#570 - Cold Email Masterclass: Everything You Need To Book Meetings in 2026

The average rep has to send 344 emails to get one reply. Cold emails are totally different game right now. AI ironically has made it easier to write emails, but it's made it much harder to get a response. But the good thing is that you can still get double digit replies over cold email. We studied 85 million cold emails together with GONG, and I'm going to share everything that we know to help you land more meetings through cold email. We're going to talk about the email framework that helps you break through the noise, subject lines that get your emails opened, and we're going to talk about follow-ups to drive replies. My name is Jason Bay. I run Outbound Squad. We've helped over 250 sales teams like Shopify, GONG, Zoom, and Rippling send higher quality cold emails to book meetings with senior buyers. Let's dig in. Part one, the reply method framework. So there's five parts to a great email. So the first parts of subject line, we're going to cover that in the next section, but what's really important is that we do not talk about our product. We don't do any type of pitching. The number one goal of the subject line is to drive an open. The second part of the email is relevance. So the very first line of the email needs to open with something about the buyer that shows that you're reaching out on purpose. The third part of the email is the problem. The problem answers this question why change? It's the thing that will compel the buyer to take action. The next part of the email is the value and social proof. The data from GONG shows that you will increase the reply rate by more than 40% if we share a relevant company that's similar to the one that we're reaching out to. And last but not least, call to action. We need to be very specific about what we are asking the buyer to do. So let's start with a bad example of an email. So let's give some quick context. This company sells a marketing solution that helps with a lot of the automation that's required to deliver personalized email campaigns. Stuff that really converts really well for B2C businesses, especially is extremely hard to do without a bunch of manual intensive labor. They can make a campaign launch take weeks or months instead of days. So subject lines. Rule of thumb with subject line is you want this to look like an internal email. You want it to be short and sweet less than five words is what the data shows. And you can see that this subject line here, quick question about your campaign workflows. It just screams sales email. I would be very surprised if a buyer would open up this email. So what we're looking for in the first line of the email is relevance. There needs to be something that is like obvious in this email that I am reaching out to you on purpose. And what you can see in this email is it's really generic. I'm wanting to know like what campaigns did you see? What are you seeing us doing that stuck out to you? The second line of the email we want to call at a problem. And this email actually doesn't do a terrible job in that. It says a lot of the teams I talk to are trying to move faster, but they're stuck waiting on code. It still feels very generic for this buyer. In ops, we want to get much more specific around campaigns, build times, etc. The next thing we want to do is talk about value and social proof. And you can see here it doesn't do a terrible job of talking about what they do, but it doesn't drop any social proof. This client works with amazing companies that they could drop here and they don't drop any of those. And the last but not least, the call to action. It's not bad. We really want to use a closed-ended call to action that can be answered with a simple yes or no. Something interest-based, maybe you're giving something valuable in return for their time. This CTA is not too bad. Would it make sense to have a quick chat about how we might build the help? So let's look at the after version of this email, the rewrite. So the subject line. What you can see in the subject line is we've clearly called out a business priority that T-Mobile has been talking about publicly. And it's 5G revenue. So if I work on the marketing team and I see something related to 5G revenue, I'm likely going to open that. And the first line of the email, 5G and fiber campaigns look very tailored and personalized. You can tell it is calling out specific projects and things that they are seeing the buyer doing. That's second line, the problem statement. Multiple builds, QA and compliance checks can take weeks or even months if ops is the bottleneck. The really big problem is that things take longer than they should. We needed to launch today. We needed to launch tomorrow. It takes weeks or months. And ops, marketing ops, this is the persona being the bottleneck. That's the big thing that we want to call out that this rep did great. The third line, social proof. What we want to do is name drop and we want to be really specific around the value that we can bring. So Amazon used blank solution to launch hundreds of personalized landing pages in the email campaigns in a day instead of weeks. And then last but not least, call to action. Something short, sweet, yes or no answer. Can I show you how? I think that we could upgrade the CTA, which I will talk about later in this master class, but it's not a bad start. So the after email, I would likely give maybe an 8.3, 8.4. The before email, I might give like a 7.1 or 7.2. So let's do a deep dive on the framework. So that first line, the reason. This is where I showed the prospect that I did my homework. The data, everything