I can share my screen. Can you guys can everyone see? Yeah, go ahead and let us know in the chat. You guys give us a yes real quick. If you can see back screen here, everyone could start with a yes. And if you could give me everyone could jump in the chat and give me a one if you are in sales development. Two, if your sales development leader, three, if you're an AE, four, if you're an AE leader, five, if your sales enablement. And six of your sales ops. So I can have kind of the. Look for a background. A lot of ones and three's it looks like. Breeze. So a lot of sales sales Devon and AE. Cool. That's really helpful. So why don't I jump in here? So today, I wanted to go into four different pieces. So, you know, like I mentioned, I know that Jason sent out the session. On how to personalize it scale. So in that session, I dive really deep into what are all the different things that you can scale. Personalize premises that you can incorporate. And then how can you maintain consistency of messaging? So just a little bit of back point. You know, I started this journey a couple of years ago. Whenever I realize I ask myself two questions and the questions were, you know, remain the same for me today. I remember laying on my
apartment floor and I was at SDR and I was getting some pretty good results, but I wanted some amazing results. And so I'll ask you those those same questions today. The first question that I asked myself is, who in here and if you could jump into chat, who in here responds to unpersonalized messaging by taking a meeting with a vendor that you don't know? A lot of notes. One yes. One yes. One ha ha ha. Right so mostly knows. So now I'm going to ask you a second question that I asked myself, who in here thinks that your prospect is different than you and your prospects are different than you in that regard? So a bunch of notes. So that was the hunch that I had was I thought, hey, I personally don't respond to unpersonalized messaging and I don't think my prospects do either. And so the answer I know here is some level of personalization. So I have to figure out how to make a prototype and then how to scale that in terms of personalization. So today, you know, I wanted to jump into four different pieces. Number one, I wanted to start with how you can find your buyer starting at a new company. I think that's a big struggle for people of like, how do I identify my buyer personas? I get a different story from marketing than I get from the sales rep that I get from the CSM. So if I'm new at an org, how do I identify my buyer persona and how I can speak to them in a compelling way? Number two, I wanted to go into the structure of a full comprehensive playbook of how can you maximize all of the leads coming to you and how can you maximize all of the outbound plays that you potentially could do incorporating personalization to drive the most results? Number three, I want to go into and this might seem odd, but the third part, I'm going to go into how do you scale any sales technique? A lot of really good sales technique out there. You know, you have namely, you have Sandler, MJ Hoffman, you have Spin, Medic, Challenger, you know, you have John Barrows, bunch of different people out there. A lot seem to be teaching different technique items. Some of them are incorporated with, you know, other different methodology. So I want to enable everyone today to walk away from this session and be able to watch any sales trainer that you want and incorporate their methodology or their template into your sequences so that you yourself can beta test who is the best, who's advice should I follow and what actually works for me within my business. So I want to enable people basically in step three to stop listening to me. You know, if like, how do I walk away from a session and if someone gives me a really good technique that I think will work, how do I, I put that in my infrastructure within my sequences to see if it actually works and then double down on it, on it if it does. And then number four, I'm going to go very in depth into, you know, and I hope that everyone watched the first session on how to personalize the scale. Mainly I focus in the first email in that session. I'm going to go into all of the follow-up emails for the entire breadth of the sequence in step number four. So I'm going to give you the personal, my personal sequences that we're following over here at Corus. So if you haven't listened to a lot of sales training, if you don't have a lot of methodology, you know, within you or you, you know, don't know really where to start, you can use my infrastructure, you know, kind of as a default as you work out your tenure and sales. So first let's start with finding my body, finding your bio. Five steps to finding a buyer. And this is just the personal infrastructure of how I find my buyer whenever I come into any company. So most people will enter into an organization and in some of the onboarding sessions, they'll be usually told by the marketing team, you know, they'll say like, hey, here's our buyer persona sheet, here's our competitive sheets, and here are five buyer personas, like for instance, over at Corus, we sell into sales ops, sales enablement, sales leaders, rev leaders, and sales development leaders. And so you'll get this kind of sheet from marketing, and it's all good intent, like they're trying to do their best to give you some kind of war deck or talk track, etc. You know, of how you should speak to someone within that buyer persona to make them want a meeting. Could be just my experience, but I want to get a little bit gritty of them that. So the first thing that I do with any company is when I enter into the organization, especially for SMB and Midmarket, if you're working with that kind of organization, I immediately go to the case studies, you know, on the website, and understand from a high level, you know, who bought my product, and why did they buy my product? What did they buy my product for? And how, what were the different goals within that buyer persona? I then, you're going to think I'm insane, but I call those people in the case study. I asked the rep, I'm like, hey, you sold into, you know, Jason, Jason, are you okay if I reach out to Jason? And I reach out to Jason and say, hey, I'm not annoying on boarding rep. And this is very ad hoc, but I call them and I ask them for 30 minutes of their time, because this could, again, just be my experience, but usually there's a different story of record than there is on record. Yeah, well, you're going to ask different questions too, than the person building the case study probably asked them. Absolutely. And so they're thinking through from a marketing perspective, you know, what would be good for SEO, what would be generation, etc. And I want to personally go find out the details, you know, typically when I see people post