that we saw was very conclusive. And honestly, none of it really surprised me. The GONG data showed that, hey, if we personalized an email, if we put a trigger in there, if we put something about the buyer that gives context into why we're reaching out, your reply rate will, on average, increase by five times. You will have a 10% reply rate compared to a 2% reply rate. We also really found some interesting data on the types of personalization that works best. So for example, for trying to reach out to a director plus persona, so this is someone that's in a leadership position, director, VPC, sweet, these folks are much closer to the business outcome. They respond much better to company level personalization. So that's going to have a 50% higher reply rate when we reference something about the company. So a company project versus something at the contact level, something about them where they went to school, what you saw on their LinkedIn profile, etc. So we want to call out for senior leaders something going on at the company. So the next part of the email, the problem. This really answers the why change. Why should I do anything differently from what I'm doing right now? When we lead with problems and priorities, we will boost reply rates by more than 20%. When we talk about ROI, platform, AI is kind of the hot thing right now. And I know that everyone has like an AI budget and buyers are looking for AI-enabled solutions. But you should not put that in your cold emails. You can see it has a significant impact on decreasing the reply rate when we use these types of buzzwords. The next part of the email is value and social proof. We have to show the prospect that we're up here. So a couple of quick guidelines here. If you're going to name drop companies, you want to make sure to name drop companies that are very similar to the buyer that you're reaching out to. So for example, we used Amazon when we were reaching out to T-Mobile. If you were reaching out to Outbound Squad, a small training firm, you wouldn't want to name drop T-Mobile in Amazon. These are companies that are nothing like our company. I would want to know what consulting firms, training shops, etc. that you've worked with. So when we leverage social proof effectively, we will boost replies by as much as 41%. The CTA, last part of the email, we want to make it specific, closed ended, and very easy to respond to. The common mistakes that I see here are ending an email with how to question Mark. Like you want to have a specific call to action. The second thing is having multiple call to actions. So maybe we link to a case study, an article, and then we ask them for time. We're asking too many different things. You can always send another email. You're only allowed to use one call to action. So there are four types of CTAs that we looked at with GONG. The worst CTA to use ironically is asking for time. So the very thing that you want, you should not ask for in the cold email. Your reply rate will decrease by as much as 44%. If we use CTAs like, are you free for 15 minutes tomorrow? So the second type of CTA is an open ended question. These are really terrible CTAs, and I know that we're taught in sales to ask open ended questions. That's really great when you're having a live conversation over the phone, over a Zoom call, whatever it might be. With email, if you ask an open ended question, it requires a tremendous amount of effort to respond to. So we don't want to ask questions like, what's your biggest challenge with? You shouldn't ask questions that start with how? None of that kind of stuff. You want yes or no answers. And then there are interest-based CTAs. These were really popular two or three years ago. They can work really well. But essentially what you're asking for is interest instead of time. Would it be worth a quick chat? Are you interested in chatting further? Would it be interesting to do a deeper dive? Where's a quick look? Anything like that that's a yes or no answer? That is getting a much smaller commitment, a commitment of interest versus time. You're much more likely to book a meeting when you can get that micro commitment first. Last but not least, this was the coolest part of the study. We found that offer-based CTAs will increase reply rates by up to 28%. So in other words, if we are able to give the buyer something in return for their time, we find that the reply rate is the highest of any CTA that you could possibly use. So let's talk about the different types of offers you can use. And then I want to give you an example. So the first type of offer, if we were to think about these as, you know, easy, medium and hard, the first type is selling the blind date. This is something every single person can do. Regardless of your role, we're going to pitch the expertise of the person that the buyer is going to be meeting with. So let's say that you sell edtech. The blind date might be with you because you were a previous teacher, right? You've been in the game for a decade. You have insights that you could share. If you're an SDR and you're pitching the experience of your account executive who's close some big logos, you can say, "I'd like to introduce you to so-and-so who's worked with XYZ companies." You could pitch the expertise of a solutions expert or a sales engineer. So if you sell cybersecurity and you have a technical person that can join the first call, you can sell their expertise. And I'll show you an example email of what that was. that looks like here. So if we look at this email, same one is before the T-Mobile, subject lines 5G revenue, first part, the relevance piece is the same, the problem piece is the same, but if you start to look at the social proof element, we are dropping social proof and an offer at the same time. Our optimization specialist, Adam, has worked with Amazon to launch hundreds of personalized landing pages and email campaigns in a day instead of weeks. Can I connect you to so you can see how? The second type of offer, the medium, if you will, these are one to many offers. These are high quality, reusable insights that feel tailored because it's something relevant to maybe their persona or industry. If I had to give you an example, we worked with a company that sells into e-commerce businesses and they sell a CX solution. So outsourced customer support essentially. They've misch shopped 300 e-commerce companies and what they would look at was like the average response time to chat, the channels they operated in, their business hours, etc. So in an email or a cold call, what they could do is say, hey, your response time via chat is three times longer than XYZ competitors. You might be losing sales to them. Can I walk you through the rest of the insights that we learned from analyzing 300 plus other e-commerce businesses? That is the perfect setup for a sales call right there where you're giving them valuable insight. Offer number three, the last one, these are a bit tougher. This is going to apply mostly to enterprise and strap wraps. These are one to one offers. So I worked with another company that sold a solution that would help with shopping cart conversion. So they would actually record a video of themselves buying something on the website and showing all of the leaky parts of their sales funnel or how they didn't get an email when they added something to the cart but didn't buy it. You could offer cybersecurity audits, right? You could offer free data. Maybe if that's something that you sell. There's all kinds of things that you can do on a one to one basis for that customer to benchmark them compared to competitors, whatever might be. Those offers can work really great as well. Okay, last but not least, format is so important because if your email is formatted in a way that feels incredibly hard to read, digest, or just really high effort to figure out what to do with, it's not going to get open to red. So it really starts with the format of the email and the length of the email. So a good rule of thumb here is you want it to be formatted so that I could open it up on a mobile phone without scrolling. So typically that means four to five sentences and under 100 words. Paragraph structure, I want one max, two short sentences per paragraph. It needs to be really easy to skim lots of white space and very low effort to read and respond to. So if you're a complete email framework, let's go to part two subject lines because it's impossible to get a reply to an email that never gets opened. Okay, so top reps are able to drive more than twice the opens as average reps. So there's a couple of things here, length. So the first part is we want to keep it short one to four words is what the data shows. Open rate is going to be the highest when it's one to four words and we want to match internal communication style. So if we can use words and phrases that the buyer would use when they're communicating with their peers or sending internal emails, that's going to have the highest open rates. Second thing, language to avoid. There's very specific things that we found in the data that you want to avoid that will impact the open rates in a negative way. We don't want to use any marketing speak. AI, platform, industry buzzwords, all in one, single pane of glass, none of that belongs in the subject line. Numbers and questions. We want to avoid using numbers, questions, 10x percentage increases. None of that stuff should go in the subject line because again, it violates rule number one. It does not match internal communication style that is not how your buyer talks to their peers. Social proof. This was actually a surprising thing in the data. Social proof works really well in the body of the email, but we don't want to name drop customers that we've worked with into the subject line. So the language that we should use is priority based language that speaks to the prospects world. We should be using words, phrases, project names, stuff that they would recognize that looks like it's from a peer. So priorities. These are specific initiatives. If it's a publicly traded company, a lot of this is public information. Like I can drop that into the subject line, current solutions and problems. So if there's a really sticky problem that you help with, like you could drop that into the subject line and then aspirations. If there's anything that they hope to achieve that's really easy to drop, that would be recognizable. We can do that as well. We want to resist talking about our solution. And last but not least before we go into the frameworks, capitalization matters. What we've noticed is that all lower case subject lines tend to have the highest open rates followed by sentence case, capitalization. So capitalizing the first letter of the first word. What does not work as well as capitalizing the first letter of every word in the subject line because again, that is not how buyers will typically write emails to people that they know. Alright, so let me give you seven subject line formulas. So you can see what this looks like in action. The example client that I'm working with here is one that sells a solution to clinical operations and helps them start studies faster and helps them get done on time. So the first framework is pervasive problems. So these are macro problems that almost everyone