on LinkedIn, some of the people that I know, I'll call them and be like, did you really do this thing? And they're like, not actually really the story is x, y and z, but the public facing story was different. And so the first thing I want to understand is what was the real skinny behind, why someone bought my product and how happy are they? What did they initially buy it for and how are they using it today is the first thing that I want to understand. And the reason I start with case studies, this is someone who is obviously pleased with your product, that they're willing, you know, to go and record for you, so they'll probably take a call. The second thing that I do is I interview customers. So I go to I would start with anyone who's above a certain NPS score and I again would usually it's a good way to multi-thread within your organization and kind of get some buy-in or relationship with like CSM's or AES and say like, hey, you know, I notice you sold these five market accounts. Do you like do you mind that I reach out to them? And I would interview the customers who were in the case studies. So like case studies are usually good for one thing in specific but I want to know an aggregate why are people buying my product. And so again, I would make sure that your customers are happy, you know, and double click it with your CSM to make sure that they're okay for you to reach out. But I would reach out to those customers and the economic buyer and the decision maker and try to understand if they're willing to give me the time, why they bought the product and what they run into in their day to day. Third step I would do is I would actually go to whatever buyer persona you sell into like sales leaders as our biggest buyer persona for chorus. I would go in the industry to five of that actual role and I would ask them to give me an hour to talk about their day to day and what they actually care about. I would not pitch them on my product. I would not under you know try to be doing it to pull anything. I would simply be curious on that line of like what do you run into in your day to day and what do you care about. And I would start my mind crafting through like okay this is what they care about. These are the problems they have. These are the things they run into and the things that they want and start brainstorming in my mind. How does our product fit into that? I'll leave you to pain or you know highlight a pleasure for my prospect. So I can help start graphing out like typically I'm going to these are the five things that I'm going to probably hit on within a demo with someone you will always want to run discovery but you want to come in with a good top you know five points of things that I think will help them in their day to day. So I would start by going to five people within that role asking them to give you an hour and then just going deep on everything that they care about and in my experience I mean I want to link in you can call you can actually go to my account and see it if you don't believe me as about a year ago. I was selling into CIOs and I'm like hey I'm not a CIO I need to know what a CIO does anyone want to help me and I hope from Dell reaches out randomly and says like hey yeah I'll take a meeting and I was like wait seriously like that's how this works jump on the phone with them for two hours and marches through everything that he cares about in his day to day and again I would be smart enough not to pitch your product like really go in there to understand and seek to understand but in my experience people especially if they're at that decision maker level they want to help people and they want to mentor and they want to give some level of advice so I think you just need to be diligent enough to find a mingo after them. The fourth thing that I would do is I would go to the buyer percent of that you sell into internally so I would go to you know for instance the sales leader chorus and say like hey you know what do you go run into in your day to day and how does chorus solve for the things that you really care about so you can really understand
understand from a high level and a detailed view both. What value does your internal buyer persona care about? I have the luxury of selling into luxury and pain of selling into sales leaders. I have found it really relieving that I am typically selling into a buyer persona that I understand because I'm selling into SDR leaders. I buy in large, know what they care about in their day to day. I would be very, very focused on like axiomatically what do they care about and what is running through their mind. And then the last thing that I would do, sorry, last two things is I would go to my sales people then and say like, hey, how are you selling, you know, who are you selling to and what pain points and talk trucks are resonating. And then I would lastly go to marketing. Then I would go to marketing and say, hey, what's your understanding of our buyer persona's? What do you think that they care about? So I mean, there's two or three types of thinking. There is deductive, inductive, and abductive. Deductive means you start with a theory and you confirm it. Inductive is where the goal minus to me is like, how do I find out what actually cares someone cares about and then reinvent the wheel of saying like, you know, personalization of scale is a great example of that of like, I want to find out what works and find a way to scale it as opposed to coming up with a theory and then confirming it or just confirming it. So I'd start with the source and work my way out. So that was a long wind. That's how I'd find my buyer and I would start with that. You really need to understand who your buyer is and what they run into and what they care about before you start thinking about your product. So I would spend, you know, quite a bit of time on the front end if I were onboarding or if you haven't done it, you know, within your own organization, you know, you need to be able to not be full of crap, you know, so to speak and be able to eloquently speak, you know, about what they care about because you can read them, you know, you know, you know what they're running into. Now let's get into playbook. So playbook, I really started from a place of, there's three types of leads from my perspective. There's inbound, which is demo request and chat box. There's outbound, which is completely cold. The person doesn't know who I am. And then there's a lot of categories in between. So I have nicknamed these internally as postbound. So postbound to me is anyone who is not a true handraiser. They don't necessarily want my product yet, but they have had some kind of interaction with chorus. So great examples of those. I have divided postbound leads, if you will, into two different buckets internally. On the left, you'll see the postbound, a bucket of postbound premises that I would mention for context to my buyer. And then on the right, you're going to see a bucket of postbound premises that I would not mention to my buyer. So on the left, you know, for example, you know, we've got content downloads or event attendees or webinar registrants, let's say to a webinar like this, or executive term, you know, like they have bought chorus at one org and moved on to a second org. That's within ICP that we haven't sold into. So it's pretty easy to guess that they would, hopefully, value, you know, what chorus does and we can sell into them again. You've got a list over here, but for me, graphic triggers like hyper growth, you know, maybe they have a common VC and common with you, demoed in the past or LinkedIn engagement. And then on the right hand side, you have a list of buckets of premises that I would not mention. I would not mention this is the reason for your outreach, but I would, I would know that this probably makes them more buyer ready. So a great example of that is number two, company funding. You know, chorus just raised $45 million and I've been getting hammered with emails of people basically prospecting into me saying like, Hey, you have a whole lot of money. You know, you want to buy my shit because I sell my money. That one's been overdone quite a bit in the last five, 10 years, I would say. They're like, congrats on your funding. You want to buy my shit? And I'm like, are you or are you? And it's bizarre. Like I've seen it. I mean, I'm inundated. I am just flooded with messages from random people, just value prop and me over and over. So, you know, yes, I probably am more buyer ready. Now I've got a lot of cash, right? So we're probably going to be doing tech stack or hiring people or et cetera. But, you know, just like anything, you don't want to walk up to someone, you know, and just say like, Hey, you know, I just heard that you walked into an inheritance. Do you want to hang out? I think you'd combine this in really cool jewelry. Or you're newly single and you put your status on Facebook or something and someone's like, Hey, I saw that you're single. You know, it's like, okay. You know, all right. Christina asked a question actually, is do referrals fit into here somewhere? If someone says, Hey, I have this person that you should maybe reach out to, or is that more of like a cold outbound at that point or mix of the two? Yeah. I mean, there's true post bound and then there's plays, if you will. Plays are, you know, they are, they're more interesting to you because of a certain aspect. So referral. Great example of that. And I didn't put referral on here, but I use it quite a bit. That I would mention the premise. Okay. I rely on it in no case scenario. Do I think you should rely on this premise for the breadth of your messaging? This is just to build a sequence off of and then you personalize from there. So we'll go how you do that. But that's a great question. You know, I would put referrals over in bucket one of like you want to mention that someone sent their way, yeah, you their way. However, I would still make it about them. There's nothing worse than an email where they're like, Hey, blank city should take a meeting with me and you're like, all right. Like, you know, the person's my boss or I want to win points with them. I will take the meeting. But from square one, you want to always make it about the person who you're speaking with. So these are all of the different scenarios that I build these sequences off of within outreach for my reps. And TLDR won't go too deep into it, but I am ranking every single month based on conversion ratios of what sequences, you know, are causing the most people to take meetings with me. The best meetings with me in terms of company size and best in terms of company type or person's title. And then what is the result from those meetings like are we winning more clothes, one business off of, you know, event attendees or webinar registrants, but content downloads, you know, we actually have the most meetings from and what's important to me. So I am being very, I'm very, very focused on what are the results from these sequences. So I'm ranking from my reps all of these sequences and number order. And basically they just come into outreach in the morning or whatever sales engagement tool you're using, you do it with sales off to and they are basically going to sequence one. And then if they have a task to, they're writing it, and then they go to task two and three and four and five and six. And I'm re ranking these sequences, you know, it's shuffling the order based on where I'm seeing the most, where they're seeing the most conversion for them. So I tell them, I'm like, don't get, don't get married to you should call on content downloads first. Just get married to the idea that you need to count. So I will just change the numbers for them at the beginning of every month, you know, so that they have the highest likelihood of booking a meeting with whatever person they're talking to based on data. But this is the comprehensive book. Apart from cold outbound, we have one sequence that's just cold outbound, meaning there has been no trigger at all. But this is the comprehensive book for everything except for cold outbound. And you have like over a dozen of these playbooks, essentially, our sequences for every scenario. And that's kind of the point behind this is that you're creating very specialized messaging for every type of scenario so that you have something that you can measure and refine and improve and optimize and that sort of thing. Yes, exactly. I was listening to say other people and everything that they care about. And then I'm listening to marketing and everything that they care about. And I'm combining all of those, you know, premises to say like, hey, so we have a sequence that's a content download sequence. You know, we have a sequence that's the event attendee sequence. And a sequence is the webinar, a registration sequence. And most of these sequences, I'm going to go into the structure in a second. But most of them are identical in terms of what action that they're taking and when. Just being the premise and messaging a little bit and it's helping me measure it. So we have, you know, we have 13 sequences in here. And I'm certain to flush out a few more. But these are the ones that we have. We have played out here at Corus. You have email opens, website use, etc. You know, dark funnel G2, six cents, Bumbora, you know, our different dark funnel providers that basically if you're researching on G2, you know, then we can tell from an account level and then we automate to where we kick in, you know, someone, you know, usually it's on the account level, not the contact level. So it'll say, I'm from Drift is researching you in Boston. And so within our CRM, basically, you need a very great ops person for this level.