is experiencing on the persona level. So if I'm ahead of clinical operations, participants dropping out of the studies is something that's very top of mind for me. So the subject line is just going to be participant dropouts. And you know what, if you want to use one word, you could probably just use dropouts. The second framework is an industry trend. So this is something that might be industry wide. So it just doesn't just affect the person and the types of buyers that you're reaching out to at effects an entire industry. So remote engagement is something that is really big for any clinical ops buyer. There's an example I love to use with a company that sells an automated welding solution, welding talent and a shortage of that talent is an industry wide problem. And their subject line was one word, well, there's had a 92% open rate. So the third framework is company and organization initiatives. So if it's a publicly traded company or they post online and you can find triggers, they would indicate that they might have a problem. I'm going to drop that into the subject line. So what you see here is FAPI trial recruitment. FAPI is the name of a study. Trial recruitment is what they're likely working on. I just dropped that in three words subject line works great. The fourth framework is exact leadership quotes. So this would primarily be for a publicly traded company where you pull a quote in that a CEO or someone in the C suite, let's say shared. This can work really well if you can get that information. The example is Rick's comments on site interests. And they talked a lot about site interest. I'm just going to drop that into the subject line. The fifth framework is people on their team or shared connections. I love this one. So if you're selling to a leader and the product or solution would be used by the people on their team, I can look on LinkedIn for people's names and I can drop that into the subject line. So this was Carol's upcoming study. So Carol is a clinical operations manager who is likely project managing these studies. We drop Carol's name in there, upcoming study. Six is short pattern interrupts. So again, we could just use a one word, one off off the cuff looking email that someone might send internally if they noticed a quick problem. So the one word subject line here was delays. That was a really, really great one that we saw a lot of success because trial delays are the number one thing that these folks are worried about. So delays and then last but not least, competitor shares. So if there is a very strong competitor that they work against that you might have worked with, this kind of violates the social proof data that we talked about, but I have seen this work pretty well. A Moderna is the number one competitor of this account that we're researching. And if we had insight around what they were doing, we could just say Moderna or C Moderna. We're just going to drop the name of the competitor into the subject line. Let's start with some sequencing fundamentals. Key point number one that I want to talk about is tiering. The reason why it's really important to tier your efforts is it requires, on average, 12 to 15 touches to get in contact with a prospect. You don't have enough time in your day, in your week to treat every prospect equally, nor is every meeting worth an equal amount to you. So for example, if you sell an HR solution, a meeting with a VP of HR, let's say, is much more valuable than a meeting with a HR manager. And it's going to take a lot more effort to get a hold of that senior HR leader than an HR manager. So we're going to tier our sequences. We're going to keep it really simple. You're going to have a high-touch sequence, which gets very customized. It's multi-channel. You're going to use this for senior stakeholders. Your dream accounts, those A tier, tier one accounts, whatever you want to call them, the ones that are a really great fit that can do massive business with you, and then large deal sizes. So if you see potential based on your research for an account that has the opportunity to be a really big deal for you, this is where we're going to invest more effort. It's going to have all the phone calls, emails, and social touches. The second type of sequence is a low-touch sequence. This is mostly going to be automated, and it might mostly be single-channel, like email, for example, because it's really easy to automate. And you might throw a phone call or two in there if the prospect is opening up the emails that you're sending them. So what you want to decide is who is deserving of your tier one efforts versus your tier two efforts, your high-touch versus your low-touch. Key point number two, let's talk about the data. So the data-backed outreach blueprint looks like this, whatever you do. It needs to be multi-day. So it needs to be spread out over three to four weeks. It doesn't make sense to do all of those touches in one day, and it doesn't make sense to spread it out over an entire quarter. The data shows that three to four weeks is the optimal spread. It needs to be multi-touch, so 12 to 15 touches, and then it needs to be multi-channel. So those 12 to 15 touches are going to be spread across email, phone, and social. So if you're just doing this for the first time, you don't have a lot of data, a great place to start looks something like the diagram that you see here. What we're going to do in week one, and week two and week three is we're going to have five touches each week. On average, two phone calls a week, you're going to have two emails per week, and then one social touch. So the very first time that you reach out to someone, the technique