of detail. Shout out to John Sweet or Ops person, but basically if someone from Drift research is chorus, then anyone who's in the CRM from Drift is within a title that we want to sell into kicks into the G2 buyer, buyer intent sequence automatically for the reps to call on. So they're just going from sequence to sequence based on data and what I've seen over the last month. And they're just going, is there anyone in sequence one that has a task to do? Is there anyone in sequence to do as a task to do, etc, etc. down to sequence 15 in their day to day. So I'm taking off of these reps for the leaders in the room, most of the list cleaning, most of the who and what account, most of, you know, etc. and basically having them spend all of their calories on what is that personalized premise? And how do I hook that into my value prop so I can marry structure, structure and creativity both? The structure of every single sequence that we run over here at chorus is 16 steps over 21 days. And it is comprised of 10 call calls, five emails and one step where they do LinkedIn research. This step at the beginning, they are coming in and they are basically going to the person's LinkedIn profile and they are hunting three different personalized premises that they can tie back to chorus. That's the rule for us of like whatever premise you're going to pick, you need to be able in your mind to relate that to chorus of no what angle you're going to go. So if I'm going to pick grilling, for instance, like, hey, Jason, reach my out reaches, I notice your grilling of fishy and auto, you know, when it comes to grilling, it's all about highlighting the best flavors. What if you could highlight the best flavors of your sales conversations, you know, and drive more quota to even as a result? Like, you know, that's cheesy, but you get the gist of like, I'm putting them thing through. Can I relate any of this stuff to what chorus does? And that's kind of the precursor for them picking on a premise. And this is the personalization at scale stuff goes into this more in depth. And I'm going to just throw this in. You guys to the chat again here in a second when I find it. But that's where you'll get like the really the deep dive into that stuff. And it's great. It's like two hours just full of like, like the most in depth shit you've ever seen when it comes to like personalization and then how to connect it and like all that other stuff. So I'll throw that into the chat because I think there's some people here. It looks like that may not have watched that kind of change to watch it yet. Yeah. That's awesome. If you're watching their recording, you know, whenever this is replayed, I would stop what you're doing right now. For those of you who are alive, I'm really sorry. Right now you're going to have to watch through this. But that's a really good place to start. But basically I am and I'm going to touch on it today. But I am teasing at having them tease out, you know, the great thing about the first step when they go to someone's LinkedIn profile. I mean, everyone who's who has been in the industry for any period of time, whether that be 15 minutes or 15 years knows that data is rough. Yeah. Contact emails being accurate, you know, them working at that company being accurate, their title being accurate, their phone number being accurate. It's like that is 70% of the battle is how do I find a person that is at an account that could bias that would be a good buyer for me that's in the right role? What's their contact data and what's their phone number is 70% of it? So, you know, I'm having my reps send out personalized messaging. So the first step I want them to do, you know, other than teasing out these three personalized premises, is they're going to this person's profile and they're using LinkedIn to understand like maybe this person left the company, you know, maybe this person isn't the actual role that our CRM data says. So it's a good way for them to trim out some of these people who aren't actually buyers right at the beginning. So they're only focusing on people that could buy our product. So step one again, they're going to the LinkedIn profile, making sure that they still work for the company, that they are the right buyer persona and then they're teasing out three personalized premises. They're storing them in outreach, you know, for that will fuel the rest of the sequence. But in terms of the actual structure of the sequence and you'll see what days I'm having them do which step here. You know, we can send the deck out afterwards for anyone who wants to build this in. But essentially, the theory behind it is I actually based it off of MJ Hoffman's studies, the author of Why Ui Now. He basically did a pretty in depth study on what cadence of actions you should do in when and keep in mind he's kind of pre social media. I hope he's not listening to this, but he built his media. You know, so it was more landlines and heavy cold call. But basically his research proved is that the later five minutes before the hour and after the hour later throughout the day and later throughout the week are going to be your best cold calling time. So in my experience and my personal belief is Monday morning, there's not a shot in hell that you were going to get a hold of me. Like internal fires, coffee in my stomach, I got to get stuff done. Friday afternoon at 330 or 345, I'm kind of looking for that one thing to stay busy, but not open up a huge project. And so that's a great time, you know, where you're more likely to get a hold of me. Certainly over the phone, I would say email and phone both, but he he understood two things that you should call later in the day, later throughout the week. So he has his reps take Monday off and start Tuesday Wednesday Thursday, Friday from 3 until 9 p.m. because he calls on West Coast and he's based in Boston. So not 855 p.m., his reps are calling on a Friday because of the conversion ratios. And I'm like, it makes sense. It makes sense that when you like to send emails is when everyone else likes to too. So you need to flip it and basically bump the chance that you are one of two emails as opposed to one of 10 that that person is receiving. But he also did a lot of analysis on how aggressive you should be in the sequence. And what he found is that basically if you are more aggressive in the beginning and then you start pedering off near the end of the sequence that you are teaching your prospect that if you, if they just wait long enough, you will eventually go away. So he flipped it on a TED and I followed, you know, his research and doing that and then actually I saw some great results near the end of the sequence of I'm easier in the beginning in terms of time and then I'm more aggressive in the back end. So they get to know me, they know that I know them. I'm hitting them with some personalized premises, I'm warming them up, you know, and you'll see I want you to think of this sequence in five different pods. First pod is cold email, cold call, cold call on day 1-1-2 then these are business days, you know, then day 8-8-9, I wait at seven day Delta, here, or six day Delta, you know, then day 8-8-9 I go into cold email, cold, cold, cold call, then I wait four days, cold email, cold, cold, cold, cold, and then here near the end of the sequence, you're going cold email, cold call, cold call, you know, cold email, cold call, cold call, cold, cold, cold email, you know, near the end. So in my experience, this is where you're going to see a lot of results, this first step, you know, if like, especially if you're personalized, I'm going to see a lot of conversion and then right in here, because they're like, holy shit, if I don't pick up the phone, like, this person is not going to go away and so, you know, if you're loaded with a personalized premise, you're not going to make the map. You know, I haven't seen it happen, if you are unpersonalized and you are just blanket pitching, they're going to get pissed. But if you have this one article that they wrote where you saw this line, you know, and you saw them on a podcast, and based on that research, you're going to value hook into something that you think could help them speed up, you know, eliminate, add to blah, blah, blah, they're day, you know, in my experience, if you're aggressive, matched with, you are relevant and personalized, people don't get upset with the level of aggression where they start to get mad is if you're mass blasting and then you're super aggressive on that end. So, you know, if nothing else, I feel like, you know, they kind of respect that you did that level of granular research, because no one else is doing it on the market. So, any who, that is the structure of every sequence that we do. I'll briefly touch on this for a couple of minutes, because I want to make sure we're on time here. But go to that personalization scale session, but the premise buckets of personalized, what I'm personalizing based on, I lump into five buckets. Again, I'm going to make you guys watch the session, but there's basically five buckets of personalized premises that you can personalize on at the contact level. So, I'm not going to talk about Jason's company, your industry segment or role. I'm going to talk about Jason. So, any first bucket of self-authored content, anything Jason wrote, webinars, articles or posts that he didn't on LinkedIn, Bucket 2 is engaged content, you know, but so anything he liked shared or commented on, but he didn't author himself. These are ranked in terms of conversion. So, Bucket 1, you're going to get the most responses. 2, you know, 3, 4 and 5. And if I had to guess, for instance, why Bucket 2, you get less.
responses is you're not giving them the ego stroke of validating their work. Yep. After this session, I'm going to walk around in this apartment and I'm going to wonder one thing. I want you guys to jump in the chat and tell me what your guess is on what that one thing is. There you go. Braiding got it. How I did. Let's prolong our absence. Thank you. I really got it. I'm going to wonder whether you liked me and I'm going to wonder whether you found value from this content and whether it was worth your time. Whenever you jump into bucket one and you start talking about their work, it's almost stronger than complimenting them directly. Instead of saying, "You're obsessed with someone," you're saying, "I'm obsessed with something you did," which is almost even stronger, just less creepy and it's stronger. Psychologically for them. Bucket one is self-authored content. Two is anything that they engage with on LinkedIn but did not through themself. Bucket three is self-attributed traits, profile line, headline, company line, anything they wrote about themself. Four is going to be junk drawer, school's attended personal interest, hobbies, careful. Remember that whatever you pick, you have to relate back to your product. So if you pick someone's school, I don't know what the rules are, but you have to find a way to relate that back to your product. So any who in junk drawer, in my experience, certain personas really like this, marketing HR, some sales leaders, sales development leaders really like this. Some personas don't back end engineers, CIOs, finances, iffy. So it's dependent on your buyer persona. And then the last one, if I can't find anything for personalized premise is company level, M&A, post blogs, hiring website language, but you have to tease out some kind of detail. You need to make sure that the prospect knows that you know who they are. So saying, "I notice your company is growing," and "I notice your company grew 73% and just hired a new VP of sales." One, someone doesn't know if you're a mass-blaster personalized, and one they're positive of it. So if you do all of that work to personalize to someone, you need to make it apparent to them. I would less generic to the better, because a lot of people are trying to send out cadences and sequences that make it look like they're personalized when they're not. So I'd spit some kind of detail to make them understand very quickly at a glance that you know exactly who they are, because you know something that they've done in specific, that it couldn't be a mass-blaster cadence is what I'm looking to achieve. How you can build those buckets in, again, these buckets in and all the personalized premises, and I'm going to showcase outreach here today, but full disclosure, you can do it with any sales engagement provider, Zaynant, sales law, etc. And outreach, basically, if you hit custom tags, you have 35 by default, you can expand it to 50, but I basically have ironed in all of these different personalized premises for my reps, so that basically they can, you know, when they go to the LinkedIn profile, they pull out three premises, they can throw them in these custom tags, and they can hit save, because the one thing that I wanted to do was I wanted to save their time. Yeah, so this will automatically populate, because some people may not be using sales engagement tools, in which you could probably create these fields in your CRM as well. But the idea here is it looks like it automatically will throw that link until when you go right into email, you don't have to spend another five minutes searching for stuff. It's just right there. Is the premise behind this? Yes, bingo. And number two is people don't pick up on the first dial. Yeah. They pick up on dial 800, you know. So it's like, I didn't want the reps to have to research every single time that they're dialing someone. Number one, number two, one of the biggest things I was running into, when I first started doing this was I had my reps putting it into a sheet, and then someone would pick up and they'd be like, oh shit, reset sheet. They're like shuffling back and forth between all the tabs on their computer, because they didn't expect someone to pick up. And so I wanted to make it a really clean user flow, you know, that when that person picks up, you can you can spit this personalized data within the first 20 seconds of the call, so that they don't hang up on you. So this really personalization, at the base of it, it prevents people hanging up on us, because we are giving them some detail about themself and asking them a question right off the bat. I go deeper into the call call track, you know, within personalization at scale. But yeah, if you throw it into one of these custom fields, you hit save. And then every single time that I call, I did my friend Scott Barker for this one. I've heated a post on seeing his believing and I put a little excerpt in