that we're going to leverage is this idea of doing a triple or a double touch. You're never going to send an email without making a phone call. You're never going to make a phone call without sending an email. You're never going to send a connect on LinkedIn without bumping them via email. All of the channels work well and better together. So in that first touch, I'm going to call. I'm going to leave a voicemail if they don't pick up. I'm going to email, and then I'm going to hit them on social. Pro tip with voicemail. Don't ask for a call back. Ask them to look at something that is much more low friction, the email that you just sent that. So the second set of touches that you're going to do is another phone call. You're not going to leave a voicemail this time and you're going to do a bump email. So this bump email, it's going to be an email that's threaded into the same email thread. So you're not going to send a new email chain. It's got the same subject line. You sent that longer first email that we just spent a ton of time creating. And we're going to bump it with something shorter. The idea here is that it's one sentence and you're really pushing people back to look at that first email. So keep point number three. Let's talk more about bump emails because there are a lot of different types and you don't want to just send the same email over and over and over again. So the data here was really interesting. So if we use case studies and case study language, Beth had mixed results with this by the way. That is actually one of the styles of bumps that we recommend. But when you don't do this correctly, it could reduce the reply rate by as much as 47%. If you ask for a quick chat, it's going to reduce the reply rate by as much as 2%. But when we mix in things like thoughts, any thoughts, when we have short CTA language, pick up emails, when done correctly, I'll give you some examples of that. It can increase the reply rates by as much as 89%. So let's look at some more examples. I really like what we call the interest bump. So the interest bump is you're basically going to do a very similar CTA that you did before asking for interest. So you might say something like, hey, is this worth a quick chat to see how this could reduce study build times? The second type of bump email is what's called an offer bump. So we just talked about offers earlier. So you can repitch the offer. So that might look something like, hey, can I connect you with Tom to share how similar Hitchmanifactures are dealing with the wilder shortage? I ran a cart audit and found three opportunities to increase AOV here. Where's a quick chat to dig in? There is an any thoughts bump. This is probably the most overused bump email at this point in sales, especially if you consume content on YouTube or LinkedIn like this. But it just works. Really well, it's a version of any thoughts you could drop in the person's first name, any thoughts you could get more specific around the subject area that you want to talk about. So that might sound like, hey, any thoughts on reducing the need for devs? There's the quick chat bump. So this is one where you're going to make a very specific ask for time. Any chance you're free next Tuesday at 2pm or 3pm to dig in more. There's the case study bump. So you could simply link to a case study with no other ask outside of that. Hey, here's how obsoleteers at Caterpillar are leveraging automation to replace welders. And then last but not least, the breakup bump. So we don't want to use cheesy breakup bumps. I would avoid the weird cheesy memes here. Hey, would this be more relevant to Dave over in manufacturing? So you could basically ask, am I reaching out to the right person or not? All right. So now you have everything that you need to write, a great email, make sure it gets open, and then make sure it drives replies so that you can book a shit ton of meetings. Okay. From here, we have two resources for you. Once free. So if you want my exact outbound sequence template, make sure to check it out below. It's got a ton of great templates in there, sequence examples, et cetera. The second thing that you can do is grab our cold email course. I partnered up with 30 NPC and Gong. We created a really great course that's going to help you do everything from leveraging AI so that you don't have to do this from scratch every time, design messaging that execs really care about. There's some great exercises on how to tease out buyer language and problems in the voice of your customer. It increases the success rates of this just massively when you're able to do that. And then really how to avoid getting con in the spam filter and make sure that you're doing everything right to book meetings. So what are you waiting for? Go grab the cold email course. Today's show is brought to you by Insightly. The CRM helps you spot deal risk early. So pipe reviews actually drive your number. One question I ask in nearly every deal review is what do we need to get in our next interaction with the customer? If my rep can't answer that question, the deal has a risk and I have something I can coach to. We'll take guide with our friends at Insightly CRM on how to run pipe reviews that surface real risk and get deals moving again. And you can get it for free at the link in the show notes. Today's show is brought to you by Consensus, which helps you demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learned in discovery. Number two, how we solve those problems. And number three, what does success look like today slide? You can steal that exact 30-MPC Demo Deck template powered by Consensus. Go check it out in the show notes.