here. And then every single time, you know, that I call Scott, whenever he finally does pick up, I don't have to shuffle anywhere. I can just, you know, put this, say this premise very, very quickly. How I pair these together is basically, you know, like we, like I mentioned up here for the bucket, see if two kinds of buckets, premises that you or scenarios that sequences you can build based on a premise, and sequences where I would still create the sequence, but I wouldn't mention the premise. If you have a postbound premise, let's say they downloaded content, you know, they're in that sequence, then I would, I would mention the postbound premise of like, hey Jason, we think my outreach, as I noticed, you attended this webinar with the, think outside the script tour. I say, but more importantly, and then I say something about them. But more importantly, I saw you with this article on LinkedIn where you're talking about scaling effective teams. Yeah, I think this is a really common thing because there's some people that call inbound, you know, content downloads. So people that have downloaded a need book or signed up for a webinar, and that's not a true inbound lead because this person didn't say I wanted demo. So you're not only just referencing, because someone asked this question, I get asked this a lot too. You're not just saying, I say, you sign up for a webinar, you also got to do a little bit more digging than that to find out actual reason why a conversation makes sense right now. The fact that they signed up for the webinar just makes it a little bit warmer than doing it completely cold outreach. 3,000%. Any true rap knows that inbound is not, it's not the same. Demo request and content download is not the same because if they wanted a demo, when they downloaded your content, there was a demo request button. So they didn't, they didn't request a demo for a reason, you know, that reason, some kind of objection. A lot of times, sometimes it's false objection, sometimes it's not, but there is some kind of reason there. So you have to do almost the same exact work as an outbound deal. It's just a little bit warmer. So I always, in every context, you want to make it about your buyer, your buyer, your buyer, your buyer, your buyer, your buyer. So, you know, I don't want to hear about chorus, you know, like it's like that I downloaded your content, you know, people don't care, that they attended the webinar event attendee. I mean, people after they got after this, if you email them and send like, hey, do you want a demo of chorus? No one would respond to that, right? So it's like, you want to couch it with dynamic tags, we'll go in how to do that. You want to couch it with the dynamic tags, say, but more importantly, and then make it about them. More importantly, I don't want to talk about chorus and our content and our webinars. We're the hero there. Yeah. I want to talk about you and all the stuff that you've done said, engage with, et cetera, because this chat to be an effective one needs to be about them. So for the majority of our sequences, where we're mentioning this, it's going to be a postbound premise with transition, but more importantly, and then a summary of something they've done. If it's a cold outbound sequence, it's going to be a personalized summary, and then I push them to put an excerpt in there. So I say, hey, Jason, reason for my outreach is, you know, I saw you with this article on LinkedIn. We're talking about scaling in effective teams. One thing that stood up to me is where you said, it all comes down to quality conversations. So in either case scenario, you want to have two pieces, either the postbound premise, and then a summary or a summary in the next served, if it isn't a postbound sequence. So that's the sequencing work on what sequences you want to build. I mean, in review here, the 13 that we're running over at Corus, five that you don't mention that the premises are all personalized, and these eight where you're giving the postbound premise with a dynamic tag to couch it, transition, but more importantly, and then making it about them. I want to briefly touch on how you can scale any sales technique, and then I'll go into the follow up emails. Scaling any sales technique is actually not that tough. All I need to do is this. I'll let you read it later. I'm not going to spend too much time here because I want to get into the follow up email so you guys have a structure as a takeaway. But basically, when I'm listening to any trainer, all I do is I think when they say, like, oh, you should do this. Here's the email that you should send, and it's all about deposits, or it's all about whatever. Like, the way dude, like, how does this actually fit into a strategy? I'm like, whenever I see any trainer training on any ad hoc item that there's
training on. I'm like, this might work, but if this isn't within a sequence and if it's not scaled, I loved when Mani, CEO of Outreach, he said that on the flip the script where he said, "If you can't scale it, it means nothing." And I'm like, "Mani, you could not be more correct. You could not be more correct." So you're going to learn a lot of different techniques from a lot of different people with a lot of different opinions on LinkedIn. And I'm certainly not here to say who's more valid, et cetera. What I'm here to say is, "Any time that someone tells you a sales technique, like, let's say they give you an example of an email, I think through the following steps, I break down the number of sentences in that email. I understand with each sentence, a sentence, what is being accomplished in the root of it? Like, is it an intro? Are they saying the reason for your Outreach, like Jump Arrows, or are they doing some kind of deposit, or etc? Like, what is being accomplished in that sentence? I think about what is being accomplished, sorry, what is being accomplished overall in the email? What's being accomplished in each sentence? And then I break that down and I self-label the technique." So I'm like, okay, what they're doing here is a great example is their pattern interrupting. They're not uninterrupting by saying something different that hasn't been said before. So a great example of that is the rule of free of like, "Hey, Jason, did you drop by our booth because you wanted to learn more about chorus, you wanted to learn more about sales conversations, or because you wanted the sweet swag that we were giving away for free and you wanted me not to bother you?" Yeah. You know, it's like business reason, business reason, and then funny reason that makes the prospect like you more. I would take a screenshot. I took a screenshot of this. This is really good for anyone that consumes a lot of content on this stuff. If you've run it through these questions, I guess these sort of checklist of things, it's going to help you actually understand why it works so that you can make it your own and that's the hardest part consuming content, especially on prospecting is like, how do I apply this to my situation? And without actually hiring someone like back to come into your company and do that for you, usually we got to do it ourselves, right? This is awesome. Three, three thousand percent. And I also, I wonder a lot, you know, I look at a lot of content and you always wonder, people just want the best thing, right? The best hook, the best objection handling line, the best thing. And so I usually, I want to understand for me and for my business, which technique works the best. And so I basically run through this checklist. I think through the number of sentences in the email, I think through what's being accomplished overall for the email, like what's the goal of it? Are they asking for a demo? Is it, you know, just a response email? Is it a nurture email? What's being accomplished in every line? Can I break that down and label the technique that they're doing? Can I write in step five as I write in an example for reference for my reps of like, hey, you need to do a pattern interrupt here. Here's an example of one that you can do. But, you know, feel free to do some kind of pattern interrupt. It's like, you know, I'm not going to tell you you need a subway sandwich, but you need some kind of sandwich. So whether you go to whatever, blimpies or quiznos or whatever, it's like you need to be doing that in this moment and you need to be interrupting that buyer seller dance, the toxic buyer seller dance and making them see you as different. Here's an example of that, but go ahead and this is what needs to be accomplished with the thing. So a lot of, I think the strongest leader is someone who is okay with being replaceable. A, you know, here's what needs to be accomplished and this is the base of it, but you go, you go show me how you, you can make this at your own and you can do it. So I write an example for reference within the sequence. I train on multiple examples, you know, I beta test out responses and the types of responses I'm getting and the outcome of those responses, I adjust accordingly to that data. And then the last step for me is the most important or one of the most important is I leverage all the people that I hire. I'm like, Hey, I need a new hook. Who can come up with a new good hook? It needs to have two pieces and it needs to achieve this and then I kick it out to my team and they have fueled most of the content that I'm doing is fueled by people coming up with awesome ideas and then me figuring out what's the base technique and then the ones that work leveraging it across the rest of the team to do it. So our team is an organism that is constantly learning from one another. So we're learning very, very quickly. Someone has a good hook. We deploy it to the rest of the team and then we're like, okay, so what was effective about this thing and then how can I, how can I do it in several different ways? So great example of that is in the hook line and the value prop line, I came up with the middle structure of like, you know, what if you could x, y, and z. And then we got to the point where we're like, imagine if you could x, y, and z. And then I have an idea on how you could x, y, and z. All three accomplishing the same thing, different words, but same same goal. So this is a great, it's a dense slide cerebral, but it's a great way to understand if I'm listening to all of these people in the market and the stuff that I like, I'm going to put these following steps into place, figure out what works, you know, and then breathe off of off of that technique that's being deployed. So that's it in terms of sales technique. I'm going to, I'm probably going to go after the hourful disclosure, what on I do 15 minutes on follow-up emails, pass the first email if that's okay, Jason, you know, for anyone who wants to stay on the line. Yeah, I want to share a couple things in case someone has to hop off. I'm going to link to this YouTube link that I just threw in is the entire flip the script content. You guys like, there's just master classes in everything about objection handling and personalization. I've already shared the personalization one a bunch. And then also I want to drop in Bex linked in. Make sure to connect with her and say hi after this if you got to jump, but we're going to go over extra, the replay is going to be available later. It's going to get posted tonight. So I would definitely, you know, check it out, but she was kind enough to spend some extra time with us here. So I want to just want to make sure if people got to jump off back that they have a way to check out your stuff. Proceed. It took a couple of days. I'm too long-winded. I need to go on that. I do the same thing. As far as the follow-up emails, again in that session, it will, I go into further depth of how to write the first email. But I wanted to give, I mean, I don't know if you've caught you caught it, but in this sequence, you know, there are five emails in total that I am writing. One on day one, day eight, day 13, and then two more, we have a break at be mail in day 18. So I wanted to go into what the actual technique is behind those follow-up emails. So let's start with the first email and I'll try to sum all this up in 15 minutes. The first email, you know, and I go into it more in this session. So I'm going to make you guys watch that. But the first email, I basically am in my first line. It's my longest line. I am picking out a personalized premise and I'm giving them a summary and then some kind of excerpt. So it says, "Reason for my outreach is, you know, I saw you wrote this article, you know, on scaling effective teams. One line it said up to me is it all comes down to good conversations." The second line, medium length, is the value prop where I hook my value prop into the personalization and I do that in three different parts. The first part of the line is where I am tying three words from the end of the first line into the beginning of this line. The second part to a hook is I'm navigating my way back to buyer persona and then the third part of the hook is I'm saying and blank as a result and I put the one thing they care about. So, you know, in that example, I would say, "What if you could, you said, it all comes down to great conversations. What if you could ensure your reps, you know, over at Octa are having great conversations like you mentioned, building more rapport with your buyer, and exceeding more quota as a result. So, you just want to state the one thing that they care about in the middle of that hook and there are three different ways that I'm doing that. Imagine if, what if and I have an idea on how you could X." So, that value prop is going to be the medium length and basically the goal of that line and this is where good and great reps are made, meaning how well you can hook the personalization to what's relevant to them and talk about what they actually care about in a fluid and brief way is where you're going to get the majority of your buyers. This is the hardest line. So, this is where I want my reps, you know, spending most of their calories is how do I sum this up? How do I structure this in a way to where it makes sense to this person? You've seen a lot of 10, 80, 10 in the industry. They're saying, you know, "Hey Jason, I know whatever, hi back. I noticed you went to Texas Z&M. We at Drift helped convert more website use in two clothes, one business." And I'm like, "There's no tie here." So, this is where in my experience where buyers are hungry to see you prove personalization in and of itself means nothing or very little. It's different, but it means very little.
You need to, or at least in my experience, you need to, like, this is the most important line of, I'm not full of crap. I teased out that quote because it actually means something to me. It was the perfect timing because it hooks in here. So that's where I'm going in the second line, value problem. Third line, it's my shortest line. I'm going into CTA or call to action where I'm requesting one time to unpack how VPs of sales leverage chorus to drive more quota attainment. And I usually give them a barter. And if you're not in pre-- and I promise I won't hammer you with follow-up if you're not in press. And then the last line, I do what's called the push pull technique. So basically, I give them a reprieve. I say either way, I want to give them the reprieve of whether they have a meeting with me or not, whether they buy from me or not, whether they give me what I want or not. Either way, they need to keep the good stuff coming. I'm a fan, thanks for the article. And this is a good place to intertwine COVID language, if you will. Either way, I hope you're staying safe during everything that's going on in the world. So I've seen a lot of people lead with COVID and be like, hope that you're safe. Hope that you're-- you and your family are OK during this time. Number one, it causes pattern recognition in their head and they're like delete. Number two, it comes off as insincere in my experience. And they're like, you don't know my kids. So stop talking about them. And number three, we're-- Don't talk about people's kids. It's weird. And number three, in my experience, it's like if you're not careful, they think that you're monetizing a pandemic. That was a good one. So we didn't quite get the whole audio portion in there because it cut off on Zoom actually now that I'm listening to it. So we definitely have the full version in the webinar. So make sure to check that out at tour.blasfulprospecting.com for the replay. It's also linked up in the show notes there. So if you get your phone open, it's linked up right there. You should see a link to catch the full talk. But yeah, my apologies. I wasn't expecting for the idea to be cut off. Sometimes I have some issues with Zoom and recording the audio bits of it, especially. So make sure to check that out. I think you'll really dig the rest of the talks on the tour as well. My biggest takeaway from this is how to scale any sales technique. I thought that was really cool because I consume a lot of sales content by getting it in a way that's actually being implemented either by myself or by our clients is a bit of a challenge sometimes. So thinking about the specific parts that you can scale will really help make sure that the time you're spending and investing in consuming content is actually paying off and putting more appointments under a calendar or closing more sales. So thanks for tuning in. Again, check out tour.blasfulprospecting.com. And we'll talk to you soon. See ya.
Podcast Summary
Key Points:
The biggest challenge in outbound prospecting is creating effective follow-up sequences after the first email, as many reps struggle with what to say in subsequent touches without being a pest.
Beck Holland emphasizes personalization at scale, arguing that unpersonalized messaging rarely works and that reps must find ways to scale relevant, tailored outreach.
The session covers four key areas
Beck recommends starting with case studies, then interviewing actual customers and industry peers to understand real buyer motivations, rather than relying solely on marketing personas.
The goal is to enable reps to test and adopt techniques from various sales methodologies, using data to double down on what works.
Summary:
In this podcast episode, Jason Bay interviews Beck Holland, CEO and Founder of Flip the Script, to address the common mystery of outbound prospecting sequences. Beck explains that many reps feel lost after the first email, unsure how to craft unique follow-ups without annoying prospects. She argues that the rise of sales engagement tools has led to a culture of mass automation, where reps lose sight of their true goal: selling more effectively. The key is to personalize at scale, as most people don’t respond to unpersonalized messages.
Beck outlines a four-part approach to solving this. First, she advises finding your buyer by going beyond marketing personas: start with case studies, then interview those customers to learn the real reasons they bought. Next, interview industry peers in the same role to understand their daily challenges, without pitching your product. This helps craft relevant messaging. Second, structure a comprehensive playbook that maximizes lead conversion through personalized outbound plays. Third, learn to scale any sales technique by incorporating proven methodologies (like Sandler or Challenger) into your sequences and testing them. Finally, Beck provides her personal follow-up email sequences as a default template, showing how to maintain personalization across multiple touches. The overall goal is to help reps stop guessing and use data-driven, scalable personalization to achieve 35%+ response rates.
FAQs
The main challenge is figuring out what to say after the first email, how to follow up without being a pest, and how to scale personalization to get a 35%+ response rate.
Sales culture shifted from field sales to automation with sales engagement tools, leading to mass messaging. This caused a loss of focus on the goal of selling more, making sequences confusing.
Start by reviewing case studies on your website to understand who bought your product and why, then contact those customers directly for deeper insights.
Case studies often have a polished story, but interviewing customers gives you the real reasons they bought and how they use the product, helping you craft better messaging.
Take their methodologies and incorporate them into your sequences as beta tests, then analyze results to see what works for your business and double down on it.
To understand their day-to-day challenges and priorities without pitching your product, so you can tailor your messaging to their real needs.
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